NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	197.08
Volume:	211.703
LogP:	3.451
LogD:	3.383
LogS:	-3.418
# Rotatable Bonds:	0
TPSA:	36.02
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	1.983
Fsp3:	0.077
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.874
MDCK Permeability:	1.2994284588785376e-05
Pgp-inhibitor:	0.019
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.798
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.706
Plasma Protein Binding (PPB):	95.28919219970703%
Volume Distribution (VD):	0.748
Pgp-substrate:	1.9346354007720947%

ADMET: Metabolism

CYP1A2-inhibitor:	0.989
CYP1A2-substrate:	0.866
CYP2C19-inhibitor:	0.626
CYP2C19-substrate:	0.16
CYP2C9-inhibitor:	0.272
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.86
CYP2D6-substrate:	0.925
CYP3A4-inhibitor:	0.379
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	8.506
Half-life (T1/2):	0.597

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.138
Drug-inuced Liver Injury (DILI):	0.651
AMES Toxicity:	0.891
Rat Oral Acute Toxicity:	0.765
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.937
Carcinogencity:	0.8
Eye Corrosion:	0.173
Eye Irritation:	0.992
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC212535

Natural Product ID:	NPC212535
*Common Name:**	3-Methyl-9H-Carbazol-2-Ol
IUPAC Name:	3-methyl-9H-carbazol-2-ol
Synonyms:
Standard InCHIKey:	ZLOJFAGTWDOURE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H11NO/c1-8-6-10-9-4-2-3-5-11(9)14-12(10)7-13(8)15/h2-7,14-15H,1H3
SMILES:	Cc1cc2c(cc1O)[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1927325
PubChem CID:	3459141
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
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000023]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[11473432]
NPO18135	Clausena vestita	Species	Rutaceae	Eukaryota	whole plants	Yunnan Province, China	2008-JAN	PMID[22093759]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	Roots	n.a.	n.a.	PMID[8991951]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644081]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27746	Taxus mairei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18135	Clausena vestita	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19266	Clausena excavata	Species	Rutaceae	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	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	14400.0	nM	PMID[571045]
NPT27	Others	Unspecified		IC50	=	85200.0	nM	PMID[571045]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	=	41500.0	nM	PMID[571046]

☑ 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 NPC212535 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	733
0.1-0.2	4857
0.2-0.3	12510
0.3-0.4	9784
0.4-0.5	10089
0.5-0.6	2750
0.6-0.7	1524
0.7-0.8	366
0.8-0.85	43
0.85-0.9	28
0.9-0.95	10
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC94943
0.9817	High Similarity	NPC190007
0.9448	High Similarity	NPC474409
0.931	High Similarity	NPC70956
0.931	High Similarity	NPC153042
0.931	High Similarity	NPC243834
0.9222	High Similarity	NPC72980
0.9222	High Similarity	NPC88363
0.905	High Similarity	NPC475085
0.905	High Similarity	NPC475112
0.905	High Similarity	NPC291535
0.9017	High Similarity	NPC246700
0.887	High Similarity	NPC131017
0.8852	High Similarity	NPC193777
0.882	High Similarity	NPC70259
0.88	High Similarity	NPC128751
0.8764	High Similarity	NPC43787
0.8764	High Similarity	NPC205934
0.875	High Similarity	NPC106833
0.875	High Similarity	NPC469497
0.8722	High Similarity	NPC72211
0.8703	High Similarity	NPC210828
0.8703	High Similarity	NPC86834
0.8696	High Similarity	NPC476106
0.8663	High Similarity	NPC23294
0.8636	High Similarity	NPC46580
0.8617	High Similarity	NPC48353
0.861	High Similarity	NPC303951
0.8602	High Similarity	NPC39679
0.8497	Intermediate Similarity	NPC96890
0.8486	Intermediate Similarity	NPC162484
0.8482	Intermediate Similarity	NPC3207
0.8478	Intermediate Similarity	NPC476044
0.8478	Intermediate Similarity	NPC267423
0.8466	Intermediate Similarity	NPC84478
0.8432	Intermediate Similarity	NPC199277
0.8432	Intermediate Similarity	NPC135887
0.8415	Intermediate Similarity	NPC306376
0.8394	Intermediate Similarity	NPC247803
0.8368	Intermediate Similarity	NPC87413
0.836	Intermediate Similarity	NPC209769
0.8351	Intermediate Similarity	NPC473179
0.8325	Intermediate Similarity	NPC294620
0.8308	Intermediate Similarity	NPC150239
0.8306	Intermediate Similarity	NPC242209
0.829	Intermediate Similarity	NPC183407
0.827	Intermediate Similarity	NPC128823
0.8265	Intermediate Similarity	NPC477532
0.8263	Intermediate Similarity	NPC201697
0.8242	Intermediate Similarity	NPC99666
0.8214	Intermediate Similarity	NPC174760
0.8177	Intermediate Similarity	NPC242928
0.8158	Intermediate Similarity	NPC4687
0.8158	Intermediate Similarity	NPC249583
0.8156	Intermediate Similarity	NPC204717
0.8135	Intermediate Similarity	NPC308137
0.8135	Intermediate Similarity	NPC310211
0.8128	Intermediate Similarity	NPC329747
0.8125	Intermediate Similarity	NPC11464
0.8115	Intermediate Similarity	NPC470931
0.8111	Intermediate Similarity	NPC314002
0.8101	Intermediate Similarity	NPC220765
0.8095	Intermediate Similarity	NPC134848
0.8083	Intermediate Similarity	NPC9894
0.8066	Intermediate Similarity	NPC171171
0.806	Intermediate Similarity	NPC473185
0.8054	Intermediate Similarity	NPC326634
0.8053	Intermediate Similarity	NPC470930
0.8051	Intermediate Similarity	NPC116238
0.8021	Intermediate Similarity	NPC475910
0.802	Intermediate Similarity	NPC252251
0.801	Intermediate Similarity	NPC330009
0.8	Intermediate Similarity	NPC223427
0.8	Intermediate Similarity	NPC141353
0.8	Intermediate Similarity	NPC106937
0.798	Intermediate Similarity	NPC209174
0.7978	Intermediate Similarity	NPC184964
0.797	Intermediate Similarity	NPC169402
0.796	Intermediate Similarity	NPC179287
0.7957	Intermediate Similarity	NPC276517
0.7946	Intermediate Similarity	NPC324149
0.7941	Intermediate Similarity	NPC477531
0.7929	Intermediate Similarity	NPC46561
0.791	Intermediate Similarity	NPC211416
0.7901	Intermediate Similarity	NPC176127
0.7895	Intermediate Similarity	NPC232727
0.7889	Intermediate Similarity	NPC478032
0.7879	Intermediate Similarity	NPC60553
0.7876	Intermediate Similarity	NPC283117
0.7872	Intermediate Similarity	NPC77555
0.7868	Intermediate Similarity	NPC470549
0.7865	Intermediate Similarity	NPC285558
0.7864	Intermediate Similarity	NPC473182
0.7861	Intermediate Similarity	NPC162748
0.7845	Intermediate Similarity	NPC474798
0.7842	Intermediate Similarity	NPC249040
0.7842	Intermediate Similarity	NPC11017
0.7828	Intermediate Similarity	NPC170114
0.7819	Intermediate Similarity	NPC13880
0.7816	Intermediate Similarity	NPC16667
0.7811	Intermediate Similarity	NPC198503
0.7809	Intermediate Similarity	NPC34508
0.7806	Intermediate Similarity	NPC294375
0.78	Intermediate Similarity	NPC193267
0.78	Intermediate Similarity	NPC213530
0.7789	Intermediate Similarity	NPC293151
0.7788	Intermediate Similarity	NPC473187
0.7778	Intermediate Similarity	NPC118228
0.7772	Intermediate Similarity	NPC475070
0.7771	Intermediate Similarity	NPC159319
0.7766	Intermediate Similarity	NPC12344
0.7761	Intermediate Similarity	NPC477533
0.776	Intermediate Similarity	NPC62069
0.7751	Intermediate Similarity	NPC473183
0.7751	Intermediate Similarity	NPC6786
0.775	Intermediate Similarity	NPC264285
0.7747	Intermediate Similarity	NPC314394
0.7745	Intermediate Similarity	NPC202503
0.774	Intermediate Similarity	NPC473184
0.7727	Intermediate Similarity	NPC471080
0.7727	Intermediate Similarity	NPC469592
0.7717	Intermediate Similarity	NPC476319
0.7711	Intermediate Similarity	NPC208084
0.7696	Intermediate Similarity	NPC476167
0.7692	Intermediate Similarity	NPC183777
0.768	Intermediate Similarity	NPC470500
0.7677	Intermediate Similarity	NPC128084
0.7677	Intermediate Similarity	NPC316981
0.767	Intermediate Similarity	NPC32028
0.7665	Intermediate Similarity	NPC167860
0.7665	Intermediate Similarity	NPC123976
0.7657	Intermediate Similarity	NPC131718
0.7654	Intermediate Similarity	NPC179365
0.765	Intermediate Similarity	NPC74969
0.7647	Intermediate Similarity	NPC51388
0.7644	Intermediate Similarity	NPC192315
0.7644	Intermediate Similarity	NPC132329
0.7641	Intermediate Similarity	NPC45190
0.7641	Intermediate Similarity	NPC300156
0.7637	Intermediate Similarity	NPC270009
0.7632	Intermediate Similarity	NPC472193
0.7632	Intermediate Similarity	NPC251090
0.7629	Intermediate Similarity	NPC476098
0.7622	Intermediate Similarity	NPC473189
0.7614	Intermediate Similarity	NPC315214
0.7614	Intermediate Similarity	NPC473181
0.7614	Intermediate Similarity	NPC47298
0.7614	Intermediate Similarity	NPC476116
0.7612	Intermediate Similarity	NPC314552
0.7611	Intermediate Similarity	NPC259545
0.7602	Intermediate Similarity	NPC124005
0.76	Intermediate Similarity	NPC67056
0.7598	Intermediate Similarity	NPC280548
0.7592	Intermediate Similarity	NPC156704
0.7586	Intermediate Similarity	NPC86078
0.7586	Intermediate Similarity	NPC285469
0.7581	Intermediate Similarity	NPC160381
0.7581	Intermediate Similarity	NPC314573
0.7579	Intermediate Similarity	NPC195314
0.7576	Intermediate Similarity	NPC199667
0.7576	Intermediate Similarity	NPC5145
0.7574	Intermediate Similarity	NPC469594
0.7574	Intermediate Similarity	NPC184408
0.7571	Intermediate Similarity	NPC102423
0.7566	Intermediate Similarity	NPC280964
0.7566	Intermediate Similarity	NPC114335
0.7566	Intermediate Similarity	NPC141915
0.7565	Intermediate Similarity	NPC213308
0.7562	Intermediate Similarity	NPC469928
0.7554	Intermediate Similarity	NPC192270
0.755	Intermediate Similarity	NPC266931
0.755	Intermediate Similarity	NPC478074
0.7543	Intermediate Similarity	NPC26850
0.7542	Intermediate Similarity	NPC154293
0.7541	Intermediate Similarity	NPC472443
0.7538	Intermediate Similarity	NPC53144
0.7531	Intermediate Similarity	NPC473587
0.7529	Intermediate Similarity	NPC38736
0.7529	Intermediate Similarity	NPC207726
0.7526	Intermediate Similarity	NPC307963
0.7525	Intermediate Similarity	NPC80596
0.7514	Intermediate Similarity	NPC471294
0.7514	Intermediate Similarity	NPC19679
0.7512	Intermediate Similarity	NPC16352
0.7512	Intermediate Similarity	NPC475253
0.7512	Intermediate Similarity	NPC477861
0.75	Intermediate Similarity	NPC474188
0.75	Intermediate Similarity	NPC296527
0.75	Intermediate Similarity	NPC132642
0.75	Intermediate Similarity	NPC473180
0.7488	Intermediate Similarity	NPC2497
0.7488	Intermediate Similarity	NPC303658
0.7488	Intermediate Similarity	NPC277351
0.7488	Intermediate Similarity	NPC473041
0.7485	Intermediate Similarity	NPC475428
0.7474	Intermediate Similarity	NPC329793
0.7474	Intermediate Similarity	NPC121772
0.7474	Intermediate Similarity	NPC315491
0.7474	Intermediate Similarity	NPC45459
0.7473	Intermediate Similarity	NPC329688

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 NPC212535 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	678
0.2-0.3	796
0.3-0.4	1583
0.4-0.5	2930
0.5-0.6	2034
0.6-0.7	593
0.7-0.8	80
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD1325	Approved
0.8421	Intermediate Similarity	NPD1326	Approved
0.8182	Intermediate Similarity	NPD4511	Phase 1
0.8065	Intermediate Similarity	NPD7948	Phase 1
0.8011	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD802	Phase 2
0.8	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3003	Approved
0.7789	Intermediate Similarity	NPD3814	Phase 1
0.7744	Intermediate Similarity	NPD2916	Discontinued
0.7744	Intermediate Similarity	NPD5658	Approved
0.774	Intermediate Similarity	NPD1921	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD1768	Approved
0.7696	Intermediate Similarity	NPD8395	Approved
0.7696	Intermediate Similarity	NPD8396	Approved
0.7665	Intermediate Similarity	NPD1592	Phase 3
0.7641	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD1685	Approved
0.7614	Intermediate Similarity	NPD1684	Approved
0.7612	Intermediate Similarity	NPD5164	Discontinued
0.7604	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5902	Approved
0.76	Intermediate Similarity	NPD5903	Approved
0.7552	Intermediate Similarity	NPD2727	Phase 2
0.7541	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD1038	Approved
0.7514	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2794	Discontinued
0.7474	Intermediate Similarity	NPD484	Approved
0.7473	Intermediate Similarity	NPD5065	Approved
0.7435	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD1392	Approved
0.7414	Intermediate Similarity	NPD2882	Phase 1
0.7402	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6975	Discontinued
0.7396	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6159	Phase 2
0.7389	Intermediate Similarity	NPD5612	Discontinued
0.7363	Intermediate Similarity	NPD5936	Approved
0.7363	Intermediate Similarity	NPD5939	Approved
0.7358	Intermediate Similarity	NPD3127	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7558	Phase 2
0.7356	Intermediate Similarity	NPD4462	Approved
0.7356	Intermediate Similarity	NPD4463	Approved
0.7354	Intermediate Similarity	NPD2383	Phase 1
0.7351	Intermediate Similarity	NPD8386	Phase 2
0.7333	Intermediate Similarity	NPD2175	Phase 3
0.7333	Intermediate Similarity	NPD2176	Approved
0.7333	Intermediate Similarity	NPD2177	Approved
0.733	Intermediate Similarity	NPD5913	Phase 3
0.733	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD3330	Phase 1
0.7317	Intermediate Similarity	NPD6985	Discontinued
0.7314	Intermediate Similarity	NPD6158	Phase 2
0.7314	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3404	Approved
0.7282	Intermediate Similarity	NPD7194	Discontinued
0.7278	Intermediate Similarity	NPD5140	Approved
0.7278	Intermediate Similarity	NPD5138	Approved
0.7263	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD2844	Phase 3
0.725	Intermediate Similarity	NPD7453	Approved
0.725	Intermediate Similarity	NPD7452	Approved
0.725	Intermediate Similarity	NPD7222	Phase 2
0.7249	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5901	Discontinued
0.7231	Intermediate Similarity	NPD5003	Discontinued
0.722	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4418	Discontinued
0.7216	Intermediate Similarity	NPD3791	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5067	Phase 2
0.7192	Intermediate Similarity	NPD5066	Phase 2
0.7158	Intermediate Similarity	NPD2762	Phase 2
0.715	Intermediate Similarity	NPD5632	Approved
0.7128	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD8403	Phase 1
0.7114	Intermediate Similarity	NPD5530	Phase 1
0.7112	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1554	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD2565	Phase 2
0.7098	Intermediate Similarity	NPD2564	Approved
0.7092	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6290	Phase 2
0.7074	Intermediate Similarity	NPD3920	Phase 2
0.7071	Intermediate Similarity	NPD3825	Phase 3
0.7059	Intermediate Similarity	NPD2381	Approved
0.7059	Intermediate Similarity	NPD2380	Approved
0.7059	Intermediate Similarity	NPD2382	Approved
0.7056	Intermediate Similarity	NPD1219	Approved
0.7056	Intermediate Similarity	NPD1218	Approved
0.705	Intermediate Similarity	NPD3931	Approved
0.705	Intermediate Similarity	NPD3928	Approved
0.7041	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6595	Phase 3
0.7027	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5937	Approved
0.7024	Intermediate Similarity	NPD6220	Phase 3
0.7024	Intermediate Similarity	NPD4502	Phase 2
0.7019	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6492	Phase 2
0.7	Intermediate Similarity	NPD2468	Approved
0.7	Intermediate Similarity	NPD4203	Approved
0.7	Intermediate Similarity	NPD2469	Approved
0.7	Intermediate Similarity	NPD4204	Approved
0.6995	Remote Similarity	NPD7603	Discontinued
0.6995	Remote Similarity	NPD8431	Approved
0.6995	Remote Similarity	NPD4948	Discontinued
0.698	Remote Similarity	NPD4795	Phase 2
0.698	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD2781	Approved
0.6971	Remote Similarity	NPD5254	Discontinued
0.6963	Remote Similarity	NPD5596	Phase 2
0.6959	Remote Similarity	NPD1534	Approved
0.6959	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD925	Approved
0.6957	Remote Similarity	NPD2780	Approved
0.6957	Remote Similarity	NPD926	Approved
0.6957	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2782	Approved
0.6954	Remote Similarity	NPD6590	Discontinued
0.6952	Remote Similarity	NPD7418	Discontinued
0.695	Remote Similarity	NPD1740	Approved
0.695	Remote Similarity	NPD1739	Approved
0.6946	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD7219	Approved
0.6934	Remote Similarity	NPD7221	Approved
0.6931	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5512	Phase 3
0.6919	Remote Similarity	NPD1262	Discovery
0.6915	Remote Similarity	NPD9690	Approved
0.6905	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7112	Discontinued
0.6887	Remote Similarity	NPD7726	Phase 1
0.6885	Remote Similarity	NPD112	Approved
0.6885	Remote Similarity	NPD9705	Discontinued
0.6881	Remote Similarity	NPD6494	Phase 2
0.6878	Remote Similarity	NPD2187	Approved
0.6878	Remote Similarity	NPD6376	Discontinued
0.6878	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD2189	Approved
0.6878	Remote Similarity	NPD5100	Phase 3
0.6872	Remote Similarity	NPD3835	Phase 3
0.6872	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD3833	Phase 3
0.6872	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD3017	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6452	Discontinued
0.6854	Remote Similarity	NPD1954	Phase 1
0.6852	Remote Similarity	NPD7555	Discontinued
0.6847	Remote Similarity	NPD4886	Phase 2
0.6845	Remote Similarity	NPD7474	Suspended
0.6842	Remote Similarity	NPD2144	Approved
0.684	Remote Similarity	NPD5930	Phase 3
0.6835	Remote Similarity	NPD3746	Discontinued
0.683	Remote Similarity	NPD4350	Approved
0.683	Remote Similarity	NPD4349	Approved
0.6828	Remote Similarity	NPD424	Approved
0.6828	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD425	Approved
0.6825	Remote Similarity	NPD482	Approved
0.6816	Remote Similarity	NPD3100	Discontinued
0.6816	Remote Similarity	NPD6473	Phase 1
0.6806	Remote Similarity	NPD4079	Approved
0.6806	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4076	Approved
0.6796	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4403	Phase 3
0.6791	Remote Similarity	NPD5021	Discontinued
0.6791	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD4401	Phase 2
0.6789	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD3986	Discontinued
0.6784	Remote Similarity	NPD3810	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4600	Approved
0.6782	Remote Similarity	NPD4601	Approved
0.678	Remote Similarity	NPD8364	Approved
0.678	Remote Similarity	NPD8363	Approved
0.6776	Remote Similarity	NPD6736	Discontinued
0.6776	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD3224	Phase 2
0.6763	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6242	Discontinued
0.6758	Remote Similarity	NPD5617	Suspended
0.6754	Remote Similarity	NPD3505	Approved
0.6754	Remote Similarity	NPD3506	Approved
0.6749	Remote Similarity	NPD6145	Phase 1
0.6748	Remote Similarity	NPD5429	Discontinued
0.6746	Remote Similarity	NPD7069	Discontinued

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