haemanthamine (Q27106819)

(1R,13R,15S,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol

inferred from SMILES

1 reference

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(1S,13R,15R,18S)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol

1 reference

inferred from SMILES

chemical structure

Haemanthamine.svg
435 × 490; 19 KB

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mass

301.131408±0 dalton

1 reference

(+)-Haemanthamine (English)

(1S,13R,15S,18S)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol

5 October 2016

stereoisomer of

1 reference

(1R,13S,15S,18S)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol

inferred from InChIKey

1 reference

(1S,13R,15R,18R)-15-methoxy-5,7-dioxa-12-azapentacyclo[10.5.2.01,13.02,10.04,8]nonadeca-2,4(8),9,16-tetraen-18-ol

inferred from InChI

1 reference

inferred from InChI

chemical formula

C₁₇H₁₉NO₄

1 reference

(+)-Haemanthamine (English)

5 October 2016

canonical SMILES

COC1CC2C3(C=C1)C(CN2CC4=CC5=C(C=C34)OCO5)O

1 reference

(+)-Haemanthamine (English)

5 October 2016

OC1CN2CC3=CC=4OCOC4C=C3C51C=CC(OC)CC25

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isomeric SMILES

CO[C@H]1C[C@H]2[C@@]3(C=C1)[C@H](CN2CC4=CC5=C(C=C34)OCO5)O

1 reference

(+)-Haemanthamine (English)

5 October 2016

CO[C@@H]1C=C[C@@]23c4cc5c(cc4CN(C[C@H]2O)[C@H]3C1)OCO5

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found in taxon

Narcissus confusus

3 references

Solid-phase extraction and reversed-phase high-performance liquid chromatography of the five major alkaloids in Narcissus confusus.

Alkaloids from Narcissus confusus

Molecular structure of haemanthamine, an alkaloid from Narcissus confusus

Sternbergia sicula

1 reference

Four New Crinine-Type Alkaloids from Sternbergia Species

Sternbergia lutea

1 reference

Four New Crinine-Type Alkaloids from Sternbergia Species

Narcissus pseudonarcissus subsp. pallidiflorus

1 reference

A heterodimer alkaloid from Narcissus pallidiflorus

Pancratium canariense

1 reference

Pancratium canariense as an important source of amaryllidaceae alkaloids

Habranthus brachyandrus

1 reference

Chemical constituents of the bulbs of Habranthus brachyandrus and their cytotoxic activities

Narcissus obesus

1 reference

Narcissus Alkaloids, XVII. Obesine, a Novel Alkaloid from Narcissus, obesus

Narcissus tazetta

1 reference

Narcisine, an alkaloid from Narcissus tazetta

Hymenocallis littoralis

1 reference

Lycorine alkaloids from Hymenocallis littoralis

Crinum asiaticum

1 reference

New Alkaloids from Crinum asiaticum

Crinum glaucum

1 reference

Choline esterase inhibitory properties of alkaloids from two Nigerian Crinum species

Crinum jagus

1 reference

Choline esterase inhibitory properties of alkaloids from two Nigerian Crinum species

George lily, Scarborough lily

1 reference

Alkaloids from Cyrtanthus elatus

Eucharis amazonica

1 reference

Alkaloids from Eucharis amazonica (Amaryllidaceae).

Hippeastrum puniceum

1 reference

Alkaloids of the epigeal organs ofHippeastrum equestre

Hippeastrum

1 reference

Alkaloids of Hippeastrum glaucescens

Hymenocallis rotata

1 reference

Alkaloidal constituents of Hymenocallis rotata Herb. (Amaryllidaceae).

Narcissus asturiensis

1 reference

Alkaloids from Narcissus asturiensis

Narcissus cuneiflorus

1 reference

Alkaloids from Narcissus asturiensis

Narcissus primigenius

1 reference

Alkaloids from Narcissus primigenius

Pancratium maritimum

1 reference

New Alkaloids from Pancratium maritimum L

Pancratium sickenbergeri

1 reference

Two New Alkaloids of the Crinane Series from Pancratium sickenbergeri

Sternbergia clusiana

1 reference

Alkaloids of Sternbergia clusiana and their Analgesic Effects

Zephyranthes citrina

1 reference

Crinane and lycorane type alkaloids from Zephyranthes citrina

Zephyranthes flava

1 reference

Alkaloids of zephyranthes flava

Zephyranthes rosea

1 reference

(+)-Epimaritidine, an alkaloid from Zephyranthes rosea

Zephyranthes candida

1 reference

Cytotoxic alkaloids from the whole plants of Zephyranthes candida

Hippeastrum morelianum

1 reference

Alkaloids from Hippeastrum morelianum Lem. (Amaryllidaceae)

Hippeastrum papilio

1 reference

Alkaloids from Hippeastrum papilio.

Phaedranassa dubia

1 reference

In vitro antiprotozoal activity of alkaloids from Phaedranassa dubia (Amaryllidaceae)

Sprekelia formosissima

1 reference

Antiproliferative amaryllidaceae alkaloids isolated from the bulbs of Sprekelia formosissima and Hymenocallis x festalis

Narcissus hispanicus

3 references

Alkaloids from Narcissus confusus

Solid-phase extraction and reversed-phase high-performance liquid chromatography of the five major alkaloids in Narcissus confusus.

Molecular structure of haemanthamine, an alkaloid from Narcissus confusus

Pyrolirion flavum

1 reference

Alkaloids of zephyranthes flava

Narcissus

1 reference

Alkaloid content of different bulb parts of Narcissus cv. Ice Follies

Urceolina amazonica

1 reference

Alkaloids from Eucharis amazonica (Amaryllidaceae).

Narcissus minor

1 reference

Alkaloids from Narcissus asturiensis

Galanthus elwesii

2 references

Intraspecific variability in the alkaloid metabolism of Galanthus elwesii

Alkaloide vonSprekelia formosissima, Galanthus Elwesii, Zephyranthes candida undCrinum Powellii (VIII. Mitteil. über Amaryllidaceen-Alkaloide1))

Scadoxus multiflorus

2 references

Isocarbostyril alkaloids from Haemanthus kalbreyeri

Alkaloids of Haemanthus kalbreyeri

Narcissus bulbocodium

1 reference

Narcissus Alkaloids, XVII. Obesine, a Novel Alkaloid from Narcissus, obesus

Ismene longipetala

1 reference

Alkaloide aus Urceolina-, Hymenocallis-, Elisena-, Calostemma-, Eustephia- und Hippeastrum-Arten

Hippeastrum vittatum

1 reference

Alkaloide vonChlidanthus fragrans,Vallota purpurea,Nerine undulata undHippeastrum vittatum (XI. Mitteil. über Amaryllidaceen-Alkaloide)

Stenomesson miniatum

1 reference

Alkaloide aus Urceolina-, Hymenocallis-, Elisena-, Calostemma-, Eustephia- und Hippeastrum-Arten

Amaryllidaceae

3 references

Capillary gas chromatography-mass spectrometry of Amaryllidaceae alkaloids

(+)-Narcidine, a New Alkaloid from Narcissus pseudonarcissus

O-Methyloduline and N-demethylmasonine, alkaloids from Narcissus pseudonarcissus

Narcissus pseudonarcissus

1 reference

O-Methyloduline and N-demethylmasonine, alkaloids from Narcissus pseudonarcissus

Identifiers

InChI

InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15+,16+,17+/m1/s1

1 reference

(+)-Haemanthamine (English)

InChI=1S/C17H19NO4/c1-20-11-2-3-17-12-6-14-13(21-9-22-14)4-10(12)7-18(8-16(17)19)15(17)5-11/h2-4,6,11,15-16,19H,5,7-9H2,1H3/t11-,15+,16-,17+/m1/s1

5 October 2016

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InChIKey

YGPRSGKVLATIHT-HSHDSVGOSA-N

2 references

(+)-Haemanthamine (English)

5 October 2016

YGPRSGKVLATIHT-BEMMVCDISA-N

ChEBI release 2020-09-01

0 references

2 references

Haemanthamine (English)

YGPRSGKVLATIHT-HSHDSVGOSA-N

5 October 2016

InChIKey

9 April 2021

https://commonchemistry.cas.org/detail?cas_rn=466-75-1

1 reference

(3beta,11R,13beta,19alpha)-3-Methoxy-1,2-didehydrocrinan-11-ol (English)

5 October 2016

1 reference

(+)-Haemanthamine (English)

5 October 2016

ChEBI ID

5600

mapping relation type

1 reference

Haemanthamine (English)

5 October 2016

1 reference

DSSTOX compound identifier

(+)-HAEMANTHAMINE (English)

5 October 2016

1 reference

0 references

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1 reference

Haemanthamine (English)

5 October 2016

0 references

1 reference

Haemanthamine (English)