NPASS Natural Product

Natural Product: NPC287118

Natural Product ID:	NPC287118
Common Name:	3Alpha-Acetoxy-27-Hydroxylup-20(29)-En-24-Oic Acid
IUPAC Name:	(1R,3aR,5aS,5bR,7aR,8R,9R,11aR,11bR,13aR,13bR)-9-acetyloxy-5a-(hydroxymethyl)-3a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-8-carboxylic acid
Synonyms:
Molecular Formula:	C32H50O5
Standard InCHIKey:	SFMBHTKBXIQXHJ-LBIUZANVSA-N
Standard InCHI:	InChI=1S/C32H50O5/c1-19(2)21-10-13-28(4)16-17-32(18-33)22(26(21)28)8-9-23-29(5)14-12-25(37-20(3)34)31(7,27(35)36)24(29)11-15-30(23,32)6/h21-26,33H,1,8-18H2,2-7H3,(H,35,36)/t21-,22+,23+,24+,25+,26+,28+,29+,30+,31+,32-/m0/s1
Canonical SMILES:	OC[C@@]12CC[C@@]3([C@@H]([C@H]1CC[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@H]([C@]2(C)C(=O)O)OC(=O)C)[C@@H](CC3)C(=C)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
NPO10628	Boswellia papyrifera	Species	Burseraceae	Eukaryota				PMID[15730241]

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1591	Individual Protein	Prolyl endopeptidase	Homo sapiens	IC50	=	2866	nM	8691203

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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 NPC287118 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	137
0.1-0.2	954
0.2-0.3	3435
0.3-0.4	8833
0.4-0.5	7219
0.5-0.6	3729
0.6-0.7	3831
0.7-0.8	2262
0.8-0.85	390
0.85-0.9	75
0.9-0.95	16
0.95-1	8

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Similarity Score	Similarity Level	Natural Product ID
0.8265	Intermediate Similarity	NPC71706
0.8269	Intermediate Similarity	NPC146563
0.8276	Intermediate Similarity	NPC201459
0.8276	Intermediate Similarity	NPC192744
0.828	Intermediate Similarity	NPC111110

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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 NPC287118 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	150
0.1-0.2	1684
0.2-0.3	3790
0.3-0.4	2343
0.4-0.5	674
0.5-0.6	205
0.6-0.7	210
0.7-0.8	98
0.8-0.85	4
0.85-0.9	0
0.9-0.95	3
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6555	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD8380	Approved
0.6555	Remote Similarity	NPD8335	Approved
0.6555	Remote Similarity	NPD8033	Approved
0.6555	Remote Similarity	NPD5983	Phase 2

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Structure

NPC287118 OpenBabel07101719512D 37 41 0 0 1 0 0 0 0 0999 V2000 3.8757 -1.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2677 -1.9555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -4.8810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2938 1.8680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3578 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1930 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6192 1.2778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9209 -1.2301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 -4.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6192 -0.3017 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8454 -1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5362 -1.4643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3816 -2.9286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6908 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8697 -1.1070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 0.9762 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6908 -1.9524 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3816 -1.9524 0.0000 C 0 0 1 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 -1.6908 1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0724 -4.8810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8459 -1.1070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.2616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 -3.4167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 6 30 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 20 34 2 0 0 0 0 20 37 1 0 0 0 0 21 19 1 1 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 22 32 1 1 0 0 0 23 29 1 6 0 0 0 23 30 1 0 0 0 0 24 29 1 6 0 0 0 24 31 1 0 0 0 0 25 31 1 1 0 0 0 25 37 1 0 0 0 0 26 28 1 6 0 0 0 27 31 1 0 0 0 0 27 35 2 0 0 0 0 27 36 1 0 0 0 0 28 4 1 6 0 0 0 29 5 1 6 0 0 0 30 32 1 1 0 0 0 31 7 1 1 0 0 0 32 18 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	21575462
ChEMBL	CHEMBL499293
ZINC

Physicochemical Properties

Molecular Weight:	514.37
ALogP:	1.6379
MLogP:	4.43
XLogP:	9.015
# Rotatable Bonds:	13
Polar Surface Area:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	37

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