NPASS Natural Product

Natural Product: NPC233274

Natural Product ID:	NPC233274
Common Name:	Neotuberostemonine
IUPAC Name:
Synonyms:	Neotuberostemonine
Molecular Formula:	C22H33NO4
Standard InCHIKey:	GYOGHROCTSEKDY-UEIGSNQUSA-N
Standard InCHI:	InChI=1S/C22H33NO4/c1-4-13-14-7-5-6-8-23-16(17-9-11(2)21(24)26-17)10-15(19(14)23)18-12(3)22(25)27-20(13)18/h11-20H,4-10H2,1-3H3/t11-,12-,13+,14+,15-,16-,17-,18-,19+,20+/m0/s1
Canonical SMILES:	CC[C@@H]1[C@H]2CCCCN3[C@H]2[C@H]([C@H]2[C@@H]1OC(=O)[C@H]2C)C[C@H]3[C@@H]1C[C@@H](C(=O)O1)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Reference
NPO23955	Stemona sp.	Species	Stemonaceae	Eukaryota		PMID[15679323]
NPO11929	Drosera gigantea	Species	Droseraceae	Eukaryota		UNPD*
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	Rhizomes	PMID[21902195]
NPO15783	Stemona phyllantha	Species	Stemonaceae	Eukaryota	tuberous root	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota		TCM_Taiwan*
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota		HerDing*
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	tuberous root	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	Rhizomes	PMID[21902195]
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota		TCM_Taiwan*
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota		HerDing*
NPO6018	Crepis virens	Species	Asteraceae	Eukaryota		UNPD*
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota		UNPD*
NPO11455	Drechslera turcica	Species	Pleosporaceae	Eukaryota		UNPD*
NPO7468	Trichogonia gardneri	Species	Asteraceae	Eukaryota		UNPD*
NPO4458	Tarenna bipindensis	Species	Rubiaceae	Eukaryota		UNPD*
NPO8753	Axinyssa ambrosia	Species	Halichondriidae	Eukaryota		UNPD*
NPO28230	Stemona japonica	Species	Stemonaceae	Eukaryota		TM-MC*
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota		TCMID*
NPO19780	Stemona sessilifolia	Species	Stemonaceae	Eukaryota		TCMID*
NPO20195	Radix stemonae preparata	Species	Lymnaeidae	Eukaryota		TCMID*
NPO5767	Alibertia edulis	Species	Rubiaceae	Eukaryota		UNPD*

Biological Activity

Activity Type	# Activity
ED50	1
IC50	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	50000	nM	15679323
NPT938	Organism	Cavia porcellus	Cavia porcellus	ED50	=	66	umol/kg	16872143

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 NPC233274 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	94
0.1-0.2	1384
0.2-0.3	13132
0.3-0.4	10239
0.4-0.5	5571
0.5-0.6	440
0.6-0.7	18
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC194750
1.0	High Similarity	NPC287638
0.8485	Intermediate Similarity	NPC471843
0.785	Intermediate Similarity	NPC471844
0.7766	Intermediate Similarity	NPC216090
0.7544	Intermediate Similarity	NPC470538
0.7241	Intermediate Similarity	NPC39041
0.7241	Intermediate Similarity	NPC471845
0.7241	Intermediate Similarity	NPC202722
0.7241	Intermediate Similarity	NPC471846
0.7241	Intermediate Similarity	NPC241294
0.6875	Remote Similarity	NPC97336
0.6833	Remote Similarity	NPC174463
0.6822	Remote Similarity	NPC469998
0.68	Remote Similarity	NPC280903
0.6726	Remote Similarity	NPC265094
0.6721	Remote Similarity	NPC11379
0.6721	Remote Similarity	NPC230849
0.6694	Remote Similarity	NPC473477
0.6667	Remote Similarity	NPC470537
0.6614	Remote Similarity	NPC173173
0.6604	Remote Similarity	NPC322966
0.6381	Remote Similarity	NPC277918
0.6357	Remote Similarity	NPC212106
0.633	Remote Similarity	NPC476019
0.6136	Remote Similarity	NPC215507
0.6134	Remote Similarity	NPC271562
0.6	Remote Similarity	NPC203170
0.6	Remote Similarity	NPC469999
0.5954	Remote Similarity	NPC474371
0.5948	Remote Similarity	NPC220111
0.5917	Remote Similarity	NPC86906
0.5909	Remote Similarity	NPC52533
0.5893	Remote Similarity	NPC312637
0.5887	Remote Similarity	NPC469466
0.5854	Remote Similarity	NPC63511
0.584	Remote Similarity	NPC477963
0.5814	Remote Similarity	NPC470593
0.5814	Remote Similarity	NPC470594
0.5806	Remote Similarity	NPC58281
0.5806	Remote Similarity	NPC474459
0.5797	Remote Similarity	NPC474210
0.5794	Remote Similarity	NPC135431
0.5785	Remote Similarity	NPC233256
0.5785	Remote Similarity	NPC195841
0.5784	Remote Similarity	NPC109510
0.5784	Remote Similarity	NPC208657
0.576	Remote Similarity	NPC474452
0.5758	Remote Similarity	NPC211848
0.5755	Remote Similarity	NPC474754
0.5748	Remote Similarity	NPC271115
0.5748	Remote Similarity	NPC209252
0.5736	Remote Similarity	NPC475340
0.5728	Remote Similarity	NPC55508
0.5726	Remote Similarity	NPC472313
0.5714	Remote Similarity	NPC474348
0.5714	Remote Similarity	NPC325117
0.5714	Remote Similarity	NPC233108
0.5714	Remote Similarity	NPC326651
0.5714	Remote Similarity	NPC322319
0.5714	Remote Similarity	NPC309731
0.5704	Remote Similarity	NPC309249
0.5703	Remote Similarity	NPC28542
0.5702	Remote Similarity	NPC475239
0.5701	Remote Similarity	NPC134227
0.5692	Remote Similarity	NPC88190
0.568	Remote Similarity	NPC79238
0.5678	Remote Similarity	NPC220234
0.5672	Remote Similarity	NPC476501
0.5669	Remote Similarity	NPC470540
0.5664	Remote Similarity	NPC323156
0.5662	Remote Similarity	NPC307165
0.5659	Remote Similarity	NPC476952
0.5649	Remote Similarity	NPC238323
0.5645	Remote Similarity	NPC473994
0.5636	Remote Similarity	NPC65133
0.5635	Remote Similarity	NPC43648
0.5631	Remote Similarity	NPC474755
0.563	Remote Similarity	NPC476497
0.5619	Remote Similarity	NPC471046
0.5615	Remote Similarity	NPC138534
0.5615	Remote Similarity	NPC477986
0.5607	Remote Similarity	NPC73013

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC233274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	84
0.1-0.2	1143
0.2-0.3	4481
0.3-0.4	2741
0.4-0.5	589
0.5-0.6	99
0.6-0.7	24
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6577	Remote Similarity	NPD3715	Approved
0.6577	Remote Similarity	NPD3713	Approved
0.6577	Remote Similarity	NPD3714	Approved
0.65	Remote Similarity	NPD8144	Approved
0.65	Remote Similarity	NPD8143	Approved
0.6339	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD8040	Discontinued
0.6325	Remote Similarity	NPD6920	Discontinued
0.6289	Remote Similarity	NPD2696	Approved
0.6289	Remote Similarity	NPD2694	Approved
0.6289	Remote Similarity	NPD2697	Approved
0.6289	Remote Similarity	NPD2695	Approved
0.6154	Remote Similarity	NPD7911	Approved
0.6154	Remote Similarity	NPD7986	Approved
0.6154	Remote Similarity	NPD7987	Approved
0.6154	Remote Similarity	NPD7912	Approved
0.6122	Remote Similarity	NPD3725	Approved
0.6122	Remote Similarity	NPD3726	Approved
0.6036	Remote Similarity	NPD2682	Approved
0.6	Remote Similarity	NPD7755	Approved
0.6	Remote Similarity	NPD7990	Approved
0.6	Remote Similarity	NPD7989	Approved
0.6	Remote Similarity	NPD7754	Approved
0.6	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD8298	Phase 2
0.5962	Remote Similarity	NPD617	Approved
0.5897	Remote Similarity	NPD8418	Phase 2
0.5887	Remote Similarity	NPD8077	Approved
0.5887	Remote Similarity	NPD8078	Approved
0.582	Remote Similarity	NPD6415	Discontinued
0.5736	Remote Similarity	NPD7519	Approved
0.5736	Remote Similarity	NPD7518	Approved
0.5736	Remote Similarity	NPD7517	Approved
0.5669	Remote Similarity	NPD7916	Approved
0.5669	Remote Similarity	NPD7915	Approved
0.561	Remote Similarity	NPD8140	Approved
0.561	Remote Similarity	NPD8307	Discontinued

Structure

CID233274 OpenBabel06191716032D 27 31 0 0 1 0 0 0 0 0999 V2000 -0.9889 1.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3619 2.2569 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0704 -1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1229 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2764 3.3981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0291 3.3190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6883 2.9218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5054 2.7308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6018 1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4263 0.3601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5529 1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4013 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7431 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0140 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0140 1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4752 1.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7431 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5529 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4263 1.9781 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 7.3619 0.0813 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0933 -1.7796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6018 0.3601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 10 16 1 0 0 0 0 11 2 1 6 0 0 0 11 21 1 0 0 0 0 12 3 1 6 0 0 0 12 18 1 0 0 0 0 12 22 1 0 0 0 0 13 4 1 6 0 0 0 13 14 1 0 0 0 0 13 20 1 0 0 0 0 14 7 1 1 0 0 0 14 19 1 0 0 0 0 15 10 1 1 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 23 1 6 0 0 0 17 9 1 6 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 19 23 1 0 0 0 0 20 27 1 0 0 0 0 21 24 2 0 0 0 0 21 26 1 0 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11667940
ChEMBL	CHEMBL479493
ZINC

Physicochemical Properties

Molecular Weight:	375.24
ALogP:	-1.0397
MLogP:	3.33
XLogP:	3.179
# Rotatable Bonds:	5
Polar Surface Area:	55.84
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	27

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