NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	213.08
Volume:	220.493
LogP:	2.964
LogD:	3.141
LogS:	-3.556
# Rotatable Bonds:	1
TPSA:	45.25
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.652
Synthetic Accessibility Score:	1.909
Fsp3:	0.077
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.949
MDCK Permeability:	1.4628305507358164e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.605

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.464
Plasma Protein Binding (PPB):	94.26641082763672%
Volume Distribution (VD):	0.648
Pgp-substrate:	4.675131797790527%

ADMET: Metabolism

CYP1A2-inhibitor:	0.991
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.564
CYP2C19-substrate:	0.274
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.782
CYP2D6-substrate:	0.923
CYP3A4-inhibitor:	0.467
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	8.409
Half-life (T1/2):	0.724

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.75
AMES Toxicity:	0.899
Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.897
Skin Sensitization:	0.93
Carcinogencity:	0.818
Eye Corrosion:	0.157
Eye Irritation:	0.988
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC199277

Natural Product ID:	NPC199277
*Common Name:**	2-Methoxy-9H-Carbazol-3-Ol
IUPAC Name:	2-methoxy-9H-carbazol-3-ol
Synonyms:
Standard InCHIKey:	KDLDZUFUKYBJCQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H11NO2/c1-16-13-7-11-9(6-12(13)15)8-4-2-3-5-10(8)14-11/h2-7,14-15H,1H3
SMILES:	COc1cc2c(cc1O)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2037028
PubChem CID:	15182256
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11720530]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724858]
NPO29161	Hyptis urticoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19265396]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[21774474]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22050382]
NPO4806	Clausena wallichii	Species	Rutaceae	Eukaryota	Roots	n.a.	n.a.	PMID[22482432]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	Guam Island, Pacific Ocean	n.a.	PMID[23164710]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26203536]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28951079]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29161	Hyptis urticoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29321	Octopus octopodia	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29028	Cicer cuneatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28943	Daldinia vernicosa	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27603	Populus candicans	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28735	Helicia erratica	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25073	Saccharina latissima	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29497	Delphinium speciosum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29461	Sarcophyton infundibuliforme	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28427	Gutenbergia marginata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29387	Eudendrium racemosum	Species	Eudendriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27349	Rhododendron edgeworthii	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28639	Trixis grisebachii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25248	Gloydius blomhoffii	Species	Viperidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29035	Pseudomonas cichorii	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29073	Ipomoea carnea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28500	Griselinia scandens	Species	Griseliniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29518	Nardia scalaris	Species	Solenostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29095	Yucca elata	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29180	Monachosorum maximowiczii	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28993	Streptomyces venezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28961	Croton hutchinsonianus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29070	Bulbine asphodeloides	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28544	Podocalyx loranthoides	Species	Picrodendraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4806	Clausena wallichii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23710	Otholobium pubescens	Species	Fabaceae	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	3
MIC	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	213000.0	nM	PMID[502092]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	31400.0	nM	PMID[502092]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	27400.0	nM	PMID[502092]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128.0	ug.mL-1	PMID[502092]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[502092]

☑ 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 NPC199277 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	654
0.1-0.2	4269
0.2-0.3	13148
0.3-0.4	4968
0.4-0.5	12986
0.5-0.6	4516
0.6-0.7	1682
0.7-0.8	389
0.8-0.85	64
0.85-0.9	16
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC135887
0.9115	High Similarity	NPC316981
0.8973	High Similarity	NPC131017
0.8969	High Similarity	NPC266931
0.8953	High Similarity	NPC193777
0.8877	High Similarity	NPC70956
0.8877	High Similarity	NPC243834
0.8698	High Similarity	NPC223427
0.8629	High Similarity	NPC48353
0.8601	High Similarity	NPC162484
0.8587	High Similarity	NPC84478
0.8549	High Similarity	NPC475085
0.8549	High Similarity	NPC291535
0.8549	High Similarity	NPC475112
0.8533	High Similarity	NPC176127
0.8522	High Similarity	NPC280272
0.8482	Intermediate Similarity	NPC153042
0.8474	Intermediate Similarity	NPC326634
0.847	Intermediate Similarity	NPC88363
0.8453	Intermediate Similarity	NPC474409
0.8432	Intermediate Similarity	NPC212535
0.8421	Intermediate Similarity	NPC473182
0.8389	Intermediate Similarity	NPC473183
0.837	Intermediate Similarity	NPC72980
0.8342	Intermediate Similarity	NPC72211
0.8342	Intermediate Similarity	NPC94943
0.8333	Intermediate Similarity	NPC251090
0.8325	Intermediate Similarity	NPC476106
0.8299	Intermediate Similarity	NPC128823
0.8294	Intermediate Similarity	NPC473184
0.8294	Intermediate Similarity	NPC277351
0.8291	Intermediate Similarity	NPC201697
0.8289	Intermediate Similarity	NPC190007
0.8238	Intermediate Similarity	NPC70259
0.8229	Intermediate Similarity	NPC307963
0.8218	Intermediate Similarity	NPC469592
0.8218	Intermediate Similarity	NPC471080
0.8209	Intermediate Similarity	NPC87413
0.8207	Intermediate Similarity	NPC312872
0.8201	Intermediate Similarity	NPC204385
0.8195	Intermediate Similarity	NPC473179
0.8187	Intermediate Similarity	NPC205934
0.8187	Intermediate Similarity	NPC43787
0.8143	Intermediate Similarity	NPC252251
0.8115	Intermediate Similarity	NPC128751
0.8115	Intermediate Similarity	NPC246700
0.8115	Intermediate Similarity	NPC242928
0.8115	Intermediate Similarity	NPC296527
0.8109	Intermediate Similarity	NPC209769
0.8107	Intermediate Similarity	NPC193267
0.8107	Intermediate Similarity	NPC213530
0.8085	Intermediate Similarity	NPC206201
0.8084	Intermediate Similarity	NPC295228
0.8083	Intermediate Similarity	NPC99666
0.8073	Intermediate Similarity	NPC469497
0.8073	Intermediate Similarity	NPC76748
0.8073	Intermediate Similarity	NPC106833
0.8071	Intermediate Similarity	NPC329747
0.8069	Intermediate Similarity	NPC11464
0.8066	Intermediate Similarity	NPC477531
0.8063	Intermediate Similarity	NPC46580
0.806	Intermediate Similarity	NPC39679
0.806	Intermediate Similarity	NPC475910
0.8058	Intermediate Similarity	NPC46561
0.8058	Intermediate Similarity	NPC469594
0.8058	Intermediate Similarity	NPC247803
0.8031	Intermediate Similarity	NPC92111
0.803	Intermediate Similarity	NPC267423
0.803	Intermediate Similarity	NPC232727
0.8029	Intermediate Similarity	NPC477532
0.8019	Intermediate Similarity	NPC209174
0.801	Intermediate Similarity	NPC249583
0.801	Intermediate Similarity	NPC4687
0.8009	Intermediate Similarity	NPC473185
0.8	Intermediate Similarity	NPC179287
0.8	Intermediate Similarity	NPC62069
0.8	Intermediate Similarity	NPC285558
0.799	Intermediate Similarity	NPC112206
0.799	Intermediate Similarity	NPC202605
0.7989	Intermediate Similarity	NPC474798
0.7981	Intermediate Similarity	NPC150239
0.798	Intermediate Similarity	NPC176538
0.7969	Intermediate Similarity	NPC66083
0.796	Intermediate Similarity	NPC300156
0.796	Intermediate Similarity	NPC45190
0.7958	Intermediate Similarity	NPC314002
0.7952	Intermediate Similarity	NPC211416
0.794	Intermediate Similarity	NPC476044
0.791	Intermediate Similarity	NPC470930
0.7906	Intermediate Similarity	NPC204717
0.79	Intermediate Similarity	NPC66815
0.7895	Intermediate Similarity	NPC174760
0.7889	Intermediate Similarity	NPC234197
0.7889	Intermediate Similarity	NPC329793
0.7885	Intermediate Similarity	NPC89549
0.788	Intermediate Similarity	NPC6786
0.7868	Intermediate Similarity	NPC13880
0.7864	Intermediate Similarity	NPC478074
0.7854	Intermediate Similarity	NPC217554
0.7853	Intermediate Similarity	NPC220765
0.7843	Intermediate Similarity	NPC325297
0.7833	Intermediate Similarity	NPC321428
0.7824	Intermediate Similarity	NPC171171
0.7817	Intermediate Similarity	NPC276517
0.7816	Intermediate Similarity	NPC308137
0.7816	Intermediate Similarity	NPC310211
0.7805	Intermediate Similarity	NPC167860
0.7805	Intermediate Similarity	NPC123976
0.78	Intermediate Similarity	NPC249040
0.7799	Intermediate Similarity	NPC173080
0.7794	Intermediate Similarity	NPC470931
0.7789	Intermediate Similarity	NPC306376
0.7788	Intermediate Similarity	NPC3207
0.7788	Intermediate Similarity	NPC170114
0.7773	Intermediate Similarity	NPC60621
0.7763	Intermediate Similarity	NPC11408
0.7762	Intermediate Similarity	NPC148409
0.7762	Intermediate Similarity	NPC208084
0.7756	Intermediate Similarity	NPC469589
0.775	Intermediate Similarity	NPC18487
0.7748	Intermediate Similarity	NPC284141
0.7745	Intermediate Similarity	NPC474595
0.774	Intermediate Similarity	NPC470549
0.774	Intermediate Similarity	NPC116238
0.7739	Intermediate Similarity	NPC77555
0.7739	Intermediate Similarity	NPC474188
0.7737	Intermediate Similarity	NPC96890
0.7737	Intermediate Similarity	NPC184964
0.7736	Intermediate Similarity	NPC118121
0.7729	Intermediate Similarity	NPC203168
0.7718	Intermediate Similarity	NPC471304
0.7718	Intermediate Similarity	NPC219664
0.7716	Intermediate Similarity	NPC195268
0.7716	Intermediate Similarity	NPC133140
0.7714	Intermediate Similarity	NPC204446
0.7714	Intermediate Similarity	NPC303658
0.7705	Intermediate Similarity	NPC26850
0.7696	Intermediate Similarity	NPC304183
0.7681	Intermediate Similarity	NPC208284
0.768	Intermediate Similarity	NPC42591
0.7677	Intermediate Similarity	NPC279401
0.7677	Intermediate Similarity	NPC79293
0.7667	Intermediate Similarity	NPC169402
0.7647	Intermediate Similarity	NPC476581
0.7647	Intermediate Similarity	NPC36229
0.7647	Intermediate Similarity	NPC16452
0.7644	Intermediate Similarity	NPC283152
0.7642	Intermediate Similarity	NPC86078
0.7642	Intermediate Similarity	NPC132642
0.7637	Intermediate Similarity	NPC26872
0.7633	Intermediate Similarity	NPC199667
0.763	Intermediate Similarity	NPC184408
0.763	Intermediate Similarity	NPC473822
0.7628	Intermediate Similarity	NPC202503
0.7628	Intermediate Similarity	NPC200888
0.7626	Intermediate Similarity	NPC280964
0.7626	Intermediate Similarity	NPC141915
0.7626	Intermediate Similarity	NPC114335
0.7624	Intermediate Similarity	NPC477019
0.7621	Intermediate Similarity	NPC210828
0.7621	Intermediate Similarity	NPC86834
0.7619	Intermediate Similarity	NPC8022
0.7619	Intermediate Similarity	NPC470799
0.7608	Intermediate Similarity	NPC162530
0.7608	Intermediate Similarity	NPC474594
0.7606	Intermediate Similarity	NPC310118
0.7596	Intermediate Similarity	NPC23294
0.7593	Intermediate Similarity	NPC110151
0.7592	Intermediate Similarity	NPC288943
0.7591	Intermediate Similarity	NPC473187
0.7588	Intermediate Similarity	NPC475190
0.7585	Intermediate Similarity	NPC473181
0.7583	Intermediate Similarity	NPC314552
0.7574	Intermediate Similarity	NPC476582
0.7574	Intermediate Similarity	NPC4071
0.7574	Intermediate Similarity	NPC476578
0.7568	Intermediate Similarity	NPC41501
0.7563	Intermediate Similarity	NPC477186
0.7561	Intermediate Similarity	NPC475070
0.756	Intermediate Similarity	NPC53069
0.756	Intermediate Similarity	NPC202768
0.756	Intermediate Similarity	NPC296482
0.756	Intermediate Similarity	NPC94157
0.7559	Intermediate Similarity	NPC477533
0.7548	Intermediate Similarity	NPC5145
0.7548	Intermediate Similarity	NPC303951
0.7547	Intermediate Similarity	NPC96321
0.7547	Intermediate Similarity	NPC473041
0.7537	Intermediate Similarity	NPC315957
0.7537	Intermediate Similarity	NPC121772
0.7526	Intermediate Similarity	NPC258773
0.7526	Intermediate Similarity	NPC314394
0.7524	Intermediate Similarity	NPC472111
0.7523	Intermediate Similarity	NPC198503
0.7512	Intermediate Similarity	NPC134848
0.7512	Intermediate Similarity	NPC242209
0.7512	Intermediate Similarity	NPC246518
0.7512	Intermediate Similarity	NPC476098
0.7512	Intermediate Similarity	NPC9894
0.75	Intermediate Similarity	NPC31930

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 NPC199277 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	727
0.2-0.3	868
0.3-0.4	1642
0.4-0.5	2850
0.5-0.6	1962
0.6-0.7	607
0.7-0.8	105
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9005	High Similarity	NPD5658	Approved
0.8358	Intermediate Similarity	NPD5903	Approved
0.8358	Intermediate Similarity	NPD5902	Approved
0.8325	Intermediate Similarity	NPD3003	Approved
0.8317	Intermediate Similarity	NPD5612	Discontinued
0.8229	Intermediate Similarity	NPD1038	Approved
0.8172	Intermediate Similarity	NPD3920	Phase 2
0.8112	Intermediate Similarity	NPD1768	Approved
0.8041	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.802	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD1954	Phase 1
0.7921	Intermediate Similarity	NPD7452	Approved
0.7921	Intermediate Similarity	NPD7222	Phase 2
0.7921	Intermediate Similarity	NPD7453	Approved
0.7865	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD1392	Approved
0.7824	Intermediate Similarity	NPD6494	Phase 2
0.7817	Intermediate Similarity	NPD4418	Discontinued
0.781	Intermediate Similarity	NPD5930	Phase 3
0.7766	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7558	Phase 2
0.7725	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3924	Approved
0.7716	Intermediate Similarity	NPD3922	Approved
0.7716	Intermediate Similarity	NPD3923	Approved
0.7716	Intermediate Similarity	NPD3921	Approved
0.7714	Intermediate Similarity	NPD6985	Discontinued
0.7678	Intermediate Similarity	NPD7194	Discontinued
0.7655	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD4885	Approved
0.7583	Intermediate Similarity	NPD5164	Discontinued
0.7561	Intermediate Similarity	NPD4795	Phase 2
0.756	Intermediate Similarity	NPD3815	Phase 1
0.756	Intermediate Similarity	NPD3816	Phase 1
0.7538	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD1739	Approved
0.7537	Intermediate Similarity	NPD1740	Approved
0.7512	Intermediate Similarity	NPD5067	Phase 2
0.7512	Intermediate Similarity	NPD4502	Phase 2
0.7512	Intermediate Similarity	NPD5066	Phase 2
0.7488	Intermediate Similarity	NPD3825	Phase 3
0.7475	Intermediate Similarity	NPD7948	Phase 1
0.7465	Intermediate Similarity	NPD5632	Approved
0.7456	Intermediate Similarity	NPD6243	Phase 3
0.7456	Intermediate Similarity	NPD6244	Phase 3
0.7452	Intermediate Similarity	NPD2189	Approved
0.7452	Intermediate Similarity	NPD2187	Approved
0.7443	Intermediate Similarity	NPD8512	Phase 3
0.7441	Intermediate Similarity	NPD1322	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD4083	Discontinued
0.7411	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5905	Phase 1
0.7395	Intermediate Similarity	NPD6242	Discontinued
0.7387	Intermediate Similarity	NPD6964	Approved
0.7387	Intermediate Similarity	NPD6963	Approved
0.7376	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD484	Approved
0.7364	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8403	Phase 1
0.7349	Intermediate Similarity	NPD3875	Discontinued
0.7347	Intermediate Similarity	NPD4203	Approved
0.7347	Intermediate Similarity	NPD4204	Approved
0.7345	Intermediate Similarity	NPD4876	Phase 3
0.7345	Intermediate Similarity	NPD4875	Phase 3
0.7345	Intermediate Similarity	NPD6517	Phase 3
0.733	Intermediate Similarity	NPD4511	Phase 1
0.733	Intermediate Similarity	NPD4996	Approved
0.733	Intermediate Similarity	NPD4995	Approved
0.7327	Intermediate Similarity	NPD802	Phase 2
0.7317	Intermediate Similarity	NPD8396	Approved
0.7317	Intermediate Similarity	NPD8395	Approved
0.7292	Intermediate Similarity	NPD1326	Approved
0.7292	Intermediate Similarity	NPD1325	Approved
0.7291	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD4925	Approved
0.7281	Intermediate Similarity	NPD6230	Discontinued
0.7273	Intermediate Similarity	NPD5530	Phase 1
0.7273	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD3763	Approved
0.7269	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD8091	Phase 3
0.7265	Intermediate Similarity	NPD4080	Discontinued
0.7234	Intermediate Similarity	NPD7955	Approved
0.7234	Intermediate Similarity	NPD7956	Approved
0.7228	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5913	Phase 3
0.722	Intermediate Similarity	NPD5003	Discontinued
0.7216	Intermediate Similarity	NPD677	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6590	Discontinued
0.7189	Intermediate Similarity	NPD3258	Approved
0.7182	Intermediate Similarity	NPD7719	Discontinued
0.7175	Intermediate Similarity	NPD6962	Phase 2
0.7171	Intermediate Similarity	NPD5512	Phase 3
0.7167	Intermediate Similarity	NPD7859	Phase 2
0.7164	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD2177	Approved
0.715	Intermediate Similarity	NPD2176	Approved
0.715	Intermediate Similarity	NPD3814	Phase 1
0.715	Intermediate Similarity	NPD2175	Phase 3
0.7143	Intermediate Similarity	NPD3354	Phase 2
0.713	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5833	Phase 1
0.7117	Intermediate Similarity	NPD4328	Approved
0.7097	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6736	Discontinued
0.7091	Intermediate Similarity	NPD7219	Approved
0.7091	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7221	Approved
0.7085	Intermediate Similarity	NPD5559	Phase 2
0.7083	Intermediate Similarity	NPD7803	Approved
0.7083	Intermediate Similarity	NPD3257	Approved
0.7071	Intermediate Similarity	NPD7479	Phase 2
0.7064	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4034	Approved
0.7062	Intermediate Similarity	NPD32	Approved
0.7062	Intermediate Similarity	NPD4035	Approved
0.7062	Intermediate Similarity	NPD4122	Approved
0.7062	Intermediate Similarity	NPD4036	Approved
0.7062	Intermediate Similarity	NPD4039	Approved
0.7062	Intermediate Similarity	NPD4038	Approved
0.7062	Intermediate Similarity	NPD31	Approved
0.7062	Intermediate Similarity	NPD4037	Approved
0.7062	Intermediate Similarity	NPD4033	Approved
0.7054	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1592	Phase 3
0.7043	Intermediate Similarity	NPD5051	Phase 1
0.7042	Intermediate Similarity	NPD2916	Discontinued
0.7039	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD4373	Phase 2
0.703	Intermediate Similarity	NPD5256	Discontinued
0.7027	Intermediate Similarity	NPD1305	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5936	Approved
0.7023	Intermediate Similarity	NPD5416	Discontinued
0.7023	Intermediate Similarity	NPD5939	Approved
0.7014	Intermediate Similarity	NPD6991	Approved
0.701	Intermediate Similarity	NPD2843	Phase 2
0.701	Intermediate Similarity	NPD2845	Phase 2
0.7009	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4897	Phase 2
0.7	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD8364	Approved
0.6996	Remote Similarity	NPD8363	Approved
0.6995	Remote Similarity	NPD5429	Discontinued
0.6995	Remote Similarity	NPD6290	Phase 2
0.6995	Remote Similarity	NPD2749	Discontinued
0.699	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD5641	Discontinued
0.6974	Remote Similarity	NPD4454	Phase 2
0.6972	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3886	Phase 1
0.6964	Remote Similarity	NPD3259	Approved
0.6951	Remote Similarity	NPD6246	Approved
0.6944	Remote Similarity	NPD4131	Phase 3
0.6944	Remote Similarity	NPD6220	Phase 3
0.6942	Remote Similarity	NPD3634	Approved
0.6942	Remote Similarity	NPD3633	Approved
0.6942	Remote Similarity	NPD6569	Phase 2
0.694	Remote Similarity	NPD7620	Phase 2
0.6939	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6159	Phase 2
0.6927	Remote Similarity	NPD2564	Approved
0.6927	Remote Similarity	NPD2565	Phase 2
0.6923	Remote Similarity	NPD774	Phase 3
0.692	Remote Similarity	NPD5539	Phase 2
0.6919	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7708	Approved
0.6915	Remote Similarity	NPD3037	Phase 1
0.6912	Remote Similarity	NPD2383	Phase 1
0.691	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4952	Phase 3
0.6901	Remote Similarity	NPD3397	Phase 2
0.6897	Remote Similarity	NPD2762	Phase 2
0.6895	Remote Similarity	NPD8466	Approved
0.6895	Remote Similarity	NPD8467	Approved
0.6895	Remote Similarity	NPD8427	Approved
0.6895	Remote Similarity	NPD8465	Approved
0.6895	Remote Similarity	NPD8429	Approved
0.6895	Remote Similarity	NPD8428	Approved
0.6894	Remote Similarity	NPD5007	Approved
0.689	Remote Similarity	NPD6988	Phase 1
0.689	Remote Similarity	NPD2952	Discontinued
0.6888	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD7672	Approved
0.6884	Remote Similarity	NPD7671	Approved
0.6883	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6251	Discontinued
0.687	Remote Similarity	NPD5805	Approved
0.6869	Remote Similarity	NPD6150	Discontinued
0.6867	Remote Similarity	NPD7067	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