NPASS Compound

Structure

CID76213 OpenBabel06191715412D 21 23 0 0 1 0 0 0 0 0999 V2000 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 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 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 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 1.7321 -0.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 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 2.5981 1.5000 0.0000 C 0 0 2 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 2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 4 1 0 0 0 0 2 11 2 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 13 2 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 12 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 15 8 1 6 0 0 0 15 18 1 0 0 0 0 16 17 2 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	285.14
Volume:	298.468
LogP:	0.962
LogD:	2.368
LogS:	-2.447
# Rotatable Bonds:	3
TPSA:	61.72
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	2.732
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.078
MDCK Permeability:	1.3597411452792585e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.553
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135
Plasma Protein Binding (PPB):	50.226478576660156%
Volume Distribution (VD):	1.915
Pgp-substrate:	39.650936126708984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.276
CYP1A2-substrate:	0.905
CYP2C19-inhibitor:	0.34
CYP2C19-substrate:	0.295
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.667
CYP2D6-inhibitor:	0.725
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.698

ADMET: Excretion

Clearance (CL):	11.999
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.403
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.068
AMES Toxicity:	0.48
Rat Oral Acute Toxicity:	0.702
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.914
Carcinogencity:	0.048
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.845

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC76213

Natural Product ID:	NPC76213
*Common Name:**	(R)-(+)-Coclaurine
IUPAC Name:	(1R)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Synonyms:	(+)-1R-Cocluaurine; (R)-(+)-Coclaurine
Standard InCHIKey:	LVVKXRQZSRUVPY-OAHLLOKOSA-N
Standard InCHI:	InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m1/s1
SMILES:	COc1cc2CCN[C@@H](c2cc1O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256448
PubChem CID:	440989
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0000054] Benzylisoquinolines

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(88)80746-5]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94986-0]
NPO25388	Siliquariaspongia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10425118]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575964]
NPO27931	Caulerpa taxifolia	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16563751]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	root bark	Buea, Southwest Province, Cameroon	1997-JUL	PMID[17125223]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	flower	n.a.	PMID[17679444]
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18980381]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23132311]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[8289066]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	roots	n.a.	n.a.	PMID[8450318]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8759160]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917283]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12170	Solanum indicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27912	Cocculus laurifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26332	Ramalina tumidula	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27617	Phoenix dactylifera	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27703	Eclipta erecta	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27838	Rebutia marsoneri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27666	Sophora tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27468	Rhizopogon roseolus	Species	Rhizopogonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27869	Bombacopsis glabra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27216	Oreodaphne porosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO27522	Gongronella urceolifera	Species	Cunninghamellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25388	Siliquariaspongia japonica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3849	Cyclea barbata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27686	Aglaia odorata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27931	Caulerpa taxifolia	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27976	Astragalus wootoni	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27646	Cystoseira baccata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27803	Cercidiphyllum japonicum	Species	Cercidiphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27726	Diplocarpon mali	Species	Dermateaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27739	Erythrina mildbraedii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18354	Meiothermus ruber	Species	Thermaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	2
IC50	2
Others	1

Activity Type	# Activity
Individual Protein	2
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1858	Individual Protein	Dopamine D2 receptor	Rattus norvegicus	IC50	=	130.0	nM	PMID[496487]
NPT1857	Individual Protein	Dopamine D1 receptor	Rattus norvegicus	IC50	=	240.0	nM	PMID[496487]
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	EC50	=	0.8	ug.mL-1	PMID[496486]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	2800.0	nM	PMID[496488]
NPT27	Others	Unspecified		TI	=	125.0	n.a.	PMID[496488]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC76213 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	267
0.1-0.2	1654
0.2-0.3	9741
0.3-0.4	8056
0.4-0.5	6755
0.5-0.6	11534
0.6-0.7	3553
0.7-0.8	811
0.8-0.85	168
0.85-0.9	86
0.9-0.95	59
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC277669
0.9859	High Similarity	NPC60538
0.9859	High Similarity	NPC207824
0.9724	High Similarity	NPC2295
0.9724	High Similarity	NPC477564
0.958	High Similarity	NPC191376
0.958	High Similarity	NPC179825
0.958	High Similarity	NPC321505
0.9514	High Similarity	NPC24233
0.9514	High Similarity	NPC147390
0.9514	High Similarity	NPC246587
0.9514	High Similarity	NPC428
0.9514	High Similarity	NPC476571
0.9514	High Similarity	NPC135538
0.9507	High Similarity	NPC294249
0.9441	High Similarity	NPC185838
0.9315	High Similarity	NPC477565
0.9315	High Similarity	NPC103379
0.9281	High Similarity	NPC81247
0.9281	High Similarity	NPC35627
0.9281	High Similarity	NPC476573
0.9252	High Similarity	NPC151895
0.9252	High Similarity	NPC220858
0.9252	High Similarity	NPC88249
0.9252	High Similarity	NPC97221
0.9252	High Similarity	NPC192768
0.9216	High Similarity	NPC4138
0.9216	High Similarity	NPC121275
0.9216	High Similarity	NPC284183
0.9178	High Similarity	NPC476151
0.9155	High Similarity	NPC211468
0.9155	High Similarity	NPC219233
0.9155	High Similarity	NPC170170
0.9133	High Similarity	NPC249797
0.9133	High Similarity	NPC5238
0.9133	High Similarity	NPC127674
0.9133	High Similarity	NPC276588
0.9133	High Similarity	NPC39701
0.9133	High Similarity	NPC207757
0.9133	High Similarity	NPC172765
0.9133	High Similarity	NPC184026
0.9133	High Similarity	NPC469817
0.9133	High Similarity	NPC189266
0.9133	High Similarity	NPC193949
0.9133	High Similarity	NPC54379
0.9133	High Similarity	NPC2413
0.9133	High Similarity	NPC278799
0.9133	High Similarity	NPC295691
0.9133	High Similarity	NPC110416
0.9133	High Similarity	NPC204828
0.9091	High Similarity	NPC323123
0.9091	High Similarity	NPC314682
0.9085	High Similarity	NPC253429
0.9045	High Similarity	NPC475215
0.9045	High Similarity	NPC108434
0.9028	High Similarity	NPC213206
0.9028	High Similarity	NPC328750
0.9028	High Similarity	NPC188163
0.9028	High Similarity	NPC474915
0.8987	High Similarity	NPC66341
0.8987	High Similarity	NPC477020
0.8987	High Similarity	NPC192135
0.8981	High Similarity	NPC477562
0.8981	High Similarity	NPC26240
0.8981	High Similarity	NPC69712
0.8981	High Similarity	NPC109925
0.8896	High Similarity	NPC166014
0.8896	High Similarity	NPC27410
0.8881	High Similarity	NPC301050
0.8881	High Similarity	NPC131204
0.8874	High Similarity	NPC82285
0.8874	High Similarity	NPC133011
0.8831	High Similarity	NPC111485
0.8824	High Similarity	NPC203784
0.8824	High Similarity	NPC170503
0.8824	High Similarity	NPC126519
0.8824	High Similarity	NPC147091
0.8803	High Similarity	NPC160692
0.8776	High Similarity	NPC136860
0.8776	High Similarity	NPC128019
0.8776	High Similarity	NPC476567
0.8765	High Similarity	NPC474507
0.8758	High Similarity	NPC173416
0.8758	High Similarity	NPC187022
0.8758	High Similarity	NPC476577
0.8758	High Similarity	NPC148709
0.8758	High Similarity	NPC80129
0.8732	High Similarity	NPC300020
0.8732	High Similarity	NPC302171
0.8732	High Similarity	NPC33338
0.8726	High Similarity	NPC238530
0.8726	High Similarity	NPC232514
0.8726	High Similarity	NPC276944
0.8671	High Similarity	NPC317272
0.8671	High Similarity	NPC264850
0.8671	High Similarity	NPC13916
0.8671	High Similarity	NPC250846
0.8671	High Similarity	NPC42549
0.8671	High Similarity	NPC256012
0.8671	High Similarity	NPC268503
0.8671	High Similarity	NPC240841
0.8667	High Similarity	NPC210437
0.8667	High Similarity	NPC106295
0.8667	High Similarity	NPC476144
0.8667	High Similarity	NPC16107
0.8667	High Similarity	NPC51957
0.8662	High Similarity	NPC324144
0.8627	High Similarity	NPC37272
0.8625	High Similarity	NPC152212
0.8618	High Similarity	NPC274026
0.8616	High Similarity	NPC158376
0.8616	High Similarity	NPC12053
0.8616	High Similarity	NPC81218
0.8616	High Similarity	NPC306555
0.8616	High Similarity	NPC145832
0.8616	High Similarity	NPC117188
0.8616	High Similarity	NPC205421
0.8616	High Similarity	NPC474931
0.8609	High Similarity	NPC7467
0.8609	High Similarity	NPC475959
0.8608	High Similarity	NPC13504
0.8608	High Similarity	NPC306843
0.8608	High Similarity	NPC96603
0.8608	High Similarity	NPC78222
0.8608	High Similarity	NPC253043
0.8608	High Similarity	NPC477563
0.8608	High Similarity	NPC136508
0.8608	High Similarity	NPC212794
0.8608	High Similarity	NPC196447
0.8608	High Similarity	NPC24465
0.8606	High Similarity	NPC135772
0.8598	High Similarity	NPC312918
0.8598	High Similarity	NPC476574
0.8598	High Similarity	NPC477561
0.8598	High Similarity	NPC155442
0.8581	High Similarity	NPC186063
0.8562	High Similarity	NPC83198
0.8562	High Similarity	NPC204908
0.8544	High Similarity	NPC1229
0.8544	High Similarity	NPC475393
0.8535	High Similarity	NPC249274
0.8535	High Similarity	NPC205167
0.8526	High Similarity	NPC79328
0.8506	High Similarity	NPC26601
0.85	High Similarity	NPC210140
0.8481	Intermediate Similarity	NPC60186
0.8466	Intermediate Similarity	NPC477558
0.8462	Intermediate Similarity	NPC160193
0.8462	Intermediate Similarity	NPC160931
0.8462	Intermediate Similarity	NPC37205
0.8447	Intermediate Similarity	NPC66573
0.8442	Intermediate Similarity	NPC81733
0.8442	Intermediate Similarity	NPC326316
0.8438	Intermediate Similarity	NPC86144
0.8438	Intermediate Similarity	NPC304659
0.8411	Intermediate Similarity	NPC130926
0.8408	Intermediate Similarity	NPC475326
0.8405	Intermediate Similarity	NPC232386
0.8405	Intermediate Similarity	NPC152680
0.8405	Intermediate Similarity	NPC190783
0.8402	Intermediate Similarity	NPC48490
0.8402	Intermediate Similarity	NPC175890
0.8402	Intermediate Similarity	NPC274661
0.8402	Intermediate Similarity	NPC11296
0.8402	Intermediate Similarity	NPC82457
0.8395	Intermediate Similarity	NPC168753
0.8395	Intermediate Similarity	NPC118274
0.8385	Intermediate Similarity	NPC298979
0.8375	Intermediate Similarity	NPC134858
0.8354	Intermediate Similarity	NPC329969
0.8353	Intermediate Similarity	NPC60295
0.8353	Intermediate Similarity	NPC191132
0.8344	Intermediate Similarity	NPC239775
0.8344	Intermediate Similarity	NPC29647
0.8343	Intermediate Similarity	NPC186546
0.8343	Intermediate Similarity	NPC476576
0.8333	Intermediate Similarity	NPC470324
0.8323	Intermediate Similarity	NPC476568
0.8322	Intermediate Similarity	NPC172403
0.8313	Intermediate Similarity	NPC233650
0.8313	Intermediate Similarity	NPC189470
0.8312	Intermediate Similarity	NPC219162
0.8312	Intermediate Similarity	NPC92541
0.8311	Intermediate Similarity	NPC193528
0.831	Intermediate Similarity	NPC318965
0.828	Intermediate Similarity	NPC138487
0.828	Intermediate Similarity	NPC41178
0.828	Intermediate Similarity	NPC216459
0.8272	Intermediate Similarity	NPC204947
0.8269	Intermediate Similarity	NPC210148
0.8269	Intermediate Similarity	NPC233029
0.8261	Intermediate Similarity	NPC209377
0.8261	Intermediate Similarity	NPC2770
0.8261	Intermediate Similarity	NPC39103
0.8253	Intermediate Similarity	NPC114364
0.8253	Intermediate Similarity	NPC320223
0.8242	Intermediate Similarity	NPC199465
0.8242	Intermediate Similarity	NPC128560
0.8242	Intermediate Similarity	NPC229166
0.8239	Intermediate Similarity	NPC59028

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC76213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	713
0.2-0.3	1079
0.3-0.4	1661
0.4-0.5	2721
0.5-0.6	1838
0.6-0.7	693
0.7-0.8	236
0.8-0.85	27
0.85-0.9	8
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9028	High Similarity	NPD4664	Clinical (unspecified phase)
0.88	High Similarity	NPD6030	Approved
0.88	High Similarity	NPD6031	Approved
0.8784	High Similarity	NPD3845	Phase 1
0.8758	High Similarity	NPD7298	Approved
0.8667	High Similarity	NPD4584	Approved
0.8658	High Similarity	NPD2422	Clinical (unspecified phase)
0.8553	High Similarity	NPD4010	Discontinued
0.8503	High Similarity	NPD1632	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD4017	Approved
0.8344	Intermediate Similarity	NPD5241	Discontinued
0.8333	Intermediate Similarity	NPD4772	Phase 2
0.8333	Intermediate Similarity	NPD4773	Phase 2
0.8333	Intermediate Similarity	NPD3060	Approved
0.8333	Intermediate Similarity	NPD2898	Approved
0.8313	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD3055	Approved
0.831	Intermediate Similarity	NPD3053	Approved
0.8303	Intermediate Similarity	NPD6297	Approved
0.8228	Intermediate Similarity	NPD2977	Approved
0.8228	Intermediate Similarity	NPD2978	Approved
0.8194	Intermediate Similarity	NPD3639	Approved
0.8194	Intermediate Similarity	NPD3641	Approved
0.8194	Intermediate Similarity	NPD3640	Phase 3
0.8182	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD2420	Approved
0.8117	Intermediate Similarity	NPD2421	Approved
0.8113	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6853	Approved
0.8107	Intermediate Similarity	NPD8053	Approved
0.8107	Intermediate Similarity	NPD8054	Approved
0.8107	Intermediate Similarity	NPD6851	Approved
0.8095	Intermediate Similarity	NPD2674	Phase 3
0.8092	Intermediate Similarity	NPD4162	Approved
0.8075	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7833	Phase 2
0.8075	Intermediate Similarity	NPD7831	Phase 2
0.8037	Intermediate Similarity	NPD6107	Approved
0.8027	Intermediate Similarity	NPD5718	Phase 2
0.8012	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2489	Approved
0.8	Intermediate Similarity	NPD27	Approved
0.7988	Intermediate Similarity	NPD4166	Phase 2
0.7986	Intermediate Similarity	NPD5310	Approved
0.7986	Intermediate Similarity	NPD5311	Approved
0.7959	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD823	Approved
0.7933	Intermediate Similarity	NPD817	Approved
0.7905	Intermediate Similarity	NPD3145	Approved
0.7905	Intermediate Similarity	NPD3144	Approved
0.7852	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1424	Approved
0.7831	Intermediate Similarity	NPD2969	Approved
0.7831	Intermediate Similarity	NPD2970	Approved
0.7829	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3051	Approved
0.7771	Intermediate Similarity	NPD6071	Discontinued
0.777	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5160	Discontinued
0.7742	Intermediate Similarity	NPD5177	Phase 3
0.7738	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1136	Approved
0.7733	Intermediate Similarity	NPD1130	Approved
0.7733	Intermediate Similarity	NPD1132	Approved
0.773	Intermediate Similarity	NPD2563	Approved
0.773	Intermediate Similarity	NPD2560	Approved
0.7725	Intermediate Similarity	NPD4083	Discontinued
0.7692	Intermediate Similarity	NPD8251	Approved
0.7692	Intermediate Similarity	NPD8252	Approved
0.7692	Intermediate Similarity	NPD8099	Discontinued
0.7683	Intermediate Similarity	NPD6788	Approved
0.7682	Intermediate Similarity	NPD3059	Approved
0.7682	Intermediate Similarity	NPD3062	Approved
0.7682	Intermediate Similarity	NPD3061	Approved
0.7677	Intermediate Similarity	NPD7153	Discontinued
0.7674	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD601	Approved
0.7667	Intermediate Similarity	NPD598	Approved
0.7667	Intermediate Similarity	NPD597	Approved
0.7658	Intermediate Similarity	NPD3124	Discontinued
0.7647	Intermediate Similarity	NPD8156	Discontinued
0.7647	Intermediate Similarity	NPD6895	Approved
0.7647	Intermediate Similarity	NPD6896	Approved
0.7628	Intermediate Similarity	NPD2460	Phase 3
0.7628	Intermediate Similarity	NPD2459	Approved
0.7628	Intermediate Similarity	NPD2458	Approved
0.7616	Intermediate Similarity	NPD3532	Approved
0.7616	Intermediate Similarity	NPD3530	Approved
0.7616	Intermediate Similarity	NPD3531	Approved
0.761	Intermediate Similarity	NPD2874	Phase 2
0.7607	Intermediate Similarity	NPD5720	Discontinued
0.7605	Intermediate Similarity	NPD7802	Discontinued
0.7602	Intermediate Similarity	NPD7479	Phase 2
0.7597	Intermediate Similarity	NPD2154	Approved
0.7597	Intermediate Similarity	NPD2155	Approved
0.7597	Intermediate Similarity	NPD2156	Approved
0.7597	Intermediate Similarity	NPD1753	Discontinued
0.7588	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD3054	Approved
0.7582	Intermediate Similarity	NPD2986	Phase 2
0.7582	Intermediate Similarity	NPD5314	Approved
0.7582	Intermediate Similarity	NPD3052	Approved
0.7582	Intermediate Similarity	NPD2989	Phase 2
0.7557	Intermediate Similarity	NPD7906	Approved
0.7547	Intermediate Similarity	NPD7598	Phase 2
0.7545	Intermediate Similarity	NPD4666	Phase 3
0.7544	Intermediate Similarity	NPD4873	Discontinued
0.7543	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4578	Approved
0.7529	Intermediate Similarity	NPD7313	Approved
0.7529	Intermediate Similarity	NPD4577	Approved
0.7529	Intermediate Similarity	NPD7311	Approved
0.7529	Intermediate Similarity	NPD7310	Approved
0.7529	Intermediate Similarity	NPD7312	Approved
0.7529	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5976	Discontinued
0.7515	Intermediate Similarity	NPD5977	Approved
0.7515	Intermediate Similarity	NPD5978	Approved
0.75	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3645	Discontinued
0.7486	Intermediate Similarity	NPD6618	Phase 2
0.7486	Intermediate Similarity	NPD7309	Approved
0.7485	Intermediate Similarity	NPD5709	Phase 3
0.7484	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3936	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2653	Approved
0.7453	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3109	Approved
0.7451	Intermediate Similarity	NPD3110	Approved
0.7434	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4055	Discovery
0.7423	Intermediate Similarity	NPD4005	Discontinued
0.7423	Intermediate Similarity	NPD824	Approved
0.7421	Intermediate Similarity	NPD2677	Approved
0.7421	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4727	Phase 1
0.7401	Intermediate Similarity	NPD4663	Approved
0.74	Intermediate Similarity	NPD9621	Approved
0.74	Intermediate Similarity	NPD9620	Approved
0.74	Intermediate Similarity	NPD9619	Approved
0.7397	Intermediate Similarity	NPD2668	Approved
0.7397	Intermediate Similarity	NPD2667	Approved
0.7391	Intermediate Similarity	NPD3536	Discontinued
0.7391	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4475	Approved
0.7386	Intermediate Similarity	NPD4474	Approved
0.7383	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2120	Phase 2
0.7374	Intermediate Similarity	NPD2490	Approved
0.7374	Intermediate Similarity	NPD2488	Approved
0.7365	Intermediate Similarity	NPD2230	Approved
0.7365	Intermediate Similarity	NPD2232	Approved
0.7365	Intermediate Similarity	NPD2233	Approved
0.7362	Intermediate Similarity	NPD3687	Approved
0.7362	Intermediate Similarity	NPD3686	Approved
0.7358	Intermediate Similarity	NPD6331	Phase 2
0.7358	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3637	Approved
0.7351	Intermediate Similarity	NPD3635	Approved
0.7351	Intermediate Similarity	NPD3636	Approved
0.7349	Intermediate Similarity	NPD4585	Approved
0.7346	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7526	Approved
0.7346	Intermediate Similarity	NPD52	Approved
0.7342	Intermediate Similarity	NPD4257	Approved
0.7342	Intermediate Similarity	NPD4256	Phase 2
0.7341	Intermediate Similarity	NPD5313	Approved
0.7341	Intermediate Similarity	NPD6042	Phase 2
0.7341	Intermediate Similarity	NPD3933	Discontinued
0.7341	Intermediate Similarity	NPD5312	Approved
0.7341	Intermediate Similarity	NPD42	Phase 2
0.7341	Intermediate Similarity	NPD5096	Phase 3
0.7341	Intermediate Similarity	NPD5095	Phase 3
0.7333	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7110	Phase 1
0.7329	Intermediate Similarity	NPD4093	Discontinued
0.7325	Intermediate Similarity	NPD3156	Discontinued
0.7324	Intermediate Similarity	NPD9377	Approved
0.7324	Intermediate Similarity	NPD9379	Approved
0.7315	Intermediate Similarity	NPD9622	Approved
0.7315	Intermediate Similarity	NPD1669	Approved
0.7312	Intermediate Similarity	NPD3692	Discontinued
0.7308	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4236	Phase 3
0.7296	Intermediate Similarity	NPD4237	Approved
0.7284	Intermediate Similarity	NPD4123	Phase 3
0.7278	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7124	Phase 2
0.7267	Intermediate Similarity	NPD4481	Phase 3
0.7256	Intermediate Similarity	NPD1969	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1973	Approved
0.7256	Intermediate Similarity	NPD1972	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data