NPASS Natural Product

Natural Product: NPC123544

Natural Product ID:	NPC123544
Common Name:	Gericudranin D
IUPAC Name:	(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-6,8-bis[(4-hydroxyphenyl)methyl]-2,3-dihydrochromen-4-one
Synonyms:	Gericudranin D
Molecular Formula:	C29H24O8
Standard InCHIKey:	LHFMOLHENFWCMZ-WUFINQPMSA-N
Standard InCHI:	InChI=1S/C29H24O8/c30-18-7-1-15(2-8-18)13-21-24(33)22(14-16-3-9-19(31)10-4-16)29-23(25(21)34)26(35)27(36)28(37-29)17-5-11-20(32)12-6-17/h1-12,27-28,30-34,36H,13-14H2/t27-,28+/m0/s1
Canonical SMILES:	Oc1ccc(cc1)Cc1c(O)c(Cc2ccc(cc2)O)c(c2c1O[C@H](c1ccc(cc1)O)[C@H](C2=O)O)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
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits			PMID[19113968]

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Biological Activity

Activity Type	# Activity
ED50	5
IC50	1

Activity Type	# Activity
Cell Line	5
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000	nM	25211145
NPT2	Others	Unspecified		ED50	=	9.5	ug/ml	8254344
NPT371	Cell Line	UO-31	Homo sapiens	ED50	=	5.2	ug/ml	25646964
NPT386	Cell Line	KM12	Homo sapiens	ED50	=	5	ug/ml	25646964
NPT390	Cell Line	LOX IMVI	Homo sapiens	ED50	=	16.6	ug/ml	8254344
NPT5528	Cell Line	MOLT-4F	Homo sapiens	ED50	=	8.9	ug/ml	8254344

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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 NPC123544 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	344
0.1-0.2	1158
0.2-0.3	2412
0.3-0.4	5849
0.4-0.5	7070
0.5-0.6	3070
0.6-0.7	4025
0.7-0.8	3740
0.8-0.85	1871
0.85-0.9	1108
0.9-0.95	236
0.95-1	6

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Similarity Score	Similarity Level	Natural Product ID
0.9051	High Similarity	NPC470326
0.9057	High Similarity	NPC476247
0.9057	High Similarity	NPC473012
0.9057	High Similarity	NPC44947
0.9057	High Similarity	NPC473011

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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 NPC123544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	851
0.2-0.3	1599
0.3-0.4	2596
0.4-0.5	1994
0.5-0.6	1133
0.6-0.7	452
0.7-0.8	150
0.8-0.85	32
0.85-0.9	19
0.9-0.95	6
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7039	Intermediate Similarity	NPD2403	Approved
0.7039	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4661	Approved
0.7041	Intermediate Similarity	NPD4662	Approved
0.7041	Intermediate Similarity	NPD7447	Phase 1

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Structure

NPC123544 OpenBabel07101718242D 37 41 0 0 1 0 0 0 0 0999 V2000 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 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 -0.8660 -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 -0.8660 2.5000 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 6.0622 -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 -1.7321 -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 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 0.0000 -2.0000 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 -0.8660 -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 6.0622 -0.5000 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 -2.5981 2.5000 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 -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 1.7321 -2.0000 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 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 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 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 7 1 0 0 0 0 1 15 2 0 0 0 0 2 8 2 0 0 0 0 2 15 1 0 0 0 0 3 9 1 0 0 0 0 3 16 2 0 0 0 0 4 10 2 0 0 0 0 4 16 1 0 0 0 0 5 11 1 0 0 0 0 5 17 2 0 0 0 0 6 12 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 20 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 14 22 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 24 1 0 0 0 0 22 29 2 0 0 0 0 23 25 2 0 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 26 27 1 0 0 0 0 26 35 2 0 0 0 0 27 28 1 0 0 0 0 27 36 1 1 0 0 0 28 17 1 6 0 0 0 28 37 1 0 0 0 0 29 37 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44559901
ChEMBL	CHEMBL510170
ZINC

Physicochemical Properties

Molecular Weight:	500.15
ALogP:	-2.4748
MLogP:	3.77
XLogP:	3.702
# Rotatable Bonds:	11
Polar Surface Area:	147.68
# H-Bond Aceptor:	2
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	37

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