NPASS Compound

Structure

CID57512 OpenBabel06191715392D 26 28 0 0 0 0 0 0 0 0999 V2000 0.5000 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1603 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6962 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4282 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8301 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2942 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6028 -3.6103 0.0000 Cl 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 5 1 0 0 0 0 4 12 2 0 0 0 0 5 17 2 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 13 2 0 0 0 0 9 18 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 21 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 22 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	337.13
Volume:	345.316
LogP:	2.791
LogD:	2.795
LogS:	-4.662
# Rotatable Bonds:	3
TPSA:	49.69
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	2.497
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	1.9685352526721545e-05
Pgp-inhibitor:	0.869
Pgp-substrate:	0.941
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.892
Plasma Protein Binding (PPB):	84.71464538574219%
Volume Distribution (VD):	1.237
Pgp-substrate:	5.359897613525391%

ADMET: Metabolism

CYP1A2-inhibitor:	0.524
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.759
CYP2C19-substrate:	0.373
CYP2C9-inhibitor:	0.77
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.941
CYP3A4-inhibitor:	0.661
CYP3A4-substrate:	0.601

ADMET: Excretion

Clearance (CL):	5.72
Half-life (T1/2):	0.426

ADMET: Toxicity

hERG Blockers:	0.185
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.863
AMES Toxicity:	0.817
Rat Oral Acute Toxicity:	0.071
Maximum Recommended Daily Dose:	0.817
Skin Sensitization:	0.253
Carcinogencity:	0.558
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.747

Download Data

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

Natural Product: NPC57512

Natural Product ID:	NPC57512
*Common Name:**	Palmatrubine
IUPAC Name:	2,3,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-9-ol;chloride
Synonyms:
Standard InCHIKey:	DFUDAUWKWTTXFV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H19NO4.ClH/c1-23-17-5-4-12-8-16-14-10-19(25-3)18(24-2)9-13(14)6-7-21(16)11-15(12)20(17)22;/h4-5,8-11H,6-7H2,1-3H3;1H
SMILES:	COc1cc2c(cc1OC)CCn1c2cc2ccc(c(=O)c2c1)OC.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2270069
PubChem CID:	10547385
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001909] Protoberberine alkaloids and derivatives

*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
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[11000020]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[17340259]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21401114]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28836430]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13757	Coptis japonica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5649	Coptis chinensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29008	Coptis teeta	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	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
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Unit	Reference
NPT822	Organism	Lemna minor	Lemna minor	Activity	=	%	PMID[516131]
NPT823	Organism	Agrostis stolonifera var. palustris	Agrostis stolonifera var. palustris	Activity	=	%	PMID[516131]
NPT824	Organism	Ustilago maydis	Ustilago maydis	Inhibition	=	%	PMID[516131]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Inhibition	=	%	PMID[516131]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	Inhibition	=	%	PMID[516131]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	Inhibition	=	%	PMID[516131]
NPT827	Organism	Mycosphaerella graminicola	Mycosphaerella graminicola	Inhibition	=	%	PMID[516131]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Inhibition	=	%	PMID[516131]
NPT829	Organism	Puccinia recondita	Puccinia recondita	Activity	=	%	PMID[516131]
NPT825	Organism	Phytophthora infestans	Phytophthora infestans	Activity	=	%	PMID[516131]
NPT828	Organism	Phaeosphaeria nodorum	Phaeosphaeria nodorum	Activity	=	%	PMID[516131]
NPT830	Organism	Blumeria graminis f. sp. tritici	Blumeria graminis f. sp. tritici	Activity	=	%	PMID[516131]

☑ 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 NPC57512 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	496
0.1-0.2	3487
0.2-0.3	12877
0.3-0.4	3552
0.4-0.5	14426
0.5-0.6	5824
0.6-0.7	1687
0.7-0.8	298
0.8-0.85	42
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9795	High Similarity	NPC476580
0.9477	High Similarity	NPC306669
0.9286	High Similarity	NPC476569
0.9241	High Similarity	NPC4669
0.9073	High Similarity	NPC476579
0.8608	High Similarity	NPC106786
0.8581	High Similarity	NPC85747
0.8581	High Similarity	NPC8337
0.8562	High Similarity	NPC59567
0.8356	Intermediate Similarity	NPC160193
0.8302	Intermediate Similarity	NPC93593
0.8301	Intermediate Similarity	NPC136860
0.8301	Intermediate Similarity	NPC476567
0.8301	Intermediate Similarity	NPC128019
0.8293	Intermediate Similarity	NPC471604
0.8289	Intermediate Similarity	NPC213206
0.8289	Intermediate Similarity	NPC188163
0.8289	Intermediate Similarity	NPC474915
0.8289	Intermediate Similarity	NPC328750
0.8224	Intermediate Similarity	NPC314682
0.821	Intermediate Similarity	NPC226428
0.8165	Intermediate Similarity	NPC223125
0.8148	Intermediate Similarity	NPC118804
0.8113	Intermediate Similarity	NPC476568
0.8089	Intermediate Similarity	NPC210437
0.8089	Intermediate Similarity	NPC106295
0.8089	Intermediate Similarity	NPC16107
0.8089	Intermediate Similarity	NPC476144
0.8089	Intermediate Similarity	NPC51957
0.8077	Intermediate Similarity	NPC130926
0.8063	Intermediate Similarity	NPC223124
0.8061	Intermediate Similarity	NPC3375
0.8061	Intermediate Similarity	NPC255607
0.8038	Intermediate Similarity	NPC7467
0.8	Intermediate Similarity	NPC119669
0.7987	Intermediate Similarity	NPC196026
0.7987	Intermediate Similarity	NPC200555
0.7977	Intermediate Similarity	NPC116007
0.7974	Intermediate Similarity	NPC253429
0.7962	Intermediate Similarity	NPC185838
0.7947	Intermediate Similarity	NPC160692
0.7937	Intermediate Similarity	NPC151895
0.7937	Intermediate Similarity	NPC192768
0.7937	Intermediate Similarity	NPC97221
0.7937	Intermediate Similarity	NPC88249
0.7937	Intermediate Similarity	NPC220858
0.7925	Intermediate Similarity	NPC475959
0.7925	Intermediate Similarity	NPC135538
0.7925	Intermediate Similarity	NPC428
0.7925	Intermediate Similarity	NPC246587
0.7925	Intermediate Similarity	NPC147390
0.7925	Intermediate Similarity	NPC476571
0.7925	Intermediate Similarity	NPC24233
0.7908	Intermediate Similarity	NPC131204
0.7908	Intermediate Similarity	NPC301050
0.7908	Intermediate Similarity	NPC7018
0.7879	Intermediate Similarity	NPC475780
0.7862	Intermediate Similarity	NPC321505
0.7862	Intermediate Similarity	NPC476151
0.7862	Intermediate Similarity	NPC179825
0.7862	Intermediate Similarity	NPC191376
0.7852	Intermediate Similarity	NPC172403
0.7844	Intermediate Similarity	NPC39103
0.7844	Intermediate Similarity	NPC2770
0.7844	Intermediate Similarity	NPC231198
0.784	Intermediate Similarity	NPC233029
0.784	Intermediate Similarity	NPC210148
0.7831	Intermediate Similarity	NPC153631
0.7826	Intermediate Similarity	NPC274026
0.7818	Intermediate Similarity	NPC216816
0.7812	Intermediate Similarity	NPC130941
0.7811	Intermediate Similarity	NPC470324
0.7778	Intermediate Similarity	NPC274441
0.7778	Intermediate Similarity	NPC81733
0.7778	Intermediate Similarity	NPC326316
0.7771	Intermediate Similarity	NPC83511
0.7764	Intermediate Similarity	NPC219162
0.7764	Intermediate Similarity	NPC103379
0.7764	Intermediate Similarity	NPC477565
0.7764	Intermediate Similarity	NPC92541
0.7744	Intermediate Similarity	NPC295691
0.7744	Intermediate Similarity	NPC2413
0.7744	Intermediate Similarity	NPC127674
0.7744	Intermediate Similarity	NPC39701
0.7744	Intermediate Similarity	NPC216459
0.7744	Intermediate Similarity	NPC189266
0.7744	Intermediate Similarity	NPC325871
0.7744	Intermediate Similarity	NPC278799
0.7744	Intermediate Similarity	NPC184026
0.7744	Intermediate Similarity	NPC5238
0.7744	Intermediate Similarity	NPC204828
0.7744	Intermediate Similarity	NPC193949
0.7744	Intermediate Similarity	NPC138487
0.7744	Intermediate Similarity	NPC249797
0.7744	Intermediate Similarity	NPC80129
0.7744	Intermediate Similarity	NPC110416
0.7744	Intermediate Similarity	NPC99659
0.7744	Intermediate Similarity	NPC207757
0.7744	Intermediate Similarity	NPC276588
0.7744	Intermediate Similarity	NPC54379
0.7744	Intermediate Similarity	NPC172765
0.7744	Intermediate Similarity	NPC41178
0.7744	Intermediate Similarity	NPC187022
0.7744	Intermediate Similarity	NPC469817
0.773	Intermediate Similarity	NPC148898
0.773	Intermediate Similarity	NPC37272
0.773	Intermediate Similarity	NPC82285
0.773	Intermediate Similarity	NPC133011
0.7727	Intermediate Similarity	NPC11147
0.7727	Intermediate Similarity	NPC209195
0.7727	Intermediate Similarity	NPC13826
0.7697	Intermediate Similarity	NPC146288
0.7697	Intermediate Similarity	NPC247639
0.7697	Intermediate Similarity	NPC25084
0.7688	Intermediate Similarity	NPC222524
0.7669	Intermediate Similarity	NPC218575
0.7665	Intermediate Similarity	NPC135006
0.7661	Intermediate Similarity	NPC474708
0.7657	Intermediate Similarity	NPC298339
0.7654	Intermediate Similarity	NPC207824
0.7654	Intermediate Similarity	NPC60538
0.7651	Intermediate Similarity	NPC476572
0.7647	Intermediate Similarity	NPC284842
0.764	Intermediate Similarity	NPC144863
0.764	Intermediate Similarity	NPC95075
0.764	Intermediate Similarity	NPC90844
0.764	Intermediate Similarity	NPC253883
0.7636	Intermediate Similarity	NPC78733
0.7622	Intermediate Similarity	NPC470924
0.7605	Intermediate Similarity	NPC59028
0.7605	Intermediate Similarity	NPC111485
0.7605	Intermediate Similarity	NPC92191
0.7602	Intermediate Similarity	NPC475845
0.7602	Intermediate Similarity	NPC86469
0.759	Intermediate Similarity	NPC147091
0.759	Intermediate Similarity	NPC234392
0.759	Intermediate Similarity	NPC31311
0.7586	Intermediate Similarity	NPC241704
0.7562	Intermediate Similarity	NPC294249
0.7561	Intermediate Similarity	NPC76213
0.7561	Intermediate Similarity	NPC277669
0.756	Intermediate Similarity	NPC205167
0.7546	Intermediate Similarity	NPC44869
0.7544	Intermediate Similarity	NPC474324
0.7544	Intermediate Similarity	NPC57812
0.7543	Intermediate Similarity	NPC21885
0.7532	Intermediate Similarity	NPC118419
0.753	Intermediate Similarity	NPC244112
0.7528	Intermediate Similarity	NPC214629
0.7515	Intermediate Similarity	NPC58661
0.7514	Intermediate Similarity	NPC303581
0.7514	Intermediate Similarity	NPC67978
0.75	Intermediate Similarity	NPC66573
0.75	Intermediate Similarity	NPC32154
0.75	Intermediate Similarity	NPC477080
0.75	Intermediate Similarity	NPC27887
0.7486	Intermediate Similarity	NPC5167
0.7485	Intermediate Similarity	NPC170503
0.7485	Intermediate Similarity	NPC186063
0.7485	Intermediate Similarity	NPC203784
0.7485	Intermediate Similarity	NPC126519
0.7471	Intermediate Similarity	NPC475393
0.7471	Intermediate Similarity	NPC324144
0.7471	Intermediate Similarity	NPC233650
0.747	Intermediate Similarity	NPC477564
0.747	Intermediate Similarity	NPC2295
0.7468	Intermediate Similarity	NPC476570
0.7468	Intermediate Similarity	NPC231572
0.7456	Intermediate Similarity	NPC166014
0.7456	Intermediate Similarity	NPC160298
0.7456	Intermediate Similarity	NPC249274
0.7456	Intermediate Similarity	NPC477559
0.7456	Intermediate Similarity	NPC232924
0.7456	Intermediate Similarity	NPC266753
0.7456	Intermediate Similarity	NPC27410
0.7456	Intermediate Similarity	NPC306902
0.744	Intermediate Similarity	NPC475326
0.7429	Intermediate Similarity	NPC308267
0.7427	Intermediate Similarity	NPC253043
0.7427	Intermediate Similarity	NPC136508
0.7427	Intermediate Similarity	NPC134858
0.7427	Intermediate Similarity	NPC276944
0.7427	Intermediate Similarity	NPC477563
0.7427	Intermediate Similarity	NPC232514
0.7427	Intermediate Similarity	NPC121275
0.7427	Intermediate Similarity	NPC78222
0.7427	Intermediate Similarity	NPC212794
0.7427	Intermediate Similarity	NPC284183
0.7427	Intermediate Similarity	NPC24465
0.7427	Intermediate Similarity	NPC4138
0.7427	Intermediate Similarity	NPC238530
0.7427	Intermediate Similarity	NPC302527
0.7427	Intermediate Similarity	NPC13504
0.7427	Intermediate Similarity	NPC167546
0.7427	Intermediate Similarity	NPC306843
0.7427	Intermediate Similarity	NPC16805
0.7427	Intermediate Similarity	NPC96603
0.7427	Intermediate Similarity	NPC196447
0.7412	Intermediate Similarity	NPC60186
0.7412	Intermediate Similarity	NPC24954

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 NPC57512 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	725
0.2-0.3	932
0.3-0.4	1381
0.4-0.5	2755
0.5-0.6	2214
0.6-0.7	761
0.7-0.8	75
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD3640	Phase 3
0.8333	Intermediate Similarity	NPD3639	Approved
0.8333	Intermediate Similarity	NPD3641	Approved
0.8289	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6031	Approved
0.8101	Intermediate Similarity	NPD6030	Approved
0.8089	Intermediate Similarity	NPD4584	Approved
0.7866	Intermediate Similarity	NPD5978	Approved
0.7866	Intermediate Similarity	NPD5977	Approved
0.7811	Intermediate Similarity	NPD2898	Approved
0.7744	Intermediate Similarity	NPD7298	Approved
0.7738	Intermediate Similarity	NPD6107	Approved
0.7669	Intermediate Similarity	NPD4017	Approved
0.7657	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD4166	Phase 2
0.7582	Intermediate Similarity	NPD5718	Phase 2
0.7576	Intermediate Similarity	NPD4772	Phase 2
0.7576	Intermediate Similarity	NPD4773	Phase 2
0.7553	Intermediate Similarity	NPD4859	Phase 1
0.7515	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6618	Phase 2
0.7486	Intermediate Similarity	NPD7291	Discontinued
0.7471	Intermediate Similarity	NPD5312	Approved
0.7471	Intermediate Similarity	NPD5313	Approved
0.747	Intermediate Similarity	NPD7110	Phase 1
0.747	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6297	Approved
0.7381	Intermediate Similarity	NPD4585	Approved
0.7368	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1309	Phase 2
0.7353	Intermediate Similarity	NPD1307	Phase 2
0.7338	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7802	Discontinued
0.7283	Intermediate Similarity	NPD4010	Discontinued
0.7278	Intermediate Similarity	NPD2492	Phase 1
0.7263	Intermediate Similarity	NPD2968	Approved
0.7263	Intermediate Similarity	NPD2971	Approved
0.7256	Intermediate Similarity	NPD3124	Discontinued
0.7246	Intermediate Similarity	NPD824	Approved
0.7239	Intermediate Similarity	NPD5241	Discontinued
0.7233	Intermediate Similarity	NPD6895	Approved
0.7233	Intermediate Similarity	NPD6896	Approved
0.7222	Intermediate Similarity	NPD6851	Approved
0.7222	Intermediate Similarity	NPD6853	Approved
0.7216	Intermediate Similarity	NPD8251	Approved
0.7216	Intermediate Similarity	NPD8099	Discontinued
0.7216	Intermediate Similarity	NPD8252	Approved
0.7207	Intermediate Similarity	NPD7132	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6875	Approved
0.7202	Intermediate Similarity	NPD6876	Approved
0.72	Intermediate Similarity	NPD4481	Phase 3
0.7193	Intermediate Similarity	NPD6788	Approved
0.7184	Intermediate Similarity	NPD6071	Discontinued
0.7181	Intermediate Similarity	NPD5457	Discontinued
0.7176	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8156	Discontinued
0.716	Intermediate Similarity	NPD5090	Approved
0.716	Intermediate Similarity	NPD5089	Approved
0.716	Intermediate Similarity	NPD6386	Approved
0.716	Intermediate Similarity	NPD6385	Approved
0.7151	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7833	Phase 2
0.7151	Intermediate Similarity	NPD7831	Phase 2
0.7143	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2563	Approved
0.7135	Intermediate Similarity	NPD2560	Approved
0.7128	Intermediate Similarity	NPD7225	Discontinued
0.7108	Intermediate Similarity	NPD1424	Approved
0.7091	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4107	Approved
0.7074	Intermediate Similarity	NPD5071	Phase 2
0.7073	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2653	Approved
0.7059	Intermediate Similarity	NPD6873	Phase 2
0.7045	Intermediate Similarity	NPD6688	Approved
0.7045	Intermediate Similarity	NPD6687	Approved
0.7044	Intermediate Similarity	NPD3110	Approved
0.7044	Intermediate Similarity	NPD3109	Approved
0.7041	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2490	Approved
0.7027	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD2488	Approved
0.702	Intermediate Similarity	NPD8149	Discontinued
0.7	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5536	Phase 2
0.7	Intermediate Similarity	NPD6612	Phase 2
0.6984	Remote Similarity	NPD4420	Approved
0.6981	Remote Similarity	NPD2674	Phase 3
0.6971	Remote Similarity	NPD5677	Discontinued
0.6968	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4482	Phase 3
0.6957	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD2970	Approved
0.6949	Remote Similarity	NPD5242	Approved
0.6949	Remote Similarity	NPD2969	Approved
0.6946	Remote Similarity	NPD5297	Approved
0.6944	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8054	Approved
0.694	Remote Similarity	NPD8053	Approved
0.6937	Remote Similarity	NPD3142	Approved
0.6937	Remote Similarity	NPD3140	Approved
0.6931	Remote Similarity	NPD5564	Approved
0.6931	Remote Similarity	NPD2974	Approved
0.6931	Remote Similarity	NPD2973	Approved
0.6931	Remote Similarity	NPD2975	Approved
0.6927	Remote Similarity	NPD3057	Approved
0.691	Remote Similarity	NPD27	Approved
0.691	Remote Similarity	NPD2489	Approved
0.6905	Remote Similarity	NPD2335	Discontinued
0.6905	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3924	Approved
0.6898	Remote Similarity	NPD3921	Approved
0.6898	Remote Similarity	NPD3922	Approved
0.6898	Remote Similarity	NPD3923	Approved
0.6893	Remote Similarity	NPD3051	Approved
0.689	Remote Similarity	NPD3656	Approved
0.6889	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7124	Phase 2
0.6882	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4475	Approved
0.6875	Remote Similarity	NPD4474	Approved
0.6872	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2388	Discontinued
0.6853	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3920	Phase 2
0.6851	Remote Similarity	NPD3885	Approved
0.6845	Remote Similarity	NPD7668	Phase 2
0.6842	Remote Similarity	NPD7034	Discontinued
0.6842	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5005	Approved
0.6839	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2972	Approved
0.6839	Remote Similarity	NPD3533	Approved
0.6839	Remote Similarity	NPD5006	Approved
0.6833	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD4580	Approved
0.6813	Remote Similarity	NPD3144	Approved
0.6813	Remote Similarity	NPD3145	Approved
0.6813	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3060	Approved
0.6807	Remote Similarity	NPD4162	Approved
0.6807	Remote Similarity	NPD5177	Phase 3
0.6798	Remote Similarity	NPD5183	Approved
0.6798	Remote Similarity	NPD5186	Approved
0.6795	Remote Similarity	NPD1420	Approved
0.6795	Remote Similarity	NPD1421	Approved
0.6793	Remote Similarity	NPD7280	Phase 3
0.6793	Remote Similarity	NPD7281	Phase 3
0.6788	Remote Similarity	NPD2494	Approved
0.6788	Remote Similarity	NPD3450	Approved
0.6788	Remote Similarity	NPD2493	Approved
0.6788	Remote Similarity	NPD3452	Approved
0.677	Remote Similarity	NPD554	Clinical (unspecified phase)
0.676	Remote Similarity	NPD4083	Discontinued
0.6753	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD2491	Approved
0.6753	Remote Similarity	NPD3448	Approved
0.6752	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2421	Approved
0.6746	Remote Similarity	NPD2420	Approved
0.6744	Remote Similarity	NPD4005	Discontinued
0.6742	Remote Similarity	NPD2821	Approved
0.6737	Remote Similarity	NPD7669	Phase 3
0.6726	Remote Similarity	NPD3301	Approved
0.6725	Remote Similarity	NPD1670	Discontinued
0.672	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6111	Discontinued
0.6707	Remote Similarity	NPD743	Approved
0.6707	Remote Similarity	NPD4237	Approved
0.6707	Remote Similarity	NPD4236	Phase 3
0.6706	Remote Similarity	NPD3146	Approved
0.6706	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2120	Phase 2
0.6686	Remote Similarity	NPD3845	Phase 1
0.6686	Remote Similarity	NPD4210	Discontinued
0.6684	Remote Similarity	NPD4582	Approved
0.6684	Remote Similarity	NPD4583	Approved
0.6667	Remote Similarity	NPD7905	Discontinued
0.6667	Remote Similarity	NPD6748	Discontinued
0.6667	Remote Similarity	NPD6331	Phase 2
0.6667	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5676	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