NPASS Natural Product

Natural Product: NPC26033

Natural Product ID:	NPC26033
Common Name:	Orthosiphol R
IUPAC Name:	[(2S,3S,4S,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-7,10-diacetyloxy-5-benzoyloxy-2-ethenyl-3,6,10a-trihydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate
Synonyms:	Orthosiphol R
Molecular Formula:	C38H44O12
Standard InCHIKey:	UVLMOXBOUWFDIG-PQEFSWHNSA-N
Standard InCHI:	InChI=1S/C38H44O12/c1-8-36(6)29(42)27(49-32(43)22-15-11-9-12-16-22)28-37(7)24(19-25(47-20(2)39)38(28,46)34(36)45)35(4,5)30(48-21(3)40)26(41)31(37)50-33(44)23-17-13-10-14-18-23/h8-18,24-31,41-42,46H,1,19H2,2-7H3/t24-,25+,26-,27-,28+,29+,30+,31-,36-,37-,38-/m0/s1
Canonical SMILES:	C=C[C@@]1(C)[C@H](O)[C@@H](OC(=O)c2ccccc2)[C@H]2[C@@](C1=O)(O)[C@H](OC(=O)C)C[C@@H]1[C@]2(C)[C@@H](OC(=O)c2ccccc2)[C@@H](O)[C@H](C1(C)C)OC(=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	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
IC50	1

Activity Type	# Activity
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	35700	nM	12608860

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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 NPC26033 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	870
0.2-0.3	1838
0.3-0.4	3214
0.4-0.5	5885
0.5-0.6	7577
0.6-0.7	7708
0.7-0.8	3127
0.8-0.85	191
0.85-0.9	125
0.9-0.95	76
0.95-1	29

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Similarity Score	Similarity Level	Natural Product ID
0.8609	High Similarity	NPC477737
0.8609	High Similarity	NPC475552
0.8636	High Similarity	NPC133430
0.8636	High Similarity	NPC469477
0.8654	High Similarity	NPC472807

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 NPC26033 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	751
0.2-0.3	1512
0.3-0.4	2652
0.4-0.5	2299
0.5-0.6	1204
0.6-0.7	379
0.7-0.8	82
0.8-0.85	12
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
0.6545	Remote Similarity	NPD7033	Discontinued
0.6545	Remote Similarity	NPD3748	Approved
0.6552	Remote Similarity	NPD1237	Approved
0.6566	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1552	Clinical (unspecified phase)

Showing 1 to 5 of 200 entries

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Structure

CID26033 OpenBabel06191715352D 50 54 0 0 1 0 0 0 0 0999 V2000 0.4028 3.0597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5053 -1.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.7857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9643 -2.8929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4821 -3.7280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7260 1.8154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6702 -0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1532 2.1283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6808 -1.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3404 -5.7857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8457 -2.4107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6808 -0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5053 -5.3036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1755 -5.3036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0106 -1.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8457 -0.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5053 -4.3393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1755 -4.3393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -1.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5053 -0.4821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.8214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0106 -0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3404 -3.8571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8351 -0.4821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6702 -2.8929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6702 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8351 -0.4821 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6702 0.9643 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8351 -3.3750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6702 -1.9286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3404 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3404 -1.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 1.4464 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8351 -1.4464 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 -3.3404 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 -4.3393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5053 -3.3750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5053 1.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3404 0.9643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1755 -1.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 1.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8351 0.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6702 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8351 -4.3393 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5053 -0.4821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5053 -1.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 35 1 0 0 0 0 5 35 1 0 0 0 0 8 36 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 15 22 2 0 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 19 25 1 0 0 0 0 20 39 2 0 0 0 0 20 47 1 0 0 0 0 21 40 2 0 0 0 0 21 48 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 35 1 0 0 0 0 24 37 1 6 0 0 0 25 38 1 1 0 0 0 25 47 1 0 0 0 0 26 30 1 0 0 0 0 26 31 1 0 0 0 0 26 41 1 1 0 0 0 27 28 1 0 0 0 0 27 29 1 0 0 0 0 27 49 1 1 0 0 0 28 37 1 6 0 0 0 28 38 1 0 0 0 0 29 36 1 6 0 0 0 29 42 1 0 0 0 0 30 35 1 0 0 0 0 30 48 1 1 0 0 0 31 37 1 1 0 0 0 31 50 1 0 0 0 0 32 43 2 0 0 0 0 32 49 1 0 0 0 0 33 44 2 0 0 0 0 33 50 1 0 0 0 0 34 36 1 0 0 0 0 34 38 1 0 0 0 0 34 45 2 0 0 0 0 36 6 1 6 0 0 0 37 7 1 6 0 0 0 38 46 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	44583688
ChEMBL	CHEMBL508513
ZINC

Physicochemical Properties

Molecular Weight:	692.28
ALogP:	-0.3201
MLogP:	4.32
XLogP:	6.802
# Rotatable Bonds:	20
Polar Surface Area:	182.96
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	50

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