NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.11
Volume:	274.923
LogP:	0.167
LogD:	0.089
LogS:	-2.009
# Rotatable Bonds:	7
TPSA:	102.42
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	2.091
Fsp3:	0.286
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:	-5.083
MDCK Permeability:	2.46899071498774e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.675
Human Intestinal Absorption (HIA):	0.167
20% Bioavailability (F20%):	0.928
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.11
Plasma Protein Binding (PPB):	45.42218780517578%
Volume Distribution (VD):	0.465
Pgp-substrate:	46.1436653137207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.093
CYP1A2-substrate:	0.092
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.418
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.034

ADMET: Excretion

Clearance (CL):	9.689
Half-life (T1/2):	0.943

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.605
Skin Sensitization:	0.166
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.023

Download Data

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

Natural Product: NPC156704

Natural Product ID:	NPC156704
*Common Name:**	Bufobutanoic Acid
IUPAC Name:	4-[2-(5-hydroxy-1H-indol-3-yl)ethylamino]-4-oxobutanoic acid
Synonyms:	Bufobutanoic Acid
Standard InCHIKey:	HGOQFBPGMIWJLR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H16N2O4/c17-10-1-2-12-11(7-10)9(8-16-12)5-6-15-13(18)3-4-14(19)20/h1-2,7-8,16-17H,3-6H2,(H,15,18)(H,19,20)
SMILES:	c1cc2c(cc1O)c(CCN=C(CCC(=O)O)O)c[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1760552
PubChem CID:	10612485
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000183] Tryptamines and derivatives [CHEMONTID:0001637] Serotonins [CHEMONTID:0004271] N-acylserotonins

*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
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15635246]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17504571]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21185919]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	twigs and leaves	Yunnan Province, China	2008-OCT	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21954912]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22708620]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7543	Haplopappus venetus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6887	Lytanthus salicinus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	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
EC50	1
IC50	1

Activity Type	# Activity
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	350000.0	nM	PMID[466531]
NPT1	Others	Radical scavenging activity		EC50	=	38300.0	nM	PMID[466531]

☑ 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 NPC156704 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	340
0.1-0.2	2942
0.2-0.3	13730
0.3-0.4	10452
0.4-0.5	9841
0.5-0.6	2748
0.6-0.7	1941
0.7-0.8	621
0.8-0.85	59
0.85-0.9	11
0.9-0.95	11
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9392	High Similarity	NPC315491
0.9392	High Similarity	NPC45459
0.9314	High Similarity	NPC314002
0.931	High Similarity	NPC220765
0.9286	High Similarity	NPC213308
0.9261	High Similarity	NPC171171
0.9257	High Similarity	NPC204717
0.9111	High Similarity	NPC99666
0.9091	High Similarity	NPC88008
0.908	High Similarity	NPC184964
0.8811	High Similarity	NPC77555
0.8785	High Similarity	NPC46580
0.875	High Similarity	NPC307963
0.8703	High Similarity	NPC276517
0.8634	High Similarity	NPC32771
0.8587	High Similarity	NPC76748
0.8556	High Similarity	NPC251090
0.8549	High Similarity	NPC171787
0.8541	High Similarity	NPC92111
0.8534	High Similarity	NPC476098
0.8533	High Similarity	NPC296527
0.8503	High Similarity	NPC326634
0.8492	Intermediate Similarity	NPC74360
0.8469	Intermediate Similarity	NPC219087
0.8394	Intermediate Similarity	NPC475070
0.836	Intermediate Similarity	NPC222018
0.8358	Intermediate Similarity	NPC276657
0.8343	Intermediate Similarity	NPC96890
0.8343	Intermediate Similarity	NPC131718
0.8333	Intermediate Similarity	NPC266931
0.8315	Intermediate Similarity	NPC78020
0.8274	Intermediate Similarity	NPC5145
0.8263	Intermediate Similarity	NPC242209
0.8254	Intermediate Similarity	NPC106937
0.8242	Intermediate Similarity	NPC111275
0.8232	Intermediate Similarity	NPC110500
0.8232	Intermediate Similarity	NPC203468
0.8232	Intermediate Similarity	NPC149155
0.8227	Intermediate Similarity	NPC473317
0.8207	Intermediate Similarity	NPC71037
0.8197	Intermediate Similarity	NPC88363
0.8197	Intermediate Similarity	NPC283219
0.8191	Intermediate Similarity	NPC316981
0.8187	Intermediate Similarity	NPC267885
0.8182	Intermediate Similarity	NPC309845
0.8152	Intermediate Similarity	NPC15801
0.815	Intermediate Similarity	NPC477610
0.8146	Intermediate Similarity	NPC102423
0.8128	Intermediate Similarity	NPC315555
0.8128	Intermediate Similarity	NPC235684
0.8125	Intermediate Similarity	NPC90229
0.8122	Intermediate Similarity	NPC270918
0.8107	Intermediate Similarity	NPC125597
0.8105	Intermediate Similarity	NPC324149
0.8098	Intermediate Similarity	NPC126709
0.8098	Intermediate Similarity	NPC248041
0.8098	Intermediate Similarity	NPC55772
0.8085	Intermediate Similarity	NPC278434
0.8083	Intermediate Similarity	NPC306376
0.8083	Intermediate Similarity	NPC192315
0.8069	Intermediate Similarity	NPC469928
0.8068	Intermediate Similarity	NPC319232
0.8068	Intermediate Similarity	NPC24370
0.8041	Intermediate Similarity	NPC476167
0.803	Intermediate Similarity	NPC183777
0.801	Intermediate Similarity	NPC211813
0.8	Intermediate Similarity	NPC83111
0.8	Intermediate Similarity	NPC42979
0.8	Intermediate Similarity	NPC72980
0.8	Intermediate Similarity	NPC176538
0.8	Intermediate Similarity	NPC249040
0.799	Intermediate Similarity	NPC264285
0.799	Intermediate Similarity	NPC477609
0.7989	Intermediate Similarity	NPC224764
0.7978	Intermediate Similarity	NPC230869
0.7978	Intermediate Similarity	NPC313791
0.7968	Intermediate Similarity	NPC469358
0.7956	Intermediate Similarity	NPC160105
0.7947	Intermediate Similarity	NPC246700
0.7947	Intermediate Similarity	NPC128751
0.7946	Intermediate Similarity	NPC145885
0.7946	Intermediate Similarity	NPC14113
0.7946	Intermediate Similarity	NPC84827
0.7941	Intermediate Similarity	NPC476041
0.7941	Intermediate Similarity	NPC304926
0.7933	Intermediate Similarity	NPC279918
0.7917	Intermediate Similarity	NPC171393
0.7917	Intermediate Similarity	NPC295452
0.7906	Intermediate Similarity	NPC469497
0.7906	Intermediate Similarity	NPC106833
0.7903	Intermediate Similarity	NPC213468
0.79	Intermediate Similarity	NPC476465
0.7889	Intermediate Similarity	NPC282231
0.788	Intermediate Similarity	NPC314603
0.788	Intermediate Similarity	NPC474409
0.7877	Intermediate Similarity	NPC207686
0.7874	Intermediate Similarity	NPC60621
0.7872	Intermediate Similarity	NPC176127
0.7867	Intermediate Similarity	NPC326363
0.7857	Intermediate Similarity	NPC49954
0.7857	Intermediate Similarity	NPC474561
0.7853	Intermediate Similarity	NPC469786
0.7853	Intermediate Similarity	NPC469763
0.7853	Intermediate Similarity	NPC25008
0.7853	Intermediate Similarity	NPC469760
0.7853	Intermediate Similarity	NPC73952
0.7853	Intermediate Similarity	NPC469765
0.7853	Intermediate Similarity	NPC321708
0.7853	Intermediate Similarity	NPC259644
0.7845	Intermediate Similarity	NPC311276
0.784	Intermediate Similarity	NPC323752
0.7837	Intermediate Similarity	NPC16352
0.7821	Intermediate Similarity	NPC469762
0.7816	Intermediate Similarity	NPC159856
0.7814	Intermediate Similarity	NPC63751
0.7809	Intermediate Similarity	NPC75540
0.7809	Intermediate Similarity	NPC211572
0.7809	Intermediate Similarity	NPC212376
0.7809	Intermediate Similarity	NPC70922
0.7809	Intermediate Similarity	NPC80597
0.7808	Intermediate Similarity	NPC178858
0.7799	Intermediate Similarity	NPC130570
0.7795	Intermediate Similarity	NPC13880
0.7772	Intermediate Similarity	NPC476116
0.7767	Intermediate Similarity	NPC477549
0.7766	Intermediate Similarity	NPC293917
0.7765	Intermediate Similarity	NPC469785
0.776	Intermediate Similarity	NPC54988
0.7755	Intermediate Similarity	NPC153042
0.775	Intermediate Similarity	NPC470500
0.7749	Intermediate Similarity	NPC62749
0.774	Intermediate Similarity	NPC105818
0.774	Intermediate Similarity	NPC24678
0.7723	Intermediate Similarity	NPC477111
0.7721	Intermediate Similarity	NPC325976
0.7714	Intermediate Similarity	NPC314372
0.7711	Intermediate Similarity	NPC477113
0.7707	Intermediate Similarity	NPC229348
0.7696	Intermediate Similarity	NPC82370
0.7696	Intermediate Similarity	NPC208284
0.7696	Intermediate Similarity	NPC41679
0.7696	Intermediate Similarity	NPC246518
0.7689	Intermediate Similarity	NPC6215
0.7681	Intermediate Similarity	NPC469727
0.768	Intermediate Similarity	NPC138370
0.7678	Intermediate Similarity	NPC245348
0.7676	Intermediate Similarity	NPC314940
0.7676	Intermediate Similarity	NPC473764
0.7673	Intermediate Similarity	NPC193238
0.7673	Intermediate Similarity	NPC321428
0.7668	Intermediate Similarity	NPC213629
0.7665	Intermediate Similarity	NPC74153
0.7659	Intermediate Similarity	NPC128084
0.7653	Intermediate Similarity	NPC477608
0.7653	Intermediate Similarity	NPC477607
0.7653	Intermediate Similarity	NPC146724
0.765	Intermediate Similarity	NPC194640
0.765	Intermediate Similarity	NPC193761
0.765	Intermediate Similarity	NPC476874
0.765	Intermediate Similarity	NPC184225
0.7647	Intermediate Similarity	NPC11464
0.7639	Intermediate Similarity	NPC97902
0.7633	Intermediate Similarity	NPC74969
0.7633	Intermediate Similarity	NPC477110
0.7633	Intermediate Similarity	NPC330009
0.7629	Intermediate Similarity	NPC154339
0.7626	Intermediate Similarity	NPC131887
0.7621	Intermediate Similarity	NPC476287
0.7612	Intermediate Similarity	NPC223427
0.761	Intermediate Similarity	NPC9894
0.761	Intermediate Similarity	NPC294375
0.7604	Intermediate Similarity	NPC280290
0.7604	Intermediate Similarity	NPC188387
0.7604	Intermediate Similarity	NPC163421
0.7604	Intermediate Similarity	NPC94943
0.76	Intermediate Similarity	NPC190296
0.7598	Intermediate Similarity	NPC325297
0.7596	Intermediate Similarity	NPC27041
0.7592	Intermediate Similarity	NPC212535
0.7592	Intermediate Similarity	NPC48938
0.7586	Intermediate Similarity	NPC53344
0.7585	Intermediate Similarity	NPC118228
0.7576	Intermediate Similarity	NPC262898
0.7576	Intermediate Similarity	NPC227582
0.7573	Intermediate Similarity	NPC207020
0.7569	Intermediate Similarity	NPC141353
0.7566	Intermediate Similarity	NPC248454
0.7566	Intermediate Similarity	NPC59269
0.7562	Intermediate Similarity	NPC470678
0.7561	Intermediate Similarity	NPC471304
0.756	Intermediate Similarity	NPC96321
0.7559	Intermediate Similarity	NPC60006
0.7556	Intermediate Similarity	NPC153400
0.7554	Intermediate Similarity	NPC40779
0.7552	Intermediate Similarity	NPC190007
0.755	Intermediate Similarity	NPC470497
0.7548	Intermediate Similarity	NPC476161
0.7548	Intermediate Similarity	NPC142901
0.754	Intermediate Similarity	NPC252590
0.7538	Intermediate Similarity	NPC470499

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 NPC156704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	612
0.2-0.3	894
0.3-0.4	1212
0.4-0.5	2768
0.5-0.6	2289
0.6-0.7	1026
0.7-0.8	136
0.8-0.85	16
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9392	High Similarity	NPD484	Approved
0.8956	High Similarity	NPD5575	Clinical (unspecified phase)
0.875	High Similarity	NPD1038	Approved
0.8511	High Similarity	NPD7948	Phase 1
0.8449	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2094	Phase 2
0.8261	Intermediate Similarity	NPD2095	Phase 2
0.8261	Intermediate Similarity	NPD2092	Phase 2
0.8254	Intermediate Similarity	NPD802	Phase 2
0.825	Intermediate Similarity	NPD5612	Discontinued
0.8232	Intermediate Similarity	NPD482	Approved
0.8216	Intermediate Similarity	NPD2091	Phase 2
0.8216	Intermediate Similarity	NPD2096	Phase 2
0.8187	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.8159	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7968	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD5065	Approved
0.7929	Intermediate Similarity	NPD5901	Discontinued
0.7913	Intermediate Similarity	NPD6242	Discontinued
0.79	Intermediate Similarity	NPD2189	Approved
0.79	Intermediate Similarity	NPD2187	Approved
0.7895	Intermediate Similarity	NPD7603	Discontinued
0.7882	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD750	Phase 2
0.7816	Intermediate Similarity	NPD3354	Phase 2
0.7766	Intermediate Similarity	NPD3825	Phase 3
0.7766	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7739	Intermediate Similarity	NPD8073	Approved
0.7711	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7470	Discontinued
0.7689	Intermediate Similarity	NPD4845	Discontinued
0.7676	Intermediate Similarity	NPD1326	Approved
0.7676	Intermediate Similarity	NPD1325	Approved
0.7674	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD4418	Discontinued
0.7624	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7957	Phase 1
0.7622	Intermediate Similarity	NPD2844	Phase 3
0.7612	Intermediate Similarity	NPD8072	Approved
0.7602	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4511	Phase 1
0.7586	Intermediate Similarity	NPD1392	Approved
0.7563	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD4795	Phase 2
0.7488	Intermediate Similarity	NPD5559	Phase 2
0.7487	Intermediate Similarity	NPD6595	Phase 3
0.7473	Intermediate Similarity	NPD276	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1740	Approved
0.7463	Intermediate Similarity	NPD1739	Approved
0.7463	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD9690	Approved
0.7448	Intermediate Similarity	NPD3178	Discontinued
0.7446	Intermediate Similarity	NPD112	Approved
0.7446	Intermediate Similarity	NPD9705	Discontinued
0.7438	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD9695	Approved
0.7416	Intermediate Similarity	NPD4897	Phase 2
0.7415	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD8395	Approved
0.7413	Intermediate Similarity	NPD8396	Approved
0.7404	Intermediate Similarity	NPD3330	Phase 1
0.7402	Intermediate Similarity	NPD5426	Phase 3
0.7398	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7112	Discontinued
0.7379	Intermediate Similarity	NPD2916	Discontinued
0.7379	Intermediate Similarity	NPD2509	Approved
0.7379	Intermediate Similarity	NPD2510	Approved
0.7364	Intermediate Similarity	NPD4454	Phase 2
0.736	Intermediate Similarity	NPD1213	Phase 3
0.7356	Intermediate Similarity	NPD5067	Phase 2
0.7356	Intermediate Similarity	NPD5066	Phase 2
0.7356	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD8431	Approved
0.7346	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD786	Approved
0.7327	Intermediate Similarity	NPD2175	Phase 3
0.7327	Intermediate Similarity	NPD3814	Phase 1
0.7327	Intermediate Similarity	NPD2177	Approved
0.7327	Intermediate Similarity	NPD2176	Approved
0.7317	Intermediate Similarity	NPD4035	Approved
0.7317	Intermediate Similarity	NPD4034	Approved
0.7317	Intermediate Similarity	NPD4038	Approved
0.7317	Intermediate Similarity	NPD4033	Approved
0.7317	Intermediate Similarity	NPD32	Approved
0.7317	Intermediate Similarity	NPD31	Approved
0.7317	Intermediate Similarity	NPD4037	Approved
0.7317	Intermediate Similarity	NPD4039	Approved
0.7317	Intermediate Similarity	NPD4122	Approved
0.7317	Intermediate Similarity	NPD4036	Approved
0.7304	Intermediate Similarity	NPD3928	Approved
0.7304	Intermediate Similarity	NPD3931	Approved
0.7297	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD5658	Approved
0.7292	Intermediate Similarity	NPD2144	Approved
0.7287	Intermediate Similarity	NPD425	Approved
0.7287	Intermediate Similarity	NPD424	Approved
0.7286	Intermediate Similarity	NPD3404	Approved
0.7273	Intermediate Similarity	NPD5140	Approved
0.7273	Intermediate Similarity	NPD5138	Approved
0.7264	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD4948	Discontinued
0.7247	Intermediate Similarity	NPD1722	Approved
0.7247	Intermediate Similarity	NPD1592	Phase 3
0.7246	Intermediate Similarity	NPD7222	Phase 2
0.7246	Intermediate Similarity	NPD7452	Approved
0.7246	Intermediate Similarity	NPD7453	Approved
0.7245	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1768	Approved
0.7238	Intermediate Similarity	NPD8093	Discontinued
0.7234	Intermediate Similarity	NPD925	Approved
0.7234	Intermediate Similarity	NPD926	Approved
0.7233	Intermediate Similarity	NPD8272	Phase 2
0.7228	Intermediate Similarity	NPD5003	Discontinued
0.7225	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD6975	Discontinued
0.7217	Intermediate Similarity	NPD3394	Approved
0.7217	Intermediate Similarity	NPD3389	Approved
0.7217	Intermediate Similarity	NPD3393	Approved
0.7216	Intermediate Similarity	NPD6452	Discontinued
0.7209	Intermediate Similarity	NPD5507	Approved
0.7209	Intermediate Similarity	NPD5506	Approved
0.7206	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD8094	Discontinued
0.7202	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD3003	Approved
0.7195	Intermediate Similarity	NPD7558	Phase 2
0.719	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD949	Phase 1
0.7188	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3038	Discontinued
0.7172	Intermediate Similarity	NPD2383	Phase 1
0.717	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD5482	Discontinued
0.7158	Intermediate Similarity	NPD4463	Approved
0.7158	Intermediate Similarity	NPD4462	Approved
0.7158	Intermediate Similarity	NPD2781	Approved
0.7157	Intermediate Similarity	NPD4889	Approved
0.7156	Intermediate Similarity	NPD7069	Discontinued
0.715	Intermediate Similarity	NPD459	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2780	Approved
0.7143	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2952	Discontinued
0.7143	Intermediate Similarity	NPD2782	Approved
0.7136	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3006	Discontinued
0.7123	Intermediate Similarity	NPD3243	Approved
0.7115	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6665	Discontinued
0.7113	Intermediate Similarity	NPD6159	Phase 2
0.711	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD2565	Phase 2
0.71	Intermediate Similarity	NPD2564	Approved
0.7094	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7970	Approved
0.7089	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6290	Phase 2
0.7081	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD203	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7711	Discontinued
0.7077	Intermediate Similarity	NPD4079	Approved
0.7077	Intermediate Similarity	NPD4076	Approved
0.7075	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6276	Discontinued
0.707	Intermediate Similarity	NPD5632	Approved
0.7062	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5100	Phase 3
0.7048	Intermediate Similarity	NPD6376	Discontinued
0.7042	Intermediate Similarity	NPD2615	Phase 3
0.7042	Intermediate Similarity	NPD2616	Phase 3
0.704	Intermediate Similarity	NPD6494	Phase 2
0.703	Intermediate Similarity	NPD3924	Approved
0.703	Intermediate Similarity	NPD3922	Approved
0.703	Intermediate Similarity	NPD3923	Approved
0.703	Intermediate Similarity	NPD3921	Approved
0.7028	Intermediate Similarity	NPD5936	Approved
0.7028	Intermediate Similarity	NPD5939	Approved
0.7027	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD3506	Approved
0.7026	Intermediate Similarity	NPD3505	Approved
0.7024	Intermediate Similarity	NPD7777	Approved
0.7024	Intermediate Similarity	NPD53	Approved
0.7024	Intermediate Similarity	NPD7778	Approved
0.7021	Intermediate Similarity	NPD5255	Approved
0.7015	Intermediate Similarity	NPD4499	Approved
0.7014	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD8101	Phase 3
0.7011	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3100	Discontinued
0.7009	Intermediate Similarity	NPD5902	Approved
0.7009	Intermediate Similarity	NPD5903	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data