NPASS Natural Product

Natural Product: NPC86774

Natural Product ID:	NPC86774
Common Name:	(+)-(S)-Gaudichaudianic Acid
IUPAC Name:	(2S)-2-methyl-8-(3-methylbut-2-enyl)-2-(4-methylpent-3-enyl)chromene-6-carboxylic acid
Synonyms:	(+)-(S)-Gaudichaudianic Acid
Molecular Formula:	C22H28O3
Standard InCHIKey:	TXHBNVYFCZMCPB-QFIPXVFZSA-N
Standard InCHI:	InChI=1S/C22H28O3/c1-15(2)7-6-11-22(5)12-10-18-14-19(21(23)24)13-17(20(18)25-22)9-8-16(3)4/h7-8,10,12-14H,6,9,11H2,1-5H3,(H,23,24)/t22-/m0/s1
Canonical SMILES:	CC(=CCC[C@@]1(C)C=Cc2c(O1)c(CC=C(C)C)cc(c2)C(=O)O)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
NPO33179	piper sp.	Species	Piperaceae	Eukaryota				PMID[15568762]

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Biological Activity

Activity Type	# Activity
IC50	1
Others	2

Activity Type	# Activity
Organism	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT487	Organism	Cladosporium cladosporioides	Cladosporium cladosporioides	Activity	=	10	ug	20297825
NPT488	Organism	Cladosporium sphaerospermum	Cladosporium sphaerospermum	Activity	=	10	ug	Open TG-GATES in vivo data: Biochemistry
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	176500	nM	25127165

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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 NPC86774 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	213
0.1-0.2	1104
0.2-0.3	2150
0.3-0.4	5099
0.4-0.5	8035
0.5-0.6	2825
0.6-0.7	5727
0.7-0.8	4837
0.8-0.85	765
0.85-0.9	125
0.9-0.95	5
0.95-1	4

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Similarity Score	Similarity Level	Natural Product ID
0.838	Intermediate Similarity	NPC474044
0.838	Intermediate Similarity	NPC209040
0.8385	Intermediate Similarity	NPC174991
0.8392	Intermediate Similarity	NPC129650
0.8392	Intermediate Similarity	NPC79469

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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 NPC86774 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	889
0.2-0.3	1292
0.3-0.4	2243
0.4-0.5	2253
0.5-0.6	1405
0.6-0.7	613
0.7-0.8	192
0.8-0.85	25
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
0.7066	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1652	Phase 2
0.7071	Intermediate Similarity	NPD4749	Approved
0.7078	Intermediate Similarity	NPD7427	Discontinued
0.708	Intermediate Similarity	NPD1651	Approved

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Structure

NPC86774 OpenBabel07101718292D 25 26 0 0 1 0 0 0 0 0999 V2000 -3.9533 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1780 0.1378 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 -0.3105 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8320 -0.7588 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2121 0.3966 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 1.7321 -0.0000 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 2.5981 -1.5000 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 3.4641 -2.0000 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 3.4641 -3.0000 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 15 2 0 0 0 0 8 9 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 22 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 19 2 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 17 20 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 20 25 1 0 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 22 5 1 1 0 0 0 22 25 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11221505
ChEMBL	CHEMBL520792
ZINC

Physicochemical Properties

Molecular Weight:	340.20
ALogP:	4.1733
MLogP:	3.55
XLogP:	5.656
# Rotatable Bonds:	12
Polar Surface Area:	46.53
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	25

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