NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	220.12
Volume:	228.024
LogP:	-0.355
LogD:	-0.776
LogS:	0.53
# Rotatable Bonds:	3
TPSA:	59.08
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	2.808
Fsp3:	0.333
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:	-5.365
MDCK Permeability:	4.6359896259673405e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.893
20% Bioavailability (F20%):	0.957
30% Bioavailability (F30%):	0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.239
Plasma Protein Binding (PPB):	19.745773315429688%
Volume Distribution (VD):	1.662
Pgp-substrate:	80.9656982421875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.085
CYP1A2-substrate:	0.949
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.945
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.902
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.041

ADMET: Excretion

Clearance (CL):	10.116
Half-life (T1/2):	0.959

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.012
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.068
Carcinogencity:	0.171
Eye Corrosion:	0.024
Eye Irritation:	0.422
Respiratory Toxicity:	0.148

Download Data

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

Natural Product: NPC32771

Natural Product ID:	NPC32771
*Common Name:**	2-(5-Hydroxy-1H-Indol-3-Yl)-N,N-Dimethylethanamine Oxide
IUPAC Name:	2-(5-hydroxy-1H-indol-3-yl)-N,N-dimethylethanamine oxide
Synonyms:
Standard InCHIKey:	UADOMBGQYQPICP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16N2O2/c1-14(2,16)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
SMILES:	Oc1ccc2c(c1)c(CCN(=O)(C)C)c[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1779175
PubChem CID:	3083669
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0004162] Hydroxyindoles

*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	twigs and leaves	Yunnan Province, China	2008-OCT	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	twig	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]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
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]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
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]
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]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	2

Activity Type	# Activity
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	<	1000.0	nM	PMID[520194]
NPT27	Others	Unspecified		CC50	>	25000.0	nM	PMID[520194]
NPT2	Others	Unspecified		Ratio CC50/IC50	>	25.0	n.a.	PMID[520194]

☑ 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 NPC32771 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	464
0.1-0.2	4770
0.2-0.3	12552
0.3-0.4	13701
0.4-0.5	6095
0.5-0.6	2759
0.6-0.7	1630
0.7-0.8	633
0.8-0.85	64
0.85-0.9	16
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9191	High Similarity	NPC171171
0.9133	High Similarity	NPC314002
0.9075	High Similarity	NPC204717
0.9017	High Similarity	NPC220765
0.8827	High Similarity	NPC99666
0.8786	High Similarity	NPC184964
0.8736	High Similarity	NPC77555
0.8634	High Similarity	NPC156704
0.8571	High Similarity	NPC307963
0.85	High Similarity	NPC46580
0.8462	Intermediate Similarity	NPC92111
0.8407	Intermediate Similarity	NPC76748
0.8396	Intermediate Similarity	NPC315491
0.8396	Intermediate Similarity	NPC45459
0.8378	Intermediate Similarity	NPC251090
0.8352	Intermediate Similarity	NPC296527
0.8316	Intermediate Similarity	NPC475070
0.8298	Intermediate Similarity	NPC213308
0.8226	Intermediate Similarity	NPC326634
0.8085	Intermediate Similarity	NPC222018
0.8075	Intermediate Similarity	NPC106937
0.8071	Intermediate Similarity	NPC266931
0.8056	Intermediate Similarity	NPC96890
0.8046	Intermediate Similarity	NPC131718
0.8041	Intermediate Similarity	NPC88008
0.802	Intermediate Similarity	NPC316981
0.8011	Intermediate Similarity	NPC88363
0.801	Intermediate Similarity	NPC5145
0.7989	Intermediate Similarity	NPC242209
0.7917	Intermediate Similarity	NPC249040
0.7908	Intermediate Similarity	NPC171787
0.7889	Intermediate Similarity	NPC477610
0.7865	Intermediate Similarity	NPC476167
0.7861	Intermediate Similarity	NPC304926
0.7861	Intermediate Similarity	NPC476041
0.7853	Intermediate Similarity	NPC102423
0.7839	Intermediate Similarity	NPC219087
0.7831	Intermediate Similarity	NPC324149
0.7824	Intermediate Similarity	NPC176538
0.7814	Intermediate Similarity	NPC72980
0.7812	Intermediate Similarity	NPC192315
0.779	Intermediate Similarity	NPC313791
0.7766	Intermediate Similarity	NPC128751
0.7766	Intermediate Similarity	NPC246700
0.7749	Intermediate Similarity	NPC276517
0.7744	Intermediate Similarity	NPC470678
0.7734	Intermediate Similarity	NPC477609
0.7727	Intermediate Similarity	NPC476465
0.7727	Intermediate Similarity	NPC477111
0.7725	Intermediate Similarity	NPC469497
0.7725	Intermediate Similarity	NPC106833
0.7723	Intermediate Similarity	NPC476161
0.7704	Intermediate Similarity	NPC476098
0.7697	Intermediate Similarity	NPC282231
0.7696	Intermediate Similarity	NPC74360
0.7688	Intermediate Similarity	NPC476116
0.7688	Intermediate Similarity	NPC176127
0.7684	Intermediate Similarity	NPC230869
0.7667	Intermediate Similarity	NPC160105
0.7667	Intermediate Similarity	NPC474561
0.7667	Intermediate Similarity	NPC49954
0.7659	Intermediate Similarity	NPC276657
0.7657	Intermediate Similarity	NPC469786
0.7657	Intermediate Similarity	NPC25008
0.7657	Intermediate Similarity	NPC469760
0.7657	Intermediate Similarity	NPC469763
0.7657	Intermediate Similarity	NPC259644
0.7657	Intermediate Similarity	NPC469765
0.7657	Intermediate Similarity	NPC73952
0.7654	Intermediate Similarity	NPC311276
0.7653	Intermediate Similarity	NPC211813
0.764	Intermediate Similarity	NPC279918
0.7626	Intermediate Similarity	NPC477113
0.7622	Intermediate Similarity	NPC42979
0.7617	Intermediate Similarity	NPC13880
0.7614	Intermediate Similarity	NPC80597
0.7614	Intermediate Similarity	NPC70922
0.7614	Intermediate Similarity	NPC211572
0.7614	Intermediate Similarity	NPC212376
0.7614	Intermediate Similarity	NPC75540
0.7609	Intermediate Similarity	NPC224764
0.7608	Intermediate Similarity	NPC6215
0.7606	Intermediate Similarity	NPC163421
0.7606	Intermediate Similarity	NPC188387
0.7596	Intermediate Similarity	NPC474409
0.7582	Intermediate Similarity	NPC473764
0.7582	Intermediate Similarity	NPC314940
0.7577	Intermediate Similarity	NPC153042
0.7561	Intermediate Similarity	NPC264285
0.7548	Intermediate Similarity	NPC130570
0.7543	Intermediate Similarity	NPC105818
0.7543	Intermediate Similarity	NPC24678
0.7528	Intermediate Similarity	NPC469762
0.7527	Intermediate Similarity	NPC63751
0.7525	Intermediate Similarity	NPC208284
0.7514	Intermediate Similarity	NPC159856
0.7514	Intermediate Similarity	NPC314372
0.7512	Intermediate Similarity	NPC245348
0.75	Intermediate Similarity	NPC314603
0.75	Intermediate Similarity	NPC270918
0.7488	Intermediate Similarity	NPC184225
0.7487	Intermediate Similarity	NPC470500
0.7476	Intermediate Similarity	NPC60006
0.7475	Intermediate Similarity	NPC11464
0.7473	Intermediate Similarity	NPC54988
0.7472	Intermediate Similarity	NPC469785
0.7463	Intermediate Similarity	NPC476157
0.7463	Intermediate Similarity	NPC477110
0.7462	Intermediate Similarity	NPC315957
0.7459	Intermediate Similarity	NPC194640
0.745	Intermediate Similarity	NPC476121
0.745	Intermediate Similarity	NPC476124
0.7446	Intermediate Similarity	NPC252590
0.7438	Intermediate Similarity	NPC246518
0.7437	Intermediate Similarity	NPC223427
0.7423	Intermediate Similarity	NPC329541
0.7421	Intermediate Similarity	NPC94943
0.7418	Intermediate Similarity	NPC471178
0.7413	Intermediate Similarity	NPC183777
0.7407	Intermediate Similarity	NPC212535
0.7406	Intermediate Similarity	NPC477607
0.7406	Intermediate Similarity	NPC477608
0.7402	Intermediate Similarity	NPC128084
0.74	Intermediate Similarity	NPC264166
0.74	Intermediate Similarity	NPC118832
0.74	Intermediate Similarity	NPC329708
0.74	Intermediate Similarity	NPC165349
0.74	Intermediate Similarity	NPC47059
0.74	Intermediate Similarity	NPC274291
0.7399	Intermediate Similarity	NPC190296
0.738	Intermediate Similarity	NPC248454
0.7379	Intermediate Similarity	NPC469928
0.7374	Intermediate Similarity	NPC329793
0.7368	Intermediate Similarity	NPC190007
0.7368	Intermediate Similarity	NPC473317
0.7366	Intermediate Similarity	NPC478074
0.7363	Intermediate Similarity	NPC40779
0.7363	Intermediate Similarity	NPC476118
0.7361	Intermediate Similarity	NPC295228
0.7361	Intermediate Similarity	NPC477549
0.7356	Intermediate Similarity	NPC193267
0.7356	Intermediate Similarity	NPC213530
0.7354	Intermediate Similarity	NPC233936
0.735	Intermediate Similarity	NPC475774
0.7343	Intermediate Similarity	NPC469727
0.7337	Intermediate Similarity	NPC232727
0.7337	Intermediate Similarity	NPC44161
0.7337	Intermediate Similarity	NPC78020
0.7333	Intermediate Similarity	NPC16352
0.7327	Intermediate Similarity	NPC15801
0.7326	Intermediate Similarity	NPC267885
0.7316	Intermediate Similarity	NPC48938
0.7313	Intermediate Similarity	NPC285558
0.7312	Intermediate Similarity	NPC259545
0.7311	Intermediate Similarity	NPC24370
0.7311	Intermediate Similarity	NPC319232
0.7304	Intermediate Similarity	NPC85273
0.7304	Intermediate Similarity	NPC309845
0.7302	Intermediate Similarity	NPC207686
0.73	Intermediate Similarity	NPC199277
0.73	Intermediate Similarity	NPC135887
0.7295	Intermediate Similarity	NPC8022
0.7295	Intermediate Similarity	NPC470799
0.7294	Intermediate Similarity	NPC41679
0.7291	Intermediate Similarity	NPC18348
0.729	Intermediate Similarity	NPC326363
0.7287	Intermediate Similarity	NPC59269
0.7287	Intermediate Similarity	NPC111275
0.7287	Intermediate Similarity	NPC151939
0.7286	Intermediate Similarity	NPC121772
0.7283	Intermediate Similarity	NPC49217
0.7283	Intermediate Similarity	NPC108469
0.7278	Intermediate Similarity	NPC141353
0.7273	Intermediate Similarity	NPC203468
0.7273	Intermediate Similarity	NPC149155
0.7273	Intermediate Similarity	NPC110500
0.7273	Intermediate Similarity	NPC470499
0.7273	Intermediate Similarity	NPC306376
0.7273	Intermediate Similarity	NPC255110
0.7268	Intermediate Similarity	NPC473057
0.7268	Intermediate Similarity	NPC95783
0.7264	Intermediate Similarity	NPC125597
0.7264	Intermediate Similarity	NPC245816
0.7264	Intermediate Similarity	NPC476138
0.7263	Intermediate Similarity	NPC71037
0.7256	Intermediate Similarity	NPC476451
0.7255	Intermediate Similarity	NPC80596
0.7251	Intermediate Similarity	NPC280272
0.7249	Intermediate Similarity	NPC232340
0.7249	Intermediate Similarity	NPC248041
0.7249	Intermediate Similarity	NPC126709
0.7243	Intermediate Similarity	NPC201700
0.7241	Intermediate Similarity	NPC193777
0.7227	Intermediate Similarity	NPC81175
0.7225	Intermediate Similarity	NPC73767
0.7225	Intermediate Similarity	NPC469358
0.7225	Intermediate Similarity	NPC163055
0.7222	Intermediate Similarity	NPC90229
0.7213	Intermediate Similarity	NPC471177
0.7213	Intermediate Similarity	NPC48192

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 NPC32771 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	713
0.2-0.3	821
0.3-0.4	1314
0.4-0.5	2632
0.5-0.6	2296
0.6-0.7	959
0.7-0.8	161
0.8-0.85	8
0.85-0.9	6
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8778	High Similarity	NPD5575	Clinical (unspecified phase)
0.8571	High Similarity	NPD1038	Approved
0.8396	Intermediate Similarity	NPD484	Approved
0.827	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD7948	Phase 1
0.8075	Intermediate Similarity	NPD802	Phase 2
0.799	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD5612	Discontinued
0.7892	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD5065	Approved
0.7727	Intermediate Similarity	NPD2187	Approved
0.7727	Intermediate Similarity	NPD2189	Approved
0.7711	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD9695	Approved
0.7576	Intermediate Similarity	NPD4795	Phase 2
0.7561	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD4511	Phase 1
0.75	Intermediate Similarity	NPD3825	Phase 3
0.7488	Intermediate Similarity	NPD6242	Discontinued
0.7486	Intermediate Similarity	NPD1326	Approved
0.7486	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD1325	Approved
0.7462	Intermediate Similarity	NPD1740	Approved
0.7462	Intermediate Similarity	NPD1739	Approved
0.7413	Intermediate Similarity	NPD1392	Approved
0.7411	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4038	Approved
0.74	Intermediate Similarity	NPD4122	Approved
0.74	Intermediate Similarity	NPD31	Approved
0.74	Intermediate Similarity	NPD32	Approved
0.74	Intermediate Similarity	NPD4035	Approved
0.74	Intermediate Similarity	NPD4033	Approved
0.74	Intermediate Similarity	NPD4036	Approved
0.74	Intermediate Similarity	NPD4039	Approved
0.74	Intermediate Similarity	NPD4034	Approved
0.74	Intermediate Similarity	NPD4037	Approved
0.7387	Intermediate Similarity	NPD3928	Approved
0.7387	Intermediate Similarity	NPD3931	Approved
0.7366	Intermediate Similarity	NPD9690	Approved
0.7363	Intermediate Similarity	NPD5138	Approved
0.7363	Intermediate Similarity	NPD5140	Approved
0.7348	Intermediate Similarity	NPD112	Approved
0.7348	Intermediate Similarity	NPD9705	Discontinued
0.7337	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2175	Phase 3
0.7323	Intermediate Similarity	NPD2177	Approved
0.7323	Intermediate Similarity	NPD2176	Approved
0.7322	Intermediate Similarity	NPD926	Approved
0.7322	Intermediate Similarity	NPD925	Approved
0.7311	Intermediate Similarity	NPD7603	Discontinued
0.7302	Intermediate Similarity	NPD6595	Phase 3
0.7296	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD7112	Discontinued
0.7287	Intermediate Similarity	NPD2144	Approved
0.7283	Intermediate Similarity	NPD424	Approved
0.7283	Intermediate Similarity	NPD425	Approved
0.7273	Intermediate Similarity	NPD482	Approved
0.7269	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1592	Phase 3
0.7236	Intermediate Similarity	NPD8395	Approved
0.7236	Intermediate Similarity	NPD8396	Approved
0.7233	Intermediate Similarity	NPD3330	Phase 1
0.7225	Intermediate Similarity	NPD2094	Phase 2
0.7225	Intermediate Similarity	NPD2092	Phase 2
0.7225	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD2095	Phase 2
0.7206	Intermediate Similarity	NPD5658	Approved
0.7196	Intermediate Similarity	NPD4845	Discontinued
0.7192	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2091	Phase 2
0.7188	Intermediate Similarity	NPD2096	Phase 2
0.7184	Intermediate Similarity	NPD949	Phase 1
0.7184	Intermediate Similarity	NPD5067	Phase 2
0.7184	Intermediate Similarity	NPD5066	Phase 2
0.7173	Intermediate Similarity	NPD3038	Discontinued
0.7163	Intermediate Similarity	NPD5559	Phase 2
0.7158	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7453	Approved
0.7157	Intermediate Similarity	NPD7222	Phase 2
0.7157	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD7452	Approved
0.7151	Intermediate Similarity	NPD4463	Approved
0.7151	Intermediate Similarity	NPD4462	Approved
0.715	Intermediate Similarity	NPD3814	Phase 1
0.715	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5901	Discontinued
0.7129	Intermediate Similarity	NPD6975	Discontinued
0.7128	Intermediate Similarity	NPD750	Phase 2
0.7126	Intermediate Similarity	NPD786	Approved
0.712	Intermediate Similarity	NPD1685	Approved
0.712	Intermediate Similarity	NPD1684	Approved
0.7115	Intermediate Similarity	NPD2616	Phase 3
0.7115	Intermediate Similarity	NPD2615	Phase 3
0.7105	Intermediate Similarity	NPD6159	Phase 2
0.7104	Intermediate Similarity	NPD5255	Approved
0.7095	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2789	Approved
0.7077	Intermediate Similarity	NPD8431	Approved
0.7077	Intermediate Similarity	NPD2383	Phase 1
0.7065	Intermediate Similarity	NPD1768	Approved
0.7065	Intermediate Similarity	NPD5599	Discontinued
0.7053	Intermediate Similarity	NPD5100	Phase 3
0.7052	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2952	Discontinued
0.7041	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4702	Approved
0.7039	Intermediate Similarity	NPD4703	Approved
0.7035	Intermediate Similarity	NPD4418	Discontinued
0.7024	Intermediate Similarity	NPD3003	Approved
0.702	Intermediate Similarity	NPD3404	Approved
0.7019	Intermediate Similarity	NPD5939	Approved
0.7019	Intermediate Similarity	NPD5936	Approved
0.7016	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4203	Approved
0.6995	Remote Similarity	NPD4204	Approved
0.699	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3354	Phase 2
0.6979	Remote Similarity	NPD4076	Approved
0.6979	Remote Similarity	NPD4079	Approved
0.6976	Remote Similarity	NPD5426	Phase 3
0.6968	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2844	Phase 3
0.6968	Remote Similarity	NPD2781	Approved
0.6966	Remote Similarity	NPD1352	Discontinued
0.6959	Remote Similarity	NPD5596	Phase 2
0.6959	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD7558	Phase 2
0.6952	Remote Similarity	NPD2780	Approved
0.6952	Remote Similarity	NPD2782	Approved
0.6949	Remote Similarity	NPD1722	Approved
0.6942	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7470	Discontinued
0.6935	Remote Similarity	NPD3921	Approved
0.6935	Remote Similarity	NPD3924	Approved
0.6935	Remote Similarity	NPD3922	Approved
0.6935	Remote Similarity	NPD3923	Approved
0.6927	Remote Similarity	NPD3506	Approved
0.6927	Remote Similarity	NPD3505	Approved
0.6927	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6158	Phase 2
0.691	Remote Similarity	NPD3717	Discontinued
0.6908	Remote Similarity	NPD6290	Phase 2
0.6907	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD3100	Discontinued
0.69	Remote Similarity	NPD4551	Phase 2
0.6898	Remote Similarity	NPD863	Approved
0.6898	Remote Similarity	NPD861	Approved
0.6898	Remote Similarity	NPD862	Approved
0.6897	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD1622	Discontinued
0.6878	Remote Similarity	NPD6494	Phase 2
0.6875	Remote Similarity	NPD2380	Approved
0.6875	Remote Similarity	NPD2382	Approved
0.6875	Remote Similarity	NPD2381	Approved
0.6875	Remote Similarity	NPD2916	Discontinued
0.6866	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD9382	Approved
0.6865	Remote Similarity	NPD9383	Approved
0.6863	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD4502	Phase 2
0.685	Remote Similarity	NPD9689	Approved
0.685	Remote Similarity	NPD6569	Phase 2
0.6831	Remote Similarity	NPD2882	Phase 1
0.6825	Remote Similarity	NPD8093	Discontinued
0.6822	Remote Similarity	NPD2021	Discontinued
0.6821	Remote Similarity	NPD3178	Discontinued
0.6818	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8512	Phase 3
0.6806	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD8094	Discontinued
0.6791	Remote Similarity	NPD1404	Approved
0.6791	Remote Similarity	NPD687	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD1403	Approved
0.6782	Remote Similarity	NPD3395	Approved
0.6782	Remote Similarity	NPD3396	Approved
0.6778	Remote Similarity	NPD3813	Approved
0.6776	Remote Similarity	NPD2172	Phase 1
0.6768	Remote Similarity	NPD706	Phase 1
0.6763	Remote Similarity	NPD4044	Discontinued
0.6761	Remote Similarity	NPD5903	Approved
0.6761	Remote Similarity	NPD5902	Approved
0.675	Remote Similarity	NPD5117	Phase 2
0.675	Remote Similarity	NPD1213	Phase 3
0.6744	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD4454	Phase 2
0.674	Remote Similarity	NPD4875	Phase 3
0.674	Remote Similarity	NPD4876	Phase 3
0.6738	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD5999	Phase 2
0.6732	Remote Similarity	NPD6999	Discontinued
0.6732	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3013	Phase 3

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