NPASS Natural Product

Natural Product: NPC311256

Natural Product ID:	NPC311256
Common Name:	(+)-Cycloolivil
IUPAC Name:	(2S,3S,4S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-bis(hydroxymethyl)-7-methoxy-3,4-dihydro-1H-naphthalene-2,6-diol
Synonyms:	(+)-Cycloolivil
Molecular Formula:	C20H24O7
Standard InCHIKey:	KCIQZCNOUZCRGH-VOBQZIQPSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-26-17-5-11(3-4-15(17)23)19-13-7-16(24)18(27-2)6-12(13)8-20(25,10-22)14(19)9-21/h3-7,14,19,21-25H,8-10H2,1-2H3/t14-,19+,20-/m1/s1
Canonical SMILES:	COc1cc2C[C@@](O)(CO)[C@@H]([C@H](c2cc1O)c1ccc(c(c1)OC)O)CO
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10010	Evernia vulpina	Species	Parmeliaceae	Eukaryota	UNPD*
NPO10298	Symbiodinium microadriaticum	Species	Symbiodiniaceae	Eukaryota	UNPD*
NPO10745	Stereospermum personatum	Species	Bignoniaceae	Eukaryota	PMID[16309309]
NPO10825	Nerine sarniensis	Species	Amaryllidaceae	Eukaryota	UNPD*
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	TM-MC*
NPO10970	Osmorhiza aristata	Species	Apiaceae	Eukaryota	UNPD*
NPO11339	Litsea salicifolia	Species	Lauraceae	Eukaryota	UNPD*
NPO11506	Stipa vaseyi	Species	Poaceae	Eukaryota	UNPD*
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	UNPD*
NPO12118	Cleistopholis staudtii	Species	Annonaceae	Eukaryota	UNPD*

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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
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	101380	nM	16309309

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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 NPC311256 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	279
0.1-0.2	1103
0.2-0.3	2220
0.3-0.4	5300
0.4-0.5	7612
0.5-0.6	2833
0.6-0.7	5850
0.7-0.8	4466
0.8-0.85	729
0.85-0.9	434
0.9-0.95	60
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.8777	High Similarity	NPC183709
0.8777	High Similarity	NPC204347
0.8777	High Similarity	NPC475891
0.8779	High Similarity	NPC191037
0.8779	High Similarity	NPC58607

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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 NPC311256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	866
0.2-0.3	1450
0.3-0.4	2604
0.4-0.5	1990
0.5-0.6	1042
0.6-0.7	716
0.7-0.8	205
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7045	Intermediate Similarity	NPD968	Approved
0.705	Intermediate Similarity	NPD7741	Discontinued
0.7051	Intermediate Similarity	NPD1512	Approved
0.7055	Intermediate Similarity	NPD4666	Phase 3
0.7059	Intermediate Similarity	NPD6658	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID311256 OpenBabel06191716122D 27 29 0 0 1 0 0 0 0 0999 V2000 -6.0622 2.5000 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 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 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 2.5000 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 -1.2321 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2321 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 15 1 0 0 0 0 5 11 2 0 0 0 0 5 17 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 20 1 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 20 1 0 0 0 0 10 22 1 0 0 0 0 12 13 1 0 0 0 0 13 19 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 1 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 11 1 6 0 0 0 20 25 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	5316262
ChEMBL	CHEMBL516536
ZINC

Physicochemical Properties

Molecular Weight:	376.15
ALogP:	-2.6532
MLogP:	2.89
XLogP:	0.58
# Rotatable Bonds:	12
Polar Surface Area:	119.61
# H-Bond Aceptor:	3
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	27

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