NPASS Compound

Structure

CID118121 OpenBabel06191715472D 24 28 0 0 0 0 0 0 0 0999 V2000 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -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 -3.4641 -1.0000 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 12 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 15 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 13 2 0 0 0 0 7 17 1 0 0 0 0 8 14 2 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 9 24 1 0 0 0 0 10 13 1 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	319.08
Volume:	316.827
LogP:	4.206
LogD:	3.605
LogS:	-6.52
# Rotatable Bonds:	1
TPSA:	60.81
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.538
Synthetic Accessibility Score:	2.516
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.988
MDCK Permeability:	3.0731862352695316e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	93.55657958984375%
Volume Distribution (VD):	0.84
Pgp-substrate:	2.1032321453094482%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.326
CYP2C19-inhibitor:	0.944
CYP2C19-substrate:	0.145
CYP2C9-inhibitor:	0.661
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.86
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.795
CYP3A4-substrate:	0.137

ADMET: Excretion

Clearance (CL):	14.872
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.267
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.917
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.941
Carcinogencity:	0.94
Eye Corrosion:	0.003
Eye Irritation:	0.788
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC118121

Natural Product ID:	NPC118121
*Common Name:**	Decarine
IUPAC Name:	1-methoxy-[1,3]benzodioxolo[5,6-c]phenanthridin-2-ol
Synonyms:	Decarine
Standard InCHIKey:	GJJFWGQGJJGJEO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H13NO4/c1-22-19-14-8-20-18-12(11(14)4-5-15(19)21)3-2-10-6-16-17(7-13(10)18)24-9-23-16/h2-8,21H,9H2,1H3
SMILES:	COc1c(O)ccc2c1cnc1c2ccc2c1cc1OCOc1c2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458702
PubChem CID:	179640
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines 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
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(74)80113-5]
NPO20298	Zanthoxylum viride	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(75)83065-2]
NPO30267	Zanthoxylum caudatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11324918]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11324918]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662092]
NPO27680	Zanthoxylum syncarpum	Species	Rutaceae	Eukaryota	n.a.	stem	n.a.	PMID[14738394]
NPO8520	Mucor spinosus	Species	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844967]
NPO27680	Zanthoxylum syncarpum	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124784]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[1686898]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17637068]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18302336]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22432912]
NPO2330	Alchornea cordifolia	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[26724423]
NPO2330	Alchornea cordifolia	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[26724423]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14407	Stachyurus praecox	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17862	Zanthoxylum planispinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17862	Zanthoxylum planispinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23772	Tetradium glabrifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14407	Stachyurus praecox	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12487	Juniperus horizontalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10098	Glycosmis pseudoracemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17862	Zanthoxylum planispinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18894	Karenia mikimotoi	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20298	Zanthoxylum viride	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16801	Cota tinctoria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5276	Zanthoxylum decaryi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10098	Glycosmis pseudoracemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14526	Plectranthus caninus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13848	Amomum daniellii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15329	Rhizoplaca baranowii	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4424	Salvia amplexicaulis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5398	Peucedanum oroselinum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13647	Calcarisporium thermophilum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2330	Alchornea cordifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13389	Cystoseira barbatula	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7521	Hygrophorus eburneus	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15275	Briareum asbestinum	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15862	Eminium lehmannii	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14407	Stachyurus praecox	Species	Stachyuraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14947	Lathyrus tingitanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13247	Stevia pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11430	Inula grantioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6906	Atalantia wightii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10423	Sibthorpia europaea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3761	Plectosphaerella cucumerina	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1759	Alexandrium excavatum	Species	Gonyaulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14713	Bauhinia retusa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18873.2	Salmonella enterica subsp. enterica serovar bovismorbificans	Subspecies	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14567	Ursinia anethoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15020	Flindersia amboinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23772	Tetradium glabrifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17489	Myoporum acuminatum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14236	Physalis coztomatl	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8520	Mucor spinosus	Species	Mucoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12487	Juniperus horizontalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27680	Zanthoxylum syncarpum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2360	Jatropha mahafalensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15145	Rauvolfia salicifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17862	Zanthoxylum planispinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1109	Corydalis persica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3965	Corynanthe pachyceras	Species	Rubiaceae	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	4

Activity Type	# Activity
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	880.0	nM	PMID[515603]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1440.0	nM	PMID[515603]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.29	ug.mL-1	PMID[515604]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1.94	ug.mL-1	PMID[515604]

☑ 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 NPC118121 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	657
0.1-0.2	3264
0.2-0.3	12620
0.3-0.4	5411
0.4-0.5	12890
0.5-0.6	5625
0.6-0.7	1857
0.7-0.8	315
0.8-0.85	37
0.85-0.9	11
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9797	High Similarity	NPC204446
0.9645	High Similarity	NPC235076
0.95	High Similarity	NPC100079
0.95	High Similarity	NPC23614
0.9453	High Similarity	NPC46451
0.9442	High Similarity	NPC188420
0.93	High Similarity	NPC271215
0.93	High Similarity	NPC149471
0.8873	High Similarity	NPC251160
0.878	High Similarity	NPC112206
0.878	High Similarity	NPC202605
0.878	High Similarity	NPC296482
0.878	High Similarity	NPC202768
0.878	High Similarity	NPC53069
0.87	High Similarity	NPC234197
0.8689	High Similarity	NPC96405
0.8689	High Similarity	NPC171409
0.8585	High Similarity	NPC122463
0.8564	High Similarity	NPC31930
0.8537	High Similarity	NPC313189
0.8515	High Similarity	NPC477019
0.8447	Intermediate Similarity	NPC135549
0.8439	Intermediate Similarity	NPC476581
0.8439	Intermediate Similarity	NPC36229
0.8439	Intermediate Similarity	NPC16452
0.8404	Intermediate Similarity	NPC174049
0.8341	Intermediate Similarity	NPC210296
0.831	Intermediate Similarity	NPC473822
0.8309	Intermediate Similarity	NPC304183
0.8259	Intermediate Similarity	NPC133140
0.8259	Intermediate Similarity	NPC195268
0.8235	Intermediate Similarity	NPC22481
0.821	Intermediate Similarity	NPC77878
0.8195	Intermediate Similarity	NPC476578
0.8195	Intermediate Similarity	NPC476582
0.8195	Intermediate Similarity	NPC4071
0.8186	Intermediate Similarity	NPC148409
0.8182	Intermediate Similarity	NPC278525
0.8161	Intermediate Similarity	NPC108342
0.8159	Intermediate Similarity	NPC474904
0.8153	Intermediate Similarity	NPC255800
0.8153	Intermediate Similarity	NPC96584
0.8145	Intermediate Similarity	NPC201508
0.814	Intermediate Similarity	NPC173080
0.813	Intermediate Similarity	NPC183537
0.8125	Intermediate Similarity	NPC189903
0.8125	Intermediate Similarity	NPC182907
0.8122	Intermediate Similarity	NPC266931
0.8097	Intermediate Similarity	NPC217554
0.809	Intermediate Similarity	NPC179704
0.8089	Intermediate Similarity	NPC166722
0.807	Intermediate Similarity	NPC284141
0.8049	Intermediate Similarity	NPC162653
0.801	Intermediate Similarity	NPC204385
0.8009	Intermediate Similarity	NPC11408
0.799	Intermediate Similarity	NPC280964
0.799	Intermediate Similarity	NPC141915
0.799	Intermediate Similarity	NPC114335
0.7964	Intermediate Similarity	NPC214980
0.7948	Intermediate Similarity	NPC15406
0.794	Intermediate Similarity	NPC287588
0.7913	Intermediate Similarity	NPC124313
0.7909	Intermediate Similarity	NPC210434
0.7907	Intermediate Similarity	NPC316981
0.7904	Intermediate Similarity	NPC84164
0.7904	Intermediate Similarity	NPC207283
0.79	Intermediate Similarity	NPC206201
0.7897	Intermediate Similarity	NPC290689
0.7897	Intermediate Similarity	NPC11464
0.7892	Intermediate Similarity	NPC476997
0.7871	Intermediate Similarity	NPC249405
0.786	Intermediate Similarity	NPC208284
0.7857	Intermediate Similarity	NPC476998
0.7857	Intermediate Similarity	NPC476996
0.7841	Intermediate Similarity	NPC295228
0.7837	Intermediate Similarity	NPC224928
0.7833	Intermediate Similarity	NPC276674
0.7833	Intermediate Similarity	NPC33902
0.7812	Intermediate Similarity	NPC476994
0.7803	Intermediate Similarity	NPC200888
0.7797	Intermediate Similarity	NPC253675
0.7792	Intermediate Similarity	NPC132385
0.7788	Intermediate Similarity	NPC474594
0.7778	Intermediate Similarity	NPC24019
0.7778	Intermediate Similarity	NPC302001
0.7757	Intermediate Similarity	NPC474595
0.7756	Intermediate Similarity	NPC320088
0.7753	Intermediate Similarity	NPC473182
0.7736	Intermediate Similarity	NPC199277
0.7736	Intermediate Similarity	NPC135887
0.7735	Intermediate Similarity	NPC270515
0.7731	Intermediate Similarity	NPC470020
0.7729	Intermediate Similarity	NPC473183
0.7718	Intermediate Similarity	NPC312531
0.7706	Intermediate Similarity	NPC162530
0.7692	Intermediate Similarity	NPC213530
0.7692	Intermediate Similarity	NPC193267
0.7682	Intermediate Similarity	NPC473513
0.7674	Intermediate Similarity	NPC193777
0.7664	Intermediate Similarity	NPC164374
0.7664	Intermediate Similarity	NPC137929
0.7652	Intermediate Similarity	NPC476995
0.7642	Intermediate Similarity	NPC473184
0.7639	Intermediate Similarity	NPC470931
0.7632	Intermediate Similarity	NPC233334
0.763	Intermediate Similarity	NPC23080
0.763	Intermediate Similarity	NPC193906
0.763	Intermediate Similarity	NPC17677
0.7594	Intermediate Similarity	NPC212163
0.7589	Intermediate Similarity	NPC280272
0.7581	Intermediate Similarity	NPC285558
0.7577	Intermediate Similarity	NPC246381
0.7566	Intermediate Similarity	NPC202503
0.7565	Intermediate Similarity	NPC90875
0.7565	Intermediate Similarity	NPC277351
0.7562	Intermediate Similarity	NPC312872
0.7548	Intermediate Similarity	NPC112676
0.7548	Intermediate Similarity	NPC296742
0.7545	Intermediate Similarity	NPC236668
0.7544	Intermediate Similarity	NPC469792
0.7523	Intermediate Similarity	NPC295676
0.7512	Intermediate Similarity	NPC287437
0.7511	Intermediate Similarity	NPC146976
0.75	Intermediate Similarity	NPC48353
0.75	Intermediate Similarity	NPC224293
0.7488	Intermediate Similarity	NPC285941
0.7477	Intermediate Similarity	NPC18348
0.7463	Intermediate Similarity	NPC298979
0.7463	Intermediate Similarity	NPC320223
0.7463	Intermediate Similarity	NPC114364
0.7458	Intermediate Similarity	NPC208522
0.7453	Intermediate Similarity	NPC473053
0.7452	Intermediate Similarity	NPC69213
0.7451	Intermediate Similarity	NPC229166
0.7451	Intermediate Similarity	NPC128560
0.7451	Intermediate Similarity	NPC199465
0.7442	Intermediate Similarity	NPC471489
0.7441	Intermediate Similarity	NPC78284
0.744	Intermediate Similarity	NPC28425
0.7427	Intermediate Similarity	NPC311936
0.7424	Intermediate Similarity	NPC252251
0.7419	Intermediate Similarity	NPC156728
0.7419	Intermediate Similarity	NPC244606
0.7418	Intermediate Similarity	NPC70956
0.7418	Intermediate Similarity	NPC243834
0.7412	Intermediate Similarity	NPC470018
0.7409	Intermediate Similarity	NPC167860
0.7409	Intermediate Similarity	NPC123976
0.7407	Intermediate Similarity	NPC66815
0.7399	Intermediate Similarity	NPC170114
0.7391	Intermediate Similarity	NPC119579
0.7385	Intermediate Similarity	NPC323345
0.7385	Intermediate Similarity	NPC470164
0.738	Intermediate Similarity	NPC74575
0.738	Intermediate Similarity	NPC473185
0.7379	Intermediate Similarity	NPC190461
0.7373	Intermediate Similarity	NPC475774
0.7371	Intermediate Similarity	NPC470889
0.7371	Intermediate Similarity	NPC251090
0.7362	Intermediate Similarity	NPC41501
0.7359	Intermediate Similarity	NPC476999
0.7359	Intermediate Similarity	NPC477531
0.7355	Intermediate Similarity	NPC478045
0.7354	Intermediate Similarity	NPC470549
0.735	Intermediate Similarity	NPC24954
0.7343	Intermediate Similarity	NPC215747
0.7343	Intermediate Similarity	NPC192939
0.7336	Intermediate Similarity	NPC474188
0.7333	Intermediate Similarity	NPC134637
0.7333	Intermediate Similarity	NPC477186
0.7331	Intermediate Similarity	NPC99891
0.7325	Intermediate Similarity	NPC322482
0.7324	Intermediate Similarity	NPC326634
0.7324	Intermediate Similarity	NPC29472
0.7321	Intermediate Similarity	NPC8022
0.7321	Intermediate Similarity	NPC135772
0.7321	Intermediate Similarity	NPC470799
0.7316	Intermediate Similarity	NPC209174
0.7315	Intermediate Similarity	NPC11017
0.7309	Intermediate Similarity	NPC478074
0.7308	Intermediate Similarity	NPC477561
0.7308	Intermediate Similarity	NPC476574
0.7308	Intermediate Similarity	NPC312918
0.7308	Intermediate Similarity	NPC155442
0.7304	Intermediate Similarity	NPC152212
0.7295	Intermediate Similarity	NPC260118
0.7294	Intermediate Similarity	NPC223427
0.7294	Intermediate Similarity	NPC159101
0.7285	Intermediate Similarity	NPC469589
0.7285	Intermediate Similarity	NPC201697
0.7281	Intermediate Similarity	NPC232727
0.7277	Intermediate Similarity	NPC329541
0.7277	Intermediate Similarity	NPC276944
0.7277	Intermediate Similarity	NPC238530
0.7277	Intermediate Similarity	NPC232514
0.7277	Intermediate Similarity	NPC307963
0.7273	Intermediate Similarity	NPC116284
0.7265	Intermediate Similarity	NPC203168
0.726	Intermediate Similarity	NPC329708
0.726	Intermediate Similarity	NPC47059

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 NPC118121 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	683
0.2-0.3	952
0.3-0.4	1690
0.4-0.5	2686
0.5-0.6	2052
0.6-0.7	657
0.7-0.8	71
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9453	High Similarity	NPD3763	Approved
0.878	High Similarity	NPD3816	Phase 1
0.878	High Similarity	NPD3815	Phase 1
0.8259	Intermediate Similarity	NPD3924	Approved
0.8259	Intermediate Similarity	NPD3922	Approved
0.8259	Intermediate Similarity	NPD3921	Approved
0.8259	Intermediate Similarity	NPD3923	Approved
0.8153	Intermediate Similarity	NPD6494	Phase 2
0.7742	Intermediate Similarity	NPD7069	Discontinued
0.7723	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3920	Phase 2
0.771	Intermediate Similarity	NPD5530	Phase 1
0.7675	Intermediate Similarity	NPD7558	Phase 2
0.7674	Intermediate Similarity	NPD7222	Phase 2
0.7621	Intermediate Similarity	NPD7567	Approved
0.757	Intermediate Similarity	NPD6975	Discontinued
0.7558	Intermediate Similarity	NPD5658	Approved
0.7557	Intermediate Similarity	NPD5612	Discontinued
0.7532	Intermediate Similarity	NPD6230	Discontinued
0.751	Intermediate Similarity	NPD7169	Suspended
0.75	Intermediate Similarity	NPD7555	Discontinued
0.7466	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5902	Approved
0.7432	Intermediate Similarity	NPD5903	Approved
0.7431	Intermediate Similarity	NPD7452	Approved
0.7431	Intermediate Similarity	NPD7453	Approved
0.7407	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6281	Approved
0.7375	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD8091	Phase 3
0.7339	Intermediate Similarity	NPD6963	Approved
0.7339	Intermediate Similarity	NPD6964	Approved
0.7336	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD7674	Phase 3
0.7336	Intermediate Similarity	NPD7675	Phase 3
0.7311	Intermediate Similarity	NPD6569	Phase 2
0.7297	Intermediate Similarity	NPD4502	Phase 2
0.7281	Intermediate Similarity	NPD1954	Phase 1
0.7277	Intermediate Similarity	NPD1038	Approved
0.7273	Intermediate Similarity	NPD5429	Discontinued
0.726	Intermediate Similarity	NPD32	Approved
0.726	Intermediate Similarity	NPD4795	Phase 2
0.726	Intermediate Similarity	NPD4038	Approved
0.726	Intermediate Similarity	NPD4122	Approved
0.726	Intermediate Similarity	NPD4034	Approved
0.726	Intermediate Similarity	NPD4037	Approved
0.726	Intermediate Similarity	NPD4033	Approved
0.726	Intermediate Similarity	NPD4039	Approved
0.726	Intermediate Similarity	NPD4036	Approved
0.726	Intermediate Similarity	NPD4035	Approved
0.726	Intermediate Similarity	NPD31	Approved
0.7253	Intermediate Similarity	NPD4885	Approved
0.7243	Intermediate Similarity	NPD4418	Discontinued
0.7233	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5164	Discontinued
0.7208	Intermediate Similarity	NPD5488	Discontinued
0.7198	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5930	Phase 3
0.719	Intermediate Similarity	NPD4889	Approved
0.7186	Intermediate Similarity	NPD7426	Phase 1
0.7181	Intermediate Similarity	NPD7395	Discontinued
0.7176	Intermediate Similarity	NPD7948	Phase 1
0.7163	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD7671	Approved
0.7162	Intermediate Similarity	NPD7672	Approved
0.7156	Intermediate Similarity	NPD1739	Approved
0.7156	Intermediate Similarity	NPD1740	Approved
0.7155	Intermediate Similarity	NPD4875	Phase 3
0.7155	Intermediate Similarity	NPD4876	Phase 3
0.7143	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8016	Phase 3
0.7136	Intermediate Similarity	NPD1923	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD7859	Phase 2
0.713	Intermediate Similarity	NPD1856	Discontinued
0.713	Intermediate Similarity	NPD4437	Phase 3
0.7117	Intermediate Similarity	NPD1392	Approved
0.7116	Intermediate Similarity	NPD4551	Phase 2
0.7116	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3354	Phase 2
0.7101	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD2739	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6517	Phase 3
0.7082	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD5945	Phase 1
0.708	Intermediate Similarity	NPD5944	Phase 1
0.7078	Intermediate Similarity	NPD6219	Discontinued
0.7075	Intermediate Similarity	NPD4375	Approved
0.7072	Intermediate Similarity	NPD3003	Approved
0.7068	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5067	Phase 2
0.7067	Intermediate Similarity	NPD5936	Approved
0.7067	Intermediate Similarity	NPD5939	Approved
0.7067	Intermediate Similarity	NPD5066	Phase 2
0.7064	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7417	Discontinued
0.7037	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6361	Phase 2
0.7033	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3837	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5507	Approved
0.7013	Intermediate Similarity	NPD5506	Approved
0.7009	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5905	Phase 1
0.7	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7194	Discontinued
0.6996	Remote Similarity	NPD7719	Discontinued
0.6996	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD4131	Phase 3
0.6987	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6991	Approved
0.6981	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD8244	Phase 2
0.6967	Remote Similarity	NPD4204	Approved
0.6967	Remote Similarity	NPD4203	Approved
0.6957	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2334	Discontinued
0.6942	Remote Similarity	NPD6716	Phase 1
0.6941	Remote Similarity	NPD2952	Discontinued
0.694	Remote Similarity	NPD6298	Discontinued
0.6938	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD5100	Phase 3
0.6935	Remote Similarity	NPD8442	Discontinued
0.6927	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.692	Remote Similarity	NPD4995	Approved
0.692	Remote Similarity	NPD4996	Approved
0.6917	Remote Similarity	NPD5805	Approved
0.6911	Remote Similarity	NPD8101	Phase 3
0.6904	Remote Similarity	NPD2757	Phase 2
0.6901	Remote Similarity	NPD6790	Phase 1
0.6895	Remote Similarity	NPD3477	Phase 2
0.6895	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3386	Phase 2
0.6885	Remote Similarity	NPD4349	Approved
0.6885	Remote Similarity	NPD4350	Approved
0.6878	Remote Similarity	NPD4925	Approved
0.6878	Remote Similarity	NPD8052	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3825	Phase 3
0.6872	Remote Similarity	NPD1483	Discontinued
0.6872	Remote Similarity	NPD6473	Phase 1
0.687	Remote Similarity	NPD7112	Discontinued
0.6869	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2781	Approved
0.6858	Remote Similarity	NPD2916	Discontinued
0.6853	Remote Similarity	NPD6500	Approved
0.6853	Remote Similarity	NPD6501	Approved
0.6851	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3925	Approved
0.6849	Remote Similarity	NPD3396	Approved
0.6849	Remote Similarity	NPD3395	Approved
0.6845	Remote Similarity	NPD2780	Approved
0.6845	Remote Similarity	NPD2782	Approved
0.6844	Remote Similarity	NPD2060	Approved
0.6838	Remote Similarity	NPD7219	Approved
0.6838	Remote Similarity	NPD7221	Approved
0.683	Remote Similarity	NPD4044	Discontinued
0.6825	Remote Similarity	NPD6159	Phase 2
0.6824	Remote Similarity	NPD7673	Phase 3
0.6824	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7002	Clinical (unspecified phase)
0.682	Remote Similarity	NPD8063	Discontinued
0.6816	Remote Similarity	NPD4511	Phase 1
0.6814	Remote Similarity	NPD6290	Phase 2
0.681	Remote Similarity	NPD6568	Discontinued
0.681	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6985	Discontinued
0.6805	Remote Similarity	NPD4454	Phase 2
0.6802	Remote Similarity	NPD1768	Approved
0.6802	Remote Similarity	NPD2175	Phase 3
0.6802	Remote Similarity	NPD2176	Approved
0.6802	Remote Similarity	NPD2177	Approved
0.68	Remote Similarity	NPD3397	Phase 2
0.6798	Remote Similarity	NPD6262	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD4083	Discontinued
0.6792	Remote Similarity	NPD7479	Phase 2
0.6789	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD8100	Phase 3
0.6787	Remote Similarity	NPD1229	Phase 2
0.6786	Remote Similarity	NPD7955	Approved
0.6786	Remote Similarity	NPD7956	Approved
0.6784	Remote Similarity	NPD4859	Phase 1
0.6773	Remote Similarity	NPD6590	Discontinued
0.677	Remote Similarity	NPD6150	Discontinued
0.6762	Remote Similarity	NPD6607	Clinical (unspecified phase)

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