NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	255.09
Volume:	261.239
LogP:	3.323
LogD:	3.141
LogS:	-5.367
# Rotatable Bonds:	3
TPSA:	51.32
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	2.167
Fsp3:	0.133
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:	-4.94
MDCK Permeability:	8.548455298296176e-06
Pgp-inhibitor:	0.004
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.052

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.737
Plasma Protein Binding (PPB):	90.68639373779297%
Volume Distribution (VD):	0.924
Pgp-substrate:	7.034520149230957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.969
CYP2C19-inhibitor:	0.594
CYP2C19-substrate:	0.651
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.928
CYP2D6-inhibitor:	0.378
CYP2D6-substrate:	0.924
CYP3A4-inhibitor:	0.578
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	5.053
Half-life (T1/2):	0.379

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.221
Drug-inuced Liver Injury (DILI):	0.785
AMES Toxicity:	0.882
Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.738
Carcinogencity:	0.489
Eye Corrosion:	0.111
Eye Irritation:	0.983
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC46561

Natural Product ID:	NPC46561
*Common Name:**	Glycozolidal
IUPAC Name:	2,6-dimethoxy-9H-carbazole-3-carbaldehyde
Synonyms:	Glycozolidal
Standard InCHIKey:	WCKFRKXQABCDRE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H13NO3/c1-18-10-3-4-13-12(6-10)11-5-9(8-17)15(19-2)7-14(11)16-13/h3-8,16H,1-2H3
SMILES:	COc1ccc2c(c1)c1cc(C=O)c(cc1[nH]2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036045
PubChem CID:	182690
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]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19327990]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	Stems	n.a.	n.a.	PMID[22372931]
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]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	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]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19266	Clausena excavata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19266	Clausena excavata	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]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23546	Clausena lansium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	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
NON-MOLECULAR	2
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4600.0	nM	PMID[538422]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[538422]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC90	>	50000.0	nM	PMID[538423]

☑ 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 NPC46561 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	636
0.1-0.2	3650
0.2-0.3	13305
0.3-0.4	3532
0.4-0.5	14575
0.5-0.6	5019
0.6-0.7	1446
0.7-0.8	453
0.8-0.85	46
0.85-0.9	19
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9741	High Similarity	NPC310211
0.9741	High Similarity	NPC308137
0.9495	High Similarity	NPC247803
0.9482	High Similarity	NPC249583
0.943	High Similarity	NPC45190
0.94	High Similarity	NPC150239
0.9353	High Similarity	NPC198503
0.9343	High Similarity	NPC116238
0.925	High Similarity	NPC169402
0.9234	High Similarity	NPC6786
0.9184	High Similarity	NPC4687
0.9158	High Similarity	NPC208084
0.9133	High Similarity	NPC300156
0.9113	High Similarity	NPC174760
0.904	High Similarity	NPC86834
0.904	High Similarity	NPC210828
0.9	High Similarity	NPC87413
0.9	High Similarity	NPC23294
0.895	High Similarity	NPC303951
0.8937	High Similarity	NPC179287
0.8916	High Similarity	NPC3207
0.8912	High Similarity	NPC131017
0.8812	High Similarity	NPC187501
0.8756	High Similarity	NPC39679
0.8702	High Similarity	NPC280799
0.8654	High Similarity	NPC225279
0.8651	High Similarity	NPC473187
0.8627	High Similarity	NPC9894
0.8557	High Similarity	NPC162484
0.8544	High Similarity	NPC39500
0.8502	High Similarity	NPC89549
0.8431	Intermediate Similarity	NPC193777
0.8396	Intermediate Similarity	NPC144452
0.8381	Intermediate Similarity	NPC184408
0.8357	Intermediate Similarity	NPC294375
0.835	Intermediate Similarity	NPC70956
0.835	Intermediate Similarity	NPC243834
0.8308	Intermediate Similarity	NPC72211
0.8265	Intermediate Similarity	NPC160381
0.8261	Intermediate Similarity	NPC201697
0.8252	Intermediate Similarity	NPC321428
0.8211	Intermediate Similarity	NPC474688
0.8209	Intermediate Similarity	NPC70259
0.8203	Intermediate Similarity	NPC274640
0.8182	Intermediate Similarity	NPC39370
0.8174	Intermediate Similarity	NPC473186
0.8164	Intermediate Similarity	NPC283117
0.8159	Intermediate Similarity	NPC205934
0.8159	Intermediate Similarity	NPC43787
0.8152	Intermediate Similarity	NPC118228
0.8152	Intermediate Similarity	NPC16066
0.8143	Intermediate Similarity	NPC48353
0.8084	Intermediate Similarity	NPC298436
0.8075	Intermediate Similarity	NPC293151
0.8058	Intermediate Similarity	NPC475085
0.8058	Intermediate Similarity	NPC135887
0.8058	Intermediate Similarity	NPC199277
0.8058	Intermediate Similarity	NPC475112
0.8058	Intermediate Similarity	NPC291535
0.8035	Intermediate Similarity	NPC473188
0.8029	Intermediate Similarity	NPC476106
0.8028	Intermediate Similarity	NPC152768
0.8028	Intermediate Similarity	NPC148183
0.8018	Intermediate Similarity	NPC51388
0.801	Intermediate Similarity	NPC267423
0.799	Intermediate Similarity	NPC153042
0.798	Intermediate Similarity	NPC84478
0.7964	Intermediate Similarity	NPC217176
0.7962	Intermediate Similarity	NPC471304
0.7962	Intermediate Similarity	NPC269367
0.7953	Intermediate Similarity	NPC96321
0.7953	Intermediate Similarity	NPC473041
0.7929	Intermediate Similarity	NPC176127
0.7929	Intermediate Similarity	NPC212535
0.7925	Intermediate Similarity	NPC146418
0.7923	Intermediate Similarity	NPC476044
0.792	Intermediate Similarity	NPC475844
0.791	Intermediate Similarity	NPC242928
0.7909	Intermediate Similarity	NPC478078
0.79	Intermediate Similarity	NPC97746
0.7895	Intermediate Similarity	NPC470930
0.7883	Intermediate Similarity	NPC474701
0.7873	Intermediate Similarity	NPC471762
0.7854	Intermediate Similarity	NPC122436
0.785	Intermediate Similarity	NPC94943
0.7828	Intermediate Similarity	NPC157931
0.7826	Intermediate Similarity	NPC128823
0.78	Intermediate Similarity	NPC190007
0.7793	Intermediate Similarity	NPC194740
0.7778	Intermediate Similarity	NPC88363
0.7763	Intermediate Similarity	NPC60621
0.7762	Intermediate Similarity	NPC134848
0.7752	Intermediate Similarity	NPC473179
0.7742	Intermediate Similarity	NPC305984
0.7738	Intermediate Similarity	NPC21638
0.7721	Intermediate Similarity	NPC264176
0.7719	Intermediate Similarity	NPC168922
0.7717	Intermediate Similarity	NPC472099
0.7713	Intermediate Similarity	NPC252251
0.7713	Intermediate Similarity	NPC66777
0.7706	Intermediate Similarity	NPC303658
0.7703	Intermediate Similarity	NPC329747
0.7678	Intermediate Similarity	NPC223427
0.7672	Intermediate Similarity	NPC1608
0.7667	Intermediate Similarity	NPC88923
0.7667	Intermediate Similarity	NPC315634
0.7667	Intermediate Similarity	NPC100734
0.7664	Intermediate Similarity	NPC209769
0.7664	Intermediate Similarity	NPC325297
0.7653	Intermediate Similarity	NPC183777
0.7647	Intermediate Similarity	NPC246700
0.7644	Intermediate Similarity	NPC260434
0.7644	Intermediate Similarity	NPC477531
0.7636	Intermediate Similarity	NPC86078
0.7634	Intermediate Similarity	NPC311906
0.7632	Intermediate Similarity	NPC235685
0.7629	Intermediate Similarity	NPC475666
0.7626	Intermediate Similarity	NPC131885
0.7623	Intermediate Similarity	NPC470018
0.7619	Intermediate Similarity	NPC188400
0.7615	Intermediate Similarity	NPC170114
0.7612	Intermediate Similarity	NPC474798
0.7611	Intermediate Similarity	NPC475720
0.7611	Intermediate Similarity	NPC474192
0.7608	Intermediate Similarity	NPC306376
0.7605	Intermediate Similarity	NPC284685
0.7602	Intermediate Similarity	NPC477532
0.76	Intermediate Similarity	NPC209174
0.7598	Intermediate Similarity	NPC101350
0.7596	Intermediate Similarity	NPC251090
0.7589	Intermediate Similarity	NPC473185
0.7586	Intermediate Similarity	NPC81939
0.7576	Intermediate Similarity	NPC474409
0.757	Intermediate Similarity	NPC270918
0.7569	Intermediate Similarity	NPC470549
0.7564	Intermediate Similarity	NPC91868
0.7564	Intermediate Similarity	NPC63971
0.7561	Intermediate Similarity	NPC296527
0.7558	Intermediate Similarity	NPC12344
0.7557	Intermediate Similarity	NPC323969
0.7557	Intermediate Similarity	NPC477533
0.7553	Intermediate Similarity	NPC303374
0.7548	Intermediate Similarity	NPC276517
0.7546	Intermediate Similarity	NPC470020
0.7536	Intermediate Similarity	NPC329793
0.7535	Intermediate Similarity	NPC475910
0.7535	Intermediate Similarity	NPC171787
0.7524	Intermediate Similarity	NPC76748
0.7521	Intermediate Similarity	NPC478083
0.7513	Intermediate Similarity	NPC76982
0.7512	Intermediate Similarity	NPC208284
0.7512	Intermediate Similarity	NPC220337
0.7512	Intermediate Similarity	NPC13880
0.7511	Intermediate Similarity	NPC140296
0.7511	Intermediate Similarity	NPC74360
0.75	Intermediate Similarity	NPC473105
0.75	Intermediate Similarity	NPC191489
0.75	Intermediate Similarity	NPC307963
0.75	Intermediate Similarity	NPC232727
0.7489	Intermediate Similarity	NPC475816
0.7489	Intermediate Similarity	NPC475253
0.7488	Intermediate Similarity	NPC92111
0.7478	Intermediate Similarity	NPC184680
0.7477	Intermediate Similarity	NPC285558
0.7476	Intermediate Similarity	NPC128751
0.7467	Intermediate Similarity	NPC34770
0.7467	Intermediate Similarity	NPC227908
0.7465	Intermediate Similarity	NPC199667
0.7465	Intermediate Similarity	NPC11464
0.7457	Intermediate Similarity	NPC477066
0.7456	Intermediate Similarity	NPC132329
0.7455	Intermediate Similarity	NPC330009
0.7455	Intermediate Similarity	NPC205372
0.7455	Intermediate Similarity	NPC469928
0.7453	Intermediate Similarity	NPC11017
0.7453	Intermediate Similarity	NPC176538
0.7446	Intermediate Similarity	NPC470785
0.7446	Intermediate Similarity	NPC470784
0.7443	Intermediate Similarity	NPC478074
0.744	Intermediate Similarity	NPC106833
0.744	Intermediate Similarity	NPC469497
0.7436	Intermediate Similarity	NPC78609
0.7436	Intermediate Similarity	NPC160898
0.7434	Intermediate Similarity	NPC74575
0.7425	Intermediate Similarity	NPC478081
0.7425	Intermediate Similarity	NPC477067
0.7425	Intermediate Similarity	NPC478082
0.7425	Intermediate Similarity	NPC473540
0.7419	Intermediate Similarity	NPC473181
0.7416	Intermediate Similarity	NPC475190
0.7415	Intermediate Similarity	NPC270515
0.7397	Intermediate Similarity	NPC472098
0.7397	Intermediate Similarity	NPC94157
0.7397	Intermediate Similarity	NPC219087
0.7397	Intermediate Similarity	NPC473180
0.7397	Intermediate Similarity	NPC316981
0.7387	Intermediate Similarity	NPC264285
0.7384	Intermediate Similarity	NPC203373
0.738	Intermediate Similarity	NPC49547
0.7373	Intermediate Similarity	NPC17437

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 NPC46561 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	388
0.1-0.2	690
0.2-0.3	1018
0.3-0.4	1509
0.4-0.5	2872
0.5-0.6	1927
0.6-0.7	649
0.7-0.8	95
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
0.8224	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.8122	Intermediate Similarity	NPD5632	Approved
0.7963	Intermediate Similarity	NPD6242	Discontinued
0.7867	Intermediate Similarity	NPD5658	Approved
0.7841	Intermediate Similarity	NPD6790	Phase 1
0.7814	Intermediate Similarity	NPD3257	Approved
0.7719	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD5488	Discontinued
0.7671	Intermediate Similarity	NPD3258	Approved
0.7667	Intermediate Similarity	NPD7803	Approved
0.7656	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3003	Approved
0.7605	Intermediate Similarity	NPD7956	Approved
0.7605	Intermediate Similarity	NPD7955	Approved
0.76	Intermediate Similarity	NPD4952	Phase 3
0.7586	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5482	Discontinued
0.7511	Intermediate Similarity	NPD4328	Approved
0.75	Intermediate Similarity	NPD7708	Approved
0.75	Intermediate Similarity	NPD1038	Approved
0.75	Intermediate Similarity	NPD4373	Phase 2
0.75	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD4418	Discontinued
0.7445	Intermediate Similarity	NPD5479	Discontinued
0.7431	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD1768	Approved
0.738	Intermediate Similarity	NPD4885	Approved
0.7373	Intermediate Similarity	NPD8358	Approved
0.7368	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD3259	Approved
0.7352	Intermediate Similarity	NPD5416	Discontinued
0.7336	Intermediate Similarity	NPD6962	Phase 2
0.733	Intermediate Similarity	NPD5902	Approved
0.733	Intermediate Similarity	NPD5903	Approved
0.732	Intermediate Similarity	NPD8427	Approved
0.732	Intermediate Similarity	NPD8467	Approved
0.732	Intermediate Similarity	NPD8466	Approved
0.732	Intermediate Similarity	NPD8429	Approved
0.732	Intermediate Similarity	NPD8465	Approved
0.732	Intermediate Similarity	NPD8428	Approved
0.7311	Intermediate Similarity	NPD5003	Discontinued
0.7292	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8364	Approved
0.7287	Intermediate Similarity	NPD8363	Approved
0.7273	Intermediate Similarity	NPD8460	Approved
0.7273	Intermediate Similarity	NPD8459	Approved
0.7252	Intermediate Similarity	NPD5293	Phase 2
0.7232	Intermediate Similarity	NPD4429	Discontinued
0.7229	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD5612	Discontinued
0.7213	Intermediate Similarity	NPD6530	Approved
0.7213	Intermediate Similarity	NPD6531	Approved
0.7205	Intermediate Similarity	NPD8426	Approved
0.7205	Intermediate Similarity	NPD8425	Approved
0.7202	Intermediate Similarity	NPD8091	Phase 3
0.7197	Intermediate Similarity	NPD4558	Phase 2
0.719	Intermediate Similarity	NPD2565	Phase 2
0.719	Intermediate Similarity	NPD2564	Approved
0.7183	Intermediate Similarity	NPD5512	Phase 3
0.7169	Intermediate Similarity	NPD5429	Discontinued
0.7169	Intermediate Similarity	NPD1392	Approved
0.7167	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD5450	Discontinued
0.7156	Intermediate Similarity	NPD5901	Discontinued
0.7156	Intermediate Similarity	NPD7395	Discontinued
0.7156	Intermediate Similarity	NPD6138	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2916	Discontinued
0.713	Intermediate Similarity	NPD484	Approved
0.713	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD5164	Discontinued
0.7105	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3986	Discontinued
0.7091	Intermediate Similarity	NPD7222	Phase 2
0.7091	Intermediate Similarity	NPD7453	Approved
0.7091	Intermediate Similarity	NPD7452	Approved
0.7089	Intermediate Similarity	NPD7417	Discontinued
0.7087	Intermediate Similarity	NPD3920	Phase 2
0.7085	Intermediate Similarity	NPD7069	Discontinued
0.7083	Intermediate Similarity	NPD3825	Phase 3
0.708	Intermediate Similarity	NPD3354	Phase 2
0.708	Intermediate Similarity	NPD6985	Discontinued
0.7078	Intermediate Similarity	NPD4795	Phase 2
0.7073	Intermediate Similarity	NPD6228	Discontinued
0.7056	Intermediate Similarity	NPD7994	Phase 2
0.7054	Intermediate Similarity	NPD8102	Discontinued
0.7051	Intermediate Similarity	NPD1740	Approved
0.7051	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1739	Approved
0.7048	Intermediate Similarity	NPD7194	Discontinued
0.7039	Intermediate Similarity	NPD1505	Phase 2
0.7027	Intermediate Similarity	NPD4506	Discontinued
0.7026	Intermediate Similarity	NPD5559	Phase 2
0.7018	Intermediate Similarity	NPD5930	Phase 3
0.6996	Remote Similarity	NPD5022	Discontinued
0.6996	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3006	Discontinued
0.6982	Remote Similarity	NPD2187	Approved
0.6982	Remote Similarity	NPD2189	Approved
0.6979	Remote Similarity	NPD7558	Phase 2
0.6979	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3925	Approved
0.6968	Remote Similarity	NPD8403	Phase 1
0.6962	Remote Similarity	NPD5805	Approved
0.6957	Remote Similarity	NPD6995	Phase 1
0.6939	Remote Similarity	NPD8463	Approved
0.693	Remote Similarity	NPD802	Phase 2
0.6923	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4981	Phase 2
0.692	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6716	Phase 1
0.6916	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5913	Phase 3
0.6906	Remote Similarity	NPD2509	Approved
0.6906	Remote Similarity	NPD8489	Phase 1
0.6906	Remote Similarity	NPD2510	Approved
0.6903	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3945	Discontinued
0.6898	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD3289	Phase 3
0.6895	Remote Similarity	NPD3290	Approved
0.6894	Remote Similarity	NPD1867	Approved
0.6892	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5066	Phase 2
0.6889	Remote Similarity	NPD5067	Phase 2
0.6884	Remote Similarity	NPD5937	Approved
0.6878	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD6176	Phase 1
0.6872	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5532	Phase 2
0.687	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3746	Discontinued
0.6852	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7853	Phase 2
0.6847	Remote Similarity	NPD3947	Discontinued
0.6846	Remote Similarity	NPD6517	Phase 3
0.6838	Remote Similarity	NPD4845	Discontinued
0.6835	Remote Similarity	NPD6494	Phase 2
0.6833	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.683	Remote Similarity	NPD6376	Discontinued
0.6828	Remote Similarity	NPD1322	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6770	Approved
0.6824	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4500	Approved
0.6818	Remote Similarity	NPD4501	Approved
0.6818	Remote Similarity	NPD4600	Approved
0.6818	Remote Similarity	NPD4601	Approved
0.6816	Remote Similarity	NPD5530	Phase 1
0.6814	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6963	Approved
0.6807	Remote Similarity	NPD6964	Approved
0.6804	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2920	Discontinued
0.6802	Remote Similarity	NPD5513	Phase 2
0.6797	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD1325	Approved
0.6796	Remote Similarity	NPD1326	Approved
0.6792	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6787	Remote Similarity	NPD4511	Phase 1
0.6784	Remote Similarity	NPD5866	Approved
0.6784	Remote Similarity	NPD3816	Phase 1
0.6784	Remote Similarity	NPD3815	Phase 1
0.6781	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4948	Discontinued
0.6774	Remote Similarity	NPD4539	Phase 1
0.6773	Remote Similarity	NPD2778	Approved
0.6769	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7689	Approved
0.6757	Remote Similarity	NPD7627	Approved
0.6757	Remote Similarity	NPD7626	Approved
0.6751	Remote Similarity	NPD7688	Phase 1
0.6748	Remote Similarity	NPD2844	Phase 3
0.6746	Remote Similarity	NPD5399	Discovery
0.6741	Remote Similarity	NPD6245	Phase 2
0.674	Remote Similarity	NPD4502	Phase 2
0.6738	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2951	Discontinued
0.6728	Remote Similarity	NPD3924	Approved
0.6728	Remote Similarity	NPD3922	Approved
0.6728	Remote Similarity	NPD3923	Approved
0.6728	Remote Similarity	NPD3921	Approved
0.6723	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3263	Phase 3
0.6723	Remote Similarity	NPD7426	Phase 1
0.6712	Remote Similarity	NPD6550	Discontinued
0.6711	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1926	Approved
0.6696	Remote Similarity	NPD3393	Approved
0.6696	Remote Similarity	NPD3394	Approved
0.6696	Remote Similarity	NPD3389	Approved
0.6694	Remote Similarity	NPD4561	Discontinued
0.6682	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD2779	Approved
0.6681	Remote Similarity	NPD3763	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