NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	319.13
Volume:	329.797
LogP:	2.284
LogD:	2.734
LogS:	-3.947
# Rotatable Bonds:	4
TPSA:	74.58
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.729
Synthetic Accessibility Score:	3.017
Fsp3:	0.211
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:	-4.973
MDCK Permeability:	1.4150215065455996e-05
Pgp-inhibitor:	0.095
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.464
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.87
Plasma Protein Binding (PPB):	94.24932861328125%
Volume Distribution (VD):	1.075
Pgp-substrate:	3.961190938949585%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.325
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.625
CYP2D6-inhibitor:	0.811
CYP2D6-substrate:	0.7
CYP3A4-inhibitor:	0.307
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	2.123
Half-life (T1/2):	0.598

ADMET: Toxicity

hERG Blockers:	0.139
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.813
AMES Toxicity:	0.915
Rat Oral Acute Toxicity:	0.425
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.857
Carcinogencity:	0.922
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.893

Download Data

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

Natural Product: NPC477111

Natural Product ID:	NPC477111
*Common Name:**	Styelsamine B
IUPAC Name:	N-[2-(12-hydroxy-8,14-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2,4,6,9,11,13,15-octaen-10-yl)ethyl]acetamide;2,2,2-trifluoroacetic acid
Synonyms:
Standard InCHIKey:	RHLJMHQIMMOHTA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H17N3O2.C2HF3O2/c1-11(23)20-8-6-12-10-16(24)19-17-14(7-9-21-19)13-4-2-3-5-15(13)22-18(12)17;3-2(4,5)1(6)7/h2-5,7,9-10,22,24H,6,8H2,1H3,(H,20,23);(H,6,7)
SMILES:	CC(=O)NCCC1=C2C3=C(C=CN=C3C(=C1)O)C4=CC=CC=C4N2.C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558519
PubChem CID:	49797654
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000274] Acridines [CHEMONTID:0001763] Pyridoacridines [CHEMONTID:0002827] Pyrido[2,3,4-kl]acridines

*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
NPO11682	Eusynstyela latericius	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19505081]
NPO11682	Eusynstyela latericius	Species	Styelidae	Eukaryota	n.a.	Hixson Island (2145.0' S, 15017.5' E); Percy Island Group in the Central Great Barrier Reef, Queensland, Australia; Rib Reef (1828.7' S, 14652.3' E)	n.a.	PMID[19505081]
NPO11682	Eusynstyela latericius	Species	Styelidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	1600	nM	PMID[19505081]

☑ 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 NPC477111 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	453
0.1-0.2	3914
0.2-0.3	13380
0.3-0.4	13809
0.4-0.5	6509
0.5-0.6	2777
0.6-0.7	1682
0.7-0.8	164
0.8-0.85	3
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9784	High Similarity	NPC477113
0.943	High Similarity	NPC477110
0.8824	High Similarity	NPC103687
0.8824	High Similarity	NPC132631
0.8744	High Similarity	NPC477112
0.8333	Intermediate Similarity	NPC470678
0.8315	Intermediate Similarity	NPC314940
0.8315	Intermediate Similarity	NPC473764
0.8274	Intermediate Similarity	NPC476167
0.8247	Intermediate Similarity	NPC99666
0.8223	Intermediate Similarity	NPC192315
0.8204	Intermediate Similarity	NPC476161
0.8172	Intermediate Similarity	NPC252590
0.8159	Intermediate Similarity	NPC475070
0.8137	Intermediate Similarity	NPC5145
0.8125	Intermediate Similarity	NPC314002
0.8105	Intermediate Similarity	NPC478032
0.8083	Intermediate Similarity	NPC171171
0.8081	Intermediate Similarity	NPC77555
0.8073	Intermediate Similarity	NPC204717
0.8047	Intermediate Similarity	NPC476451
0.8039	Intermediate Similarity	NPC476157
0.8021	Intermediate Similarity	NPC220765
0.8018	Intermediate Similarity	NPC24802
0.7951	Intermediate Similarity	NPC18348
0.7907	Intermediate Similarity	NPC6215
0.7905	Intermediate Similarity	NPC469727
0.7905	Intermediate Similarity	NPC476041
0.7905	Intermediate Similarity	NPC304926
0.7892	Intermediate Similarity	NPC329708
0.7892	Intermediate Similarity	NPC47059
0.7892	Intermediate Similarity	NPC118832
0.7892	Intermediate Similarity	NPC165349
0.7892	Intermediate Similarity	NPC264166
0.7892	Intermediate Similarity	NPC274291
0.7865	Intermediate Similarity	NPC88363
0.7839	Intermediate Similarity	NPC329541
0.7812	Intermediate Similarity	NPC184964
0.7783	Intermediate Similarity	NPC249040
0.7756	Intermediate Similarity	NPC475774
0.7751	Intermediate Similarity	NPC208284
0.7727	Intermediate Similarity	NPC32771
0.7727	Intermediate Similarity	NPC246700
0.7723	Intermediate Similarity	NPC473312
0.7723	Intermediate Similarity	NPC156704
0.7718	Intermediate Similarity	NPC470500
0.7713	Intermediate Similarity	NPC477861
0.771	Intermediate Similarity	NPC132642
0.7703	Intermediate Similarity	NPC309845
0.77	Intermediate Similarity	NPC324149
0.7689	Intermediate Similarity	NPC470799
0.7689	Intermediate Similarity	NPC8022
0.768	Intermediate Similarity	NPC232340
0.7672	Intermediate Similarity	NPC471178
0.7668	Intermediate Similarity	NPC150048
0.7668	Intermediate Similarity	NPC203754
0.7665	Intermediate Similarity	NPC471891
0.7662	Intermediate Similarity	NPC307963
0.7656	Intermediate Similarity	NPC476116
0.7642	Intermediate Similarity	NPC237740
0.763	Intermediate Similarity	NPC94157
0.7619	Intermediate Similarity	NPC97367
0.7611	Intermediate Similarity	NPC142385
0.761	Intermediate Similarity	NPC315491
0.761	Intermediate Similarity	NPC45459
0.7604	Intermediate Similarity	NPC130570
0.76	Intermediate Similarity	NPC3715
0.7594	Intermediate Similarity	NPC266931
0.7592	Intermediate Similarity	NPC44161
0.7589	Intermediate Similarity	NPC41679
0.7588	Intermediate Similarity	NPC46580
0.7585	Intermediate Similarity	NPC245816
0.7585	Intermediate Similarity	NPC476138
0.758	Intermediate Similarity	NPC473185
0.7566	Intermediate Similarity	NPC59779
0.7566	Intermediate Similarity	NPC471177
0.7566	Intermediate Similarity	NPC124542
0.7561	Intermediate Similarity	NPC128823
0.755	Intermediate Similarity	NPC128751
0.7549	Intermediate Similarity	NPC153042
0.7536	Intermediate Similarity	NPC211813
0.7523	Intermediate Similarity	NPC469554
0.7523	Intermediate Similarity	NPC101543
0.7522	Intermediate Similarity	NPC81175
0.7512	Intermediate Similarity	NPC469497
0.7512	Intermediate Similarity	NPC106833
0.7512	Intermediate Similarity	NPC477610
0.7512	Intermediate Similarity	NPC76748
0.75	Intermediate Similarity	NPC193267
0.75	Intermediate Similarity	NPC294375
0.75	Intermediate Similarity	NPC213530
0.75	Intermediate Similarity	NPC251090
0.75	Intermediate Similarity	NPC208522
0.7475	Intermediate Similarity	NPC92111
0.7474	Intermediate Similarity	NPC259545
0.7467	Intermediate Similarity	NPC184225
0.7465	Intermediate Similarity	NPC26679
0.7463	Intermediate Similarity	NPC242928
0.7463	Intermediate Similarity	NPC296527
0.7455	Intermediate Similarity	NPC214980
0.7454	Intermediate Similarity	NPC173080
0.744	Intermediate Similarity	NPC329793
0.744	Intermediate Similarity	NPC176538
0.744	Intermediate Similarity	NPC213308
0.7435	Intermediate Similarity	NPC159319
0.7422	Intermediate Similarity	NPC295228
0.7422	Intermediate Similarity	NPC477549
0.7419	Intermediate Similarity	NPC473179
0.7412	Intermediate Similarity	NPC72905
0.7411	Intermediate Similarity	NPC180504
0.7406	Intermediate Similarity	NPC185782
0.74	Intermediate Similarity	NPC94943
0.7397	Intermediate Similarity	NPC216612
0.7393	Intermediate Similarity	NPC283117
0.7383	Intermediate Similarity	NPC202605
0.7383	Intermediate Similarity	NPC112206
0.7379	Intermediate Similarity	NPC90229
0.7366	Intermediate Similarity	NPC133366
0.7366	Intermediate Similarity	NPC49547
0.7366	Intermediate Similarity	NPC326634
0.7363	Intermediate Similarity	NPC314573
0.7361	Intermediate Similarity	NPC469928
0.7356	Intermediate Similarity	NPC19872
0.735	Intermediate Similarity	NPC190007
0.7349	Intermediate Similarity	NPC162530
0.7349	Intermediate Similarity	NPC476287
0.7344	Intermediate Similarity	NPC32028
0.7333	Intermediate Similarity	NPC476098
0.7333	Intermediate Similarity	NPC223427
0.7327	Intermediate Similarity	NPC293151
0.7327	Intermediate Similarity	NPC317030
0.7324	Intermediate Similarity	NPC209769
0.7323	Intermediate Similarity	NPC42979
0.7318	Intermediate Similarity	NPC162748
0.7317	Intermediate Similarity	NPC474177
0.7313	Intermediate Similarity	NPC473183
0.731	Intermediate Similarity	NPC224764
0.7309	Intermediate Similarity	NPC314954
0.7308	Intermediate Similarity	NPC476582
0.7308	Intermediate Similarity	NPC287437
0.7308	Intermediate Similarity	NPC476578
0.7308	Intermediate Similarity	NPC4071
0.73	Intermediate Similarity	NPC212535
0.73	Intermediate Similarity	NPC48938
0.7299	Intermediate Similarity	NPC285558
0.7297	Intermediate Similarity	NPC470018
0.7294	Intermediate Similarity	NPC477609
0.7292	Intermediate Similarity	NPC315214
0.7292	Intermediate Similarity	NPC47298
0.729	Intermediate Similarity	NPC199667
0.7286	Intermediate Similarity	NPC328596
0.7286	Intermediate Similarity	NPC328318
0.7285	Intermediate Similarity	NPC167908
0.7282	Intermediate Similarity	NPC126481
0.7277	Intermediate Similarity	NPC474707
0.7277	Intermediate Similarity	NPC314957
0.7273	Intermediate Similarity	NPC315957
0.7265	Intermediate Similarity	NPC74575
0.7265	Intermediate Similarity	NPC137353
0.7264	Intermediate Similarity	NPC476121
0.7264	Intermediate Similarity	NPC476124
0.726	Intermediate Similarity	NPC265576
0.7254	Intermediate Similarity	NPC473057
0.7246	Intermediate Similarity	NPC242209
0.7246	Intermediate Similarity	NPC222018
0.7243	Intermediate Similarity	NPC473181
0.7241	Intermediate Similarity	NPC204565
0.724	Intermediate Similarity	NPC324203
0.724	Intermediate Similarity	NPC25899
0.724	Intermediate Similarity	NPC131718
0.724	Intermediate Similarity	NPC322976
0.724	Intermediate Similarity	NPC280272
0.724	Intermediate Similarity	NPC63338
0.7235	Intermediate Similarity	NPC118228
0.7231	Intermediate Similarity	NPC63751
0.723	Intermediate Similarity	NPC88008
0.723	Intermediate Similarity	NPC193777
0.7228	Intermediate Similarity	NPC42591
0.7227	Intermediate Similarity	NPC276657
0.7225	Intermediate Similarity	NPC473184
0.7222	Intermediate Similarity	NPC473180
0.7222	Intermediate Similarity	NPC316981
0.722	Intermediate Similarity	NPC60006
0.7217	Intermediate Similarity	NPC476581
0.7217	Intermediate Similarity	NPC36229
0.7217	Intermediate Similarity	NPC16452
0.7214	Intermediate Similarity	NPC133306
0.7212	Intermediate Similarity	NPC267928
0.7209	Intermediate Similarity	NPC123976
0.7209	Intermediate Similarity	NPC11464
0.7209	Intermediate Similarity	NPC167860
0.7208	Intermediate Similarity	NPC471294
0.7206	Intermediate Similarity	NPC65215
0.7206	Intermediate Similarity	NPC230805
0.7206	Intermediate Similarity	NPC173028
0.7202	Intermediate Similarity	NPC183407
0.7198	Intermediate Similarity	NPC276517
0.7189	Intermediate Similarity	NPC478074
0.7186	Intermediate Similarity	NPC96890
0.7184	Intermediate Similarity	NPC133140

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 NPC477111 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	663
0.2-0.3	912
0.3-0.4	1505
0.4-0.5	2696
0.5-0.6	2103
0.6-0.7	948
0.7-0.8	103
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.849	Intermediate Similarity	NPD9695	Approved
0.8205	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6159	Phase 2
0.8085	Intermediate Similarity	NPD9690	Approved
0.801	Intermediate Similarity	NPD5936	Approved
0.801	Intermediate Similarity	NPD5939	Approved
0.8	Intermediate Similarity	NPD2177	Approved
0.8	Intermediate Similarity	NPD2176	Approved
0.8	Intermediate Similarity	NPD2175	Phase 3
0.7989	Intermediate Similarity	NPD9705	Discontinued
0.7989	Intermediate Similarity	NPD112	Approved
0.7971	Intermediate Similarity	NPD3330	Phase 1
0.7927	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD4035	Approved
0.7892	Intermediate Similarity	NPD4038	Approved
0.7892	Intermediate Similarity	NPD4037	Approved
0.7892	Intermediate Similarity	NPD4034	Approved
0.7892	Intermediate Similarity	NPD32	Approved
0.7892	Intermediate Similarity	NPD4036	Approved
0.7892	Intermediate Similarity	NPD31	Approved
0.7892	Intermediate Similarity	NPD4039	Approved
0.7892	Intermediate Similarity	NPD4033	Approved
0.7892	Intermediate Similarity	NPD4122	Approved
0.7882	Intermediate Similarity	NPD3928	Approved
0.7882	Intermediate Similarity	NPD3931	Approved
0.7816	Intermediate Similarity	NPD6290	Phase 2
0.7814	Intermediate Similarity	NPD7586	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7948	Phase 1
0.7783	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7603	Discontinued
0.7767	Intermediate Similarity	NPD3932	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD2616	Phase 3
0.7762	Intermediate Similarity	NPD2615	Phase 3
0.7751	Intermediate Similarity	NPD4502	Phase 2
0.7742	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.7729	Intermediate Similarity	NPD3930	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD4429	Discontinued
0.77	Intermediate Similarity	NPD3404	Approved
0.7689	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD7112	Discontinued
0.7675	Intermediate Similarity	NPD3809	Discontinued
0.7665	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD5428	Discontinued
0.7662	Intermediate Similarity	NPD1038	Approved
0.7647	Intermediate Similarity	NPD5255	Approved
0.7632	Intermediate Similarity	NPD425	Approved
0.7632	Intermediate Similarity	NPD424	Approved
0.7621	Intermediate Similarity	NPD6132	Phase 1
0.7617	Intermediate Similarity	NPD5065	Approved
0.761	Intermediate Similarity	NPD484	Approved
0.7606	Intermediate Similarity	NPD5612	Discontinued
0.7589	Intermediate Similarity	NPD6750	Phase 2
0.7573	Intermediate Similarity	NPD4511	Phase 1
0.7568	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD5999	Phase 2
0.7525	Intermediate Similarity	NPD9689	Approved
0.7525	Intermediate Similarity	NPD6569	Phase 2
0.7511	Intermediate Similarity	NPD5022	Discontinued
0.7488	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD2380	Approved
0.7487	Intermediate Similarity	NPD2382	Approved
0.7487	Intermediate Similarity	NPD2381	Approved
0.7476	Intermediate Similarity	NPD7222	Phase 2
0.7473	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4886	Phase 2
0.7415	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD3477	Phase 2
0.7411	Intermediate Similarity	NPD6494	Phase 2
0.7407	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3082	Discontinued
0.74	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4945	Discontinued
0.7397	Intermediate Similarity	NPD1856	Discontinued
0.7396	Intermediate Similarity	NPD925	Approved
0.7396	Intermediate Similarity	NPD926	Approved
0.7391	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4795	Phase 2
0.738	Intermediate Similarity	NPD6158	Phase 2
0.738	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5669	Clinical (unspecified phase)
0.7352	Intermediate Similarity	NPD7726	Phase 1
0.7337	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD6220	Phase 3
0.7327	Intermediate Similarity	NPD7423	Phase 2
0.732	Intermediate Similarity	NPD2781	Approved
0.732	Intermediate Similarity	NPD5862	Discovery
0.7315	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD9688	Approved
0.7308	Intermediate Similarity	NPD9687	Approved
0.7306	Intermediate Similarity	NPD2780	Approved
0.7306	Intermediate Similarity	NPD2782	Approved
0.7304	Intermediate Similarity	NPD7067	Approved
0.7304	Intermediate Similarity	NPD7068	Approved
0.7294	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1685	Approved
0.7292	Intermediate Similarity	NPD1684	Approved
0.7287	Intermediate Similarity	NPD2882	Phase 1
0.7286	Intermediate Similarity	NPD6975	Discontinued
0.7273	Intermediate Similarity	NPD1740	Approved
0.7273	Intermediate Similarity	NPD1739	Approved
0.7264	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1213	Phase 3
0.7253	Intermediate Similarity	NPD5644	Phase 1
0.7251	Intermediate Similarity	NPD4044	Discontinued
0.724	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5559	Phase 2
0.723	Intermediate Similarity	NPD7453	Approved
0.723	Intermediate Similarity	NPD7452	Approved
0.7222	Intermediate Similarity	NPD5100	Phase 3
0.7206	Intermediate Similarity	NPD9714	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6968	Phase 2
0.72	Intermediate Similarity	NPD6969	Phase 2
0.7198	Intermediate Similarity	NPD4999	Phase 3
0.7198	Intermediate Similarity	NPD4998	Phase 3
0.7194	Intermediate Similarity	NPD1325	Approved
0.7194	Intermediate Similarity	NPD1326	Approved
0.7184	Intermediate Similarity	NPD3923	Approved
0.7184	Intermediate Similarity	NPD3922	Approved
0.7184	Intermediate Similarity	NPD3924	Approved
0.7184	Intermediate Similarity	NPD3921	Approved
0.7182	Intermediate Similarity	NPD3402	Phase 1
0.7165	Intermediate Similarity	NPD862	Approved
0.7165	Intermediate Similarity	NPD863	Approved
0.7165	Intermediate Similarity	NPD861	Approved
0.7157	Intermediate Similarity	NPD2123	Phase 3
0.715	Intermediate Similarity	NPD802	Phase 2
0.715	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD3986	Discontinued
0.7143	Intermediate Similarity	NPD8396	Approved
0.7143	Intermediate Similarity	NPD3825	Phase 3
0.7143	Intermediate Similarity	NPD8395	Approved
0.7117	Intermediate Similarity	NPD4881	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD5528	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD5529	Phase 1
0.7115	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4375	Approved
0.7104	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5530	Phase 1
0.71	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4890	Phase 2
0.7091	Intermediate Similarity	NPD5164	Discontinued
0.7087	Intermediate Similarity	NPD6281	Approved
0.7087	Intermediate Similarity	NPD8063	Discontinued
0.7085	Intermediate Similarity	NPD6492	Phase 2
0.7085	Intermediate Similarity	NPD1954	Phase 1
0.7073	Intermediate Similarity	NPD8431	Approved
0.7073	Intermediate Similarity	NPD2383	Phase 1
0.7072	Intermediate Similarity	NPD6242	Discontinued
0.7071	Intermediate Similarity	NPD5911	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5680	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD4548	Discontinued
0.7059	Intermediate Similarity	NPD3813	Approved
0.7059	Intermediate Similarity	NPD2762	Phase 2
0.7056	Intermediate Similarity	NPD5901	Discontinued
0.7056	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7202	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD2952	Discontinued
0.7047	Intermediate Similarity	NPD9383	Approved
0.7047	Intermediate Similarity	NPD9382	Approved
0.7042	Intermediate Similarity	NPD8091	Phase 3
0.7041	Intermediate Similarity	NPD2720	Phase 1
0.7041	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4702	Approved
0.7037	Intermediate Similarity	NPD4703	Approved
0.7037	Intermediate Similarity	NPD5658	Approved
0.7037	Intermediate Similarity	NPD2187	Approved
0.7037	Intermediate Similarity	NPD2189	Approved
0.7035	Intermediate Similarity	NPD4845	Discontinued
0.7035	Intermediate Similarity	NPD8430	Approved
0.7032	Intermediate Similarity	NPD5945	Phase 1
0.7032	Intermediate Similarity	NPD5944	Phase 1
0.7031	Intermediate Similarity	NPD7558	Phase 2
0.7028	Intermediate Similarity	NPD5497	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4919	Phase 3
0.7024	Intermediate Similarity	NPD4921	Phase 3
0.7024	Intermediate Similarity	NPD4920	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4131	Phase 3
0.7018	Intermediate Similarity	NPD5066	Phase 2
0.7018	Intermediate Similarity	NPD5067	Phase 2
0.7015	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD712	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8244	Phase 2
0.6995	Remote Similarity	NPD4203	Approved
0.6995	Remote Similarity	NPD4204	Approved
0.6991	Remote Similarity	NPD7051	Phase 3
0.6991	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD3815	Phase 1
0.6986	Remote Similarity	NPD7069	Discontinued
0.6986	Remote Similarity	NPD3816	Phase 1
0.6985	Remote Similarity	NPD5934	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD2021	Discontinued
0.698	Remote Similarity	NPD1620	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD2012	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD4889	Approved
0.6972	Remote Similarity	NPD3013	Phase 3
0.6972	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4454	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