NPASS Natural Product

Natural Product: NPC116797

Natural Product ID:	NPC116797
Common Name:	Triptoquinone B
IUPAC Name:	(4bS,8S,8aR)-8-(hydroxymethyl)-4b,8-dimethyl-2-propan-2-yl-6,8a,9,10-tetrahydro-5H-phenanthrene-1,4,7-trione
Synonyms:
Molecular Formula:	C20H26O4
Standard InCHIKey:	RYYRZMIBKOKIRO-UIAACRFSSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-11(2)13-9-14(22)17-12(18(13)24)5-6-15-19(17,3)8-7-16(23)20(15,4)10-21/h9,11,15,21H,5-8,10H2,1-4H3/t15-,19+,20-/m1/s1
Canonical SMILES:	OC[C@@]1(C)C(=O)CC[C@]2([C@H]1CCC1=C2C(=O)C=C(C1=O)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
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota				PMID[10579865]

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Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	5
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1872	Cell Line	Bcap37	Homo sapiens	IC50	=	13290	nM	27133593
NPT2	Others	Unspecified		IC50	=	25980	nM	27133593
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	26300	nM	27133593
NPT75	Cell Line	U251	Homo sapiens	IC50	>	100000	nM	27133593
NPT81	Cell Line	A549	Homo sapiens	IC50	=	19910	nM	27133593
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	16690	nM	27133593

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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 NPC116797 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	109
0.1-0.2	671
0.2-0.3	3213
0.3-0.4	8539
0.4-0.5	8339
0.5-0.6	4675
0.6-0.7	3613
0.7-0.8	1536
0.8-0.85	167
0.85-0.9	26
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7978	Intermediate Similarity	NPC158030
0.7978	Intermediate Similarity	NPC73457
0.7978	Intermediate Similarity	NPC131872
0.7978	Intermediate Similarity	NPC172101
0.7978	Intermediate Similarity	NPC65120

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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 NPC116797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	124
0.1-0.2	1164
0.2-0.3	3693
0.3-0.4	2848
0.4-0.5	811
0.5-0.6	221
0.6-0.7	183
0.7-0.8	106
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6588	Remote Similarity	NPD4243	Approved
0.6593	Remote Similarity	NPD4270	Approved
0.6593	Remote Similarity	NPD4269	Approved
0.66	Remote Similarity	NPD5290	Discontinued
0.6606	Remote Similarity	NPD6868	Approved

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Structure

CID116797 OpenBabel06191715472D 24 26 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 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 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 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 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 2.5981 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 0.0000 -1.0000 0.0000 C 0 0 2 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 0.8660 0.5000 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 -0.0000 -0.0000 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 -0.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 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 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 8 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 20 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 14 17 1 0 0 0 0 14 22 2 0 0 0 0 15 19 1 1 0 0 0 15 20 1 0 0 0 0 16 20 1 0 0 0 0 16 23 2 0 0 0 0 17 19 1 0 0 0 0 18 24 2 0 0 0 0 19 3 1 1 0 0 0 20 4 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	11724191
ChEMBL	CHEMBL3800483
ZINC

Physicochemical Properties

Molecular Weight:	330.18
ALogP:	0.4036
MLogP:	3.22
XLogP:	1.39
# Rotatable Bonds:	7
Polar Surface Area:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	24

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