NPASS Natural Product

Natural Product: NPC132054

Natural Product ID:	NPC132054
Common Name:	13-Acetoxy-14-Oxocacalohastin
IUPAC Name:	[(5S)-4-formyl-9-methoxy-5-methyl-5,6-dihydrobenzo[f][1]benzofuran-3-yl]methyl acetate
Synonyms:
Molecular Formula:	C18H18O5
Standard InCHIKey:	URGRYLWWOSDITP-JTQLQIEISA-N
Standard InCHI:	InChI=1S/C18H18O5/c1-10-5-4-6-13-15(10)14(7-19)16-12(8-22-11(2)20)9-23-18(16)17(13)21-3/h4,6-7,9-10H,5,8H2,1-3H3/t10-/m0/s1
Canonical SMILES:	O=Cc1c2[C@@H](C)CC=Cc2c(c2c1c(COC(=O)C)co2)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO11820	Amomum villosum	Species	Zingiberaceae	Eukaryota	UNPD*
NPO12869	Quercus gambelii	Species	Fagaceae	Eukaryota	UNPD*
NPO15290.1	Petasites frigidus var. palmatus	Varieties	Asteraceae	Eukaryota	UNPD*
NPO16980	Callistemon lanceolatus	Species	Myrtaceae	Eukaryota	UNPD*
NPO17113	Pertusaria sulphurata	Species	Pertusariaceae	Eukaryota	UNPD*
NPO17352	Streptomyces mutabilis	Species	Streptomycetaceae	Bacteria	UNPD*
NPO17626	Gentiana algida	Species	Gentianaceae	Eukaryota	UNPD*
NPO17896	Perymenium discolor	Species	Asteraceae	Eukaryota	UNPD*
NPO18531	Streptomyces propurpuratus	Species	Streptomycetaceae	Bacteria	UNPD*
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	UNPD*

Showing 1 to 10 of 11 entries

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Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000	nM	17190472
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	>	10000	nM	17190472
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000	nM	17190472
NPT311	Cell Line	SK-LU-1	Homo sapiens	IC50	>	10000	nM	17190472
NPT380	Cell Line	U-251	Homo sapiens	IC50	>	10000	nM	17190472
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000	nM	17190472

Showing 1 to 6 of 6 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 NPC132054 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	342
0.1-0.2	1296
0.2-0.3	2484
0.3-0.4	5649
0.4-0.5	7361
0.5-0.6	3558
0.6-0.7	5140
0.7-0.8	4812
0.8-0.85	227
0.85-0.9	17
0.9-0.95	2
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.8036	Intermediate Similarity	NPC246647
0.8036	Intermediate Similarity	NPC473368
0.8036	Intermediate Similarity	NPC19600
0.8036	Intermediate Similarity	NPC123153
0.8036	Intermediate Similarity	NPC96342

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 NPC132054 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	929
0.2-0.3	1692
0.3-0.4	2692
0.4-0.5	1976
0.5-0.6	1015
0.6-0.7	396
0.7-0.8	106
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6746	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD8032	Phase 2
0.6749	Remote Similarity	NPD7874	Approved
0.6749	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.675	Remote Similarity	NPD1611	Approved

Showing 1 to 5 of 200 entries

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Structure

CID132054 OpenBabel06191715492D 23 25 0 0 1 0 0 0 0 0999 V2000 3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 5.0064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 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 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 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 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 1.8171 1.8090 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 0.9511 1.3090 0.0000 C 0 0 0 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 0 0 0 0 0 0 0 0 0 0 2.6831 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 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 0.3601 3.3122 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 2 11 1 0 0 0 0 3 21 1 0 0 0 0 4 5 1 0 0 0 0 4 6 2 0 0 0 0 5 10 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 7 19 2 0 0 0 0 8 12 1 0 0 0 0 8 22 1 0 0 0 0 9 12 2 0 0 0 0 9 23 1 0 0 0 0 10 1 1 1 0 0 0 10 15 1 0 0 0 0 11 20 2 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 17 2 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 16 18 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44566461
ChEMBL	CHEMBL463710
ZINC

Physicochemical Properties

Molecular Weight:	314.12
ALogP:	0.1957
MLogP:	2.89
XLogP:	2.953
# Rotatable Bonds:	8
Polar Surface Area:	65.74
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	23

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