NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	249.1
Volume:	249.267
LogP:	1.387
LogD:	1.599
LogS:	-2.47
# Rotatable Bonds:	4
TPSA:	60.55
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.895
Synthetic Accessibility Score:	2.225
Fsp3:	0.308
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.87
MDCK Permeability:	9.287735338148195e-06
Pgp-inhibitor:	0.025
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.518

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.69
Plasma Protein Binding (PPB):	60.885169982910156%
Volume Distribution (VD):	0.628
Pgp-substrate:	18.106264114379883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.325
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.099
CYP3A4-substrate:	0.361

ADMET: Excretion

Clearance (CL):	5.588
Half-life (T1/2):	0.735

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.426
Drug-inuced Liver Injury (DILI):	0.755
AMES Toxicity:	0.73
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.08
Skin Sensitization:	0.084
Carcinogencity:	0.345
Eye Corrosion:	0.003
Eye Irritation:	0.222
Respiratory Toxicity:	0.639

Download Data

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

Natural Product: NPC62069

Natural Product ID:	NPC62069
*Common Name:**	Semecarpifoline
IUPAC Name:	4,7-dimethoxy-3-(methoxymethyl)-1H-quinolin-2-one
Synonyms:	Semecarpifoline
Standard InCHIKey:	WBHOECNXRGZKAH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H15NO4/c1-16-7-10-12(18-3)9-5-4-8(17-2)6-11(9)14-13(10)15/h4-6H,7H2,1-3H3,(H,14,15)
SMILES:	COCc1c(O)nc2c(c1OC)ccc(c2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505570
PubChem CID:	10857848
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575945]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18163582]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20244	Melicope semecarpifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20244	Melicope semecarpifolia	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
Others	4

Activity Type	# Activity
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	85.8	%	PMID[546273]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	81.0	%	PMID[546273]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	82.7	%	PMID[546273]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	88.8	%	PMID[546273]

☑ 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 NPC62069 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	450
0.1-0.2	2995
0.2-0.3	13307
0.3-0.4	3728
0.4-0.5	12804
0.5-0.6	7455
0.6-0.7	1544
0.7-0.8	377
0.8-0.85	27
0.85-0.9	8
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9107	High Similarity	NPC283152
0.8935	High Similarity	NPC288943
0.8693	High Similarity	NPC66083
0.8689	High Similarity	NPC66815
0.8686	High Similarity	NPC42591
0.8659	High Similarity	NPC279401
0.8659	High Similarity	NPC79293
0.8598	High Similarity	NPC26872
0.8547	High Similarity	NPC469390
0.8443	Intermediate Similarity	NPC26850
0.8427	Intermediate Similarity	NPC61350
0.8294	Intermediate Similarity	NPC177404
0.8216	Intermediate Similarity	NPC243834
0.8216	Intermediate Similarity	NPC224928
0.8216	Intermediate Similarity	NPC70956
0.8201	Intermediate Similarity	NPC164374
0.8201	Intermediate Similarity	NPC137929
0.8197	Intermediate Similarity	NPC141915
0.8197	Intermediate Similarity	NPC114335
0.8197	Intermediate Similarity	NPC280964
0.8182	Intermediate Similarity	NPC161292
0.816	Intermediate Similarity	NPC60553
0.8111	Intermediate Similarity	NPC84478
0.8093	Intermediate Similarity	NPC203168
0.8083	Intermediate Similarity	NPC219664
0.8023	Intermediate Similarity	NPC312872
0.8011	Intermediate Similarity	NPC320394
0.801	Intermediate Similarity	NPC97746
0.8	Intermediate Similarity	NPC135887
0.8	Intermediate Similarity	NPC199277
0.7988	Intermediate Similarity	NPC153769
0.797	Intermediate Similarity	NPC200888
0.7958	Intermediate Similarity	NPC469440
0.7938	Intermediate Similarity	NPC469589
0.7931	Intermediate Similarity	NPC118511
0.7906	Intermediate Similarity	NPC475085
0.7906	Intermediate Similarity	NPC475112
0.7906	Intermediate Similarity	NPC291535
0.7889	Intermediate Similarity	NPC72980
0.7889	Intermediate Similarity	NPC469594
0.7887	Intermediate Similarity	NPC470931
0.7887	Intermediate Similarity	NPC475910
0.7844	Intermediate Similarity	NPC471598
0.7835	Intermediate Similarity	NPC193777
0.7826	Intermediate Similarity	NPC204385
0.7819	Intermediate Similarity	NPC131017
0.7818	Intermediate Similarity	NPC280853
0.7784	Intermediate Similarity	NPC476106
0.7784	Intermediate Similarity	NPC472111
0.7784	Intermediate Similarity	NPC304183
0.7778	Intermediate Similarity	NPC473053
0.7778	Intermediate Similarity	NPC469592
0.7778	Intermediate Similarity	NPC471080
0.7772	Intermediate Similarity	NPC223427
0.7771	Intermediate Similarity	NPC285016
0.7771	Intermediate Similarity	NPC245657
0.7766	Intermediate Similarity	NPC289786
0.7765	Intermediate Similarity	NPC474409
0.7761	Intermediate Similarity	NPC298436
0.7761	Intermediate Similarity	NPC148409
0.776	Intermediate Similarity	NPC212535
0.7758	Intermediate Similarity	NPC471596
0.7749	Intermediate Similarity	NPC280714
0.7747	Intermediate Similarity	NPC168486
0.7747	Intermediate Similarity	NPC222592
0.7744	Intermediate Similarity	NPC474595
0.773	Intermediate Similarity	NPC194040
0.7711	Intermediate Similarity	NPC473822
0.7708	Intermediate Similarity	NPC329747
0.7705	Intermediate Similarity	NPC206201
0.7696	Intermediate Similarity	NPC72211
0.7688	Intermediate Similarity	NPC474594
0.7676	Intermediate Similarity	NPC94943
0.7673	Intermediate Similarity	NPC213530
0.7673	Intermediate Similarity	NPC193267
0.7668	Intermediate Similarity	NPC232727
0.7659	Intermediate Similarity	NPC473449
0.765	Intermediate Similarity	NPC478032
0.7635	Intermediate Similarity	NPC174049
0.7634	Intermediate Similarity	NPC314573
0.7622	Intermediate Similarity	NPC190007
0.7592	Intermediate Similarity	NPC70259
0.7588	Intermediate Similarity	NPC87413
0.7582	Intermediate Similarity	NPC194724
0.7568	Intermediate Similarity	NPC176127
0.7565	Intermediate Similarity	NPC128823
0.7553	Intermediate Similarity	NPC110741
0.7551	Intermediate Similarity	NPC165349
0.7551	Intermediate Similarity	NPC118832
0.7551	Intermediate Similarity	NPC285558
0.7551	Intermediate Similarity	NPC47059
0.7551	Intermediate Similarity	NPC264166
0.7551	Intermediate Similarity	NPC274291
0.7551	Intermediate Similarity	NPC329708
0.755	Intermediate Similarity	NPC48353
0.755	Intermediate Similarity	NPC112206
0.755	Intermediate Similarity	NPC202605
0.7549	Intermediate Similarity	NPC174760
0.7545	Intermediate Similarity	NPC471594
0.7539	Intermediate Similarity	NPC205934
0.7539	Intermediate Similarity	NPC43787
0.7538	Intermediate Similarity	NPC295898
0.7537	Intermediate Similarity	NPC247803
0.7526	Intermediate Similarity	NPC11017
0.7514	Intermediate Similarity	NPC285635
0.75	Intermediate Similarity	NPC162484
0.75	Intermediate Similarity	NPC44161
0.75	Intermediate Similarity	NPC146418
0.75	Intermediate Similarity	NPC46580
0.75	Intermediate Similarity	NPC251090
0.7487	Intermediate Similarity	NPC174758
0.7487	Intermediate Similarity	NPC470586
0.7476	Intermediate Similarity	NPC122463
0.7475	Intermediate Similarity	NPC249583
0.7463	Intermediate Similarity	NPC128115
0.7463	Intermediate Similarity	NPC264176
0.7463	Intermediate Similarity	NPC316981
0.7463	Intermediate Similarity	NPC150239
0.7451	Intermediate Similarity	NPC173080
0.745	Intermediate Similarity	NPC11464
0.7446	Intermediate Similarity	NPC96890
0.7437	Intermediate Similarity	NPC39679
0.7436	Intermediate Similarity	NPC315957
0.7435	Intermediate Similarity	NPC195268
0.7435	Intermediate Similarity	NPC133140
0.743	Intermediate Similarity	NPC473057
0.7427	Intermediate Similarity	NPC477532
0.7419	Intermediate Similarity	NPC144114
0.7415	Intermediate Similarity	NPC473179
0.7411	Intermediate Similarity	NPC317572
0.7409	Intermediate Similarity	NPC13880
0.7406	Intermediate Similarity	NPC473105
0.7404	Intermediate Similarity	NPC21638
0.74	Intermediate Similarity	NPC209769
0.7398	Intermediate Similarity	NPC267423
0.7398	Intermediate Similarity	NPC476044
0.7393	Intermediate Similarity	NPC217176
0.7387	Intermediate Similarity	NPC4687
0.7387	Intermediate Similarity	NPC193238
0.7379	Intermediate Similarity	NPC469439
0.7374	Intermediate Similarity	NPC36229
0.7374	Intermediate Similarity	NPC16452
0.7374	Intermediate Similarity	NPC476581
0.7371	Intermediate Similarity	NPC153042
0.7363	Intermediate Similarity	NPC167860
0.7363	Intermediate Similarity	NPC269367
0.7363	Intermediate Similarity	NPC123976
0.736	Intermediate Similarity	NPC84508
0.7353	Intermediate Similarity	NPC3207
0.7353	Intermediate Similarity	NPC470799
0.7353	Intermediate Similarity	NPC8022
0.7348	Intermediate Similarity	NPC108469
0.7347	Intermediate Similarity	NPC234197
0.7345	Intermediate Similarity	NPC10875
0.7345	Intermediate Similarity	NPC10730
0.7343	Intermediate Similarity	NPC60621
0.7343	Intermediate Similarity	NPC310118
0.7337	Intermediate Similarity	NPC303225
0.7337	Intermediate Similarity	NPC474145
0.7337	Intermediate Similarity	NPC475841
0.7333	Intermediate Similarity	NPC110151
0.7333	Intermediate Similarity	NPC306376
0.7326	Intermediate Similarity	NPC118776
0.7322	Intermediate Similarity	NPC258773
0.7321	Intermediate Similarity	NPC179287
0.7317	Intermediate Similarity	NPC169402
0.7313	Intermediate Similarity	NPC174672
0.7312	Intermediate Similarity	NPC88363
0.7311	Intermediate Similarity	NPC201508
0.7308	Intermediate Similarity	NPC1527
0.7306	Intermediate Similarity	NPC307963
0.7304	Intermediate Similarity	NPC116238
0.7299	Intermediate Similarity	NPC476997
0.7297	Intermediate Similarity	NPC168153
0.7296	Intermediate Similarity	NPC476578
0.7296	Intermediate Similarity	NPC4071
0.7296	Intermediate Similarity	NPC476582
0.7296	Intermediate Similarity	NPC18487
0.7294	Intermediate Similarity	NPC188400
0.7291	Intermediate Similarity	NPC310211
0.7291	Intermediate Similarity	NPC308137
0.7282	Intermediate Similarity	NPC267928
0.7282	Intermediate Similarity	NPC303658
0.7278	Intermediate Similarity	NPC315214
0.7278	Intermediate Similarity	NPC47298
0.7277	Intermediate Similarity	NPC242928
0.7268	Intermediate Similarity	NPC148183
0.7268	Intermediate Similarity	NPC126481
0.7268	Intermediate Similarity	NPC152768
0.7268	Intermediate Similarity	NPC274982
0.7264	Intermediate Similarity	NPC476998
0.7264	Intermediate Similarity	NPC476996
0.7255	Intermediate Similarity	NPC266931
0.7243	Intermediate Similarity	NPC255800
0.7243	Intermediate Similarity	NPC96584
0.7238	Intermediate Similarity	NPC159319
0.7238	Intermediate Similarity	NPC32028
0.7236	Intermediate Similarity	NPC53144
0.7234	Intermediate Similarity	NPC470474
0.7234	Intermediate Similarity	NPC219963

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 NPC62069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	700
0.2-0.3	877
0.3-0.4	1302
0.4-0.5	2811
0.5-0.6	2317
0.6-0.7	733
0.7-0.8	111
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8161	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD4204	Approved
0.8101	Intermediate Similarity	NPD4203	Approved
0.8011	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD6590	Discontinued
0.779	Intermediate Similarity	NPD3920	Phase 2
0.779	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6550	Discontinued
0.7766	Intermediate Similarity	NPD4502	Phase 2
0.7744	Intermediate Similarity	NPD7222	Phase 2
0.7725	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD3386	Phase 2
0.7697	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD5512	Phase 3
0.7565	Intermediate Similarity	NPD1768	Approved
0.7563	Intermediate Similarity	NPD7453	Approved
0.7563	Intermediate Similarity	NPD7452	Approved
0.7551	Intermediate Similarity	NPD4035	Approved
0.7551	Intermediate Similarity	NPD4122	Approved
0.7551	Intermediate Similarity	NPD4037	Approved
0.7551	Intermediate Similarity	NPD4038	Approved
0.7551	Intermediate Similarity	NPD4033	Approved
0.7551	Intermediate Similarity	NPD4039	Approved
0.7551	Intermediate Similarity	NPD32	Approved
0.7551	Intermediate Similarity	NPD31	Approved
0.7551	Intermediate Similarity	NPD4034	Approved
0.7551	Intermediate Similarity	NPD4036	Approved
0.754	Intermediate Similarity	NPD4375	Approved
0.7538	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5658	Approved
0.7513	Intermediate Similarity	NPD3003	Approved
0.75	Intermediate Similarity	NPD2383	Phase 1
0.7488	Intermediate Similarity	NPD6494	Phase 2
0.7474	Intermediate Similarity	NPD2175	Phase 3
0.7474	Intermediate Similarity	NPD2177	Approved
0.7474	Intermediate Similarity	NPD2176	Approved
0.7461	Intermediate Similarity	NPD6988	Phase 1
0.7461	Intermediate Similarity	NPD1622	Discontinued
0.7448	Intermediate Similarity	NPD4418	Discontinued
0.7446	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD6159	Phase 2
0.7436	Intermediate Similarity	NPD1740	Approved
0.7436	Intermediate Similarity	NPD1739	Approved
0.7435	Intermediate Similarity	NPD3924	Approved
0.7435	Intermediate Similarity	NPD3923	Approved
0.7435	Intermediate Similarity	NPD6569	Phase 2
0.7435	Intermediate Similarity	NPD3922	Approved
0.7435	Intermediate Similarity	NPD3921	Approved
0.7424	Intermediate Similarity	NPD5530	Phase 1
0.7419	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3037	Phase 1
0.7406	Intermediate Similarity	NPD7558	Phase 2
0.7404	Intermediate Similarity	NPD6246	Approved
0.7394	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD4795	Phase 2
0.7358	Intermediate Similarity	NPD3396	Approved
0.7358	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD3395	Approved
0.7333	Intermediate Similarity	NPD2727	Phase 2
0.7323	Intermediate Similarity	NPD6991	Approved
0.7306	Intermediate Similarity	NPD4551	Phase 2
0.7306	Intermediate Similarity	NPD6361	Phase 2
0.7306	Intermediate Similarity	NPD1038	Approved
0.7304	Intermediate Similarity	NPD5903	Approved
0.7304	Intermediate Similarity	NPD5902	Approved
0.7303	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5429	Discontinued
0.73	Intermediate Similarity	NPD1392	Approved
0.7291	Intermediate Similarity	NPD7069	Discontinued
0.7285	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1684	Approved
0.7278	Intermediate Similarity	NPD1685	Approved
0.7277	Intermediate Similarity	NPD4021	Phase 2
0.7263	Intermediate Similarity	NPD5256	Discontinued
0.726	Intermediate Similarity	NPD4350	Approved
0.726	Intermediate Similarity	NPD4349	Approved
0.7258	Intermediate Similarity	NPD6641	Approved
0.7258	Intermediate Similarity	NPD6642	Approved
0.725	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD1954	Phase 1
0.7214	Intermediate Similarity	NPD6290	Phase 2
0.7212	Intermediate Similarity	NPD5930	Phase 3
0.7211	Intermediate Similarity	NPD4889	Approved
0.7208	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD677	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5612	Discontinued
0.7178	Intermediate Similarity	NPD7672	Approved
0.7178	Intermediate Similarity	NPD7671	Approved
0.7175	Intermediate Similarity	NPD2882	Phase 1
0.717	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD7194	Discontinued
0.7163	Intermediate Similarity	NPD3875	Discontinued
0.7157	Intermediate Similarity	NPD6220	Phase 3
0.7156	Intermediate Similarity	NPD3925	Approved
0.7135	Intermediate Similarity	NPD2749	Discontinued
0.7128	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD7417	Discontinued
0.7122	Intermediate Similarity	NPD3815	Phase 1
0.7122	Intermediate Similarity	NPD3816	Phase 1
0.7115	Intermediate Similarity	NPD6985	Discontinued
0.7107	Intermediate Similarity	NPD2952	Discontinued
0.7105	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6326	Phase 2
0.7089	Intermediate Similarity	NPD6327	Phase 1
0.7085	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6158	Phase 2
0.7073	Intermediate Similarity	NPD5936	Approved
0.7073	Intermediate Similarity	NPD5939	Approved
0.7072	Intermediate Similarity	NPD8359	Phase 2
0.7071	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6962	Phase 2
0.7065	Intermediate Similarity	NPD6324	Phase 1
0.7062	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6736	Discontinued
0.7048	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7395	Discontinued
0.703	Intermediate Similarity	NPD3397	Phase 2
0.703	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1229	Phase 2
0.7011	Intermediate Similarity	NPD925	Approved
0.7011	Intermediate Similarity	NPD926	Approved
0.7009	Intermediate Similarity	NPD3259	Approved
0.7005	Intermediate Similarity	NPD6251	Discontinued
0.6995	Remote Similarity	NPD6150	Discontinued
0.699	Remote Similarity	NPD5416	Discontinued
0.6986	Remote Similarity	NPD5164	Discontinued
0.6981	Remote Similarity	NPD1856	Discontinued
0.6976	Remote Similarity	NPD4437	Phase 3
0.6974	Remote Similarity	NPD2410	Phase 2
0.6972	Remote Similarity	NPD6964	Approved
0.6972	Remote Similarity	NPD6963	Approved
0.6971	Remote Similarity	NPD3525	Discontinued
0.697	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3477	Phase 2
0.6968	Remote Similarity	NPD9690	Approved
0.6963	Remote Similarity	NPD7676	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7674	Phase 3
0.6963	Remote Similarity	NPD7675	Phase 3
0.6963	Remote Similarity	NPD7426	Phase 1
0.6957	Remote Similarity	NPD861	Approved
0.6957	Remote Similarity	NPD863	Approved
0.6957	Remote Similarity	NPD862	Approved
0.6954	Remote Similarity	NPD802	Phase 2
0.6952	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.694	Remote Similarity	NPD9705	Discontinued
0.694	Remote Similarity	NPD112	Approved
0.6939	Remote Similarity	NPD2334	Discontinued
0.6937	Remote Similarity	NPD4876	Phase 3
0.6937	Remote Similarity	NPD4875	Phase 3
0.6935	Remote Similarity	NPD4673	Phase 2
0.6935	Remote Similarity	NPD2781	Approved
0.6935	Remote Similarity	NPD7948	Phase 1
0.6931	Remote Similarity	NPD4354	Approved
0.6927	Remote Similarity	NPD2916	Discontinued
0.6923	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2782	Approved
0.6919	Remote Similarity	NPD2780	Approved
0.6912	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD2917	Approved
0.6906	Remote Similarity	NPD5617	Suspended
0.6905	Remote Similarity	NPD5352	Clinical (unspecified phase)
0.69	Remote Similarity	NPD8244	Phase 2
0.6898	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6592	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD1923	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5632	Approved
0.6872	Remote Similarity	NPD6257	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD6227	Discontinued
0.6856	Remote Similarity	NPD2762	Phase 2
0.6847	Remote Similarity	NPD4858	Phase 2
0.6847	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD6208	Discontinued
0.6847	Remote Similarity	NPD5905	Phase 1
0.6844	Remote Similarity	NPD5488	Discontinued
0.6842	Remote Similarity	NPD7859	Phase 2
0.684	Remote Similarity	NPD3763	Approved
0.684	Remote Similarity	NPD3258	Approved
0.6837	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1505	Phase 2
0.6831	Remote Similarity	NPD9382	Approved
0.6831	Remote Similarity	NPD9383	Approved
0.6829	Remote Similarity	NPD8403	Phase 1

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