NPASS Natural Product

Natural Product: NPC4940

Natural Product ID:	NPC4940
Common Name:	Prinsepiol
IUPAC Name:	(3R,3aS,6R,6aS)-3,6-bis(4-hydroxy-3-methoxyphenyl)-1,3,4,6-tetrahydrofuro[3,4-c]furan-3a,6a-diol
Synonyms:	Prinsepiol
Molecular Formula:	C20H22O8
Standard InCHIKey:	IUWMJMIMXOEDKV-ZRNYENFQSA-N
Standard InCHI:	InChI=1S/C20H22O8/c1-25-15-7-11(3-5-13(15)21)17-19(23)9-28-18(20(19,24)10-27-17)12-4-6-14(22)16(8-12)26-2/h3-8,17-18,21-24H,9-10H2,1-2H3/t17-,18-,19+,20+/m1/s1
Canonical SMILES:	COc1cc(ccc1O)[C@H]1OC[C@]2([C@]1(O)CO[C@@H]2c1ccc(c(c1)OC)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	Reference
NPO10230	Heynea trijuga	Species	Meliaceae	Eukaryota	UNPD*
NPO11775	Ophelia neglecta	Species	Opheliidae	Eukaryota	UNPD*
NPO11868	Malassezia furfur	Species	Malasseziaceae	Eukaryota	UNPD*
NPO1302	Orobanche speciosa	Species	Orobanchaceae	Eukaryota	UNPD*
NPO1305	Eriophyllum confertiflorum	Species	Asteraceae	Eukaryota	UNPD*
NPO13081	Valeriana laxiflora	Species	Caprifoliaceae	Eukaryota	TCMID*
NPO13156	Cynanchum aphyllum	Species	Apocynaceae	Eukaryota	TCMID*
NPO13530	Thorectandra excavatus	Species	Thorectidae	Eukaryota	UNPD*
NPO14102	Kadsura interior	Species	Schisandraceae	Eukaryota	UNPD*
NPO14901	Neocosmospora tenuicristata	Species	Nectriaceae	Eukaryota	UNPD*

Showing 1 to 10 of 22 entries

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Biological Activity

Activity Type	# Activity
Others	4

Activity Type	# Activity
Others	2
Tissue	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	29.3	%	15270567
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	36.7	%	15270567
NPT2	Others	Unspecified		Activity	=	5.33	nM	15270567
NPT2	Others	Unspecified		Activity	=	6.7	nM	15270567

Showing 1 to 4 of 4 entries

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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 NPC4940 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	257
0.1-0.2	1012
0.2-0.3	2267
0.3-0.4	5947
0.4-0.5	7508
0.5-0.6	2566
0.6-0.7	6229
0.7-0.8	3737
0.8-0.85	807
0.85-0.9	449
0.9-0.95	82
0.95-1	28

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Similarity Score	Similarity Level	Natural Product ID
0.8846	High Similarity	NPC106511
0.8846	High Similarity	NPC8050
0.8846	High Similarity	NPC473093
0.8849	High Similarity	NPC223185
0.8849	High Similarity	NPC477702

Showing 1 to 5 of 200 entries

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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 NPC4940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	240
0.1-0.2	821
0.2-0.3	1476
0.3-0.4	2623
0.4-0.5	2009
0.5-0.6	1077
0.6-0.7	719
0.7-0.8	186
0.8-0.85	9
0.85-0.9	0
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6986	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5976	Discontinued
0.6992	Remote Similarity	NPD5451	Approved
0.6994	Remote Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD2438	Suspended

Showing 1 to 5 of 200 entries

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Structure

CID4940 OpenBabel06191715322D 28 31 0 0 1 0 0 0 0 0999 V2000 -1.0454 -5.4991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0454 5.4991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6778 -1.9494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6778 1.9494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2656 -2.7585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2656 2.7585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2765 -2.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2765 2.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2135 0.2939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2135 -0.2939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6833 -2.0540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6833 2.0540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8588 -3.6720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8588 3.6720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8643 -3.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8643 3.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0955 -1.2449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0955 1.2449 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4045 -0.2939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4045 0.2939 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4466 -4.4810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4466 4.4810 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2135 -0.8817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2135 0.8817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4576 -4.6901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4576 4.6901 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9045 -1.2449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9045 1.2449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 9 28 1 0 0 0 0 10 20 1 0 0 0 0 10 27 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 25 1 0 0 0 0 16 26 1 0 0 0 0 17 19 1 6 0 0 0 17 27 1 0 0 0 0 18 20 1 6 0 0 0 18 28 1 0 0 0 0 19 20 1 6 0 0 0 19 23 1 0 0 0 0 20 24 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	3010931
ChEMBL	CHEMBL470456
ZINC

Physicochemical Properties

Molecular Weight:	390.13
ALogP:	-2.9004
MLogP:	2.78
XLogP:	0.293
# Rotatable Bonds:	10
Polar Surface Area:	117.84
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	28

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