NPASS Natural Product

Natural Product: NPC291503

Natural Product ID:	NPC291503
Common Name:	(1S,5S,9S,10S,11R,13R)-1,11-Dihydroxypimara-8(14),15-Diene
IUPAC Name:	(4S,4aS,4bS,5R,7R,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-4,5-diol
Synonyms:
Molecular Formula:	C20H32O2
Standard InCHIKey:	XSFKYBKBHXNLJA-ASZLNGMRSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-6-19(4)11-13-7-8-15-18(2,3)10-9-16(22)20(15,5)17(13)14(21)12-19/h6,11,14-17,21-22H,1,7-10,12H2,2-5H3/t14-,15+,16+,17-,19-,20-/m1/s1
Canonical SMILES:	C=C[C@@]1(C)C[C@@H](O)[C@H]2C(=C1)CC[C@@H]1[C@]2(C)[C@@H](O)CCC1(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
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota				PMID[16309313]

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3.2	ug/ml	12880316

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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 NPC291503 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	92
0.1-0.2	770
0.2-0.3	3238
0.3-0.4	9713
0.4-0.5	7908
0.5-0.6	4281
0.6-0.7	3395
0.7-0.8	1153
0.8-0.85	194
0.85-0.9	115
0.9-0.95	26
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.8354	Intermediate Similarity	NPC470049
0.8354	Intermediate Similarity	NPC304285
0.8354	Intermediate Similarity	NPC470614
0.8354	Intermediate Similarity	NPC1272
0.8354	Intermediate Similarity	NPC87489

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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 NPC291503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	127
0.1-0.2	1161
0.2-0.3	3913
0.3-0.4	2562
0.4-0.5	915
0.5-0.6	241
0.6-0.7	175
0.7-0.8	56
0.8-0.85	6
0.85-0.9	5
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.62	Remote Similarity	NPD5344	Discontinued
0.6204	Remote Similarity	NPD6868	Approved
0.6211	Remote Similarity	NPD5284	Approved
0.6211	Remote Similarity	NPD5281	Approved
0.6214	Remote Similarity	NPD6412	Phase 2

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Structure

NPC291503 OpenBabel07101718312D 22 24 0 0 1 0 0 0 0 0999 V2000 4.2711 -1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4676 -2.4914 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 3.5640 -1.2412 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 -0.8660 -1.5000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 1.7321 0.0000 0.0000 C 0 0 2 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 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 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 1.7321 1.0000 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 1 6 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 6 0 0 0 15 18 1 0 0 0 0 15 20 1 1 0 0 0 16 20 1 6 0 0 0 16 22 1 0 0 0 0 17 20 1 1 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	11536804
ChEMBL	CHEMBL465366
ZINC

Physicochemical Properties

Molecular Weight:	304.24
ALogP:	1.3099
MLogP:	3.44
XLogP:	5.048
# Rotatable Bonds:	7
Polar Surface Area:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	22

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