NPASS Natural Product

Natural Product: NPC10010

Natural Product ID:	NPC10010
Common Name:	Pennicitrinone C
IUPAC Name:
Synonyms:	Pennicitrinone C
Molecular Formula:	C23H26O6
Standard InCHIKey:	HESPWWKIRCFDQL-MNUQUWEESA-N
Standard InCHI:	InChI=1S/C23H26O6/c1-8(12(5)24)17-11(4)20(26)19-22-18-15(29-23(19)21(17)27)7-14(25)10(3)16(18)9(2)13(6)28-22/h7-9,12-13,24,26-27H,1-6H3/t8-,9-,12+,13-/m1/s1
Canonical SMILES:	C[C@@H]([C@H](c1c(O)c2oc3cc(=O)c(c4c3c(c2c(c1C)O)O[C@@H]([C@H]4C)C)C)C)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
NPO32513	Penicillium citrinum	Under-species	NA	NA				PMID[18281952]

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Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	4
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	55300	nM	DrugMatrix in vitro pharmacology data
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000	nM	DrugMatrix in vitro pharmacology data
NPT168	Cell Line	P388	Mus musculus	IC50	>	50000	nM	DrugMatrix in vitro pharmacology data
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000	nM	17350734
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000	nM	DrugMatrix in vitro pharmacology data

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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 NPC10010 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	275
0.1-0.2	1146
0.2-0.3	2531
0.3-0.4	5753
0.4-0.5	7596
0.5-0.6	3005
0.6-0.7	4777
0.7-0.8	5392
0.8-0.85	403
0.85-0.9	9
0.9-0.95	1
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.8121	Intermediate Similarity	NPC68292
0.8121	Intermediate Similarity	NPC472800
0.8121	Intermediate Similarity	NPC248727
0.8121	Intermediate Similarity	NPC162659
0.8121	Intermediate Similarity	NPC30632

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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 NPC10010 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	922
0.2-0.3	2026
0.3-0.4	2724
0.4-0.5	1724
0.5-0.6	945
0.6-0.7	437
0.7-0.8	91
0.8-0.85	2
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
0.6615	Remote Similarity	NPD2494	Approved
0.6615	Remote Similarity	NPD2493	Approved
0.6622	Remote Similarity	NPD5283	Phase 1
0.6627	Remote Similarity	NPD2677	Approved
0.6629	Remote Similarity	NPD5709	Phase 3

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Structure

NPC10010 OpenBabel07101719522D 29 32 0 0 1 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3424 -3.3750 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.0860 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 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5605 -2.7515 0.0000 C 0 0 2 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -3.0860 0.0000 C 0 0 2 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 -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 -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 -0.8660 -1.5000 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 -1.7321 0.0000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -1.7321 -3.0000 0.0000 O 0 0 0 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 0.1715 -2.7515 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 7 14 1 0 0 0 0 7 15 2 0 0 0 0 8 1 1 1 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 9 2 1 6 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 17 2 0 0 0 0 11 20 1 0 0 0 0 12 5 1 1 0 0 0 12 24 1 0 0 0 0 13 6 1 1 0 0 0 13 28 1 0 0 0 0 14 25 2 0 0 0 0 15 18 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 19 20 2 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 26 1 0 0 0 0 21 23 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	24850196
ChEMBL	CHEMBL458391
ZINC

Physicochemical Properties

Molecular Weight:	398.17
ALogP:	-0.584
MLogP:	3.33
XLogP:	1.716
# Rotatable Bonds:	11
Polar Surface Area:	96.22
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	29

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