NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.09
Volume:	246.15
LogP:	1.983
LogD:	1.621
LogS:	-3.501
# Rotatable Bonds:	3
TPSA:	65.98
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	2.17
Fsp3:	0.143
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:	-4.773
MDCK Permeability:	1.4447712601395324e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.33
30% Bioavailability (F30%):	0.122

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.13
Plasma Protein Binding (PPB):	86.44661712646484%
Volume Distribution (VD):	0.431
Pgp-substrate:	6.637875556945801%

ADMET: Metabolism

CYP1A2-inhibitor:	0.407
CYP1A2-substrate:	0.675
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.038
CYP2D6-substrate:	0.72
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	2.016
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.887
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.753
Maximum Recommended Daily Dose:	0.801
Skin Sensitization:	0.332
Carcinogencity:	0.239
Eye Corrosion:	0.006
Eye Irritation:	0.66
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC62749

Natural Product ID:	NPC62749
*Common Name:**	Beta-Carboline-1-Propionic Acid
IUPAC Name:	3-(9H-pyrido[3,4-b]indol-1-yl)propanoic acid
Synonyms:
Standard InCHIKey:	CNUHEVWYPKFJHH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12N2O2/c17-13(18)6-5-12-14-10(7-8-15-12)9-3-1-2-4-11(9)16-14/h1-4,7-8,16H,5-6H2,(H,17,18)
SMILES:	c1ccc2c(c1)c1ccnc(CCC(=O)O)c1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512759
PubChem CID:	5375436
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19659728]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21067210]
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21067210]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368118]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667820]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22840	Casearia arguta	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21012	Mikania sessilifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9375	Medium grandiflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3576	Bersama swinnyi	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21697	Irpex pachyodon	Species	Irpicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19973	Cupania glabra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20992	Tarenna graveolens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18753	Sideritis serrata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21885	Furcraea elegans	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
ED50	1
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[564514]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	8.0	%	PMID[564514]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	39.3	%	PMID[564515]

☑ 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 NPC62749 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	358
0.1-0.2	2953
0.2-0.3	16068
0.3-0.4	16390
0.4-0.5	2662
0.5-0.6	1889
0.6-0.7	1508
0.7-0.8	768
0.8-0.85	78
0.85-0.9	20
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9112	High Similarity	NPC111275
0.8982	High Similarity	NPC78020
0.8882	High Similarity	NPC110500
0.8882	High Similarity	NPC149155
0.8882	High Similarity	NPC203468
0.8837	High Similarity	NPC55772
0.883	High Similarity	NPC267885
0.8779	High Similarity	NPC183662
0.8779	High Similarity	NPC217372
0.8779	High Similarity	NPC15573
0.8728	High Similarity	NPC219336
0.8728	High Similarity	NPC248041
0.8728	High Similarity	NPC283219
0.8728	High Similarity	NPC126709
0.8652	High Similarity	NPC321708
0.8539	High Similarity	NPC315555
0.8457	Intermediate Similarity	NPC145885
0.8457	Intermediate Similarity	NPC84827
0.8457	Intermediate Similarity	NPC14113
0.8436	Intermediate Similarity	NPC235684
0.8418	Intermediate Similarity	NPC71037
0.8418	Intermediate Similarity	NPC60621
0.8409	Intermediate Similarity	NPC213468
0.8378	Intermediate Similarity	NPC131887
0.8378	Intermediate Similarity	NPC67288
0.8362	Intermediate Similarity	NPC469896
0.8343	Intermediate Similarity	NPC175474
0.8303	Intermediate Similarity	NPC63545
0.8298	Intermediate Similarity	NPC57398
0.829	Intermediate Similarity	NPC118940
0.8266	Intermediate Similarity	NPC56233
0.8253	Intermediate Similarity	NPC179787
0.8253	Intermediate Similarity	NPC201380
0.8253	Intermediate Similarity	NPC469811
0.8247	Intermediate Similarity	NPC221100
0.8247	Intermediate Similarity	NPC234078
0.8246	Intermediate Similarity	NPC279918
0.8241	Intermediate Similarity	NPC229893
0.8226	Intermediate Similarity	NPC141454
0.8226	Intermediate Similarity	NPC227582
0.8216	Intermediate Similarity	NPC202812
0.8212	Intermediate Similarity	NPC191415
0.8204	Intermediate Similarity	NPC321911
0.8201	Intermediate Similarity	NPC476073
0.8198	Intermediate Similarity	NPC282231
0.8197	Intermediate Similarity	NPC83111
0.8191	Intermediate Similarity	NPC213308
0.8187	Intermediate Similarity	NPC230869
0.8187	Intermediate Similarity	NPC17059
0.8167	Intermediate Similarity	NPC102755
0.8167	Intermediate Similarity	NPC48938
0.8162	Intermediate Similarity	NPC88315
0.8128	Intermediate Similarity	NPC272483
0.8122	Intermediate Similarity	NPC228835
0.8114	Intermediate Similarity	NPC63751
0.8101	Intermediate Similarity	NPC248462
0.8101	Intermediate Similarity	NPC11126
0.8098	Intermediate Similarity	NPC154339
0.8095	Intermediate Similarity	NPC252338
0.8087	Intermediate Similarity	NPC278434
0.8081	Intermediate Similarity	NPC473310
0.8075	Intermediate Similarity	NPC179701
0.8066	Intermediate Similarity	NPC469358
0.8059	Intermediate Similarity	NPC469765
0.8059	Intermediate Similarity	NPC73952
0.8059	Intermediate Similarity	NPC469760
0.8059	Intermediate Similarity	NPC469786
0.8059	Intermediate Similarity	NPC325903
0.8059	Intermediate Similarity	NPC469763
0.8059	Intermediate Similarity	NPC25008
0.8059	Intermediate Similarity	NPC259644
0.8057	Intermediate Similarity	NPC49954
0.8057	Intermediate Similarity	NPC54988
0.8057	Intermediate Similarity	NPC474561
0.8043	Intermediate Similarity	NPC196251
0.8043	Intermediate Similarity	NPC111602
0.8043	Intermediate Similarity	NPC102338
0.8043	Intermediate Similarity	NPC63199
0.8033	Intermediate Similarity	NPC94752
0.8032	Intermediate Similarity	NPC262898
0.8023	Intermediate Similarity	NPC469762
0.8023	Intermediate Similarity	NPC236711
0.8012	Intermediate Similarity	NPC70922
0.8012	Intermediate Similarity	NPC212376
0.8012	Intermediate Similarity	NPC211572
0.8012	Intermediate Similarity	NPC75540
0.8012	Intermediate Similarity	NPC80597
0.801	Intermediate Similarity	NPC476874
0.8	Intermediate Similarity	NPC45459
0.8	Intermediate Similarity	NPC315491
0.799	Intermediate Similarity	NPC266249
0.7989	Intermediate Similarity	NPC474916
0.7989	Intermediate Similarity	NPC52557
0.7989	Intermediate Similarity	NPC50503
0.7978	Intermediate Similarity	NPC15102
0.7969	Intermediate Similarity	NPC165599
0.7968	Intermediate Similarity	NPC267343
0.7965	Intermediate Similarity	NPC469785
0.7959	Intermediate Similarity	NPC82370
0.7955	Intermediate Similarity	NPC160105
0.7949	Intermediate Similarity	NPC478158
0.7947	Intermediate Similarity	NPC293917
0.7944	Intermediate Similarity	NPC59269
0.7941	Intermediate Similarity	NPC476491
0.7938	Intermediate Similarity	NPC244741
0.7931	Intermediate Similarity	NPC131718
0.7927	Intermediate Similarity	NPC473376
0.7926	Intermediate Similarity	NPC220151
0.7926	Intermediate Similarity	NPC19692
0.7917	Intermediate Similarity	NPC314372
0.7908	Intermediate Similarity	NPC123839
0.7906	Intermediate Similarity	NPC313985
0.7906	Intermediate Similarity	NPC81654
0.7906	Intermediate Similarity	NPC79129
0.7906	Intermediate Similarity	NPC49196
0.7906	Intermediate Similarity	NPC195461
0.7906	Intermediate Similarity	NPC249150
0.7904	Intermediate Similarity	NPC190296
0.79	Intermediate Similarity	NPC281049
0.7887	Intermediate Similarity	NPC238457
0.788	Intermediate Similarity	NPC99939
0.788	Intermediate Similarity	NPC308931
0.7876	Intermediate Similarity	NPC476098
0.7872	Intermediate Similarity	NPC326422
0.7857	Intermediate Similarity	NPC91179
0.7853	Intermediate Similarity	NPC74413
0.7849	Intermediate Similarity	NPC213629
0.7841	Intermediate Similarity	NPC21174
0.7841	Intermediate Similarity	NPC271797
0.7841	Intermediate Similarity	NPC311276
0.7841	Intermediate Similarity	NPC194640
0.7833	Intermediate Similarity	NPC469938
0.7831	Intermediate Similarity	NPC195239
0.7831	Intermediate Similarity	NPC157828
0.7829	Intermediate Similarity	NPC122141
0.7829	Intermediate Similarity	NPC470204
0.7826	Intermediate Similarity	NPC472119
0.7826	Intermediate Similarity	NPC284678
0.7824	Intermediate Similarity	NPC260900
0.7819	Intermediate Similarity	NPC324149
0.7811	Intermediate Similarity	NPC159856
0.7809	Intermediate Similarity	NPC317430
0.7796	Intermediate Similarity	NPC472323
0.7789	Intermediate Similarity	NPC11445
0.7784	Intermediate Similarity	NPC470203
0.7778	Intermediate Similarity	NPC314603
0.7766	Intermediate Similarity	NPC138370
0.776	Intermediate Similarity	NPC15840
0.7755	Intermediate Similarity	NPC54420
0.7755	Intermediate Similarity	NPC88008
0.775	Intermediate Similarity	NPC474412
0.775	Intermediate Similarity	NPC478157
0.7749	Intermediate Similarity	NPC156704
0.7747	Intermediate Similarity	NPC248454
0.7747	Intermediate Similarity	NPC64436
0.7744	Intermediate Similarity	NPC475070
0.774	Intermediate Similarity	NPC478184
0.774	Intermediate Similarity	NPC102423
0.774	Intermediate Similarity	NPC317105
0.773	Intermediate Similarity	NPC165495
0.7719	Intermediate Similarity	NPC470111
0.7717	Intermediate Similarity	NPC314394
0.7717	Intermediate Similarity	NPC113626
0.7714	Intermediate Similarity	NPC129721
0.7713	Intermediate Similarity	NPC472112
0.7708	Intermediate Similarity	NPC192315
0.7708	Intermediate Similarity	NPC265576
0.7708	Intermediate Similarity	NPC171317
0.77	Intermediate Similarity	NPC89508
0.77	Intermediate Similarity	NPC282247
0.7697	Intermediate Similarity	NPC274229
0.7696	Intermediate Similarity	NPC102592
0.7696	Intermediate Similarity	NPC79356
0.7692	Intermediate Similarity	NPC151635
0.7692	Intermediate Similarity	NPC317701
0.7679	Intermediate Similarity	NPC115611
0.7677	Intermediate Similarity	NPC162860
0.7676	Intermediate Similarity	NPC143533
0.7673	Intermediate Similarity	NPC27041
0.7672	Intermediate Similarity	NPC117244
0.7672	Intermediate Similarity	NPC473763
0.767	Intermediate Similarity	NPC293487
0.767	Intermediate Similarity	NPC92796
0.767	Intermediate Similarity	NPC135141
0.7668	Intermediate Similarity	NPC476167
0.7665	Intermediate Similarity	NPC473362
0.7665	Intermediate Similarity	NPC166492
0.7664	Intermediate Similarity	NPC295452
0.7664	Intermediate Similarity	NPC171393
0.7657	Intermediate Similarity	NPC285469
0.7656	Intermediate Similarity	NPC167710
0.7653	Intermediate Similarity	NPC132539
0.7651	Intermediate Similarity	NPC96102
0.765	Intermediate Similarity	NPC207020
0.765	Intermediate Similarity	NPC75634
0.7647	Intermediate Similarity	NPC478077
0.7641	Intermediate Similarity	NPC193761
0.764	Intermediate Similarity	NPC40779
0.7639	Intermediate Similarity	NPC178858
0.7638	Intermediate Similarity	NPC5145

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 NPC62749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	590
0.2-0.3	959
0.3-0.4	1971
0.4-0.5	2270
0.5-0.6	1951
0.6-0.7	1020
0.7-0.8	167
0.8-0.85	3
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8882	High Similarity	NPD482	Approved
0.883	High Similarity	NPD749	Clinical (unspecified phase)
0.8743	High Similarity	NPD2091	Phase 2
0.8743	High Similarity	NPD2096	Phase 2
0.8686	High Similarity	NPD2094	Phase 2
0.8686	High Similarity	NPD2092	Phase 2
0.8686	High Similarity	NPD2095	Phase 2
0.858	High Similarity	NPD5728	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD750	Phase 2
0.8324	Intermediate Similarity	NPD6178	Phase 3
0.8307	Intermediate Similarity	NPD5426	Phase 3
0.8115	Intermediate Similarity	NPD5901	Discontinued
0.807	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD484	Approved
0.7979	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD2844	Phase 3
0.7906	Intermediate Similarity	NPD4600	Approved
0.7906	Intermediate Similarity	NPD4601	Approved
0.7865	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6595	Phase 3
0.7853	Intermediate Similarity	NPD6999	Discontinued
0.7853	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD5065	Approved
0.7831	Intermediate Similarity	NPD7619	Phase 3
0.7831	Intermediate Similarity	NPD7618	Phase 3
0.7828	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD1722	Approved
0.7727	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7666	Phase 3
0.7716	Intermediate Similarity	NPD7665	Phase 2
0.7708	Intermediate Similarity	NPD4397	Phase 1
0.7692	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7470	Discontinued
0.768	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD2896	Discontinued
0.766	Intermediate Similarity	NPD1534	Approved
0.7651	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD8073	Approved
0.7641	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD4500	Approved
0.7629	Intermediate Similarity	NPD4501	Approved
0.7619	Intermediate Similarity	NPD4499	Approved
0.7616	Intermediate Similarity	NPD1661	Suspended
0.7614	Intermediate Similarity	NPD7957	Phase 1
0.7614	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD8072	Approved
0.7596	Intermediate Similarity	NPD6165	Phase 2
0.7596	Intermediate Similarity	NPD6164	Phase 2
0.7576	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD2880	Discontinued
0.7563	Intermediate Similarity	NPD6987	Phase 1
0.7554	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD4602	Approved
0.755	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD2837	Discontinued
0.7538	Intermediate Similarity	NPD2509	Approved
0.7538	Intermediate Similarity	NPD2510	Approved
0.7515	Intermediate Similarity	NPD786	Approved
0.7513	Intermediate Similarity	NPD8431	Approved
0.75	Intermediate Similarity	NPD5017	Discontinued
0.75	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7970	Approved
0.7488	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2336	Approved
0.7486	Intermediate Similarity	NPD1037	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD6664	Approved
0.7474	Intermediate Similarity	NPD5003	Discontinued
0.7461	Intermediate Similarity	NPD7944	Discontinued
0.746	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD2144	Approved
0.7459	Intermediate Similarity	NPD7865	Approved
0.7449	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD5505	Discontinued
0.7448	Intermediate Similarity	NPD6665	Discontinued
0.7447	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD7001	Phase 3
0.7437	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD5611	Phase 2
0.7363	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD2008	Discontinued
0.734	Intermediate Similarity	NPD3038	Discontinued
0.734	Intermediate Similarity	NPD4383	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD3178	Discontinued
0.7333	Intermediate Similarity	NPD2307	Discontinued
0.7333	Intermediate Similarity	NPD6454	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5818	Discontinued
0.732	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD4336	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD4702	Approved
0.7314	Intermediate Similarity	NPD4703	Approved
0.7312	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD8093	Discontinued
0.7303	Intermediate Similarity	NPD5257	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4345	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD8272	Phase 2
0.7295	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD510	Phase 1
0.7287	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1325	Approved
0.7283	Intermediate Similarity	NPD1326	Approved
0.7282	Intermediate Similarity	NPD3394	Approved
0.7282	Intermediate Similarity	NPD3393	Approved
0.7282	Intermediate Similarity	NPD3389	Approved
0.7277	Intermediate Similarity	NPD706	Phase 1
0.7273	Intermediate Similarity	NPD3100	Discontinued
0.7273	Intermediate Similarity	NPD4181	Approved
0.7273	Intermediate Similarity	NPD2305	Discontinued
0.7259	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD5322	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7415	Suspended
0.7254	Intermediate Similarity	NPD2564	Approved
0.7254	Intermediate Similarity	NPD2565	Phase 2
0.725	Intermediate Similarity	NPD4886	Phase 2
0.724	Intermediate Similarity	NPD4948	Discontinued
0.7234	Intermediate Similarity	NPD4079	Approved
0.7234	Intermediate Similarity	NPD4076	Approved
0.7232	Intermediate Similarity	NPD4462	Approved
0.7232	Intermediate Similarity	NPD4463	Approved
0.7222	Intermediate Similarity	NPD4326	Phase 2
0.722	Intermediate Similarity	NPD2411	Approved
0.722	Intermediate Similarity	NPD5482	Discontinued
0.722	Intermediate Similarity	NPD4852	Phase 2
0.7217	Intermediate Similarity	NPD7711	Discontinued
0.7217	Intermediate Similarity	NPD7603	Discontinued
0.7216	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7948	Phase 1
0.7207	Intermediate Similarity	NPD2809	Approved
0.7196	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD4427	Phase 2
0.7192	Intermediate Similarity	NPD2442	Approved
0.7192	Intermediate Similarity	NPD2443	Approved
0.7186	Intermediate Similarity	NPD6479	Discontinued
0.7184	Intermediate Similarity	NPD8094	Discontinued
0.7181	Intermediate Similarity	NPD3506	Approved
0.7181	Intermediate Similarity	NPD3505	Approved
0.7179	Intermediate Similarity	NPD3404	Approved
0.7176	Intermediate Similarity	NPD7952	Approved
0.7176	Intermediate Similarity	NPD7953	Approved
0.7176	Intermediate Similarity	NPD7790	Approved
0.7176	Intermediate Similarity	NPD7950	Approved
0.7176	Intermediate Similarity	NPD7789	Approved
0.7176	Intermediate Similarity	NPD7951	Approved
0.7176	Intermediate Similarity	NPD7791	Approved
0.7166	Intermediate Similarity	NPD4128	Approved
0.7158	Intermediate Similarity	NPD3323	Discontinued
0.715	Intermediate Similarity	NPD3961	Discontinued
0.715	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1038	Approved
0.7143	Intermediate Similarity	NPD751	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD802	Phase 2
0.7143	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD715	Phase 3
0.7135	Intermediate Similarity	NPD2640	Approved
0.7135	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2641	Approved
0.7135	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD2172	Phase 1
0.7129	Intermediate Similarity	NPD3947	Discontinued
0.7128	Intermediate Similarity	NPD4075	Phase 2
0.7126	Intermediate Similarity	NPD1592	Phase 3
0.7114	Intermediate Similarity	NPD7187	Phase 2
0.7113	Intermediate Similarity	NPD7234	Approved
0.7113	Intermediate Similarity	NPD7233	Approved
0.7107	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5473	Discontinued
0.7103	Intermediate Similarity	NPD7731	Approved
0.7103	Intermediate Similarity	NPD7730	Approved
0.7101	Intermediate Similarity	NPD4341	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1573	Approved
0.7097	Intermediate Similarity	NPD1575	Approved
0.7092	Intermediate Similarity	NPD4922	Phase 2
0.7089	Intermediate Similarity	NPD7271	Approved
0.7086	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD424	Approved
0.7081	Intermediate Similarity	NPD425	Approved
0.7074	Intermediate Similarity	NPD4736	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