NPASS Natural Product

Natural Product: NPC16107

Natural Product ID:	NPC16107
Common Name:	2,3,9,10-Tetramethoxy-6,8,13,13A-Tetrahydro-5H-Isoquinolino[2,1-B]Isoquinoline
IUPAC Name:	2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
Synonyms:	(+/-)-Tetrahydropalmatine
Molecular Formula:	C21H25NO4
Standard InCHIKey:	AEQDJSLRWYMAQI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3
Canonical SMILES:	COc1cc2CCN3C(c2cc1OC)Cc1c(C3)c(OC)c(cc1)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO1045	Corydalis racemosa	Species	Papaveraceae	Eukaryota	TCMID*
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	TCMID*
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	TM-MC*
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	TM-MC*
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	TM-MC*
NPO14045	Corydalis decumbens	Species	Papaveraceae	Eukaryota	TCMID*
NPO14368	Stephania sinica	Species	Menispermaceae	Eukaryota	TCMID*
NPO22242	Phellodendron chinense	Species	Rutaceae	Eukaryota	TM-MC*
NPO22242.1	Phellodendron chinense var. glabriusculum	Varieties	Rutaceae	Eukaryota	TCMID*
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	TM-MC*

Showing 1 to 10 of 24 entries

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Biological Activity

Activity Type	# Activity
IC50	1
Ki	1
Potency	5

Activity Type	# Activity
Individual Protein	4
Others	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		8199.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		29092.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency		9432.9	nM	PubChem BioAssay data set
NPT296	Individual Protein	Sigma opioid receptor	Homo sapiens	Ki	=	2.5	nM	16033255
NPT677	Individual Protein	Coagulation factor III	Homo sapiens	IC50	=	14.98	nM	23199480

Showing 1 to 6 of 6 entries

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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 NPC16107 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	1209
0.2-0.3	4971
0.3-0.4	7815
0.4-0.5	3639
0.5-0.6	9140
0.6-0.7	3144
0.7-0.8	376
0.8-0.85	196
0.85-0.9	101
0.9-0.95	36
0.95-1	32

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Similarity Score	Similarity Level	Natural Product ID
0.8415	Intermediate Similarity	NPC8836
0.8415	Intermediate Similarity	NPC15414
0.8415	Intermediate Similarity	NPC42663
0.8415	Intermediate Similarity	NPC328155
0.8415	Intermediate Similarity	NPC271013

Showing 1 to 5 of 200 entries

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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 NPC16107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	729
0.2-0.3	888
0.3-0.4	1564
0.4-0.5	2673
0.5-0.6	1979
0.6-0.7	880
0.7-0.8	223
0.8-0.85	23
0.85-0.9	15
0.9-0.95	0
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7161	Intermediate Similarity	NPD6111	Discontinued
0.7172	Intermediate Similarity	NPD2594	Approved
0.7172	Intermediate Similarity	NPD2595	Approved
0.7178	Intermediate Similarity	NPD6357	Discontinued
0.7192	Intermediate Similarity	NPD3294	Phase 2

Showing 1 to 5 of 200 entries

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Structure

CID16107 OpenBabel06191715342D 26 29 0 0 1 0 0 0 0 0999 V2000 -6.0622 4.5000 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 -3.4641 5.0000 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 0.8660 1.5000 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 3.5000 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 -0.0000 2.0000 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 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 22 1 0 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 19 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5417
ChEMBL	CHEMBL187892
ZINC

Physicochemical Properties

Molecular Weight:	355.18
ALogP:	0.0968
MLogP:	3.22
XLogP:	2.548
# Rotatable Bonds:	8
Polar Surface Area:	40.16
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	26

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