NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	149.05
Volume:	147.843
LogP:	1.125
LogD:	1.39
LogS:	-2.088
# Rotatable Bonds:	0
TPSA:	56.25
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	2.354
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.631
MDCK Permeability:	8.100834747892804e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	74.54571533203125%
Volume Distribution (VD):	0.648
Pgp-substrate:	21.47966194152832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.803
CYP1A2-substrate:	0.423
CYP2C19-inhibitor:	0.151
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.83
CYP2D6-inhibitor:	0.474
CYP2D6-substrate:	0.786
CYP3A4-inhibitor:	0.078
CYP3A4-substrate:	0.115

ADMET: Excretion

Clearance (CL):	17.963
Half-life (T1/2):	0.897

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.672
AMES Toxicity:	0.693
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.554
Skin Sensitization:	0.94
Carcinogencity:	0.539
Eye Corrosion:	0.579
Eye Irritation:	0.98
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC326634

Natural Product ID:	NPC326634
*Common Name:**	1H-Indole-5,6-Diol
IUPAC Name:	1H-indole-5,6-diol
Synonyms:
Standard InCHIKey:	SGNZYJXNUURYCH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H7NO2/c10-7-3-5-1-2-9-6(5)4-8(7)11/h1-4,9-11H
SMILES:	C1=CNC2=CC(=C(C=C21)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL92636
PubChem CID:	114683
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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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
Ki	1
Others	7

Activity Type	# Activity
Individual Protein	6
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3150	Individual Protein	Catechol O-methyltransferase	Rattus norvegicus	Residual activity	=	282.0	c.p.m.	PMID[451651]
NPT3150	Individual Protein	Catechol O-methyltransferase	Rattus norvegicus	Residual activity	=	228.0	c.p.m.	PMID[451651]
NPT3150	Individual Protein	Catechol O-methyltransferase	Rattus norvegicus	Residual activity	=	0.0	%	PMID[451651]
NPT3150	Individual Protein	Catechol O-methyltransferase	Rattus norvegicus	Residual activity	=	96.0	%	PMID[451651]
NPT3150	Individual Protein	Catechol O-methyltransferase	Rattus norvegicus	K2	=	0.55	min-1	PMID[451651]
NPT3150	Individual Protein	Catechol O-methyltransferase	Rattus norvegicus	Ki	=	3460000.0	nM	PMID[451651]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	>	84.4	%	PMID[451652]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	54.4	%	PMID[451652]

☑ 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 NPC326634 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	699
0.1-0.2	8901
0.2-0.3	9302
0.3-0.4	13244
0.4-0.5	5948
0.5-0.6	2759
0.6-0.7	1453
0.7-0.8	343
0.8-0.85	34
0.85-0.9	9
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9205	High Similarity	NPC46580
0.9186	High Similarity	NPC184964
0.9186	High Similarity	NPC96890
0.9048	High Similarity	NPC316981
0.8983	High Similarity	NPC314002
0.8977	High Similarity	NPC220765
0.8927	High Similarity	NPC204717
0.8895	High Similarity	NPC99666
0.8827	High Similarity	NPC171171
0.8796	High Similarity	NPC246518
0.8608	High Similarity	NPC266931
0.8503	High Similarity	NPC77555
0.8503	High Similarity	NPC156704
0.8474	Intermediate Similarity	NPC199277
0.8474	Intermediate Similarity	NPC135887
0.8466	Intermediate Similarity	NPC213308
0.8449	Intermediate Similarity	NPC222018
0.8449	Intermediate Similarity	NPC242209
0.8449	Intermediate Similarity	NPC251090
0.8394	Intermediate Similarity	NPC88008
0.8389	Intermediate Similarity	NPC72980
0.8368	Intermediate Similarity	NPC315491
0.8368	Intermediate Similarity	NPC45459
0.8351	Intermediate Similarity	NPC18348
0.8342	Intermediate Similarity	NPC307963
0.8245	Intermediate Similarity	NPC106937
0.8226	Intermediate Similarity	NPC296527
0.8226	Intermediate Similarity	NPC32771
0.8205	Intermediate Similarity	NPC183777
0.8187	Intermediate Similarity	NPC42979
0.8182	Intermediate Similarity	NPC76748
0.8177	Intermediate Similarity	NPC224764
0.8167	Intermediate Similarity	NPC474409
0.8138	Intermediate Similarity	NPC92111
0.8125	Intermediate Similarity	NPC131718
0.8122	Intermediate Similarity	NPC325297
0.8115	Intermediate Similarity	NPC153042
0.8103	Intermediate Similarity	NPC475070
0.8087	Intermediate Similarity	NPC88363
0.8081	Intermediate Similarity	NPC5145
0.8071	Intermediate Similarity	NPC171787
0.8054	Intermediate Similarity	NPC212535
0.8034	Intermediate Similarity	NPC102423
0.8	Intermediate Similarity	NPC324149
0.8	Intermediate Similarity	NPC219087
0.798	Intermediate Similarity	NPC264285
0.797	Intermediate Similarity	NPC142901
0.7969	Intermediate Similarity	NPC13880
0.7968	Intermediate Similarity	NPC94943
0.7917	Intermediate Similarity	NPC276517
0.7914	Intermediate Similarity	NPC190007
0.79	Intermediate Similarity	NPC11464
0.7887	Intermediate Similarity	NPC192315
0.7885	Intermediate Similarity	NPC214980
0.7871	Intermediate Similarity	NPC477610
0.7865	Intermediate Similarity	NPC230869
0.7857	Intermediate Similarity	NPC232727
0.7854	Intermediate Similarity	NPC193267
0.7854	Intermediate Similarity	NPC213530
0.7846	Intermediate Similarity	NPC476167
0.7822	Intermediate Similarity	NPC128084
0.7806	Intermediate Similarity	NPC176538
0.7806	Intermediate Similarity	NPC121772
0.7806	Intermediate Similarity	NPC249040
0.7795	Intermediate Similarity	NPC306376
0.7772	Intermediate Similarity	NPC313791
0.7767	Intermediate Similarity	NPC74360
0.776	Intermediate Similarity	NPC314940
0.776	Intermediate Similarity	NPC473764
0.775	Intermediate Similarity	NPC193777
0.7749	Intermediate Similarity	NPC246700
0.7749	Intermediate Similarity	NPC128751
0.774	Intermediate Similarity	NPC16352
0.7739	Intermediate Similarity	NPC470500
0.7739	Intermediate Similarity	NPC285558
0.7732	Intermediate Similarity	NPC131017
0.7725	Intermediate Similarity	NPC84478
0.7716	Intermediate Similarity	NPC315957
0.7708	Intermediate Similarity	NPC469497
0.7708	Intermediate Similarity	NPC106833
0.7703	Intermediate Similarity	NPC211416
0.7688	Intermediate Similarity	NPC476098
0.7688	Intermediate Similarity	NPC53144
0.7674	Intermediate Similarity	NPC295228
0.7673	Intermediate Similarity	NPC80596
0.7672	Intermediate Similarity	NPC176127
0.767	Intermediate Similarity	NPC476041
0.767	Intermediate Similarity	NPC304926
0.7653	Intermediate Similarity	NPC70956
0.7653	Intermediate Similarity	NPC243834
0.7644	Intermediate Similarity	NPC276657
0.7638	Intermediate Similarity	NPC211813
0.7633	Intermediate Similarity	NPC173080
0.7633	Intermediate Similarity	NPC477609
0.7624	Intermediate Similarity	NPC279918
0.7622	Intermediate Similarity	NPC252590
0.7621	Intermediate Similarity	NPC170114
0.7608	Intermediate Similarity	NPC60621
0.7604	Intermediate Similarity	NPC11408
0.7592	Intermediate Similarity	NPC188387
0.7592	Intermediate Similarity	NPC163421
0.7582	Intermediate Similarity	NPC282231
0.7574	Intermediate Similarity	NPC270918
0.7573	Intermediate Similarity	NPC470549
0.7571	Intermediate Similarity	NPC280272
0.7561	Intermediate Similarity	NPC112206
0.7561	Intermediate Similarity	NPC48353
0.7561	Intermediate Similarity	NPC202605
0.7552	Intermediate Similarity	NPC315555
0.7549	Intermediate Similarity	NPC167860
0.7549	Intermediate Similarity	NPC123976
0.7538	Intermediate Similarity	NPC234197
0.7537	Intermediate Similarity	NPC476465
0.7536	Intermediate Similarity	NPC130570
0.7534	Intermediate Similarity	NPC217554
0.7524	Intermediate Similarity	NPC162530
0.7524	Intermediate Similarity	NPC469592
0.7524	Intermediate Similarity	NPC471080
0.7512	Intermediate Similarity	NPC200836
0.7512	Intermediate Similarity	NPC223427
0.75	Intermediate Similarity	NPC476116
0.75	Intermediate Similarity	NPC329541
0.75	Intermediate Similarity	NPC159856
0.7487	Intermediate Similarity	NPC469358
0.7477	Intermediate Similarity	NPC178858
0.7477	Intermediate Similarity	NPC473183
0.7463	Intermediate Similarity	NPC475085
0.7463	Intermediate Similarity	NPC291535
0.7463	Intermediate Similarity	NPC475112
0.7463	Intermediate Similarity	NPC85273
0.746	Intermediate Similarity	NPC111275
0.7459	Intermediate Similarity	NPC160105
0.7459	Intermediate Similarity	NPC49954
0.7459	Intermediate Similarity	NPC474561
0.7459	Intermediate Similarity	NPC54988
0.7452	Intermediate Similarity	NPC8022
0.7452	Intermediate Similarity	NPC470799
0.7452	Intermediate Similarity	NPC477110
0.7446	Intermediate Similarity	NPC40779
0.7446	Intermediate Similarity	NPC311276
0.7444	Intermediate Similarity	NPC25008
0.7444	Intermediate Similarity	NPC73952
0.7444	Intermediate Similarity	NPC469765
0.7444	Intermediate Similarity	NPC259644
0.7444	Intermediate Similarity	NPC469760
0.7444	Intermediate Similarity	NPC469786
0.7444	Intermediate Similarity	NPC469763
0.7441	Intermediate Similarity	NPC310118
0.7438	Intermediate Similarity	NPC477113
0.7436	Intermediate Similarity	NPC83111
0.7432	Intermediate Similarity	NPC284141
0.743	Intermediate Similarity	NPC110151
0.743	Intermediate Similarity	NPC6215
0.7427	Intermediate Similarity	NPC208284
0.7426	Intermediate Similarity	NPC134848
0.7426	Intermediate Similarity	NPC162484
0.7423	Intermediate Similarity	NPC278434
0.7419	Intermediate Similarity	NPC63751
0.7419	Intermediate Similarity	NPC78020
0.7418	Intermediate Similarity	NPC245348
0.7418	Intermediate Similarity	NPC469762
0.7403	Intermediate Similarity	NPC70922
0.7403	Intermediate Similarity	NPC211572
0.7403	Intermediate Similarity	NPC80597
0.7403	Intermediate Similarity	NPC75540
0.7403	Intermediate Similarity	NPC212376
0.7396	Intermediate Similarity	NPC48938
0.7395	Intermediate Similarity	NPC477608
0.7395	Intermediate Similarity	NPC477607
0.7394	Intermediate Similarity	NPC314603
0.7391	Intermediate Similarity	NPC294620
0.7387	Intermediate Similarity	NPC90229
0.7387	Intermediate Similarity	NPC474188
0.7385	Intermediate Similarity	NPC473184
0.7383	Intermediate Similarity	NPC319232
0.7383	Intermediate Similarity	NPC24370
0.7381	Intermediate Similarity	NPC469594
0.7379	Intermediate Similarity	NPC309845
0.7376	Intermediate Similarity	NPC470678
0.7373	Intermediate Similarity	NPC207686
0.7366	Intermediate Similarity	NPC477111
0.7366	Intermediate Similarity	NPC475910
0.7363	Intermediate Similarity	NPC469785
0.7363	Intermediate Similarity	NPC141353
0.7358	Intermediate Similarity	NPC473317
0.7353	Intermediate Similarity	NPC476121
0.7353	Intermediate Similarity	NPC476124
0.7344	Intermediate Similarity	NPC71037
0.7333	Intermediate Similarity	NPC24678
0.7333	Intermediate Similarity	NPC105818
0.733	Intermediate Similarity	NPC60553
0.7324	Intermediate Similarity	NPC118121
0.7303	Intermediate Similarity	NPC314372
0.7302	Intermediate Similarity	NPC60006
0.7299	Intermediate Similarity	NPC204446
0.7288	Intermediate Similarity	NPC190296
0.7286	Intermediate Similarity	NPC469928
0.7286	Intermediate Similarity	NPC183407
0.7286	Intermediate Similarity	NPC330009
0.7286	Intermediate Similarity	NPC288349

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 NPC326634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	865
0.2-0.3	704
0.3-0.4	1995
0.4-0.5	2628
0.5-0.6	1942
0.6-0.7	589
0.7-0.8	69
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8541	High Similarity	NPD5575	Clinical (unspecified phase)
0.8368	Intermediate Similarity	NPD484	Approved
0.8342	Intermediate Similarity	NPD1038	Approved
0.8245	Intermediate Similarity	NPD802	Phase 2
0.8211	Intermediate Similarity	NPD7948	Phase 1
0.815	Intermediate Similarity	NPD5612	Discontinued
0.8053	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD1392	Approved
0.7889	Intermediate Similarity	NPD5658	Approved
0.7872	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1740	Approved
0.7716	Intermediate Similarity	NPD1739	Approved
0.7665	Intermediate Similarity	NPD1768	Approved
0.7562	Intermediate Similarity	NPD4795	Phase 2
0.754	Intermediate Similarity	NPD5065	Approved
0.754	Intermediate Similarity	NPD9690	Approved
0.7537	Intermediate Similarity	NPD2187	Approved
0.7537	Intermediate Similarity	NPD2189	Approved
0.7527	Intermediate Similarity	NPD9705	Discontinued
0.7527	Intermediate Similarity	NPD112	Approved
0.7524	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7558	Phase 2
0.7464	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3003	Approved
0.7419	Intermediate Similarity	NPD6494	Phase 2
0.7413	Intermediate Similarity	NPD4511	Phase 1
0.7411	Intermediate Similarity	NPD9695	Approved
0.7406	Intermediate Similarity	NPD1954	Phase 1
0.7404	Intermediate Similarity	NPD5903	Approved
0.7404	Intermediate Similarity	NPD5902	Approved
0.7402	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3825	Phase 3
0.738	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD1325	Approved
0.738	Intermediate Similarity	NPD1326	Approved
0.7353	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD3814	Phase 1
0.7273	Intermediate Similarity	NPD3921	Approved
0.7273	Intermediate Similarity	NPD3923	Approved
0.7273	Intermediate Similarity	NPD3922	Approved
0.7273	Intermediate Similarity	NPD3924	Approved
0.7263	Intermediate Similarity	NPD482	Approved
0.726	Intermediate Similarity	NPD5067	Phase 2
0.726	Intermediate Similarity	NPD5066	Phase 2
0.723	Intermediate Similarity	NPD6242	Discontinued
0.7228	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD2176	Approved
0.7228	Intermediate Similarity	NPD2175	Phase 3
0.7228	Intermediate Similarity	NPD2177	Approved
0.7225	Intermediate Similarity	NPD3330	Phase 1
0.7225	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7603	Discontinued
0.7206	Intermediate Similarity	NPD3928	Approved
0.7206	Intermediate Similarity	NPD3931	Approved
0.7202	Intermediate Similarity	NPD8512	Phase 3
0.715	Intermediate Similarity	NPD7453	Approved
0.715	Intermediate Similarity	NPD7452	Approved
0.715	Intermediate Similarity	NPD7222	Phase 2
0.7149	Intermediate Similarity	NPD6963	Approved
0.7149	Intermediate Similarity	NPD6964	Approved
0.7143	Intermediate Similarity	NPD3816	Phase 1
0.7143	Intermediate Similarity	NPD3815	Phase 1
0.7135	Intermediate Similarity	NPD1592	Phase 3
0.7128	Intermediate Similarity	NPD2092	Phase 2
0.7128	Intermediate Similarity	NPD2094	Phase 2
0.7128	Intermediate Similarity	NPD2095	Phase 2
0.7123	Intermediate Similarity	NPD7112	Discontinued
0.7115	Intermediate Similarity	NPD2916	Discontinued
0.7114	Intermediate Similarity	NPD4418	Discontinued
0.7113	Intermediate Similarity	NPD6595	Phase 3
0.7111	Intermediate Similarity	NPD4875	Phase 3
0.7111	Intermediate Similarity	NPD4876	Phase 3
0.711	Intermediate Similarity	NPD4845	Discontinued
0.7104	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD949	Phase 1
0.7092	Intermediate Similarity	NPD2096	Phase 2
0.7092	Intermediate Similarity	NPD2091	Phase 2
0.709	Intermediate Similarity	NPD424	Approved
0.709	Intermediate Similarity	NPD425	Approved
0.7074	Intermediate Similarity	NPD5140	Approved
0.7074	Intermediate Similarity	NPD5138	Approved
0.7059	Intermediate Similarity	NPD8395	Approved
0.7059	Intermediate Similarity	NPD8396	Approved
0.7054	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD5901	Discontinued
0.7053	Intermediate Similarity	NPD2781	Approved
0.7045	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6975	Discontinued
0.7037	Intermediate Similarity	NPD2780	Approved
0.7037	Intermediate Similarity	NPD2782	Approved
0.7037	Intermediate Similarity	NPD926	Approved
0.7037	Intermediate Similarity	NPD925	Approved
0.7015	Intermediate Similarity	NPD9689	Approved
0.7015	Intermediate Similarity	NPD3404	Approved
0.7011	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6244	Phase 3
0.7	Intermediate Similarity	NPD5559	Phase 2
0.7	Intermediate Similarity	NPD6243	Phase 3
0.6986	Remote Similarity	NPD6290	Phase 2
0.6977	Remote Similarity	NPD6985	Discontinued
0.6971	Remote Similarity	NPD4035	Approved
0.6971	Remote Similarity	NPD4039	Approved
0.6971	Remote Similarity	NPD4037	Approved
0.6971	Remote Similarity	NPD4034	Approved
0.6971	Remote Similarity	NPD4033	Approved
0.6971	Remote Similarity	NPD32	Approved
0.6971	Remote Similarity	NPD4122	Approved
0.6971	Remote Similarity	NPD31	Approved
0.6971	Remote Similarity	NPD4036	Approved
0.6971	Remote Similarity	NPD4038	Approved
0.6968	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD2952	Discontinued
0.695	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7194	Discontinued
0.6943	Remote Similarity	NPD750	Phase 2
0.694	Remote Similarity	NPD7859	Phase 2
0.6934	Remote Similarity	NPD4131	Phase 3
0.6934	Remote Similarity	NPD5939	Approved
0.6934	Remote Similarity	NPD5936	Approved
0.693	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD786	Approved
0.6923	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5930	Phase 3
0.69	Remote Similarity	NPD8431	Approved
0.69	Remote Similarity	NPD2383	Phase 1
0.69	Remote Similarity	NPD6230	Discontinued
0.6898	Remote Similarity	NPD3354	Phase 2
0.6894	Remote Similarity	NPD8091	Phase 3
0.6884	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD1622	Discontinued
0.6875	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4080	Discontinued
0.6872	Remote Similarity	NPD5100	Phase 3
0.6872	Remote Similarity	NPD5905	Phase 1
0.6869	Remote Similarity	NPD2615	Phase 3
0.6869	Remote Similarity	NPD2616	Phase 3
0.6869	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD4021	Phase 2
0.6866	Remote Similarity	NPD3763	Approved
0.6854	Remote Similarity	NPD4502	Phase 2
0.6852	Remote Similarity	NPD5164	Discontinued
0.6851	Remote Similarity	NPD1722	Approved
0.685	Remote Similarity	NPD706	Phase 1
0.6847	Remote Similarity	NPD996	Phase 2
0.6847	Remote Similarity	NPD994	Phase 2
0.6837	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD2144	Approved
0.6835	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.682	Remote Similarity	NPD5632	Approved
0.6816	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4925	Approved
0.6814	Remote Similarity	NPD4551	Phase 2
0.6812	Remote Similarity	NPD9687	Approved
0.6812	Remote Similarity	NPD9688	Approved
0.6808	Remote Similarity	NPD3013	Phase 3
0.6808	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3920	Phase 2
0.6802	Remote Similarity	NPD4079	Approved
0.6802	Remote Similarity	NPD4076	Approved
0.6788	Remote Similarity	NPD2844	Phase 3
0.6786	Remote Similarity	NPD4995	Approved
0.6786	Remote Similarity	NPD4996	Approved
0.6784	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4462	Approved
0.6774	Remote Similarity	NPD4463	Approved
0.6772	Remote Similarity	NPD9382	Approved
0.6772	Remote Similarity	NPD9383	Approved
0.6766	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6569	Phase 2
0.6761	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD6159	Phase 2
0.6751	Remote Similarity	NPD3505	Approved
0.6751	Remote Similarity	NPD3506	Approved
0.6749	Remote Similarity	NPD5117	Phase 2
0.6743	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.674	Remote Similarity	NPD4454	Phase 2
0.6734	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD3038	Discontinued
0.6733	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5426	Phase 3
0.673	Remote Similarity	NPD3397	Phase 2
0.6725	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD4083	Discontinued
0.6717	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2762	Phase 2
0.6715	Remote Similarity	NPD1229	Phase 2
0.6714	Remote Similarity	NPD7947	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