NPASS Natural Product

Natural Product: NPC150506

Natural Product ID:	NPC150506
Common Name:	Norethynodrel
IUPAC Name:	(8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:	Norethynodrel; Noretynodrel; SC-4642
Molecular Formula:	C20H26O2
Standard InCHIKey:	ICTXHFFSOAJUMG-SLHNCBLASA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1
Canonical SMILES:	C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=C1CCC(=O)C2
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
NPO12584	Atractylodes chinensis	Species	Asteraceae	Eukaryota				TCMID*

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Biological Activity

Activity Type	# Activity
IC50	1
Others	3
Potency	20

Activity Type	# Activity
Individual Protein	11
Organism	1
Others	12

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	91	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	4.1	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	16	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	22387.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	7176.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	16360.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	29092.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	11374.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	2.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	8.1	nM	PubChem BioAssay data set

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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 NPC150506 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	118
0.1-0.2	1115
0.2-0.3	6010
0.3-0.4	11436
0.4-0.5	4674
0.5-0.6	4647
0.6-0.7	2320
0.7-0.8	536
0.8-0.85	31
0.85-0.9	2
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7381	Intermediate Similarity	NPC266193
0.7381	Intermediate Similarity	NPC257666
0.7381	Intermediate Similarity	NPC165711
0.7381	Intermediate Similarity	NPC106078
0.7381	Intermediate Similarity	NPC212661

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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 NPC150506 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	134
0.1-0.2	1919
0.2-0.3	4406
0.3-0.4	1897
0.4-0.5	384
0.5-0.6	177
0.6-0.7	138
0.7-0.8	80
0.8-0.85	16
0.85-0.9	2
0.9-0.95	6
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6321	Remote Similarity	NPD6614	Approved
0.6327	Remote Similarity	NPD8034	Phase 2
0.6327	Remote Similarity	NPD8035	Phase 2
0.6344	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3703	Phase 2

Showing 1 to 5 of 200 entries

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Structure

CID150506 OpenBabel06191715522D 22 25 0 0 1 0 0 0 0 0999 V2000 -0.7191 1.6138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8382 0.5194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 0.9670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5160 -3.3867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0294 -1.9340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6775 -2.9029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1915 -1.4502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5151 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8367 -1.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6767 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8370 -0.4842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1921 -3.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3542 -2.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0297 -2.9019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3539 -1.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5154 -1.4507 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6772 -1.9349 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8388 -1.4512 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8385 -0.4838 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 5.8958 -3.4017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8662 0.4997 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 3 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 6 1 0 0 0 0 4 13 1 0 0 0 0 5 7 1 0 0 0 0 5 14 1 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 2 0 0 0 0 14 21 2 0 0 0 0 15 16 1 0 0 0 0 16 8 1 6 0 0 0 16 17 1 0 0 0 0 17 6 1 1 0 0 0 17 18 1 0 0 0 0 18 19 1 6 0 0 0 19 20 1 1 0 0 0 20 22 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	6231
ChEMBL	CHEMBL1387
ZINC

Physicochemical Properties

Molecular Weight:	298.19
ALogP:	1.0092
MLogP:	3.44
XLogP:	2.48
# Rotatable Bonds:	2
Polar Surface Area:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	22

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