NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	211.06
Volume:	217.857
LogP:	3.131
LogD:	2.845
LogS:	-4.44
# Rotatable Bonds:	1
TPSA:	53.09
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.608
Synthetic Accessibility Score:	2.219
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.035
MDCK Permeability:	7.577486940135714e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.902
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.475
Plasma Protein Binding (PPB):	94.2291488647461%
Volume Distribution (VD):	0.584
Pgp-substrate:	2.9293394088745117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.992
CYP1A2-substrate:	0.185
CYP2C19-inhibitor:	0.286
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.401
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.751
CYP2D6-substrate:	0.48
CYP3A4-inhibitor:	0.475
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	4.176
Half-life (T1/2):	0.647

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.119
Drug-inuced Liver Injury (DILI):	0.807
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.546
Skin Sensitization:	0.908
Carcinogencity:	0.1
Eye Corrosion:	0.339
Eye Irritation:	0.99
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC283117

Natural Product ID:	NPC283117
*Common Name:**	O-Demethylmurrayanine
IUPAC Name:	1-hydroxy-9H-carbazole-3-carbaldehyde
Synonyms:	O-Demethylmurrayanine
Standard InCHIKey:	OYSFFQUIYNEZKX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H9NO2/c15-7-8-5-10-9-3-1-2-4-11(9)14-13(10)12(16)6-8/h1-7,14,16H
SMILES:	c1ccc2c(c1)c1cc(cc(c1[nH]2)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479681
PubChem CID:	611174
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
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1080/10412905.1999.9701119]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1080/10412905.1999.9701119]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650093]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19327990]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19459693]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	n.a.	root	n.a.	PMID[21302964]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Stems	n.a.	n.a.	PMID[22372931]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	leaf oil	n.a.	n.a.	PMID[22472691]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24798144]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[26523463]
NPO21978	Clausena harmandiana	Species	Rutaceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3236015]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29109	Clausena anisata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21978	Clausena harmandiana	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	5
Others	8

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[545478]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[545478]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	19220.0	nM	PMID[545479]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5490.0	nM	PMID[545479]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	103500.0	nM	PMID[545479]
NPT2	Others	Unspecified		Activity	=	25.2	%	PMID[545478]
NPT2	Others	Unspecified		Activity	=	40.3	%	PMID[545478]
NPT2	Others	Unspecified		Activity	=	69.4	%	PMID[545478]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[545478]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3500.0	nM	PMID[545480]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6900.0	nM	PMID[545480]

☑ 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 NPC283117 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	512
0.1-0.2	3428
0.2-0.3	13452
0.3-0.4	5632
0.4-0.5	15044
0.5-0.6	2561
0.6-0.7	1758
0.7-0.8	267
0.8-0.85	24
0.85-0.9	13
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9786	High Similarity	NPC294375
0.9531	High Similarity	NPC293151
0.9326	High Similarity	NPC118228
0.9196	High Similarity	NPC179287
0.9171	High Similarity	NPC187501
0.899	High Similarity	NPC184408
0.8955	High Similarity	NPC51388
0.8878	High Similarity	NPC9894
0.885	High Similarity	NPC208084
0.8821	High Similarity	NPC86834
0.8821	High Similarity	NPC210828
0.8806	High Similarity	NPC225279
0.8788	High Similarity	NPC39500
0.8786	High Similarity	NPC474701
0.8687	High Similarity	NPC23294
0.8636	High Similarity	NPC303951
0.8622	High Similarity	NPC45190
0.8535	High Similarity	NPC39679
0.851	High Similarity	NPC274640
0.8447	Intermediate Similarity	NPC144452
0.8431	Intermediate Similarity	NPC247803
0.8392	Intermediate Similarity	NPC249583
0.835	Intermediate Similarity	NPC150239
0.8342	Intermediate Similarity	NPC300156
0.8317	Intermediate Similarity	NPC87413
0.8316	Intermediate Similarity	NPC128823
0.831	Intermediate Similarity	NPC39370
0.8302	Intermediate Similarity	NPC473186
0.8255	Intermediate Similarity	NPC474688
0.8255	Intermediate Similarity	NPC477112
0.8244	Intermediate Similarity	NPC3207
0.8203	Intermediate Similarity	NPC475844
0.8191	Intermediate Similarity	NPC88363
0.8186	Intermediate Similarity	NPC308137
0.8186	Intermediate Similarity	NPC310211
0.8164	Intermediate Similarity	NPC46561
0.8148	Intermediate Similarity	NPC478032
0.8135	Intermediate Similarity	NPC242928
0.8125	Intermediate Similarity	NPC160381
0.8119	Intermediate Similarity	NPC321428
0.8119	Intermediate Similarity	NPC4687
0.803	Intermediate Similarity	NPC270918
0.802	Intermediate Similarity	NPC276517
0.8	Intermediate Similarity	NPC144381
0.8	Intermediate Similarity	NPC174760
0.799	Intermediate Similarity	NPC171787
0.7982	Intermediate Similarity	NPC6786
0.797	Intermediate Similarity	NPC230403
0.7949	Intermediate Similarity	NPC221873
0.7923	Intermediate Similarity	NPC76982
0.7882	Intermediate Similarity	NPC476098
0.7882	Intermediate Similarity	NPC134848
0.7882	Intermediate Similarity	NPC165599
0.7877	Intermediate Similarity	NPC198503
0.7876	Intermediate Similarity	NPC212535
0.7864	Intermediate Similarity	NPC325297
0.7857	Intermediate Similarity	NPC246700
0.7854	Intermediate Similarity	NPC183777
0.785	Intermediate Similarity	NPC141454
0.7847	Intermediate Similarity	NPC116238
0.7837	Intermediate Similarity	NPC219087
0.7824	Intermediate Similarity	NPC474798
0.7822	Intermediate Similarity	NPC213308
0.7811	Intermediate Similarity	NPC306376
0.7795	Intermediate Similarity	NPC94943
0.7793	Intermediate Similarity	NPC280799
0.7773	Intermediate Similarity	NPC169402
0.7767	Intermediate Similarity	NPC244741
0.7746	Intermediate Similarity	NPC276657
0.7744	Intermediate Similarity	NPC190007
0.7727	Intermediate Similarity	NPC83111
0.7723	Intermediate Similarity	NPC192315
0.7721	Intermediate Similarity	NPC205372
0.7704	Intermediate Similarity	NPC241025
0.7696	Intermediate Similarity	NPC474409
0.7685	Intermediate Similarity	NPC476167
0.7677	Intermediate Similarity	NPC128751
0.7673	Intermediate Similarity	NPC153042
0.7656	Intermediate Similarity	NPC303225
0.7647	Intermediate Similarity	NPC315491
0.7647	Intermediate Similarity	NPC45459
0.7642	Intermediate Similarity	NPC469928
0.7638	Intermediate Similarity	NPC106833
0.7638	Intermediate Similarity	NPC469497
0.7636	Intermediate Similarity	NPC132329
0.7617	Intermediate Similarity	NPC473179
0.7613	Intermediate Similarity	NPC473187
0.7612	Intermediate Similarity	NPC475190
0.7608	Intermediate Similarity	NPC209769
0.7598	Intermediate Similarity	NPC473188
0.7596	Intermediate Similarity	NPC53344
0.7596	Intermediate Similarity	NPC88008
0.7586	Intermediate Similarity	NPC70956
0.7586	Intermediate Similarity	NPC243834
0.7583	Intermediate Similarity	NPC12344
0.7581	Intermediate Similarity	NPC132642
0.7578	Intermediate Similarity	NPC15801
0.7576	Intermediate Similarity	NPC194040
0.7571	Intermediate Similarity	NPC309845
0.7547	Intermediate Similarity	NPC89508
0.7535	Intermediate Similarity	NPC288987
0.7512	Intermediate Similarity	NPC280714
0.7488	Intermediate Similarity	NPC264285
0.7488	Intermediate Similarity	NPC199667
0.7477	Intermediate Similarity	NPC322064
0.7477	Intermediate Similarity	NPC330009
0.7465	Intermediate Similarity	NPC31700
0.7463	Intermediate Similarity	NPC472284
0.7456	Intermediate Similarity	NPC160898
0.7454	Intermediate Similarity	NPC74360
0.7449	Intermediate Similarity	NPC72980
0.7442	Intermediate Similarity	NPC472285
0.7442	Intermediate Similarity	NPC312645
0.7441	Intermediate Similarity	NPC473181
0.7429	Intermediate Similarity	NPC193777
0.7418	Intermediate Similarity	NPC473180
0.7418	Intermediate Similarity	NPC94157
0.7416	Intermediate Similarity	NPC132539
0.7415	Intermediate Similarity	NPC156704
0.7409	Intermediate Similarity	NPC470018
0.7407	Intermediate Similarity	NPC131885
0.7402	Intermediate Similarity	NPC131017
0.7395	Intermediate Similarity	NPC477110
0.7395	Intermediate Similarity	NPC74969
0.7394	Intermediate Similarity	NPC141353
0.7393	Intermediate Similarity	NPC477111
0.7389	Intermediate Similarity	NPC99666
0.7381	Intermediate Similarity	NPC477113
0.738	Intermediate Similarity	NPC208522
0.7376	Intermediate Similarity	NPC473185
0.7373	Intermediate Similarity	NPC89549
0.7371	Intermediate Similarity	NPC82370
0.7363	Intermediate Similarity	NPC206186
0.7361	Intermediate Similarity	NPC27041
0.7361	Intermediate Similarity	NPC314552
0.735	Intermediate Similarity	NPC314002
0.7337	Intermediate Similarity	NPC220765
0.7333	Intermediate Similarity	NPC182222
0.7333	Intermediate Similarity	NPC470930
0.733	Intermediate Similarity	NPC90229
0.7324	Intermediate Similarity	NPC5145
0.7321	Intermediate Similarity	NPC291535
0.7321	Intermediate Similarity	NPC475085
0.7321	Intermediate Similarity	NPC475112
0.7321	Intermediate Similarity	NPC207686
0.7302	Intermediate Similarity	NPC250448
0.7301	Intermediate Similarity	NPC477549
0.73	Intermediate Similarity	NPC204717
0.7299	Intermediate Similarity	NPC175602
0.7297	Intermediate Similarity	NPC257851
0.7296	Intermediate Similarity	NPC473800
0.7286	Intermediate Similarity	NPC314394
0.7277	Intermediate Similarity	NPC322644
0.7273	Intermediate Similarity	NPC220851
0.7273	Intermediate Similarity	NPC471944
0.7273	Intermediate Similarity	NPC16352
0.7265	Intermediate Similarity	NPC194740
0.7256	Intermediate Similarity	NPC110182
0.7253	Intermediate Similarity	NPC165964
0.7246	Intermediate Similarity	NPC77555
0.7245	Intermediate Similarity	NPC34508
0.7244	Intermediate Similarity	NPC49547
0.7243	Intermediate Similarity	NPC471304
0.7238	Intermediate Similarity	NPC199277
0.7238	Intermediate Similarity	NPC135887
0.7231	Intermediate Similarity	NPC473764
0.7231	Intermediate Similarity	NPC314940
0.7228	Intermediate Similarity	NPC171171
0.7225	Intermediate Similarity	NPC249040
0.7222	Intermediate Similarity	NPC184964
0.722	Intermediate Similarity	NPC74575
0.722	Intermediate Similarity	NPC478078
0.7219	Intermediate Similarity	NPC13432
0.7217	Intermediate Similarity	NPC472287
0.7217	Intermediate Similarity	NPC476106
0.7217	Intermediate Similarity	NPC472286
0.7217	Intermediate Similarity	NPC473312
0.7212	Intermediate Similarity	NPC284888
0.7212	Intermediate Similarity	NPC473182
0.7206	Intermediate Similarity	NPC154339
0.7204	Intermediate Similarity	NPC223427
0.7196	Intermediate Similarity	NPC61038
0.7194	Intermediate Similarity	NPC6982
0.7192	Intermediate Similarity	NPC278434
0.7192	Intermediate Similarity	NPC46580
0.7189	Intermediate Similarity	NPC16066
0.7178	Intermediate Similarity	NPC42591
0.7176	Intermediate Similarity	NPC48353
0.7176	Intermediate Similarity	NPC118940
0.7175	Intermediate Similarity	NPC319232
0.7175	Intermediate Similarity	NPC24370
0.7175	Intermediate Similarity	NPC214142
0.7175	Intermediate Similarity	NPC202503
0.717	Intermediate Similarity	NPC470500
0.7169	Intermediate Similarity	NPC96321
0.7169	Intermediate Similarity	NPC303658
0.7165	Intermediate Similarity	NPC115232
0.7164	Intermediate Similarity	NPC176127
0.7163	Intermediate Similarity	NPC269367
0.7162	Intermediate Similarity	NPC229893

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 NPC283117 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	677
0.2-0.3	955
0.3-0.4	1446
0.4-0.5	3167
0.5-0.6	1909
0.6-0.7	604
0.7-0.8	56
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8357	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8131	Intermediate Similarity	NPD3746	Discontinued
0.7756	Intermediate Similarity	NPD5901	Discontinued
0.7709	Intermediate Similarity	NPD3986	Discontinued
0.7647	Intermediate Similarity	NPD484	Approved
0.7569	Intermediate Similarity	NPD7603	Discontinued
0.7476	Intermediate Similarity	NPD6376	Discontinued
0.7464	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5939	Approved
0.7453	Intermediate Similarity	NPD5936	Approved
0.7427	Intermediate Similarity	NPD2175	Phase 3
0.7427	Intermediate Similarity	NPD2176	Approved
0.7427	Intermediate Similarity	NPD2177	Approved
0.7426	Intermediate Similarity	NPD6456	Discontinued
0.7416	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5003	Discontinued
0.7361	Intermediate Similarity	NPD5164	Discontinued
0.7349	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD4429	Discontinued
0.732	Intermediate Similarity	NPD1325	Approved
0.732	Intermediate Similarity	NPD1326	Approved
0.7309	Intermediate Similarity	NPD5479	Discontinued
0.7291	Intermediate Similarity	NPD2564	Approved
0.7291	Intermediate Similarity	NPD2565	Phase 2
0.729	Intermediate Similarity	NPD5416	Discontinued
0.7289	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4948	Discontinued
0.7273	Intermediate Similarity	NPD4511	Phase 1
0.7268	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6290	Phase 2
0.726	Intermediate Similarity	NPD6242	Discontinued
0.7251	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD5632	Approved
0.7248	Intermediate Similarity	NPD7395	Discontinued
0.7243	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5022	Discontinued
0.723	Intermediate Similarity	NPD2916	Discontinued
0.7222	Intermediate Similarity	NPD3243	Approved
0.722	Intermediate Similarity	NPD4845	Discontinued
0.7215	Intermediate Similarity	NPD3258	Approved
0.72	Intermediate Similarity	NPD1467	Approved
0.72	Intermediate Similarity	NPD1466	Phase 3
0.7198	Intermediate Similarity	NPD5512	Phase 3
0.7181	Intermediate Similarity	NPD2951	Discontinued
0.7179	Intermediate Similarity	NPD2844	Phase 3
0.7169	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7948	Phase 1
0.7155	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3945	Discontinued
0.7136	Intermediate Similarity	NPD6159	Phase 2
0.713	Intermediate Similarity	NPD4502	Phase 2
0.711	Intermediate Similarity	NPD3257	Approved
0.7103	Intermediate Similarity	NPD5429	Discontinued
0.7095	Intermediate Similarity	NPD8395	Approved
0.7095	Intermediate Similarity	NPD8396	Approved
0.7094	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1867	Approved
0.7048	Intermediate Similarity	NPD1505	Phase 2
0.7035	Intermediate Similarity	NPD9690	Approved
0.7018	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5612	Discontinued
0.7	Intermediate Similarity	NPD3006	Discontinued
0.6995	Remote Similarity	NPD2779	Approved
0.6991	Remote Similarity	NPD4328	Approved
0.699	Remote Similarity	NPD1534	Approved
0.6983	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6995	Phase 1
0.6962	Remote Similarity	NPD3809	Discontinued
0.6961	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3178	Discontinued
0.6942	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD1038	Approved
0.6934	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7853	Phase 2
0.6923	Remote Similarity	NPD9705	Discontinued
0.6923	Remote Similarity	NPD112	Approved
0.6905	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3003	Approved
0.6895	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5482	Discontinued
0.6889	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2920	Discontinued
0.6884	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6531	Approved
0.6872	Remote Similarity	NPD6530	Approved
0.6872	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD482	Approved
0.6866	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3330	Phase 1
0.686	Remote Similarity	NPD2383	Phase 1
0.6858	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD2778	Approved
0.6852	Remote Similarity	NPD5426	Phase 3
0.6851	Remote Similarity	NPD6716	Phase 1
0.6849	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4561	Discontinued
0.6832	Remote Similarity	NPD749	Clinical (unspecified phase)
0.683	Remote Similarity	NPD4312	Approved
0.6829	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4600	Approved
0.6822	Remote Similarity	NPD4601	Approved
0.6818	Remote Similarity	NPD7470	Discontinued
0.6814	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5445	Approved
0.6808	Remote Similarity	NPD2727	Phase 2
0.6806	Remote Similarity	NPD6176	Phase 1
0.6804	Remote Similarity	NPD4506	Discontinued
0.6789	Remote Similarity	NPD7222	Phase 2
0.6789	Remote Similarity	NPD7453	Approved
0.6789	Remote Similarity	NPD7452	Approved
0.6787	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.678	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6987	Phase 1
0.6773	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD7994	Phase 2
0.6769	Remote Similarity	NPD3259	Approved
0.6767	Remote Similarity	NPD4373	Phase 2
0.6762	Remote Similarity	NPD5913	Phase 3
0.6762	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6161	Approved
0.6761	Remote Similarity	NPD6162	Approved
0.6756	Remote Similarity	NPD6770	Approved
0.6747	Remote Similarity	NPD8363	Approved
0.6747	Remote Similarity	NPD8364	Approved
0.6743	Remote Similarity	NPD7001	Phase 3
0.6735	Remote Similarity	NPD7708	Approved
0.6732	Remote Similarity	NPD5473	Discontinued
0.6732	Remote Similarity	NPD9510	Approved
0.6732	Remote Similarity	NPD7181	Phase 3
0.6726	Remote Similarity	NPD5850	Phase 3
0.6724	Remote Similarity	NPD4885	Approved
0.672	Remote Similarity	NPD1592	Phase 3
0.6718	Remote Similarity	NPD3684	Discontinued
0.6717	Remote Similarity	NPD1684	Approved
0.6717	Remote Similarity	NPD1685	Approved
0.6712	Remote Similarity	NPD8093	Discontinued
0.6711	Remote Similarity	NPD7878	Phase 2
0.671	Remote Similarity	NPD4952	Phase 3
0.6709	Remote Similarity	NPD4454	Phase 2
0.67	Remote Similarity	NPD5065	Approved
0.6698	Remote Similarity	NPD9695	Approved
0.6698	Remote Similarity	NPD3825	Phase 3
0.6698	Remote Similarity	NPD3814	Phase 1
0.6698	Remote Similarity	NPD1768	Approved
0.6697	Remote Similarity	NPD3947	Discontinued
0.6697	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD3392	Approved
0.6696	Remote Similarity	NPD7726	Phase 1
0.6696	Remote Similarity	NPD6803	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5488	Discontinued
0.6693	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8349	Phase 1
0.6683	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5658	Approved
0.6682	Remote Similarity	NPD2509	Approved
0.6682	Remote Similarity	NPD2510	Approved
0.6681	Remote Similarity	NPD6962	Phase 2
0.6681	Remote Similarity	NPD4368	Phase 2
0.6681	Remote Similarity	NPD7688	Phase 1
0.6681	Remote Similarity	NPD5805	Approved
0.668	Remote Similarity	NPD5399	Discovery
0.6667	Remote Similarity	NPD2380	Approved
0.6667	Remote Similarity	NPD7417	Discontinued
0.6667	Remote Similarity	NPD2381	Approved
0.6667	Remote Similarity	NPD408	Approved
0.6667	Remote Similarity	NPD2382	Approved
0.6667	Remote Similarity	NPD8463	Approved
0.6667	Remote Similarity	NPD2094	Phase 2
0.6667	Remote Similarity	NPD2092	Phase 2
0.6667	Remote Similarity	NPD2095	Phase 2
0.6652	Remote Similarity	NPD3263	Phase 3
0.6652	Remote Similarity	NPD5903	Approved
0.6652	Remote Similarity	NPD5902	Approved
0.6651	Remote Similarity	NPD5937	Approved
0.6637	Remote Similarity	NPD3354	Phase 2
0.6637	Remote Similarity	NPD8097	Phase 3
0.6637	Remote Similarity	NPD8096	Phase 3
0.6637	Remote Similarity	NPD5866	Approved
0.6635	Remote Similarity	NPD4499	Approved
0.6635	Remote Similarity	NPD2091	Phase 2
0.6635	Remote Similarity	NPD2096	Phase 2
0.6633	Remote Similarity	NPD972	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7803	Approved
0.6626	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD8430	Approved
0.662	Remote Similarity	NPD802	Phase 2

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