NPASS Natural Product

Natural Product: NPC114410

Natural Product ID:	NPC114410
Common Name:	Orthosiphol N
IUPAC Name:	[(2S,3S,4R,4aS,4bR,7R,8aR,9R,10aS)-3-acetyloxy-4-benzoyloxy-7-ethenyl-8a,9-dihydroxy-1,1,4a,7-tetramethyl-5,8-dioxo-2,3,4,4b,6,9,10,10a-octahydrophenanthren-2-yl] benzoate
Synonyms:	Orthosiphol N
Molecular Formula:	C36H40O10
Standard InCHIKey:	LFPSUBPBKLUQAL-OBSWDRTESA-N
Standard InCHI:	InChI=1S/C36H40O10/c1-7-34(5)19-23(38)27-35(6)24(18-25(39)36(27,43)32(34)42)33(3,4)28(45-30(40)21-14-10-8-11-15-21)26(44-20(2)37)29(35)46-31(41)22-16-12-9-13-17-22/h7-17,24-29,39,43H,1,18-19H2,2-6H3/t24-,25+,26-,27+,28+,29-,34-,35-,36-/m0/s1
Canonical SMILES:	C=C[C@@]1(C)CC(=O)[C@H]2[C@@](C1=O)(O)[C@H](O)C[C@@H]1[C@]2(C)[C@@H](OC(=O)c2ccccc2)[C@@H](OC(=O)C)[C@H](C1(C)C)OC(=O)c1ccccc1
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	UNPD*
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	UNPD*
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	UNPD*
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	UNPD*
NPO1408	Cirsium helenioides	Species	Asteraceae	Eukaryota	UNPD*
NPO14529	Asterias rubens	Species	Asteriidae	Eukaryota	UNPD*
NPO14664	Stevia salicifolia	Species	Asteraceae	Eukaryota	UNPD*
NPO14797	Orthosiphon aristatus	Species	Lamiaceae	Eukaryota	UNPD*
NPO14887	Handroanthus guayacan	Species	Bignoniaceae	Eukaryota	UNPD*
NPO16275	Pterocaulon rugosum	Species	Asteraceae	Eukaryota	UNPD*

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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	=	35.1	ug/ml	11374950
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	18.6	ug/ml	11374950

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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 NPC114410 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	249
0.1-0.2	869
0.2-0.3	1837
0.3-0.4	3211
0.4-0.5	5911
0.5-0.6	7639
0.6-0.7	7770
0.7-0.8	2996
0.8-0.85	195
0.85-0.9	132
0.9-0.95	52
0.95-1	28

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Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC39549
0.8571	High Similarity	NPC22571
0.8571	High Similarity	NPC283375
0.8571	High Similarity	NPC469647
0.8571	High Similarity	NPC469648

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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 NPC114410 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	750
0.2-0.3	1512
0.3-0.4	2653
0.4-0.5	2302
0.5-0.6	1202
0.6-0.7	379
0.7-0.8	83
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6552	Remote Similarity	NPD1237	Approved
0.6556	Remote Similarity	NPD3926	Phase 2
0.6566	Remote Similarity	NPD1471	Phase 3
0.6566	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1550	Clinical (unspecified phase)

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Structure

CID114410 OpenBabel06191715472D 46 50 0 0 1 0 0 0 0 0999 V2000 2.9568 -1.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5254 0.6088 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 1.9909 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 1.0000 0.0000 C 0 0 1 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 -1.7321 3.0000 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 -2.5981 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 -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 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 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 -0.8660 -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 -0.8660 4.5000 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 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 20 1 0 0 0 0 3 33 1 0 0 0 0 4 33 1 0 0 0 0 7 34 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 16 1 0 0 0 0 13 17 2 0 0 0 0 14 21 2 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 34 1 0 0 0 0 20 37 2 0 0 0 0 20 44 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 23 38 2 0 0 0 0 24 33 1 0 0 0 0 24 35 1 1 0 0 0 25 36 1 6 0 0 0 25 39 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 26 44 1 6 0 0 0 27 35 1 1 0 0 0 27 36 1 0 0 0 0 28 33 1 0 0 0 0 28 45 1 6 0 0 0 29 35 1 6 0 0 0 29 46 1 0 0 0 0 30 40 2 0 0 0 0 30 45 1 0 0 0 0 31 41 2 0 0 0 0 31 46 1 0 0 0 0 32 34 1 0 0 0 0 32 36 1 0 0 0 0 32 42 2 0 0 0 0 34 5 1 1 0 0 0 35 6 1 1 0 0 0 36 43 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	10258499
ChEMBL	CHEMBL447217
ZINC

Physicochemical Properties

Molecular Weight:	632.26
ALogP:	-0.0172
MLogP:	4.32
XLogP:	7.108
# Rotatable Bonds:	16
Polar Surface Area:	153.5
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	46

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