NPASS Compound

Structure

NPC470018 OpenBabel07101719522D 21 24 0 0 0 0 0 0 0 0999 V2000 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8965 -1.6241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8388 -2.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2596 -1.1898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1444 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5651 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 -2.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0196 -3.7160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 9 2 0 0 0 0 5 10 2 0 0 0 0 6 7 2 0 0 0 0 6 11 1 0 0 0 0 7 19 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 16 1 0 0 0 0 15 18 1 0 0 0 0 16 19 2 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	276.09
Volume:	284.208
LogP:	3.012
LogD:	2.802
LogS:	-6.115
# Rotatable Bonds:	1
TPSA:	65.21
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.543
Synthetic Accessibility Score:	2.362
Fsp3:	0.059
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.753
MDCK Permeability:	1.4259701856644824e-05
Pgp-inhibitor:	0.244
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.78
Plasma Protein Binding (PPB):	93.20695495605469%
Volume Distribution (VD):	0.979
Pgp-substrate:	4.141045570373535%

ADMET: Metabolism

CYP1A2-inhibitor:	0.955
CYP1A2-substrate:	0.878
CYP2C19-inhibitor:	0.451
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.693
CYP2C9-substrate:	0.73
CYP2D6-inhibitor:	0.393
CYP2D6-substrate:	0.636
CYP3A4-inhibitor:	0.555
CYP3A4-substrate:	0.159

ADMET: Excretion

Clearance (CL):	3.594
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.963
AMES Toxicity:	0.813
Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.267
Carcinogencity:	0.942
Eye Corrosion:	0.004
Eye Irritation:	0.917
Respiratory Toxicity:	0.912

Download Data

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

Natural Product: NPC470018

Natural Product ID:	NPC470018
*Common Name:**	DVXISAIJCXZAQX-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	5-Methoxy-4-amino-1-azabenzanthrone
Standard InCHIKey:	DVXISAIJCXZAQX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H12N2O2/c1-21-13-8-12-14-11(15(13)18)6-7-19-16(14)9-4-2-3-5-10(9)17(12)20/h2-8H,18H2,1H3
SMILES:	COC1=C(C2=C3C(=C1)C(=O)C4=CC=CC=C4C3=NC=C2)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1651053
PubChem CID:	50901246
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003018] Isoaporphines [CHEMONTID:0004118] Oxoisoaporphines

*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
NPO21789	Sciadotenia toxifera	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20961068]
NPO21789	Sciadotenia toxifera	Species	Menispermaceae	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	12
Others	1

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	3
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	2090.0	nM	PMID[536632]
NPT1506	Cell Line	SK-MES-1	Homo sapiens	IC50	>	2090.0	nM	PMID[536632]
NPT1505	Cell Line	J82	Homo sapiens	IC50	>	2090.0	nM	PMID[536632]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	37000.0	nM	PMID[536633]
NPT1505	Cell Line	J82	Homo sapiens	IC50	>	100000.0	nM	PMID[536634]
NPT1506	Cell Line	SK-MES-1	Homo sapiens	IC50	>	100000.0	nM	PMID[536634]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	100000.0	nM	PMID[536634]
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	37000.0	nM	PMID[536634]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	2090.0	nM	PMID[536632]
NPT2	Others	Unspecified		Ratio IC50	=	0.37	n.a.	PMID[536633]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	100000.0	nM	PMID[536633]

☑ 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 NPC470018 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	634
0.1-0.2	3662
0.2-0.3	13030
0.3-0.4	4472
0.4-0.5	15021
0.5-0.6	3583
0.6-0.7	1827
0.7-0.8	431
0.8-0.85	27
0.85-0.9	3
0.9-0.95	4
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9754	High Similarity	NPC74575
0.9565	High Similarity	NPC49547
0.9429	High Similarity	NPC470017
0.93	High Similarity	NPC470020
0.9202	High Similarity	NPC470022
0.9124	High Similarity	NPC208522
0.9	High Similarity	NPC270515
0.8649	High Similarity	NPC142385
0.8598	High Similarity	NPC322482
0.8551	High Similarity	NPC210434
0.8534	High Similarity	NPC132385
0.852	High Similarity	NPC72905
0.8507	High Similarity	NPC472061
0.8502	High Similarity	NPC137353
0.8402	Intermediate Similarity	NPC24019
0.838	Intermediate Similarity	NPC216612
0.838	Intermediate Similarity	NPC144452
0.8372	Intermediate Similarity	NPC225279
0.8288	Intermediate Similarity	NPC22481
0.8281	Intermediate Similarity	NPC474688
0.8235	Intermediate Similarity	NPC278525
0.8224	Intermediate Similarity	NPC146976
0.819	Intermediate Similarity	NPC274640
0.8178	Intermediate Similarity	NPC189903
0.8178	Intermediate Similarity	NPC182907
0.8178	Intermediate Similarity	NPC236668
0.817	Intermediate Similarity	NPC90875
0.817	Intermediate Similarity	NPC39370
0.8161	Intermediate Similarity	NPC233334
0.8133	Intermediate Similarity	NPC108342
0.8093	Intermediate Similarity	NPC39500
0.8089	Intermediate Similarity	NPC253675
0.8084	Intermediate Similarity	NPC187501
0.808	Intermediate Similarity	NPC473186
0.8073	Intermediate Similarity	NPC208084
0.8	Intermediate Similarity	NPC15406
0.8	Intermediate Similarity	NPC208284
0.7991	Intermediate Similarity	NPC475844
0.7982	Intermediate Similarity	NPC166722
0.7965	Intermediate Similarity	NPC124313
0.7965	Intermediate Similarity	NPC329631
0.7957	Intermediate Similarity	NPC207283
0.7957	Intermediate Similarity	NPC84164
0.7945	Intermediate Similarity	NPC184408
0.7928	Intermediate Similarity	NPC51388
0.7913	Intermediate Similarity	NPC210296
0.7876	Intermediate Similarity	NPC474701
0.787	Intermediate Similarity	NPC41501
0.785	Intermediate Similarity	NPC300156
0.785	Intermediate Similarity	NPC45190
0.7838	Intermediate Similarity	NPC280799
0.7828	Intermediate Similarity	NPC17565
0.7814	Intermediate Similarity	NPC193238
0.7814	Intermediate Similarity	NPC249583
0.7814	Intermediate Similarity	NPC4687
0.7812	Intermediate Similarity	NPC179287
0.7797	Intermediate Similarity	NPC477112
0.7797	Intermediate Similarity	NPC183537
0.7788	Intermediate Similarity	NPC188420
0.7783	Intermediate Similarity	NPC235685
0.7768	Intermediate Similarity	NPC122436
0.7763	Intermediate Similarity	NPC162530
0.7749	Intermediate Similarity	NPC101350
0.7741	Intermediate Similarity	NPC53534
0.7738	Intermediate Similarity	NPC293151
0.7722	Intermediate Similarity	NPC77878
0.7717	Intermediate Similarity	NPC251160
0.7706	Intermediate Similarity	NPC199667
0.7703	Intermediate Similarity	NPC195268
0.7703	Intermediate Similarity	NPC133140
0.7689	Intermediate Similarity	NPC65277
0.7682	Intermediate Similarity	NPC324361
0.7682	Intermediate Similarity	NPC149471
0.7682	Intermediate Similarity	NPC271215
0.7671	Intermediate Similarity	NPC87413
0.7661	Intermediate Similarity	NPC473181
0.7653	Intermediate Similarity	NPC476582
0.7653	Intermediate Similarity	NPC4071
0.7653	Intermediate Similarity	NPC476578
0.7647	Intermediate Similarity	NPC235076
0.7647	Intermediate Similarity	NPC118228
0.7642	Intermediate Similarity	NPC260434
0.7636	Intermediate Similarity	NPC308137
0.7636	Intermediate Similarity	NPC310211
0.7636	Intermediate Similarity	NPC474428
0.7623	Intermediate Similarity	NPC46561
0.7617	Intermediate Similarity	NPC234197
0.76	Intermediate Similarity	NPC60621
0.7594	Intermediate Similarity	NPC470023
0.7593	Intermediate Similarity	NPC245816
0.7593	Intermediate Similarity	NPC476138
0.7591	Intermediate Similarity	NPC220337
0.7588	Intermediate Similarity	NPC257851
0.7588	Intermediate Similarity	NPC478078
0.7578	Intermediate Similarity	NPC169402
0.7568	Intermediate Similarity	NPC116238
0.7568	Intermediate Similarity	NPC237740
0.7558	Intermediate Similarity	NPC476581
0.7558	Intermediate Similarity	NPC285558
0.7558	Intermediate Similarity	NPC327592
0.7558	Intermediate Similarity	NPC16452
0.7558	Intermediate Similarity	NPC36229
0.7557	Intermediate Similarity	NPC94157
0.7557	Intermediate Similarity	NPC473180
0.7555	Intermediate Similarity	NPC246381
0.7554	Intermediate Similarity	NPC6786
0.7551	Intermediate Similarity	NPC152620
0.7545	Intermediate Similarity	NPC204446
0.7545	Intermediate Similarity	NPC23614
0.7545	Intermediate Similarity	NPC309845
0.7545	Intermediate Similarity	NPC100079
0.7545	Intermediate Similarity	NPC471304
0.7534	Intermediate Similarity	NPC82548
0.7532	Intermediate Similarity	NPC148889
0.7523	Intermediate Similarity	NPC317373
0.7522	Intermediate Similarity	NPC198503
0.7512	Intermediate Similarity	NPC475774
0.7511	Intermediate Similarity	NPC46451
0.75	Intermediate Similarity	NPC174758
0.7488	Intermediate Similarity	NPC287437
0.7478	Intermediate Similarity	NPC472099
0.7478	Intermediate Similarity	NPC150239
0.7477	Intermediate Similarity	NPC264176
0.7467	Intermediate Similarity	NPC247803
0.7458	Intermediate Similarity	NPC119134
0.7455	Intermediate Similarity	NPC39679
0.7454	Intermediate Similarity	NPC477019
0.7449	Intermediate Similarity	NPC478083
0.7444	Intermediate Similarity	NPC476287
0.7435	Intermediate Similarity	NPC157931
0.7432	Intermediate Similarity	NPC9894
0.7422	Intermediate Similarity	NPC473513
0.7419	Intermediate Similarity	NPC31930
0.7417	Intermediate Similarity	NPC91868
0.7417	Intermediate Similarity	NPC63971
0.7412	Intermediate Similarity	NPC118121
0.7412	Intermediate Similarity	NPC122463
0.7409	Intermediate Similarity	NPC222561
0.7409	Intermediate Similarity	NPC283117
0.7409	Intermediate Similarity	NPC308943
0.7409	Intermediate Similarity	NPC313189
0.7403	Intermediate Similarity	NPC471762
0.7401	Intermediate Similarity	NPC174760
0.7401	Intermediate Similarity	NPC323969
0.7399	Intermediate Similarity	NPC472098
0.7395	Intermediate Similarity	NPC470021
0.7393	Intermediate Similarity	NPC242928
0.7389	Intermediate Similarity	NPC473041
0.7389	Intermediate Similarity	NPC96321
0.7389	Intermediate Similarity	NPC173080
0.7387	Intermediate Similarity	NPC123976
0.7387	Intermediate Similarity	NPC167860
0.7387	Intermediate Similarity	NPC290689
0.7383	Intermediate Similarity	NPC146724
0.7373	Intermediate Similarity	NPC176538
0.7364	Intermediate Similarity	NPC470164
0.7364	Intermediate Similarity	NPC323345
0.7357	Intermediate Similarity	NPC288987
0.7354	Intermediate Similarity	NPC146418
0.7354	Intermediate Similarity	NPC294375
0.7342	Intermediate Similarity	NPC185782
0.7339	Intermediate Similarity	NPC232727
0.7331	Intermediate Similarity	NPC15801
0.733	Intermediate Similarity	NPC84347
0.733	Intermediate Similarity	NPC135549
0.7325	Intermediate Similarity	NPC276657
0.7325	Intermediate Similarity	NPC132642
0.7321	Intermediate Similarity	NPC118940
0.7321	Intermediate Similarity	NPC296482
0.7321	Intermediate Similarity	NPC202605
0.7321	Intermediate Similarity	NPC202768
0.7321	Intermediate Similarity	NPC318299
0.7321	Intermediate Similarity	NPC38237
0.7321	Intermediate Similarity	NPC112206
0.7321	Intermediate Similarity	NPC26679
0.7321	Intermediate Similarity	NPC53069
0.7315	Intermediate Similarity	NPC90229
0.7311	Intermediate Similarity	NPC296527
0.7306	Intermediate Similarity	NPC328318
0.7306	Intermediate Similarity	NPC328596
0.7301	Intermediate Similarity	NPC274982
0.7299	Intermediate Similarity	NPC160381
0.7297	Intermediate Similarity	NPC477111
0.7297	Intermediate Similarity	NPC287208
0.7294	Intermediate Similarity	NPC315957
0.7289	Intermediate Similarity	NPC317752
0.7284	Intermediate Similarity	NPC473185
0.7277	Intermediate Similarity	NPC76748
0.7265	Intermediate Similarity	NPC174672
0.7265	Intermediate Similarity	NPC478045
0.7256	Intermediate Similarity	NPC307963
0.7256	Intermediate Similarity	NPC230403
0.7253	Intermediate Similarity	NPC66777
0.7248	Intermediate Similarity	NPC128823
0.7244	Intermediate Similarity	NPC171409
0.7244	Intermediate Similarity	NPC96405
0.7243	Intermediate Similarity	NPC92111
0.7237	Intermediate Similarity	NPC131885
0.7235	Intermediate Similarity	NPC224928
0.7234	Intermediate Similarity	NPC469554

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 NPC470018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	680
0.2-0.3	950
0.3-0.4	1339
0.4-0.5	2531
0.5-0.6	2161
0.6-0.7	1002
0.7-0.8	134
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
0.8451	Intermediate Similarity	NPD4429	Discontinued
0.8072	Intermediate Similarity	NPD5022	Discontinued
0.8037	Intermediate Similarity	NPD6242	Discontinued
0.7991	Intermediate Similarity	NPD6790	Phase 1
0.7991	Intermediate Similarity	NPD5801	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD7395	Discontinued
0.7883	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7782	Intermediate Similarity	NPD8091	Phase 3
0.7778	Intermediate Similarity	NPD5488	Discontinued
0.7746	Intermediate Similarity	NPD7925	Phase 2
0.7746	Intermediate Similarity	NPD7924	Phase 2
0.7735	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7731	Intermediate Similarity	NPD5429	Discontinued
0.7725	Intermediate Similarity	NPD6716	Phase 1
0.7717	Intermediate Similarity	NPD7069	Discontinued
0.7703	Intermediate Similarity	NPD3924	Approved
0.7703	Intermediate Similarity	NPD3922	Approved
0.7703	Intermediate Similarity	NPD3923	Approved
0.7703	Intermediate Similarity	NPD3921	Approved
0.7696	Intermediate Similarity	NPD7467	Discontinued
0.7657	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7010	Phase 3
0.7531	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD3006	Discontinued
0.7511	Intermediate Similarity	NPD3763	Approved
0.75	Intermediate Similarity	NPD6494	Phase 2
0.7489	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5482	Discontinued
0.7446	Intermediate Similarity	NPD5479	Discontinued
0.7436	Intermediate Similarity	NPD5891	Approved
0.7432	Intermediate Similarity	NPD4502	Phase 2
0.7429	Intermediate Similarity	NPD6531	Approved
0.7429	Intermediate Similarity	NPD6530	Approved
0.7424	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4795	Phase 2
0.7389	Intermediate Similarity	NPD6568	Discontinued
0.7371	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6569	Phase 2
0.7364	Intermediate Similarity	NPD5530	Phase 1
0.7336	Intermediate Similarity	NPD1856	Discontinued
0.7336	Intermediate Similarity	NPD6995	Phase 1
0.7333	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4889	Approved
0.733	Intermediate Similarity	NPD7222	Phase 2
0.7328	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3815	Phase 1
0.7321	Intermediate Similarity	NPD3816	Phase 1
0.7318	Intermediate Similarity	NPD5901	Discontinued
0.7316	Intermediate Similarity	NPD7426	Phase 1
0.7294	Intermediate Similarity	NPD1739	Approved
0.7294	Intermediate Similarity	NPD1740	Approved
0.7289	Intermediate Similarity	NPD3945	Discontinued
0.7284	Intermediate Similarity	NPD7994	Phase 2
0.7284	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD5416	Discontinued
0.7277	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4558	Phase 2
0.7269	Intermediate Similarity	NPD5512	Phase 3
0.7265	Intermediate Similarity	NPD7688	Phase 1
0.726	Intermediate Similarity	NPD3920	Phase 2
0.7257	Intermediate Similarity	NPD3257	Approved
0.7256	Intermediate Similarity	NPD1038	Approved
0.7256	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7249	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4548	Discontinued
0.724	Intermediate Similarity	NPD3947	Discontinued
0.7238	Intermediate Similarity	NPD7417	Discontinued
0.7237	Intermediate Similarity	NPD3354	Phase 2
0.7222	Intermediate Similarity	NPD4952	Phase 3
0.7218	Intermediate Similarity	NPD7708	Approved
0.721	Intermediate Similarity	NPD3259	Approved
0.721	Intermediate Similarity	NPD4845	Discontinued
0.72	Intermediate Similarity	NPD5475	Discontinued
0.7197	Intermediate Similarity	NPD8016	Phase 3
0.7197	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD5513	Phase 2
0.719	Intermediate Similarity	NPD8100	Phase 3
0.7189	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD3477	Phase 2
0.7186	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5559	Phase 2
0.7173	Intermediate Similarity	NPD6963	Approved
0.7173	Intermediate Similarity	NPD2951	Discontinued
0.7173	Intermediate Similarity	NPD6964	Approved
0.7172	Intermediate Similarity	NPD3809	Discontinued
0.7169	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD5999	Phase 2
0.7169	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4035	Approved
0.7162	Intermediate Similarity	NPD6987	Phase 1
0.7162	Intermediate Similarity	NPD4039	Approved
0.7162	Intermediate Similarity	NPD31	Approved
0.7162	Intermediate Similarity	NPD4037	Approved
0.7162	Intermediate Similarity	NPD4038	Approved
0.7162	Intermediate Similarity	NPD4034	Approved
0.7162	Intermediate Similarity	NPD4033	Approved
0.7162	Intermediate Similarity	NPD32	Approved
0.7162	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4122	Approved
0.7162	Intermediate Similarity	NPD4036	Approved
0.7162	Intermediate Similarity	NPD5632	Approved
0.7161	Intermediate Similarity	NPD3746	Discontinued
0.7161	Intermediate Similarity	NPD4885	Approved
0.7143	Intermediate Similarity	NPD4418	Discontinued
0.7143	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7131	Intermediate Similarity	NPD4373	Phase 2
0.7131	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7404	Approved
0.713	Intermediate Similarity	NPD3258	Approved
0.7125	Intermediate Similarity	NPD7885	Phase 2
0.7125	Intermediate Similarity	NPD7886	Phase 2
0.7124	Intermediate Similarity	NPD5939	Approved
0.7124	Intermediate Similarity	NPD5936	Approved
0.7123	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD1867	Approved
0.7118	Intermediate Similarity	NPD3326	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD6281	Approved
0.711	Intermediate Similarity	NPD6550	Discontinued
0.7103	Intermediate Similarity	NPD5450	Discontinued
0.7103	Intermediate Similarity	NPD7803	Approved
0.7102	Intermediate Similarity	NPD8101	Phase 3
0.71	Intermediate Similarity	NPD5850	Phase 3
0.7098	Intermediate Similarity	NPD7453	Approved
0.7098	Intermediate Similarity	NPD7452	Approved
0.7094	Intermediate Similarity	NPD9705	Discontinued
0.7094	Intermediate Similarity	NPD112	Approved
0.7087	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD8463	Approved
0.708	Intermediate Similarity	NPD1166	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5612	Discontinued
0.7072	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD7853	Phase 2
0.7067	Intermediate Similarity	NPD5658	Approved
0.7062	Intermediate Similarity	NPD6293	Clinical (unspecified phase)
0.7061	Intermediate Similarity	NPD8102	Discontinued
0.7059	Intermediate Similarity	NPD3290	Approved
0.7059	Intermediate Similarity	NPD3289	Phase 3
0.7054	Intermediate Similarity	NPD5601	Phase 2
0.7054	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3925	Approved
0.7049	Intermediate Similarity	NPD6460	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7927	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7955	Approved
0.704	Intermediate Similarity	NPD7956	Approved
0.7035	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7555	Discontinued
0.7028	Intermediate Similarity	NPD6961	Discontinued
0.7023	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8358	Approved
0.7019	Intermediate Similarity	NPD1078	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5866	Approved
0.7016	Intermediate Similarity	NPD2311	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2177	Approved
0.7014	Intermediate Similarity	NPD3825	Phase 3
0.7014	Intermediate Similarity	NPD2175	Phase 3
0.7014	Intermediate Similarity	NPD2176	Approved
0.7012	Intermediate Similarity	NPD6228	Discontinued
0.7012	Intermediate Similarity	NPD5867	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6230	Discontinued
0.7005	Intermediate Similarity	NPD2336	Approved
0.7004	Intermediate Similarity	NPD6969	Phase 2
0.7004	Intermediate Similarity	NPD6204	Clinical (unspecified phase)
0.7004	Intermediate Similarity	NPD6968	Phase 2
0.7	Intermediate Similarity	NPD3394	Approved
0.7	Intermediate Similarity	NPD3389	Approved
0.7	Intermediate Similarity	NPD5469	Phase 3
0.7	Intermediate Similarity	NPD3393	Approved
0.6996	Remote Similarity	NPD6456	Discontinued
0.6996	Remote Similarity	NPD4894	Discontinued
0.6996	Remote Similarity	NPD4881	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD1483	Discontinued
0.6996	Remote Similarity	NPD4923	Phase 1
0.6996	Remote Similarity	NPD5147	Discontinued
0.6995	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD2510	Approved
0.6991	Remote Similarity	NPD2509	Approved
0.6991	Remote Similarity	NPD2916	Discontinued
0.6987	Remote Similarity	NPD3794	Approved
0.6987	Remote Similarity	NPD4356	Discontinued
0.6987	Remote Similarity	NPD3795	Approved
0.6987	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD484	Approved
0.6982	Remote Similarity	NPD6479	Discontinued
0.6974	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4372	Phase 1
0.6971	Remote Similarity	NPD5805	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