NPASS Natural Product

Natural Product: NPC105189

Natural Product ID:	NPC105189
Common Name:	Demethylregelin
IUPAC Name:	(1R,2R,4S,4aR,6aR,6aS,6bR,8aR,12aR,14bS)-4-hydroxy-1,4a,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,5,6,6a,7,8,8a,11,12,13,14b-tetradecahydropicene-2-carboxylic acid
Synonyms:	Demethylregelin
Molecular Formula:	C30H46O4
Standard InCHIKey:	QGMNTKNSMLYTKS-BHHXOIJJSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-17-18(25(33)34)16-23(32)28(5)14-15-29(6)19(24(17)28)8-9-21-27(4)12-11-22(31)26(2,3)20(27)10-13-30(21,29)7/h8,17-18,20-21,23-24,32H,9-16H2,1-7H3,(H,33,34)/t17-,18+,20-,21+,23-,24-,27-,28-,29+,30+/m0/s1
Canonical SMILES:	OC(=O)[C@@H]1C[C@H](O)[C@]2([C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)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
NPO11194	Bombus hortorum	Species	Apidae	Eukaryota	UNPD*
NPO11599	Elaeagnus commutata	Species	Elaeagnaceae	Eukaryota	UNPD*
NPO11881	Adenopeltis colliguaya	Species	Euphorbiaceae	Eukaryota	UNPD*
NPO12416	Quercus mongolica	Species	Fagaceae	Eukaryota	UNPD*
NPO12450	Cneorum pulverulentum	Species	Rutaceae	Eukaryota	UNPD*
NPO12555	Aspergillus quadrilineatus	Species	Aspergillaceae	Eukaryota	UNPD*
NPO12680	Perityle vaseyi	Species	Asteraceae	Eukaryota	UNPD*
NPO12977	Solenopsis invicta	Species	Formicidae	Eukaryota	UNPD*
NPO13230	Pedicularis condensata	Species	Orobanchaceae	Eukaryota	UNPD*
NPO13375	Palafoxia rosea	Species	Asteraceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	100000	nM	14510595
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	Inhibition	=	26	%	14510595

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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 NPC105189 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	131
0.1-0.2	744
0.2-0.3	2909
0.3-0.4	7098
0.4-0.5	9056
0.5-0.6	4284
0.6-0.7	3609
0.7-0.8	2459
0.8-0.85	304
0.85-0.9	105
0.9-0.95	131
0.95-1	59

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Similarity Score	Similarity Level	Natural Product ID
0.8936	High Similarity	NPC233012
0.8953	High Similarity	NPC180834
0.8953	High Similarity	NPC171789
0.8966	High Similarity	NPC73038
0.8966	High Similarity	NPC235341

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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 NPC105189 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1256
0.2-0.3	3580
0.3-0.4	2714
0.4-0.5	911
0.5-0.6	221
0.6-0.7	201
0.7-0.8	119
0.8-0.85	9
0.85-0.9	2
0.9-0.95	2
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD4244	Approved
0.6667	Remote Similarity	NPD6054	Approved

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Structure

CID105189 OpenBabel06191715452D 34 38 0 0 1 0 0 0 0 0999 V2000 3.3753 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0186 -0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5058 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2191 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0629 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3753 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0629 -0.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9067 0.4872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 19 2 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 27 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 1 1 6 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 1 0 0 0 19 24 1 0 0 0 0 19 29 1 0 0 0 0 20 26 1 0 0 0 0 20 27 1 6 0 0 0 21 27 1 6 0 0 0 21 30 1 0 0 0 0 22 26 1 0 0 0 0 22 31 2 0 0 0 0 23 28 1 1 0 0 0 23 32 1 0 0 0 0 24 28 1 1 0 0 0 25 33 2 0 0 0 0 25 34 1 0 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	44559663
ChEMBL	CHEMBL518044
ZINC

Physicochemical Properties

Molecular Weight:	470.34
ALogP:	1.8443
MLogP:	4.32
XLogP:	6.667
# Rotatable Bonds:	10
Polar Surface Area:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	34

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