NPASS Natural Product

Natural Product: NPC293641

Natural Product ID:	NPC293641
Common Name:	(S)-6-Gingerol
IUPAC Name:	(5S)-5-hydroxy-1-(3-hydroxy-4-methoxyphenyl)decan-3-one
Synonyms:	(S)-6-Gingerol
Molecular Formula:	C17H26O4
Standard InCHIKey:	LPRPIMHDDACJHT-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C17H26O4/c1-3-4-5-6-14(18)12-15(19)9-7-13-8-10-17(21-2)16(20)11-13/h8,10-11,14,18,20H,3-7,9,12H2,1-2H3/t14-/m0/s1
Canonical SMILES:	CCCCC[C@@H](CC(=O)CCc1ccc(c(c1)O)OC)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
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota				PMID[15270556]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota				TM-MC*

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Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Individual Protein	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	36400	nM	15270556
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	100000	nM	15270556

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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 NPC293641 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	189
0.1-0.2	894
0.2-0.3	2095
0.3-0.4	5086
0.4-0.5	8444
0.5-0.6	2493
0.6-0.7	5830
0.7-0.8	5332
0.8-0.85	387
0.85-0.9	88
0.9-0.95	35
0.95-1	16

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Similarity Score	Similarity Level	Natural Product ID
0.8346	Intermediate Similarity	NPC204466
0.8357	Intermediate Similarity	NPC469683
0.8359	Intermediate Similarity	NPC209567
0.8369	Intermediate Similarity	NPC299090
0.8369	Intermediate Similarity	NPC283081

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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 NPC293641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	806
0.2-0.3	1473
0.3-0.4	2398
0.4-0.5	2117
0.5-0.6	1196
0.6-0.7	797
0.7-0.8	158
0.8-0.85	5
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
0.6951	Remote Similarity	NPD5844	Phase 1
0.6959	Remote Similarity	NPD6002	Phase 3
0.6959	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5762	Approved
0.6959	Remote Similarity	NPD6005	Phase 3

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Structure

CID293641 OpenBabel06191716102D 21 21 0 0 1 0 0 0 0 0999 V2000 6.9282 7.0000 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 6.0622 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 4.3301 4.5000 0.0000 C 0 0 1 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 -0.0000 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 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 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 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 14 18 1 6 0 0 0 15 19 2 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44559528
ChEMBL	CHEMBL471072
ZINC

Physicochemical Properties

Molecular Weight:	294.18
ALogP:	-2.2553
MLogP:	2.89
XLogP:	2.887
# Rotatable Bonds:	14
Polar Surface Area:	66.76
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	21

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