NPASS Compound

Structure

NPC474013 OpenBabel07101718232D 26 29 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 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 -0.8660 1.5000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 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 1.7321 -2.0000 0.0000 C 0 0 2 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 0.8660 -1.5000 0.0000 C 0 0 1 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1369 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 13 1 0 0 0 0 3 21 1 0 0 0 0 4 21 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 21 1 0 0 0 0 8 22 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 12 1 1 6 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 23 2 0 0 0 0 13 25 1 0 0 0 0 14 9 1 6 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 22 1 1 0 0 0 17 11 1 1 0 0 0 17 26 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 6 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 1 0 0 0 22 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	382.094
LogP:	5.384
LogD:	4.756
LogS:	-4.658
# Rotatable Bonds:	2
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.712
Synthetic Accessibility Score:	4.708
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.732
MDCK Permeability:	2.375094663875643e-05
Pgp-inhibitor:	0.745
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.841

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.256
Plasma Protein Binding (PPB):	95.89330291748047%
Volume Distribution (VD):	1.385
Pgp-substrate:	7.354490280151367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.519
CYP2C9-substrate:	0.55
CYP2D6-inhibitor:	0.056
CYP2D6-substrate:	0.317
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.396

ADMET: Excretion

Clearance (CL):	6.013
Half-life (T1/2):	0.274

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.517
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.365
Skin Sensitization:	0.533
Carcinogencity:	0.428
Eye Corrosion:	0.011
Eye Irritation:	0.024
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC474013

Natural Product ID:	NPC474013
*Common Name:**	12-Deoxy-Sucutinirane A
IUPAC Name:	[(4aS,5S,6aS,7R,10aR,11aS,11bR)-4,4,7,11b-tetramethyl-9-oxo-2,3,4a,5,6,6a,7,10a,11,11a-decahydro-1H-naphtho[2,1-f][1]benzofuran-5-yl] acetate
Synonyms:
Standard InCHIKey:	AXXGVIAGQXWYPN-DMWQAZAYSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-12-14-9-18(25-13(2)23)20-21(3,4)7-6-8-22(20,5)16(14)11-17-15(12)10-19(24)26-17/h10,12,14,16-18,20H,6-9,11H2,1-5H3/t12-,14+,16+,17-,18+,20+,22-/m1/s1
SMILES:	CC1C2CC(C3C(CCCC3(C2CC4C1=CC(=O)O4)C)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458318
PubChem CID:	44561378
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO28335	Bowdichia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524584]
NPO28335	Bowdichia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19361174]
NPO28335	Bowdichia nitida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO28335	Bowdichia nitida	Species	Fabaceae	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

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	32000.0	nM	PMID[532743]
NPT27	Others	Unspecified		IC50	>	100.0	ug.mL-1	PMID[532742]

☑ 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 NPC474013 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	211
0.1-0.2	1389
0.2-0.3	4810
0.3-0.4	13575
0.4-0.5	9632
0.5-0.6	6395
0.6-0.7	5064
0.7-0.8	1438
0.8-0.85	153
0.85-0.9	26
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9294	High Similarity	NPC329842
0.9167	High Similarity	NPC93411
0.9146	High Similarity	NPC96055
0.9136	High Similarity	NPC471218
0.8953	High Similarity	NPC302280
0.8953	High Similarity	NPC78973
0.8929	High Similarity	NPC131813
0.8916	High Similarity	NPC318515
0.878	High Similarity	NPC170303
0.8778	High Similarity	NPC51499
0.875	High Similarity	NPC7349
0.875	High Similarity	NPC189206
0.8736	High Similarity	NPC8062
0.8721	High Similarity	NPC106332
0.8681	High Similarity	NPC325229
0.8681	High Similarity	NPC275086
0.8675	High Similarity	NPC256112
0.8667	High Similarity	NPC194132
0.8659	High Similarity	NPC469802
0.8652	High Similarity	NPC105490
0.8652	High Similarity	NPC140277
0.8652	High Similarity	NPC84893
0.8605	High Similarity	NPC166857
0.8571	High Similarity	NPC476927
0.8556	High Similarity	NPC276110
0.8554	High Similarity	NPC25554
0.8539	High Similarity	NPC53555
0.8523	High Similarity	NPC280149
0.8523	High Similarity	NPC221111
0.8506	High Similarity	NPC473879
0.8495	Intermediate Similarity	NPC247701
0.8495	Intermediate Similarity	NPC222875
0.8495	Intermediate Similarity	NPC268829
0.8495	Intermediate Similarity	NPC25177
0.8495	Intermediate Similarity	NPC295110
0.8488	Intermediate Similarity	NPC286153
0.8471	Intermediate Similarity	NPC306951
0.8462	Intermediate Similarity	NPC209297
0.8462	Intermediate Similarity	NPC475380
0.8452	Intermediate Similarity	NPC286786
0.8444	Intermediate Similarity	NPC201725
0.8444	Intermediate Similarity	NPC477722
0.8427	Intermediate Similarity	NPC472811
0.8415	Intermediate Similarity	NPC184737
0.8409	Intermediate Similarity	NPC177141
0.8387	Intermediate Similarity	NPC117685
0.8387	Intermediate Similarity	NPC201406
0.8387	Intermediate Similarity	NPC251680
0.8372	Intermediate Similarity	NPC472442
0.837	Intermediate Similarity	NPC476768
0.837	Intermediate Similarity	NPC231751
0.837	Intermediate Similarity	NPC100912
0.837	Intermediate Similarity	NPC311241
0.837	Intermediate Similarity	NPC475446
0.8353	Intermediate Similarity	NPC474193
0.8353	Intermediate Similarity	NPC139206
0.8353	Intermediate Similarity	NPC311070
0.8353	Intermediate Similarity	NPC12283
0.8353	Intermediate Similarity	NPC477124
0.8353	Intermediate Similarity	NPC472440
0.8353	Intermediate Similarity	NPC132386
0.8352	Intermediate Similarity	NPC472441
0.8352	Intermediate Similarity	NPC474909
0.8333	Intermediate Similarity	NPC139692
0.8333	Intermediate Similarity	NPC290495
0.8333	Intermediate Similarity	NPC472812
0.8333	Intermediate Similarity	NPC472303
0.8333	Intermediate Similarity	NPC162615
0.8333	Intermediate Similarity	NPC152778
0.8333	Intermediate Similarity	NPC205034
0.8333	Intermediate Similarity	NPC38232
0.8333	Intermediate Similarity	NPC195334
0.8316	Intermediate Similarity	NPC180204
0.8316	Intermediate Similarity	NPC281378
0.8316	Intermediate Similarity	NPC187302
0.8316	Intermediate Similarity	NPC112009
0.8316	Intermediate Similarity	NPC160583
0.8316	Intermediate Similarity	NPC189588
0.8316	Intermediate Similarity	NPC97487
0.8316	Intermediate Similarity	NPC10232
0.8316	Intermediate Similarity	NPC45897
0.8316	Intermediate Similarity	NPC196471
0.8315	Intermediate Similarity	NPC310479
0.8298	Intermediate Similarity	NPC11974
0.8293	Intermediate Similarity	NPC470751
0.8293	Intermediate Similarity	NPC470750
0.828	Intermediate Similarity	NPC72647
0.828	Intermediate Similarity	NPC278673
0.828	Intermediate Similarity	NPC107806
0.828	Intermediate Similarity	NPC218107
0.8261	Intermediate Similarity	NPC16967
0.8261	Intermediate Similarity	NPC94905
0.8261	Intermediate Similarity	NPC8954
0.8242	Intermediate Similarity	NPC469697
0.8235	Intermediate Similarity	NPC200513
0.8235	Intermediate Similarity	NPC2524
0.8222	Intermediate Similarity	NPC72845
0.8222	Intermediate Similarity	NPC177641
0.8222	Intermediate Similarity	NPC289479
0.8214	Intermediate Similarity	NPC269791
0.8214	Intermediate Similarity	NPC281880
0.8214	Intermediate Similarity	NPC268827
0.8202	Intermediate Similarity	NPC82876
0.8202	Intermediate Similarity	NPC170633
0.8191	Intermediate Similarity	NPC38855
0.8191	Intermediate Similarity	NPC474190
0.8191	Intermediate Similarity	NPC324841
0.8191	Intermediate Similarity	NPC471413
0.8172	Intermediate Similarity	NPC477719
0.8172	Intermediate Similarity	NPC151681
0.8172	Intermediate Similarity	NPC175351
0.8172	Intermediate Similarity	NPC132753
0.8172	Intermediate Similarity	NPC110937
0.8172	Intermediate Similarity	NPC38530
0.8172	Intermediate Similarity	NPC477718
0.8172	Intermediate Similarity	NPC84335
0.8172	Intermediate Similarity	NPC224356
0.8172	Intermediate Similarity	NPC121402
0.8161	Intermediate Similarity	NPC35933
0.8161	Intermediate Similarity	NPC30984
0.8161	Intermediate Similarity	NPC189311
0.8144	Intermediate Similarity	NPC220217
0.8144	Intermediate Similarity	NPC119855
0.8144	Intermediate Similarity	NPC51719
0.8144	Intermediate Similarity	NPC186668
0.814	Intermediate Similarity	NPC42476
0.8132	Intermediate Similarity	NPC474185
0.8132	Intermediate Similarity	NPC476304
0.8125	Intermediate Similarity	NPC254202
0.8125	Intermediate Similarity	NPC472821
0.8118	Intermediate Similarity	NPC108476
0.8118	Intermediate Similarity	NPC159148
0.8111	Intermediate Similarity	NPC161638
0.8111	Intermediate Similarity	NPC182136
0.8111	Intermediate Similarity	NPC273199
0.8105	Intermediate Similarity	NPC471412
0.8105	Intermediate Similarity	NPC168319
0.8105	Intermediate Similarity	NPC473160
0.8105	Intermediate Similarity	NPC194028
0.8095	Intermediate Similarity	NPC44083
0.8095	Intermediate Similarity	NPC153987
0.8095	Intermediate Similarity	NPC242767
0.809	Intermediate Similarity	NPC472302
0.809	Intermediate Similarity	NPC472809
0.809	Intermediate Similarity	NPC226863
0.809	Intermediate Similarity	NPC472810
0.8085	Intermediate Similarity	NPC92275
0.8068	Intermediate Similarity	NPC474970
0.8068	Intermediate Similarity	NPC471219
0.8068	Intermediate Similarity	NPC475069
0.8068	Intermediate Similarity	NPC175145
0.8065	Intermediate Similarity	NPC472363
0.8065	Intermediate Similarity	NPC234993
0.8065	Intermediate Similarity	NPC473153
0.8065	Intermediate Similarity	NPC154526
0.8065	Intermediate Similarity	NPC260796
0.8065	Intermediate Similarity	NPC190713
0.8065	Intermediate Similarity	NPC88009
0.8065	Intermediate Similarity	NPC242848
0.8065	Intermediate Similarity	NPC134072
0.8065	Intermediate Similarity	NPC162346
0.8065	Intermediate Similarity	NPC472362
0.8061	Intermediate Similarity	NPC471205
0.8046	Intermediate Similarity	NPC30486
0.8046	Intermediate Similarity	NPC32223
0.8043	Intermediate Similarity	NPC91010
0.8043	Intermediate Similarity	NPC191521
0.8043	Intermediate Similarity	NPC324078
0.8043	Intermediate Similarity	NPC476186
0.8043	Intermediate Similarity	NPC161998
0.8043	Intermediate Similarity	NPC470255
0.8043	Intermediate Similarity	NPC104925
0.8043	Intermediate Similarity	NPC298973
0.8043	Intermediate Similarity	NPC57117
0.8041	Intermediate Similarity	NPC189616
0.8041	Intermediate Similarity	NPC165969
0.8022	Intermediate Similarity	NPC110923
0.8022	Intermediate Similarity	NPC49420
0.8022	Intermediate Similarity	NPC74296
0.8022	Intermediate Similarity	NPC234335
0.8021	Intermediate Similarity	NPC283343
0.8021	Intermediate Similarity	NPC273668
0.8021	Intermediate Similarity	NPC476081
0.8021	Intermediate Similarity	NPC258547
0.8021	Intermediate Similarity	NPC475038
0.8021	Intermediate Similarity	NPC476769
0.8021	Intermediate Similarity	NPC109195
0.8021	Intermediate Similarity	NPC162973
0.8	Intermediate Similarity	NPC472240
0.8	Intermediate Similarity	NPC262858
0.8	Intermediate Similarity	NPC219285
0.8	Intermediate Similarity	NPC228251
0.8	Intermediate Similarity	NPC293044
0.8	Intermediate Similarity	NPC473647
0.8	Intermediate Similarity	NPC50488
0.8	Intermediate Similarity	NPC474396
0.8	Intermediate Similarity	NPC476767
0.8	Intermediate Similarity	NPC474012
0.8	Intermediate Similarity	NPC246028
0.8	Intermediate Similarity	NPC477716

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 NPC474013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1510
0.2-0.3	4033
0.3-0.4	2357
0.4-0.5	644
0.5-0.6	240
0.6-0.7	153
0.7-0.8	27
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8478	Intermediate Similarity	NPD7638	Approved
0.8387	Intermediate Similarity	NPD7639	Approved
0.8387	Intermediate Similarity	NPD7640	Approved
0.8235	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6051	Approved
0.7849	Intermediate Similarity	NPD7900	Approved
0.7849	Intermediate Similarity	NPD7748	Approved
0.7849	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4225	Approved
0.7692	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6409	Approved
0.7667	Intermediate Similarity	NPD7521	Approved
0.7667	Intermediate Similarity	NPD7146	Approved
0.7667	Intermediate Similarity	NPD7334	Approved
0.7667	Intermediate Similarity	NPD5330	Approved
0.7667	Intermediate Similarity	NPD6684	Approved
0.7653	Intermediate Similarity	NPD7632	Discontinued
0.7634	Intermediate Similarity	NPD7515	Phase 2
0.7604	Intermediate Similarity	NPD7902	Approved
0.7556	Intermediate Similarity	NPD1694	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD6903	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.7386	Intermediate Similarity	NPD7525	Registered
0.7315	Intermediate Similarity	NPD7327	Approved
0.7315	Intermediate Similarity	NPD7328	Approved
0.7273	Intermediate Similarity	NPD7645	Phase 2
0.7263	Intermediate Similarity	NPD5693	Phase 1
0.7248	Intermediate Similarity	NPD7516	Approved
0.7216	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3573	Approved
0.7188	Intermediate Similarity	NPD6399	Phase 3
0.7184	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD8377	Approved
0.7182	Intermediate Similarity	NPD8294	Approved
0.7117	Intermediate Similarity	NPD8296	Approved
0.7117	Intermediate Similarity	NPD8380	Approved
0.7117	Intermediate Similarity	NPD8335	Approved
0.7117	Intermediate Similarity	NPD8033	Approved
0.7117	Intermediate Similarity	NPD8379	Approved
0.7117	Intermediate Similarity	NPD8378	Approved
0.7115	Intermediate Similarity	NPD6686	Approved
0.7097	Intermediate Similarity	NPD3618	Phase 1
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7083	Intermediate Similarity	NPD8035	Phase 2
0.7083	Intermediate Similarity	NPD8034	Phase 2
0.7065	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7115	Discovery
0.7053	Intermediate Similarity	NPD6904	Approved
0.7053	Intermediate Similarity	NPD6080	Approved
0.7053	Intermediate Similarity	NPD6673	Approved
0.7053	Intermediate Similarity	NPD5328	Approved
0.7048	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6881	Approved
0.6952	Remote Similarity	NPD7320	Approved
0.6952	Remote Similarity	NPD6899	Approved
0.6951	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6008	Approved
0.6907	Remote Similarity	NPD6079	Approved
0.69	Remote Similarity	NPD6083	Phase 2
0.69	Remote Similarity	NPD6084	Phase 2
0.6887	Remote Similarity	NPD6372	Approved
0.6887	Remote Similarity	NPD6373	Approved
0.687	Remote Similarity	NPD7507	Approved
0.6857	Remote Similarity	NPD5697	Approved
0.6857	Remote Similarity	NPD5701	Approved
0.6822	Remote Similarity	NPD7290	Approved
0.6822	Remote Similarity	NPD6883	Approved
0.6822	Remote Similarity	NPD7102	Approved
0.6818	Remote Similarity	NPD6942	Approved
0.6818	Remote Similarity	NPD7339	Approved
0.6792	Remote Similarity	NPD6011	Approved
0.6771	Remote Similarity	NPD5208	Approved
0.6768	Remote Similarity	NPD6001	Approved
0.6765	Remote Similarity	NPD6648	Approved
0.6759	Remote Similarity	NPD6649	Approved
0.6759	Remote Similarity	NPD6847	Approved
0.6759	Remote Similarity	NPD6617	Approved
0.6759	Remote Similarity	NPD6650	Approved
0.6759	Remote Similarity	NPD8130	Phase 1
0.6759	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6869	Approved
0.6742	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6098	Approved
0.6735	Remote Similarity	NPD6050	Approved
0.6729	Remote Similarity	NPD6014	Approved
0.6729	Remote Similarity	NPD6012	Approved
0.6729	Remote Similarity	NPD6013	Approved
0.6702	Remote Similarity	NPD4786	Approved
0.6702	Remote Similarity	NPD3133	Approved
0.6702	Remote Similarity	NPD3666	Approved
0.6702	Remote Similarity	NPD3665	Phase 1
0.6702	Remote Similarity	NPD3668	Phase 3
0.67	Remote Similarity	NPD5695	Phase 3
0.6699	Remote Similarity	NPD5344	Discontinued
0.6697	Remote Similarity	NPD8297	Approved
0.6697	Remote Similarity	NPD6882	Approved
0.6695	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6634	Remote Similarity	NPD5221	Approved
0.6634	Remote Similarity	NPD5222	Approved
0.6634	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4697	Phase 3
0.6633	Remote Similarity	NPD5692	Phase 3
0.6629	Remote Similarity	NPD8039	Approved
0.6627	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4755	Approved
0.6569	Remote Similarity	NPD5173	Approved
0.6566	Remote Similarity	NPD7637	Suspended
0.6566	Remote Similarity	NPD5694	Approved
0.6531	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4195	Approved
0.6518	Remote Similarity	NPD6868	Approved
0.6476	Remote Similarity	NPD5211	Phase 2
0.6471	Remote Similarity	NPD7732	Phase 3
0.6465	Remote Similarity	NPD5207	Approved
0.6442	Remote Similarity	NPD5286	Approved
0.6442	Remote Similarity	NPD5285	Approved
0.6442	Remote Similarity	NPD4700	Approved
0.6442	Remote Similarity	NPD4696	Approved
0.6421	Remote Similarity	NPD6695	Phase 3
0.6404	Remote Similarity	NPD6335	Approved
0.64	Remote Similarity	NPD6411	Approved
0.6392	Remote Similarity	NPD4623	Approved
0.6392	Remote Similarity	NPD4519	Discontinued
0.6392	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5223	Approved
0.6374	Remote Similarity	NPD6117	Approved
0.6372	Remote Similarity	NPD6274	Approved
0.6364	Remote Similarity	NPD4753	Phase 2
0.6355	Remote Similarity	NPD5141	Approved
0.6354	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD7101	Approved
0.6348	Remote Similarity	NPD7100	Approved
0.6346	Remote Similarity	NPD5290	Discontinued
0.6339	Remote Similarity	NPD4632	Approved
0.6333	Remote Similarity	NPD6924	Approved
0.6333	Remote Similarity	NPD6926	Approved
0.6327	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5224	Approved
0.6321	Remote Similarity	NPD5226	Approved
0.6321	Remote Similarity	NPD4633	Approved
0.6321	Remote Similarity	NPD5225	Approved
0.6316	Remote Similarity	NPD4223	Phase 3
0.6316	Remote Similarity	NPD4221	Approved
0.6316	Remote Similarity	NPD6317	Approved
0.6304	Remote Similarity	NPD6116	Phase 1
0.63	Remote Similarity	NPD5785	Approved
0.6292	Remote Similarity	NPD4243	Approved
0.6292	Remote Similarity	NPD5777	Approved
0.6289	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5329	Approved
0.6277	Remote Similarity	NPD4695	Discontinued
0.6264	Remote Similarity	NPD8264	Approved
0.6262	Remote Similarity	NPD5174	Approved
0.6262	Remote Similarity	NPD4754	Approved
0.6262	Remote Similarity	NPD5175	Approved
0.6262	Remote Similarity	NPD6052	Approved
0.6261	Remote Similarity	NPD6314	Approved
0.6261	Remote Similarity	NPD6313	Approved
0.625	Remote Similarity	NPD6053	Discontinued
0.625	Remote Similarity	NPD4137	Phase 3
0.6239	Remote Similarity	NPD6412	Phase 2
0.6239	Remote Similarity	NPD6909	Approved
0.6239	Remote Similarity	NPD6908	Approved
0.6238	Remote Similarity	NPD5281	Approved
0.6238	Remote Similarity	NPD5284	Approved
0.6237	Remote Similarity	NPD6697	Approved
0.6237	Remote Similarity	NPD6115	Approved
0.6237	Remote Similarity	NPD6118	Approved
0.6237	Remote Similarity	NPD6114	Approved
0.6224	Remote Similarity	NPD5279	Phase 3
0.6214	Remote Similarity	NPD5654	Approved
0.62	Remote Similarity	NPD6101	Approved
0.62	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD6933	Approved
0.6195	Remote Similarity	NPD7094	Approved
0.6195	Remote Similarity	NPD6858	Approved
0.6195	Remote Similarity	NPD8133	Approved
0.6186	Remote Similarity	NPD4197	Approved
0.6182	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4691	Approved
0.618	Remote Similarity	NPD4747	Approved
0.6176	Remote Similarity	NPD5778	Approved
0.6176	Remote Similarity	NPD5779	Approved
0.6174	Remote Similarity	NPD6009	Approved
0.617	Remote Similarity	NPD6929	Approved
0.6162	Remote Similarity	NPD7524	Approved
0.6162	Remote Similarity	NPD7750	Discontinued
0.6154	Remote Similarity	NPD7614	Phase 1
0.6154	Remote Similarity	NPD5349	Clinical (unspecified phase)

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