NPASS Natural Product

Natural Product: NPC265211

Natural Product ID:	NPC265211
Common Name:	(3S,7S)-5,6-Dehydro-4''-De-O-Methylcentrolobine
IUPAC Name:	4-[2-[(2S,6S)-6-(4-hydroxyphenyl)-3,6-dihydro-2H-pyran-2-yl]ethyl]phenol
Synonyms:
Molecular Formula:	C19H20O3
Standard InCHIKey:	WNMSDVNIAXMQRI-MOPGFXCFSA-N
Standard InCHI:	InChI=1S/C19H20O3/c20-16-9-4-14(5-10-16)6-13-18-2-1-3-19(22-18)15-7-11-17(21)12-8-15/h1,3-5,7-12,18-21H,2,6,13H2/t18-,19+/m1/s1
Canonical SMILES:	Oc1ccc(cc1)CC[C@H]1CC=C[C@H](O1)c1ccc(cc1)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
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds			PMID[11325233]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota				TCMID*

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Biological Activity

Activity Type	# Activity
ED50	2

Activity Type	# Activity
Cell Line	1
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		ED50	>	0.1	nM	11325233
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	79.4	nM	11325233

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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 NPC265211 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	188
0.1-0.2	991
0.2-0.3	2043
0.3-0.4	6612
0.4-0.5	7252
0.5-0.6	3684
0.6-0.7	6948
0.7-0.8	2909
0.8-0.85	223
0.85-0.9	27
0.9-0.95	8
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.8049	Intermediate Similarity	NPC47283
0.8049	Intermediate Similarity	NPC129570
0.8049	Intermediate Similarity	NPC72529
0.8049	Intermediate Similarity	NPC45774
0.8051	Intermediate Similarity	NPC282255

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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 NPC265211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	822
0.2-0.3	1116
0.3-0.4	2533
0.4-0.5	2274
0.5-0.6	1228
0.6-0.7	784
0.7-0.8	182
0.8-0.85	5
0.85-0.9	5
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6978	Remote Similarity	NPD6190	Approved
0.6983	Remote Similarity	NPD9608	Approved
0.6983	Remote Similarity	NPD3047	Approved
0.6983	Remote Similarity	NPD3046	Approved
0.6983	Remote Similarity	NPD3048	Approved

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Structure

CID265211 OpenBabel06191716062D 22 24 0 0 1 0 0 0 0 0999 V2000 0.0000 -2.0000 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 0.8660 -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 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 -2.5981 -0.5000 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 -0.5000 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 -4.3301 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 3.4641 0.0000 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 -3.4641 -0.0000 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 -5.1962 1.0000 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 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 4.3301 1.5000 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 1 2 1 0 0 0 0 1 3 2 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 9 1 0 0 0 0 4 14 2 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 13 1 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 18 13 1 6 0 0 0 18 22 1 0 0 0 0 19 15 1 6 0 0 0 19 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44584770
ChEMBL	CHEMBL454764
ZINC

Physicochemical Properties

Molecular Weight:	296.14
ALogP:	-0.6777
MLogP:	3.22
XLogP:	4.259
# Rotatable Bonds:	6
Polar Surface Area:	49.69
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	22

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