NPASS Natural Product

Natural Product: NPC72667

Natural Product ID:	NPC72667
Common Name:	5,6-Dehydrosugiol
IUPAC Name:	(4aS)-6-hydroxy-1,1,4a-trimethyl-7-propan-2-yl-3,4-dihydro-2H-phenanthren-9-one
Synonyms:
Molecular Formula:	C20H26O2
Standard InCHIKey:	HUMGJQLBBAYPNM-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-12(2)13-9-14-15(10-16(13)21)20(5)8-6-7-19(3,4)18(20)11-17(14)22/h9-12,21H,6-8H2,1-5H3/t20-/m1/s1
Canonical SMILES:	O=C1C=C2C(C)(C)CCC[C@@]2(c2c1cc(C(C)C)c(c2)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	Isolation Part	Collection Location	Collection Time	Reference
NPO18892	Salvinia molesta	Species	Salviniaceae	Eukaryota	Whole Plants	East Texas, USA	2009-2011	PMID[24210499]
NPO2267	Liatris tenuifolia	Species	Asteraceae	Eukaryota				UNPD*
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota				TCM_Taiwan*
NPO7646	Edgeworthia chrysantha	Species	Thymelaeaceae	Eukaryota				UNPD*
NPO8215	Crepis zacintha	Species	Asteraceae	Eukaryota				UNPD*

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Biological Activity

Activity Type	# Activity
GI50	5

Activity Type	# Activity
Cell Line	3
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	92780	nM	24210499
NPT2	Others	Unspecified		GI50	>	100000	nM	24210499
NPT306	Cell Line	PC-3	Homo sapiens	GI50	>	100000	nM	24210499
NPT81	Cell Line	A549	Homo sapiens	GI50	=	84520	nM	24210499

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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 NPC72667 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	230
0.1-0.2	1208
0.2-0.3	1909
0.3-0.4	4796
0.4-0.5	7496
0.5-0.6	5536
0.6-0.7	6497
0.7-0.8	2794
0.8-0.85	307
0.85-0.9	86
0.9-0.95	16
0.95-1	14

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Similarity Score	Similarity Level	Natural Product ID
0.8321	Intermediate Similarity	NPC471974
0.8321	Intermediate Similarity	NPC469680
0.8321	Intermediate Similarity	NPC61398
0.8333	Intermediate Similarity	NPC131684
0.8333	Intermediate Similarity	NPC79933

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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 NPC72667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	999
0.2-0.3	1142
0.3-0.4	2414
0.4-0.5	2321
0.5-0.6	1353
0.6-0.7	538
0.7-0.8	111
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6719	Remote Similarity	NPD940	Approved
0.6719	Remote Similarity	NPD1932	Approved
0.6719	Remote Similarity	NPD846	Approved
0.673	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.673	Remote Similarity	NPD2801	Approved

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Structure

CID72667 OpenBabel06191715412D 22 24 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 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 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 -0.8660 -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 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 3.4641 -2.0000 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 -0.0000 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 -2.0000 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 0.0000 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 0 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 1.7321 -3.0000 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 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 18 2 0 0 0 0 12 13 1 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	14827280
ChEMBL	CHEMBL3093123
ZINC

Physicochemical Properties

Molecular Weight:	298.19
ALogP:	1.0375
MLogP:	3.44
XLogP:	5.233
# Rotatable Bonds:	7
Polar Surface Area:	37.3
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	22

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