NPASS Natural Product

Natural Product: NPC473265

Natural Product ID:	NPC473265
Common Name:	Anomanolide F
IUPAC Name:	(1R,4R,5R)-4-hydroxy-4,5-dimethyl-7-[(4S,5R,8S,9S,10R,13S,14S,16R,17S)-4,5,16,17-tetrahydroxy-10,13-dimethyl-1-oxo-4,6,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxabicyclo[3.2.1]octan-3-one
Synonyms:	Anomanolide F
Molecular Formula:	C28H40O8
Standard InCHIKey:	IIXRXLFGAXOZNE-VOWCFRKOSA-N
Standard InCHI:	InChI=1S/C28H40O8/c1-23-12-17(18(13-23)36-22(32)26(23,4)33)28(35)21(31)11-16-14-7-10-27(34)20(30)6-5-19(29)25(27,3)15(14)8-9-24(16,28)2/h5-6,14-18,20-21,30-31,33-35H,7-13H2,1-4H3/t14-,15+,16+,17?,18-,20+,21-,23-,24+,25+,26+,27+,28-/m1/s1
Canonical SMILES:	O[C@@H]1C[C@@H]2[C@]([C@@]1(O)C1C[C@@]3(C[C@H]1OC(=O)[C@]3(C)O)C)(C)CC[C@H]1[C@H]2CC[C@]2([C@]1(C)C(=O)C=C[C@@H]2O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	stems, roots, and leaves	Da-Han Mountain, Kaohsiung, Taiwan	2004-OCT	PMID[17417907]

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Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell Line	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20	ug/ml	20886871
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20	ug/ml	16417306
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20	ug/ml	10650083
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20	ug/ml	19410459

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Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC473265 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	983
0.2-0.3	2818
0.3-0.4	4941
0.4-0.5	8207
0.5-0.6	6556
0.6-0.7	4409
0.7-0.8	2398
0.8-0.85	340
0.85-0.9	45
0.9-0.95	3
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.8175	Intermediate Similarity	NPC135038
0.8182	Intermediate Similarity	NPC202889
0.8182	Intermediate Similarity	NPC255017
0.8182	Intermediate Similarity	NPC51978
0.8182	Intermediate Similarity	NPC25909

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Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC473265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	1443
0.2-0.3	3607
0.3-0.4	2505
0.4-0.5	793
0.5-0.6	322
0.6-0.7	156
0.7-0.8	104
0.8-0.85	37
0.85-0.9	4
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.661	Remote Similarity	NPD6098	Approved
0.661	Remote Similarity	NPD5690	Phase 2
0.6612	Remote Similarity	NPD5694	Approved
0.6612	Remote Similarity	NPD8034	Phase 2
0.6612	Remote Similarity	NPD6050	Approved

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Structure

NPC473265 OpenBabel07101718292D 36 41 0 0 1 0 0 0 0 0999 V2000 -6.6549 4.6028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 3.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6315 2.4964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2704 3.2702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1013 4.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2923 3.4781 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.1877 4.4727 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7682 3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7704 4.1363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4677 3.4829 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1369 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5603 2.3340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4040 3.1315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 3.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1985 3.7527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 5 6 2 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 10 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 24 1 0 0 0 0 10 27 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 23 1 0 0 0 0 13 23 1 0 0 0 0 14 7 1 1 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 25 1 6 0 0 0 16 24 1 6 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 18 13 1 1 0 0 0 18 36 1 0 0 0 0 19 25 1 0 0 0 0 19 29 2 0 0 0 0 20 27 1 6 0 0 0 20 30 1 0 0 0 0 21 28 1 1 0 0 0 21 31 1 0 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 22 36 1 0 0 0 0 23 26 1 1 0 0 0 24 28 1 1 0 0 0 25 27 1 6 0 0 0 26 4 1 1 0 0 0 26 33 1 0 0 0 0 27 34 1 6 0 0 0 28 35 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	44423064
ChEMBL	CHEMBL388494
ZINC

Physicochemical Properties

Molecular Weight:	504.27
ALogP:	-1.2575
MLogP:	3.66
XLogP:	2.107
# Rotatable Bonds:	10
Polar Surface Area:	144.52
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	36

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