NPASS Natural Product

Natural Product: NPC5671

Natural Product ID:	NPC5671
Common Name:	Penicitrinol B
IUPAC Name:
Synonyms:
Molecular Formula:	C24H28O6
Standard InCHIKey:	YWUROUQKOJZPEJ-ZPLCETTNSA-N
Standard InCHI:	InChI=1S/C24H28O6/c1-9-13(5)28-22-18-16(8-15(25)11(3)17(9)18)29-23-19(22)21(26)12(4)20-10(2)14(6)30-24(20,23)27-7/h8-10,13-14,22,25H,1-7H3/t9-,10-,13-,14-,22-,24-/m1/s1
Canonical SMILES:	CO[C@@]12O[C@@H]([C@H](C1=C(C)C(=O)C1=C2Oc2cc(O)c(c3c2[C@H]1O[C@@H]([C@H]3C)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
NPO32513	Penicillium citrinum	Under-species	NA	NA				PMID[18281952]
NPO33186	penicillium citrinum hgy1-5	Species	Aspergillaceae	Eukaryota				PMID[21761866]

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Biological Activity

Activity Type	# Activity
IC50	8

Activity Type	# Activity
Cell Line	7
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	=	291300	nM	18020419
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000	nM	10.1039/C4MD00124A
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000	nM	9249973
NPT168	Cell Line	P388	Mus musculus	IC50	>	50000	nM	9249973
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	50000	nM	9249973
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000	nM	11473434
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000	nM	9249973
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000	nM	23586757

Showing 1 to 8 of 8 entries

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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 NPC5671 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	350
0.1-0.2	1292
0.2-0.3	2431
0.3-0.4	5481
0.4-0.5	7296
0.5-0.6	3662
0.6-0.7	4300
0.7-0.8	4628
0.8-0.85	1340
0.85-0.9	108
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.84	Intermediate Similarity	NPC476216
0.8402	Intermediate Similarity	NPC297531
0.8402	Intermediate Similarity	NPC213936
0.8409	Intermediate Similarity	NPC471688
0.8409	Intermediate Similarity	NPC476159

Showing 1 to 5 of 200 entries

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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 NPC5671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	907
0.2-0.3	1766
0.3-0.4	2657
0.4-0.5	2000
0.5-0.6	978
0.6-0.7	358
0.7-0.8	140
0.8-0.85	16
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
0.6811	Remote Similarity	NPD2296	Approved
0.6814	Remote Similarity	NPD2972	Approved
0.6814	Remote Similarity	NPD3533	Approved
0.6823	Remote Similarity	NPD1729	Discontinued
0.6831	Remote Similarity	NPD7615	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

NPC5671 OpenBabel07101719252D 30 34 0 0 1 0 0 0 0 0999 V2000 5.9111 1.5320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7886 -0.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 1.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9802 1.1667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4152 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9226 0.3980 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5491 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.6910 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 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 4.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2857 -0.0362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 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 11 1 0 0 0 0 4 12 1 0 0 0 0 7 27 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 1 1 6 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 2 1 6 0 0 0 10 14 1 0 0 0 0 10 20 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 20 2 0 0 0 0 12 21 1 0 0 0 0 13 5 1 1 0 0 0 13 28 1 0 0 0 0 14 6 1 1 0 0 0 14 30 1 0 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 20 24 1 0 0 0 0 21 26 2 0 0 0 0 22 18 1 1 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 29 1 0 0 0 0 24 27 1 6 0 0 0 24 30 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	24862577
ChEMBL	CHEMBL458573
ZINC

Physicochemical Properties

Molecular Weight:	412.19
ALogP:	0.186
MLogP:	3.44
XLogP:	1.831
# Rotatable Bonds:	9
Polar Surface Area:	78.13
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	30

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