NPASS Natural Product

Natural Product: NPC185590

Natural Product ID:	NPC185590
Common Name:	Dauricumine
IUPAC Name:
Synonyms:	Dauricumine
Molecular Formula:	C19H24ClNO6
Standard InCHIKey:	FSXRARBVZZKCGJ-WPLONRSQSA-N
Standard InCHI:	InChI=1S/C19H24ClNO6/c1-21-6-5-17-8-10(22)14(26-3)16(27-4)18(17,21)9-12(20)19(17)13(23)7-11(25-2)15(19)24/h7,12,15,24H,5-6,8-9H2,1-4H3/t12-,15-,17+,18+,19+/m0/s1
Canonical SMILES:	COC1=CC(=O)[C@@]2([C@H]1O)[C@@H](Cl)C[C@@]13[C@@]2(CCN1C)CC(=O)C(=C3OC)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO20751	Hypserpa nitida	Species	Menispermaceae	Eukaryota	PMID[17723297]
NPO15557	Menispermi rhizoma	NA	NA	NA	TCMSP*
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	TM-MC*

Biological Activity

Activity Type	# Activity
IC50	2
Others	3

Activity Type	# Activity
Organism	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		CC50	=	2193000	nM	17723297
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	1312000	nM	17723297
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	3291000	nM	17723297
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.67		17723297
NPT2	Others	Unspecified		Ratio CC50/IC50	<	1		17723297

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 NPC185590 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	110
0.1-0.2	848
0.2-0.3	4405
0.3-0.4	16521
0.4-0.5	8079
0.5-0.6	911
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC15440
1.0	High Similarity	NPC264958
0.9571	High Similarity	NPC44200
0.9571	High Similarity	NPC12124
0.9286	High Similarity	NPC266697
0.9259	High Similarity	NPC45813
0.6755	Remote Similarity	NPC470539
0.6733	Remote Similarity	NPC476951
0.6443	Remote Similarity	NPC88190
0.6419	Remote Similarity	NPC476952
0.6387	Remote Similarity	NPC215507
0.6093	Remote Similarity	NPC235625
0.6078	Remote Similarity	NPC23963
0.6054	Remote Similarity	NPC473232
0.6026	Remote Similarity	NPC474371
0.5987	Remote Similarity	NPC106791
0.5987	Remote Similarity	NPC201889
0.5987	Remote Similarity	NPC96731
0.5918	Remote Similarity	NPC470535
0.5909	Remote Similarity	NPC11379
0.5909	Remote Similarity	NPC230849
0.5882	Remote Similarity	NPC471673
0.5879	Remote Similarity	NPC88943
0.5878	Remote Similarity	NPC470536
0.5871	Remote Similarity	NPC238323
0.586	Remote Similarity	NPC204639
0.5849	Remote Similarity	NPC471086
0.5838	Remote Similarity	NPC314050
0.5838	Remote Similarity	NPC315809
0.5828	Remote Similarity	NPC193471
0.5828	Remote Similarity	NPC130124
0.5817	Remote Similarity	NPC147707
0.58	Remote Similarity	NPC470534
0.58	Remote Similarity	NPC47857
0.58	Remote Similarity	NPC181510
0.58	Remote Similarity	NPC168758
0.5799	Remote Similarity	NPC276822
0.5796	Remote Similarity	NPC280498
0.5793	Remote Similarity	NPC70369
0.5786	Remote Similarity	NPC470537
0.5779	Remote Similarity	NPC156336
0.5779	Remote Similarity	NPC200412
0.5779	Remote Similarity	NPC120599
0.5776	Remote Similarity	NPC477988
0.5774	Remote Similarity	NPC803
0.5772	Remote Similarity	NPC474725
0.5767	Remote Similarity	NPC313348
0.5767	Remote Similarity	NPC475987
0.5762	Remote Similarity	NPC474497
0.5758	Remote Similarity	NPC230889
0.575	Remote Similarity	NPC173173
0.574	Remote Similarity	NPC956
0.5695	Remote Similarity	NPC30911
0.5695	Remote Similarity	NPC316984
0.5689	Remote Similarity	NPC25025
0.5687	Remote Similarity	NPC280903
0.5677	Remote Similarity	NPC284656
0.5677	Remote Similarity	NPC471109
0.5669	Remote Similarity	NPC472001
0.5667	Remote Similarity	NPC471400
0.5664	Remote Similarity	NPC135576
0.5664	Remote Similarity	NPC93271
0.566	Remote Similarity	NPC477985
0.566	Remote Similarity	NPC326386
0.566	Remote Similarity	NPC471087
0.5658	Remote Similarity	NPC275100
0.5658	Remote Similarity	NPC35069
0.5658	Remote Similarity	NPC314550
0.5658	Remote Similarity	NPC258711
0.5655	Remote Similarity	NPC473396
0.5649	Remote Similarity	NPC202722
0.5649	Remote Similarity	NPC39041
0.5649	Remote Similarity	NPC471846
0.5649	Remote Similarity	NPC241294
0.5649	Remote Similarity	NPC471845
0.5644	Remote Similarity	NPC120335
0.5641	Remote Similarity	NPC323532
0.5641	Remote Similarity	NPC35037
0.564	Remote Similarity	NPC201899
0.564	Remote Similarity	NPC471674
0.5638	Remote Similarity	NPC475800
0.5634	Remote Similarity	NPC469819
0.5634	Remote Similarity	NPC114162
0.5629	Remote Similarity	NPC470529
0.5629	Remote Similarity	NPC470531
0.5629	Remote Similarity	NPC470533
0.5629	Remote Similarity	NPC470527
0.5629	Remote Similarity	NPC470530
0.5629	Remote Similarity	NPC196073
0.5629	Remote Similarity	NPC195435
0.5629	Remote Similarity	NPC470532
0.5629	Remote Similarity	NPC470528
0.5617	Remote Similarity	NPC471471
0.5617	Remote Similarity	NPC164476
0.5616	Remote Similarity	NPC471401
0.5602	Remote Similarity	NPC243902

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC185590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	108
0.1-0.2	664
0.2-0.3	3562
0.3-0.4	3904
0.4-0.5	848
0.5-0.6	75
0.6-0.7	0
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
0.5901	Remote Similarity	NPD6845	Suspended
0.5818	Remote Similarity	NPD6333	Approved
0.5818	Remote Similarity	NPD6334	Approved
0.575	Remote Similarity	NPD6033	Approved
0.5741	Remote Similarity	NPD7260	Phase 2
0.574	Remote Similarity	NPD5193	Discontinued
0.5714	Remote Similarity	NPD8384	Approved
0.5695	Remote Similarity	NPD2204	Approved
0.5652	Remote Similarity	NPD8337	Approved
0.5652	Remote Similarity	NPD8336	Approved

Structure

CID185590 OpenBabel06191715562D 27 30 0 0 1 0 0 0 0 0999 V2000 -0.8645 -0.5027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1366 1.0375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.9039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0776 2.8695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4461 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7341 -0.4178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4307 2.7499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1691 2.0874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4461 3.3398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8772 1.9650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7120 2.0882 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5463 2.5678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.3398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2687 1.2978 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7230 2.0874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4461 0.8351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.8351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4461 1.6704 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7054 3.0882 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.8976 4.1218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8791 3.1764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4507 0.4133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7747 1.8648 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4515 4.1218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6261 2.0874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 17 1 0 0 0 0 6 21 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 12 1 0 0 0 0 10 14 1 0 0 0 0 10 22 2 0 0 0 0 11 15 1 0 0 0 0 11 25 1 0 0 0 0 12 19 1 6 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 23 2 0 0 0 0 14 16 2 0 0 0 0 14 26 1 0 0 0 0 15 19 1 6 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 18 1 6 0 0 0 18 9 1 1 0 0 0 18 21 1 0 0 0 0 19 17 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	11741544
ChEMBL	CHEMBL391835
ZINC

Physicochemical Properties

Molecular Weight:	397.13
ALogP:	-1.3627
MLogP:	2.67
XLogP:	-0.174
# Rotatable Bonds:	9
Polar Surface Area:	85.3
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	27

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