NPASS Natural Product

Natural Product: NPC222688

Natural Product ID:	NPC222688
Common Name:	(3S,4S,5R)-4-[(2R,3R)-2,3-Dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-Tetrahydroxy-10,13-Dimethyl-6-Oxo-1,2,3,4,9,11,12,15,16,17-Decahydrocyclopenta[A]Phenanthren-17-Yl]Butyl]-3,5-Dimethyloxolan-2-One
IUPAC Name:	(3S,4S,5R)-4-[(2R,3R)-2,3-dihydroxy-3-[(2S,3R,5S,9R,10R,13R,14S,17S)-2,3,5,14-tetrahydroxy-10,13-dimethyl-6-oxo-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]butyl]-3,5-dimethyloxolan-2-one
Synonyms:
Molecular Formula:	C29H44O9
Standard InCHIKey:	YQCOGGGDJXBMBU-JIVHLSMOSA-N
Standard InCHI:	InChI=1S/C29H44O9/c1-14-16(15(2)38-24(14)34)10-22(32)27(5,35)21-7-9-28(36)18-11-23(33)29(37)13-20(31)19(30)12-26(29,4)17(18)6-8-25(21,28)3/h11,14-17,19-22,30-32,35-37H,6-10,12-13H2,1-5H3/t14-,15+,16-,17-,19-,20+,21-,22+,25+,26+,27+,28+,29+/m0/s1
Canonical SMILES:	O[C@H]1C[C@]2(C)[C@H]3CC[C@]4([C@@](C3=CC(=O)[C@@]2(C[C@H]1O)O)(O)CC[C@@H]4[C@]([C@@H](C[C@@H]1[C@@H](C)OC(=O)[C@H]1C)O)(O)C)C
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
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	flowering whole plant			PMID[10425119]

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Biological Activity

Activity Type	# Activity
Others	8

Activity Type	# Activity
Cell Line	4
Others	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	0	%	10.1007/s00044-011-9568-6
NPT2	Others	Unspecified		Activity	=	100	%	DrugMatrix in vivo data: Pathology
NPT2	Others	Unspecified		Activity	=	51.9	%	23587837
NPT2	Others	Unspecified		Activity	=	80.2	%	20738102
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70	%	7807122
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80	%	18529046
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80	%	19555122
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80	%	17145798

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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 NPC222688 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	178
0.1-0.2	919
0.2-0.3	2761
0.3-0.4	4642
0.4-0.5	8689
0.5-0.6	5949
0.6-0.7	4494
0.7-0.8	2772
0.8-0.85	386
0.85-0.9	87
0.9-0.95	12
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC279478
0.8333	Intermediate Similarity	NPC297179
0.8333	Intermediate Similarity	NPC118638
0.8333	Intermediate Similarity	NPC196921
0.8333	Intermediate Similarity	NPC50535

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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 NPC222688 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	180
0.1-0.2	1404
0.2-0.3	3587
0.3-0.4	2539
0.4-0.5	857
0.5-0.6	275
0.6-0.7	159
0.7-0.8	120
0.8-0.85	37
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6724	Remote Similarity	NPD5208	Approved
0.6742	Remote Similarity	NPD4522	Approved
0.6746	Remote Similarity	NPD5168	Approved
0.678	Remote Similarity	NPD5778	Approved
0.678	Remote Similarity	NPD5779	Approved

Showing 1 to 5 of 200 entries

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Structure

NPC222688 OpenBabel07101718322D 38 42 0 0 1 0 0 0 0 0999 V2000 -7.1222 -1.7691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3903 -5.2123 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 -3.6502 -4.7382 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 -4.1369 -2.0000 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 -3.5491 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 -3.2248 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 -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 0 0 0 0 0 0 0 0 0 0 -7.2267 -2.7636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8903 -4.3463 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4836 -3.4328 0.0000 C 0 0 1 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -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 -4.8363 -3.9680 0.0000 C 0 0 2 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 -8.0927 -3.2636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8581 -3.7601 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -4.9190 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 -9.0063 -2.8569 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9071 -4.0691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -0.5865 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 -7.8848 -4.2418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 6 8 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 21 1 0 0 0 0 8 25 1 0 0 0 0 9 28 1 0 0 0 0 10 22 1 0 0 0 0 11 18 2 0 0 0 0 11 23 1 0 0 0 0 12 19 1 0 0 0 0 12 26 1 0 0 0 0 13 20 1 0 0 0 0 13 29 1 0 0 0 0 14 1 1 1 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 2 1 1 0 0 0 15 16 1 0 0 0 0 15 38 1 0 0 0 0 16 10 1 6 0 0 0 17 18 1 0 0 0 0 17 26 1 1 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 31 1 1 0 0 0 21 25 1 1 0 0 0 21 27 1 0 0 0 0 22 27 1 0 0 0 0 22 32 1 6 0 0 0 23 29 1 0 0 0 0 23 33 2 0 0 0 0 24 34 2 0 0 0 0 24 38 1 0 0 0 0 25 28 1 1 0 0 0 26 29 1 1 0 0 0 27 5 1 6 0 0 0 27 35 1 0 0 0 0 28 36 1 6 0 0 0 29 37 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	12442769
ChEMBL	CHEMBL494049
ZINC

Physicochemical Properties

Molecular Weight:	536.30
ALogP:	-1.746
MLogP:	3.66
XLogP:	0.43
# Rotatable Bonds:	15
Polar Surface Area:	164.75
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	38

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