NPASS Compound

Structure

CID112206 OpenBabel06191715462D 24 27 0 0 0 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 6.0622 4.5000 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 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 3.4641 3.0000 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 1.7321 1.0000 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 2.5981 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 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 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 N 0 3 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 5.1962 4.0000 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 4 2 0 0 0 0 3 11 1 0 0 0 0 4 16 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 20 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 13 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 18 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 M CHG 1 20 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.12
Volume:	329.339
LogP:	3.361
LogD:	3.389
LogS:	-4.826
# Rotatable Bonds:	2
TPSA:	62.8
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.712
Synthetic Accessibility Score:	2.875
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.299
MDCK Permeability:	1.117528972827131e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.272
Plasma Protein Binding (PPB):	92.92115020751953%
Volume Distribution (VD):	0.864
Pgp-substrate:	7.276340007781982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.788
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.291
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.505
CYP2D6-inhibitor:	0.412
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	10.808
Half-life (T1/2):	0.606

ADMET: Toxicity

hERG Blockers:	0.209
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.308
AMES Toxicity:	0.438
Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.938
Carcinogencity:	0.16
Eye Corrosion:	0.003
Eye Irritation:	0.483
Respiratory Toxicity:	0.888

Download Data

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

Natural Product: NPC112206

Natural Product ID:	NPC112206
*Common Name:**	Stepharanine
IUPAC Name:	3,9-dimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2,10-diol
Synonyms:	stepharanine
Standard InCHIKey:	BENXORZPKXUGMY-UHFFFAOYSA-O
Standard InCHI:	InChI=1S/C19H17NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,7-10H,5-6H2,1-2H3,(H-,21,22)/p+1
SMILES:	COc1cc2CC[n+]3cc4c(ccc(c4OC)O)cc3-c2cc1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251229
PubChem CID:	10358881
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
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3987/COM-96-7609.]
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858757]
NPO25677	Xylopia parviflora	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[15081299]
NPO25677	Xylopia parviflora	Species	Annonaceae	Eukaryota	n.a.	bark	n.a.	PMID[15081299]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038566]
NPO16437	Stephania venosa	Species	Menispermaceae	Eukaryota	n.a.	tuber	n.a.	PMID[16640839]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[16964757]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[17340259]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994701]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18081254]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18829331]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[20030508]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	tubers	n.a.	n.a.	PMID[20594848]
NPO24893	Polyalthia nemoralis	Species	Annonaceae	Eukaryota	n.a.	branch	n.a.	PMID[21809577]
NPO24893	Polyalthia nemoralis	Species	Annonaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21809577]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22737858]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23059629]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23194502]
NPO31236	Stephania dentifolia	Species	Menispermaceae	Eukaryota	n.a.	root	n.a.	PMID[23713286]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25277281]
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	aerial parts	Alpa Corral, Cordoba, Argentina	2008-Aug	PMID[25517209]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	tuber	n.a.	PMID[25670016]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28836430]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32058719]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3728032]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30169	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24050	Stephania glabra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24893	Polyalthia nemoralis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25677	Xylopia parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1315	Sinomenium acutum	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]
NPO24050	Stephania glabra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24893	Polyalthia nemoralis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24050	Stephania glabra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12773	Stephania tetrandra	Species	Menispermaceae	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]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	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]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2341	Fibraurea recisa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13962	Corydalis turtschaninovii	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24893	Polyalthia nemoralis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13528	Funneliformis mosseae	Species	Glomeraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19027	Passiflora coccinea	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16437	Stephania venosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22738	Horsfieldia iryaghedhi	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23414	Karwinskia subcordata	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25734	Tinospora sagittata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23282	Russula paludosa	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1315	Sinomenium acutum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24050	Stephania glabra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10008	Tinospora capillipes	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23885	Agathosma bisulca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24365	Hymenoxys ivesiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12773	Stephania tetrandra	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29471	Achyrocline satureioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1327	Heliothis maritima	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO827	Corydalis yanhusuo	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23550	Maytenus octogona	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24183	Brickellia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25677	Xylopia parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25345	Corydalis ternata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23461	Medicago hispida	Species	Fabaceae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	>	2500.0	nM	PMID[487747]

☑ 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 NPC112206 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	528
0.1-0.2	2940
0.2-0.3	13666
0.3-0.4	4113
0.4-0.5	12039
0.5-0.6	6734
0.6-0.7	2154
0.7-0.8	440
0.8-0.85	40
0.85-0.9	24
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC202605
0.9628	High Similarity	NPC36229
0.9628	High Similarity	NPC476581
0.9628	High Similarity	NPC16452
0.9468	High Similarity	NPC31930
0.9362	High Similarity	NPC476582
0.9362	High Similarity	NPC4071
0.9362	High Similarity	NPC476578
0.9282	High Similarity	NPC53069
0.9282	High Similarity	NPC296482
0.9282	High Similarity	NPC202768
0.9086	High Similarity	NPC96405
0.9086	High Similarity	NPC171409
0.9043	High Similarity	NPC195268
0.9043	High Similarity	NPC133140
0.9026	High Similarity	NPC313189
0.8955	High Similarity	NPC473822
0.8937	High Similarity	NPC201508
0.8832	High Similarity	NPC135549
0.8794	High Similarity	NPC290689
0.878	High Similarity	NPC118121
0.878	High Similarity	NPC122463
0.8762	High Similarity	NPC255800
0.8762	High Similarity	NPC96584
0.8718	High Similarity	NPC477019
0.8683	High Similarity	NPC174049
0.8585	High Similarity	NPC100079
0.8585	High Similarity	NPC23614
0.8585	High Similarity	NPC204446
0.8528	High Similarity	NPC234197
0.8495	Intermediate Similarity	NPC173080
0.848	Intermediate Similarity	NPC266931
0.8454	Intermediate Similarity	NPC46451
0.8439	Intermediate Similarity	NPC235076
0.8431	Intermediate Similarity	NPC251160
0.839	Intermediate Similarity	NPC149471
0.839	Intermediate Similarity	NPC271215
0.8389	Intermediate Similarity	NPC214980
0.8333	Intermediate Similarity	NPC295228
0.831	Intermediate Similarity	NPC476997
0.8283	Intermediate Similarity	NPC224928
0.8271	Intermediate Similarity	NPC469792
0.8271	Intermediate Similarity	NPC476998
0.8271	Intermediate Similarity	NPC476996
0.8252	Intermediate Similarity	NPC316981
0.8244	Intermediate Similarity	NPC188420
0.8224	Intermediate Similarity	NPC476994
0.8213	Intermediate Similarity	NPC236668
0.8173	Intermediate Similarity	NPC141915
0.8173	Intermediate Similarity	NPC280964
0.8173	Intermediate Similarity	NPC114335
0.8173	Intermediate Similarity	NPC146976
0.816	Intermediate Similarity	NPC280272
0.8109	Intermediate Similarity	NPC287437
0.8105	Intermediate Similarity	NPC312872
0.8056	Intermediate Similarity	NPC246381
0.8027	Intermediate Similarity	NPC15406
0.8019	Intermediate Similarity	NPC213530
0.8019	Intermediate Similarity	NPC193267
0.8009	Intermediate Similarity	NPC473513
0.8	Intermediate Similarity	NPC47059
0.8	Intermediate Similarity	NPC165349
0.8	Intermediate Similarity	NPC118832
0.8	Intermediate Similarity	NPC329708
0.8	Intermediate Similarity	NPC264166
0.8	Intermediate Similarity	NPC274291
0.7991	Intermediate Similarity	NPC210434
0.799	Intermediate Similarity	NPC135887
0.799	Intermediate Similarity	NPC199277
0.7964	Intermediate Similarity	NPC476995
0.7961	Intermediate Similarity	NPC470164
0.7961	Intermediate Similarity	NPC304183
0.7961	Intermediate Similarity	NPC323345
0.7952	Intermediate Similarity	NPC162530
0.7937	Intermediate Similarity	NPC217554
0.7936	Intermediate Similarity	NPC24019
0.7933	Intermediate Similarity	NPC469589
0.7919	Intermediate Similarity	NPC204385
0.7911	Intermediate Similarity	NPC284141
0.7885	Intermediate Similarity	NPC470931
0.7883	Intermediate Similarity	NPC473183
0.7864	Intermediate Similarity	NPC469440
0.7861	Intermediate Similarity	NPC329541
0.7857	Intermediate Similarity	NPC210296
0.7848	Intermediate Similarity	NPC11408
0.7826	Intermediate Similarity	NPC164374
0.7826	Intermediate Similarity	NPC137929
0.7826	Intermediate Similarity	NPC285558
0.781	Intermediate Similarity	NPC11464
0.781	Intermediate Similarity	NPC470020
0.7798	Intermediate Similarity	NPC200888
0.7793	Intermediate Similarity	NPC473184
0.7789	Intermediate Similarity	NPC471178
0.7788	Intermediate Similarity	NPC472111
0.7783	Intermediate Similarity	NPC473053
0.7778	Intermediate Similarity	NPC475774
0.7773	Intermediate Similarity	NPC134637
0.7767	Intermediate Similarity	NPC148409
0.7761	Intermediate Similarity	NPC469390
0.775	Intermediate Similarity	NPC477186
0.7748	Intermediate Similarity	NPC22481
0.7739	Intermediate Similarity	NPC77878
0.7739	Intermediate Similarity	NPC276674
0.7739	Intermediate Similarity	NPC33902
0.7729	Intermediate Similarity	NPC270515
0.7725	Intermediate Similarity	NPC167860
0.7725	Intermediate Similarity	NPC123976
0.7716	Intermediate Similarity	NPC206201
0.7714	Intermediate Similarity	NPC18348
0.7713	Intermediate Similarity	NPC90875
0.7712	Intermediate Similarity	NPC132385
0.7706	Intermediate Similarity	NPC322482
0.7703	Intermediate Similarity	NPC233334
0.7692	Intermediate Similarity	NPC278525
0.7679	Intermediate Similarity	NPC108342
0.7667	Intermediate Similarity	NPC193777
0.7662	Intermediate Similarity	NPC320088
0.7662	Intermediate Similarity	NPC183537
0.7658	Intermediate Similarity	NPC476999
0.765	Intermediate Similarity	NPC61350
0.7644	Intermediate Similarity	NPC182907
0.7644	Intermediate Similarity	NPC66815
0.7644	Intermediate Similarity	NPC189903
0.7634	Intermediate Similarity	NPC253675
0.7621	Intermediate Similarity	NPC119134
0.7619	Intermediate Similarity	NPC295691
0.7619	Intermediate Similarity	NPC278799
0.7619	Intermediate Similarity	NPC207757
0.7619	Intermediate Similarity	NPC54379
0.7619	Intermediate Similarity	NPC184026
0.7619	Intermediate Similarity	NPC189266
0.7619	Intermediate Similarity	NPC276588
0.7619	Intermediate Similarity	NPC469817
0.7619	Intermediate Similarity	NPC110416
0.7619	Intermediate Similarity	NPC5238
0.7619	Intermediate Similarity	NPC2413
0.7619	Intermediate Similarity	NPC204828
0.7619	Intermediate Similarity	NPC193949
0.7619	Intermediate Similarity	NPC172765
0.7619	Intermediate Similarity	NPC127674
0.7619	Intermediate Similarity	NPC39701
0.7619	Intermediate Similarity	NPC249797
0.7617	Intermediate Similarity	NPC471080
0.7617	Intermediate Similarity	NPC469592
0.7611	Intermediate Similarity	NPC166722
0.761	Intermediate Similarity	NPC251090
0.7606	Intermediate Similarity	NPC208284
0.7598	Intermediate Similarity	NPC307963
0.7594	Intermediate Similarity	NPC174672
0.7594	Intermediate Similarity	NPC174758
0.7592	Intermediate Similarity	NPC177404
0.7592	Intermediate Similarity	NPC471177
0.7592	Intermediate Similarity	NPC59779
0.7592	Intermediate Similarity	NPC124542
0.759	Intermediate Similarity	NPC66573
0.7589	Intermediate Similarity	NPC473182
0.7577	Intermediate Similarity	NPC41501
0.7573	Intermediate Similarity	NPC243834
0.7573	Intermediate Similarity	NPC70956
0.7571	Intermediate Similarity	NPC210256
0.7561	Intermediate Similarity	NPC326634
0.7558	Intermediate Similarity	NPC469594
0.755	Intermediate Similarity	NPC62069
0.7549	Intermediate Similarity	NPC99666
0.7548	Intermediate Similarity	NPC11017
0.7547	Intermediate Similarity	NPC82548
0.7535	Intermediate Similarity	NPC474594
0.7526	Intermediate Similarity	NPC26850
0.7525	Intermediate Similarity	NPC66083
0.7524	Intermediate Similarity	NPC223427
0.7523	Intermediate Similarity	NPC473185
0.7523	Intermediate Similarity	NPC110151
0.7512	Intermediate Similarity	NPC232727
0.7512	Intermediate Similarity	NPC289786
0.75	Intermediate Similarity	NPC474595
0.75	Intermediate Similarity	NPC92111
0.7489	Intermediate Similarity	NPC107123
0.7488	Intermediate Similarity	NPC48353
0.7488	Intermediate Similarity	NPC474188
0.7475	Intermediate Similarity	NPC283152
0.7467	Intermediate Similarity	NPC99891
0.7465	Intermediate Similarity	NPC170114
0.7465	Intermediate Similarity	NPC475910
0.7464	Intermediate Similarity	NPC176538
0.7464	Intermediate Similarity	NPC315957
0.7455	Intermediate Similarity	NPC310118
0.7451	Intermediate Similarity	NPC76748
0.7446	Intermediate Similarity	NPC124313
0.7435	Intermediate Similarity	NPC84164
0.7435	Intermediate Similarity	NPC207283
0.7419	Intermediate Similarity	NPC470549
0.7409	Intermediate Similarity	NPC54066
0.7407	Intermediate Similarity	NPC192768
0.7407	Intermediate Similarity	NPC97221
0.7407	Intermediate Similarity	NPC88249
0.7407	Intermediate Similarity	NPC151895
0.7407	Intermediate Similarity	NPC220858
0.7406	Intermediate Similarity	NPC475070
0.7402	Intermediate Similarity	NPC296527
0.7395	Intermediate Similarity	NPC129897

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 NPC112206 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	679
0.2-0.3	890
0.3-0.4	1297
0.4-0.5	2592
0.5-0.6	2263
0.6-0.7	955
0.7-0.8	175
0.8-0.85	7
0.85-0.9	1
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9282	High Similarity	NPD3816	Phase 1
0.9282	High Similarity	NPD3815	Phase 1
0.9043	High Similarity	NPD3922	Approved
0.9043	High Similarity	NPD3923	Approved
0.9043	High Similarity	NPD3921	Approved
0.9043	High Similarity	NPD3924	Approved
0.8457	Intermediate Similarity	NPD3920	Phase 2
0.8454	Intermediate Similarity	NPD3763	Approved
0.8326	Intermediate Similarity	NPD6494	Phase 2
0.8272	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.8265	Intermediate Similarity	NPD6569	Phase 2
0.8164	Intermediate Similarity	NPD7069	Discontinued
0.8072	Intermediate Similarity	NPD6230	Discontinued
0.8061	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.801	Intermediate Similarity	NPD7222	Phase 2
0.8	Intermediate Similarity	NPD4036	Approved
0.8	Intermediate Similarity	NPD4037	Approved
0.8	Intermediate Similarity	NPD4122	Approved
0.8	Intermediate Similarity	NPD4039	Approved
0.8	Intermediate Similarity	NPD4035	Approved
0.8	Intermediate Similarity	NPD32	Approved
0.8	Intermediate Similarity	NPD31	Approved
0.8	Intermediate Similarity	NPD4034	Approved
0.8	Intermediate Similarity	NPD4033	Approved
0.8	Intermediate Similarity	NPD4038	Approved
0.7971	Intermediate Similarity	NPD5658	Approved
0.7961	Intermediate Similarity	NPD5530	Phase 1
0.7902	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7897	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD7675	Phase 3
0.788	Intermediate Similarity	NPD7674	Phase 3
0.7879	Intermediate Similarity	NPD8091	Phase 3
0.7877	Intermediate Similarity	NPD5612	Discontinued
0.7861	Intermediate Similarity	NPD4551	Phase 2
0.7828	Intermediate Similarity	NPD7558	Phase 2
0.7805	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4889	Approved
0.7768	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7453	Approved
0.7751	Intermediate Similarity	NPD7452	Approved
0.7744	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD4375	Approved
0.7732	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7426	Phase 1
0.7689	Intermediate Similarity	NPD4131	Phase 3
0.7661	Intermediate Similarity	NPD1954	Phase 1
0.7656	Intermediate Similarity	NPD4795	Phase 2
0.765	Intermediate Similarity	NPD7169	Suspended
0.7647	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4418	Discontinued
0.7634	Intermediate Similarity	NPD6963	Approved
0.7634	Intermediate Similarity	NPD6964	Approved
0.7633	Intermediate Similarity	NPD6219	Discontinued
0.7629	Intermediate Similarity	NPD7859	Phase 2
0.761	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3477	Phase 2
0.7606	Intermediate Similarity	NPD4502	Phase 2
0.76	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD1038	Approved
0.7581	Intermediate Similarity	NPD5903	Approved
0.7581	Intermediate Similarity	NPD5902	Approved
0.7551	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD4203	Approved
0.7538	Intermediate Similarity	NPD4204	Approved
0.7538	Intermediate Similarity	NPD3386	Phase 2
0.7535	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6501	Approved
0.7523	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD6500	Approved
0.7521	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD6361	Phase 2
0.7512	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD4876	Phase 3
0.7511	Intermediate Similarity	NPD4875	Phase 3
0.75	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1856	Discontinued
0.75	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD5930	Phase 3
0.7489	Intermediate Similarity	NPD7555	Discontinued
0.7465	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1740	Approved
0.7464	Intermediate Similarity	NPD1739	Approved
0.7463	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7454	Intermediate Similarity	NPD5944	Phase 1
0.7454	Intermediate Similarity	NPD5945	Phase 1
0.7437	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2781	Approved
0.7436	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2782	Approved
0.7423	Intermediate Similarity	NPD2780	Approved
0.7419	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD1392	Approved
0.7406	Intermediate Similarity	NPD3397	Phase 2
0.7404	Intermediate Similarity	NPD2952	Discontinued
0.7397	Intermediate Similarity	NPD6568	Discontinued
0.7393	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7393	Intermediate Similarity	NPD6975	Discontinued
0.7391	Intermediate Similarity	NPD3396	Approved
0.7391	Intermediate Similarity	NPD3395	Approved
0.7389	Intermediate Similarity	NPD4885	Approved
0.7383	Intermediate Similarity	NPD7671	Approved
0.7383	Intermediate Similarity	NPD7672	Approved
0.7379	Intermediate Similarity	NPD4372	Phase 1
0.7378	Intermediate Similarity	NPD7567	Approved
0.7376	Intermediate Similarity	NPD5147	Discontinued
0.7371	Intermediate Similarity	NPD3003	Approved
0.7361	Intermediate Similarity	NPD5067	Phase 2
0.7361	Intermediate Similarity	NPD5066	Phase 2
0.7359	Intermediate Similarity	NPD1483	Discontinued
0.7358	Intermediate Similarity	NPD4044	Discontinued
0.7358	Intermediate Similarity	NPD6991	Approved
0.7349	Intermediate Similarity	NPD4437	Phase 3
0.733	Intermediate Similarity	NPD2334	Discontinued
0.7325	Intermediate Similarity	NPD2757	Phase 2
0.7321	Intermediate Similarity	NPD7948	Phase 1
0.7318	Intermediate Similarity	NPD3354	Phase 2
0.7317	Intermediate Similarity	NPD4021	Phase 2
0.7308	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7112	Discontinued
0.7286	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD8063	Discontinued
0.7281	Intermediate Similarity	NPD4080	Discontinued
0.7277	Intermediate Similarity	NPD7719	Discontinued
0.7273	Intermediate Similarity	NPD5905	Phase 1
0.7273	Intermediate Similarity	NPD4083	Discontinued
0.7257	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5100	Phase 3
0.7249	Intermediate Similarity	NPD4584	Approved
0.7245	Intermediate Similarity	NPD925	Approved
0.7245	Intermediate Similarity	NPD926	Approved
0.724	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1622	Discontinued
0.7225	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6590	Discontinued
0.7216	Intermediate Similarity	NPD5255	Approved
0.7209	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5601	Phase 2
0.7207	Intermediate Similarity	NPD7194	Discontinued
0.7198	Intermediate Similarity	NPD8016	Phase 3
0.7198	Intermediate Similarity	NPD6281	Approved
0.7198	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD8442	Discontinued
0.7193	Intermediate Similarity	NPD4995	Approved
0.7193	Intermediate Similarity	NPD4996	Approved
0.7186	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1034	Phase 3
0.7184	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7620	Phase 2
0.7176	Intermediate Similarity	NPD5429	Discontinued
0.7173	Intermediate Similarity	NPD8101	Phase 3
0.7171	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD3825	Phase 3
0.7167	Intermediate Similarity	NPD6790	Phase 1
0.7156	Intermediate Similarity	NPD6262	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4349	Approved
0.7149	Intermediate Similarity	NPD4350	Approved
0.7149	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD4925	Approved
0.7143	Intermediate Similarity	NPD5506	Approved
0.7143	Intermediate Similarity	NPD5529	Phase 1
0.7143	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5507	Approved
0.7136	Intermediate Similarity	NPD4921	Phase 3
0.7136	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2917	Approved
0.7136	Intermediate Similarity	NPD4919	Phase 3
0.7136	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD2060	Approved
0.7129	Intermediate Similarity	NPD6159	Phase 2
0.7129	Intermediate Similarity	NPD1032	Phase 2
0.7124	Intermediate Similarity	NPD6246	Approved
0.7117	Intermediate Similarity	NPD4989	Phase 2
0.7109	Intermediate Similarity	NPD2482	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD6592	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7807	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6242	Discontinued
0.7098	Intermediate Similarity	NPD8479	Phase 2
0.7097	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6290	Phase 2
0.7095	Intermediate Similarity	NPD802	Phase 2
0.7095	Intermediate Similarity	NPD8244	Phase 2
0.7089	Intermediate Similarity	NPD2175	Phase 3
0.7089	Intermediate Similarity	NPD5999	Phase 2
0.7089	Intermediate Similarity	NPD1768	Approved
0.7089	Intermediate Similarity	NPD2177	Approved
0.7089	Intermediate Similarity	NPD3541	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2176	Approved
0.7089	Intermediate Similarity	NPD6276	Discontinued
0.7085	Intermediate Similarity	NPD5862	Discovery
0.7085	Intermediate Similarity	NPD7395	Discontinued
0.7083	Intermediate Similarity	NPD5539	Phase 2

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