NPASS Compound

Structure

NPC38830 OpenBabel07101718242D 25 27 0 0 1 0 0 0 0 0999 V2000 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 0.3660 -3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 -5.9641 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 -4.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -3.3660 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 -1.7321 -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 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 -1.7321 -2.0000 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3660 -5.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 -5.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 12 2 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 6 24 1 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 15 1 0 0 0 0 13 14 2 0 0 0 0 13 16 1 0 0 0 0 15 20 1 6 0 0 0 16 22 2 0 0 0 0 17 20 1 0 0 0 0 17 21 1 0 0 0 0 18 21 1 1 0 0 0 18 25 1 0 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 20 5 1 6 0 0 0 21 14 1 6 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.18
Volume:	365.445
LogP:	3.302
LogD:	2.638
LogS:	-4.989
# Rotatable Bonds:	6
TPSA:	55.9
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	5.232
Fsp3:	0.524
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:	-4.822
MDCK Permeability:	3.1389037758344784e-05
Pgp-inhibitor:	0.964
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.137
Plasma Protein Binding (PPB):	79.08356475830078%
Volume Distribution (VD):	2.117
Pgp-substrate:	16.90265464782715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.842
CYP2C19-inhibitor:	0.567
CYP2C19-substrate:	0.839
CYP2C9-inhibitor:	0.159
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.48
CYP3A4-substrate:	0.791

ADMET: Excretion

Clearance (CL):	10.78
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.571
Drug-inuced Liver Injury (DILI):	0.239
AMES Toxicity:	0.118
Rat Oral Acute Toxicity:	0.877
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.925
Carcinogencity:	0.879
Eye Corrosion:	0.747
Eye Irritation:	0.068
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC38830

Natural Product ID:	NPC38830
*Common Name:**	Trigonochinene D
IUPAC Name:	methyl 3-[(1aS,3R,4R,8aS)-8-ethenyl-4,7-dimethyl-6-oxo-3-prop-1-en-2-yl-2,3-dihydro-1aH-naphtho[4,4a-b]oxiren-4-yl]propanoate
Synonyms:	trigonochinene D
Standard InCHIKey:	OLVDZXLYEJAWNY-NSGGIEJNSA-N
Standard InCHI:	InChI=1S/C21H26O4/c1-7-14-13(4)16(22)11-17-20(5,9-8-19(23)24-6)15(12(2)3)10-18-21(14,17)25-18/h7,11,15,18H,1-2,8-10H2,3-6H3/t15-,18+,20-,21-/m1/s1
SMILES:	COC(=O)CC[C@]1(C)[C@H](C[C@H]2[C@@]3(C1=CC(=O)C(=C3C=C)C)O2)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516273
PubChem CID:	25019249
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001729] Oxepanes

*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
NPO12404	Trigonostemon chinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611050]
NPO12404	Trigonostemon chinensis	Species	Euphorbiaceae	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
MIC	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	25.0	ug.mL-1	PMID[530406]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	50.0	ug.mL-1	PMID[530406]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[530406]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	50.0	ug.mL-1	PMID[530406]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	50.0	ug.mL-1	PMID[530406]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[530406]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[530406]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[530406]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	50.0	ug.mL-1	PMID[530406]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[530406]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	50.0	ug.mL-1	PMID[530406]

☑ 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 NPC38830 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	233
0.1-0.2	1223
0.2-0.3	3935
0.3-0.4	9192
0.4-0.5	13629
0.5-0.6	8074
0.6-0.7	4906
0.7-0.8	1445
0.8-0.85	54
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8913	High Similarity	NPC477130
0.8913	High Similarity	NPC477129
0.8889	High Similarity	NPC284561
0.8876	High Similarity	NPC181327
0.883	High Similarity	NPC110937
0.871	High Similarity	NPC470697
0.8696	High Similarity	NPC49420
0.8681	High Similarity	NPC118011
0.8681	High Similarity	NPC73995
0.8681	High Similarity	NPC36668
0.8652	High Similarity	NPC476678
0.8632	High Similarity	NPC38530
0.8632	High Similarity	NPC84335
0.8587	High Similarity	NPC220454
0.8587	High Similarity	NPC469595
0.8587	High Similarity	NPC212679
0.8571	High Similarity	NPC215831
0.8571	High Similarity	NPC477128
0.8556	High Similarity	NPC220478
0.8542	High Similarity	NPC264378
0.8478	Intermediate Similarity	NPC173042
0.8469	Intermediate Similarity	NPC155332
0.8469	Intermediate Similarity	NPC32577
0.8469	Intermediate Similarity	NPC114540
0.8444	Intermediate Similarity	NPC189311
0.8438	Intermediate Similarity	NPC2049
0.8427	Intermediate Similarity	NPC193198
0.8421	Intermediate Similarity	NPC295347
0.8387	Intermediate Similarity	NPC152467
0.8387	Intermediate Similarity	NPC474842
0.8387	Intermediate Similarity	NPC469372
0.8387	Intermediate Similarity	NPC475965
0.8384	Intermediate Similarity	NPC475526
0.8384	Intermediate Similarity	NPC329345
0.8384	Intermediate Similarity	NPC471365
0.8384	Intermediate Similarity	NPC471364
0.8384	Intermediate Similarity	NPC132395
0.8384	Intermediate Similarity	NPC473283
0.8367	Intermediate Similarity	NPC168319
0.8367	Intermediate Similarity	NPC194028
0.8351	Intermediate Similarity	NPC57079
0.8351	Intermediate Similarity	NPC316598
0.8351	Intermediate Similarity	NPC108368
0.8333	Intermediate Similarity	NPC30486
0.8315	Intermediate Similarity	NPC268122
0.83	Intermediate Similarity	NPC470297
0.8298	Intermediate Similarity	NPC473944
0.8265	Intermediate Similarity	NPC266955
0.8247	Intermediate Similarity	NPC151488
0.8247	Intermediate Similarity	NPC208094
0.8242	Intermediate Similarity	NPC177932
0.8235	Intermediate Similarity	NPC318363
0.8235	Intermediate Similarity	NPC473482
0.8235	Intermediate Similarity	NPC475418
0.8229	Intermediate Similarity	NPC183012
0.8222	Intermediate Similarity	NPC118423
0.8222	Intermediate Similarity	NPC222358
0.8218	Intermediate Similarity	NPC477125
0.8191	Intermediate Similarity	NPC8062
0.8182	Intermediate Similarity	NPC115899
0.8172	Intermediate Similarity	NPC93411
0.8172	Intermediate Similarity	NPC226863
0.8172	Intermediate Similarity	NPC24816
0.8172	Intermediate Similarity	NPC472302
0.8163	Intermediate Similarity	NPC252295
0.8155	Intermediate Similarity	NPC475065
0.8155	Intermediate Similarity	NPC469370
0.8152	Intermediate Similarity	NPC168248
0.8144	Intermediate Similarity	NPC260796
0.8144	Intermediate Similarity	NPC112654
0.8137	Intermediate Similarity	NPC329048
0.8137	Intermediate Similarity	NPC330011
0.8132	Intermediate Similarity	NPC139566
0.8125	Intermediate Similarity	NPC473435
0.8125	Intermediate Similarity	NPC84893
0.8125	Intermediate Similarity	NPC473431
0.8125	Intermediate Similarity	NPC471078
0.8125	Intermediate Similarity	NPC473280
0.8119	Intermediate Similarity	NPC189616
0.8119	Intermediate Similarity	NPC118911
0.8111	Intermediate Similarity	NPC471218
0.8105	Intermediate Similarity	NPC303697
0.81	Intermediate Similarity	NPC273005
0.81	Intermediate Similarity	NPC31058
0.81	Intermediate Similarity	NPC469606
0.81	Intermediate Similarity	NPC320447
0.809	Intermediate Similarity	NPC268827
0.8085	Intermediate Similarity	NPC5509
0.8081	Intermediate Similarity	NPC476299
0.8081	Intermediate Similarity	NPC474012
0.8077	Intermediate Similarity	NPC253906
0.8065	Intermediate Similarity	NPC477228
0.8061	Intermediate Similarity	NPC285513
0.8061	Intermediate Similarity	NPC254496
0.8041	Intermediate Similarity	NPC33473
0.8041	Intermediate Similarity	NPC476519
0.8041	Intermediate Similarity	NPC209355
0.8039	Intermediate Similarity	NPC266570
0.8039	Intermediate Similarity	NPC469607
0.8022	Intermediate Similarity	NPC22611
0.8021	Intermediate Similarity	NPC205034
0.8021	Intermediate Similarity	NPC162615
0.8021	Intermediate Similarity	NPC79117
0.8021	Intermediate Similarity	NPC475657
0.8021	Intermediate Similarity	NPC139692
0.8021	Intermediate Similarity	NPC152778
0.802	Intermediate Similarity	NPC72151
0.8019	Intermediate Similarity	NPC122056
0.8	Intermediate Similarity	NPC221111
0.8	Intermediate Similarity	NPC25554
0.8	Intermediate Similarity	NPC161638
0.8	Intermediate Similarity	NPC475665
0.8	Intermediate Similarity	NPC472637
0.8	Intermediate Similarity	NPC470960
0.8	Intermediate Similarity	NPC310479
0.8	Intermediate Similarity	NPC115862
0.8	Intermediate Similarity	NPC280149
0.7981	Intermediate Similarity	NPC137911
0.7981	Intermediate Similarity	NPC228477
0.798	Intermediate Similarity	NPC471582
0.798	Intermediate Similarity	NPC176845
0.798	Intermediate Similarity	NPC478056
0.7979	Intermediate Similarity	NPC473879
0.7979	Intermediate Similarity	NPC196407
0.7961	Intermediate Similarity	NPC473284
0.7961	Intermediate Similarity	NPC133422
0.7959	Intermediate Similarity	NPC301534
0.7959	Intermediate Similarity	NPC307164
0.7959	Intermediate Similarity	NPC106425
0.7959	Intermediate Similarity	NPC250757
0.7959	Intermediate Similarity	NPC151725
0.7959	Intermediate Similarity	NPC202833
0.7959	Intermediate Similarity	NPC122324
0.7957	Intermediate Similarity	NPC473226
0.7941	Intermediate Similarity	NPC472868
0.7935	Intermediate Similarity	NPC474359
0.7935	Intermediate Similarity	NPC219011
0.7935	Intermediate Similarity	NPC60951
0.7935	Intermediate Similarity	NPC470011
0.7935	Intermediate Similarity	NPC306951
0.7921	Intermediate Similarity	NPC476081
0.7917	Intermediate Similarity	NPC186363
0.7917	Intermediate Similarity	NPC252433
0.7917	Intermediate Similarity	NPC233345
0.7912	Intermediate Similarity	NPC94200
0.7912	Intermediate Similarity	NPC123880
0.7912	Intermediate Similarity	NPC256112
0.7912	Intermediate Similarity	NPC200513
0.7912	Intermediate Similarity	NPC178676
0.7912	Intermediate Similarity	NPC471159
0.79	Intermediate Similarity	NPC470906
0.79	Intermediate Similarity	NPC471413
0.79	Intermediate Similarity	NPC54705
0.79	Intermediate Similarity	NPC117685
0.7895	Intermediate Similarity	NPC288699
0.7895	Intermediate Similarity	NPC115179
0.7895	Intermediate Similarity	NPC474844
0.7895	Intermediate Similarity	NPC475049
0.7895	Intermediate Similarity	NPC177141
0.7895	Intermediate Similarity	NPC106040
0.7889	Intermediate Similarity	NPC195424
0.7885	Intermediate Similarity	NPC476802
0.7885	Intermediate Similarity	NPC322903
0.7885	Intermediate Similarity	NPC89171
0.7879	Intermediate Similarity	NPC100912
0.7879	Intermediate Similarity	NPC474343
0.7879	Intermediate Similarity	NPC10057
0.7879	Intermediate Similarity	NPC170131
0.7879	Intermediate Similarity	NPC253826
0.7879	Intermediate Similarity	NPC202705
0.7872	Intermediate Similarity	NPC30421
0.7872	Intermediate Similarity	NPC312561
0.7865	Intermediate Similarity	NPC184737
0.7864	Intermediate Similarity	NPC478052
0.7864	Intermediate Similarity	NPC34768
0.7857	Intermediate Similarity	NPC171395
0.7857	Intermediate Similarity	NPC474909
0.7857	Intermediate Similarity	NPC134067
0.785	Intermediate Similarity	NPC471204
0.7849	Intermediate Similarity	NPC110405
0.7849	Intermediate Similarity	NPC474013
0.7843	Intermediate Similarity	NPC120321
0.7843	Intermediate Similarity	NPC475050
0.7843	Intermediate Similarity	NPC473624
0.7843	Intermediate Similarity	NPC254202
0.7843	Intermediate Similarity	NPC23584
0.7841	Intermediate Similarity	NPC40353
0.7835	Intermediate Similarity	NPC476597
0.7835	Intermediate Similarity	NPC476598
0.7835	Intermediate Similarity	NPC271652
0.783	Intermediate Similarity	NPC474315
0.7826	Intermediate Similarity	NPC194637
0.7826	Intermediate Similarity	NPC53867
0.7822	Intermediate Similarity	NPC472643
0.7822	Intermediate Similarity	NPC93744
0.7822	Intermediate Similarity	NPC118174
0.7822	Intermediate Similarity	NPC471412
0.7822	Intermediate Similarity	NPC310981
0.7822	Intermediate Similarity	NPC476888
0.7822	Intermediate Similarity	NPC282524

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 NPC38830 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1395
0.2-0.3	3504
0.3-0.4	2485
0.4-0.5	1068
0.5-0.6	306
0.6-0.7	159
0.7-0.8	31
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8242	Intermediate Similarity	NPD1694	Approved
0.7912	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD3573	Approved
0.7798	Intermediate Similarity	NPD7115	Discovery
0.7755	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7748	Approved
0.7755	Intermediate Similarity	NPD7900	Approved
0.7692	Intermediate Similarity	NPD6008	Approved
0.7579	Intermediate Similarity	NPD7146	Approved
0.7579	Intermediate Similarity	NPD7334	Approved
0.7579	Intermediate Similarity	NPD5330	Approved
0.7579	Intermediate Similarity	NPD7521	Approved
0.7579	Intermediate Similarity	NPD6409	Approved
0.7579	Intermediate Similarity	NPD6684	Approved
0.7551	Intermediate Similarity	NPD5693	Phase 1
0.7551	Intermediate Similarity	NPD5694	Approved
0.7551	Intermediate Similarity	NPD7515	Phase 2
0.7528	Intermediate Similarity	NPD8039	Approved
0.7525	Intermediate Similarity	NPD7902	Approved
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7638	Approved
0.7449	Intermediate Similarity	NPD5692	Phase 3
0.7449	Intermediate Similarity	NPD5207	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6903	Approved
0.7423	Intermediate Similarity	NPD5737	Approved
0.7423	Intermediate Similarity	NPD6672	Approved
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7374	Intermediate Similarity	NPD6050	Approved
0.734	Intermediate Similarity	NPD5209	Approved
0.7315	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD6399	Phase 3
0.729	Intermediate Similarity	NPD5697	Approved
0.7282	Intermediate Similarity	NPD4225	Approved
0.7248	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6001	Approved
0.7222	Intermediate Similarity	NPD6011	Approved
0.7222	Intermediate Similarity	NPD6881	Approved
0.7222	Intermediate Similarity	NPD6899	Approved
0.7216	Intermediate Similarity	NPD3618	Phase 1
0.7212	Intermediate Similarity	NPD6648	Approved
0.72	Intermediate Similarity	NPD5281	Approved
0.72	Intermediate Similarity	NPD6411	Approved
0.72	Intermediate Similarity	NPD5284	Approved
0.7196	Intermediate Similarity	NPD6675	Approved
0.7196	Intermediate Similarity	NPD6402	Approved
0.7196	Intermediate Similarity	NPD5739	Approved
0.7196	Intermediate Similarity	NPD7128	Approved
0.7172	Intermediate Similarity	NPD6904	Approved
0.7172	Intermediate Similarity	NPD6673	Approved
0.7172	Intermediate Similarity	NPD6080	Approved
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.7156	Intermediate Similarity	NPD6012	Approved
0.7156	Intermediate Similarity	NPD6013	Approved
0.7156	Intermediate Similarity	NPD6014	Approved
0.713	Intermediate Similarity	NPD5701	Approved
0.7129	Intermediate Similarity	NPD5779	Approved
0.7129	Intermediate Similarity	NPD5778	Approved
0.7091	Intermediate Similarity	NPD6883	Approved
0.7091	Intermediate Similarity	NPD7102	Approved
0.7091	Intermediate Similarity	NPD7290	Approved
0.7071	Intermediate Similarity	NPD5208	Approved
0.7064	Intermediate Similarity	NPD7320	Approved
0.703	Intermediate Similarity	NPD6079	Approved
0.7027	Intermediate Similarity	NPD6847	Approved
0.7027	Intermediate Similarity	NPD6650	Approved
0.7027	Intermediate Similarity	NPD6649	Approved
0.7027	Intermediate Similarity	NPD8130	Phase 1
0.7027	Intermediate Similarity	NPD6617	Approved
0.7027	Intermediate Similarity	NPD6869	Approved
0.7019	Intermediate Similarity	NPD5959	Approved
0.7019	Intermediate Similarity	NPD6083	Phase 2
0.7019	Intermediate Similarity	NPD6084	Phase 2
0.701	Intermediate Similarity	NPD3668	Phase 3
0.7	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD6051	Approved
0.7	Intermediate Similarity	NPD5328	Approved
0.7	Intermediate Similarity	NPD6372	Approved
0.7	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6373	Approved
0.699	Remote Similarity	NPD5654	Approved
0.6979	Remote Similarity	NPD3667	Approved
0.6964	Remote Similarity	NPD8297	Approved
0.6964	Remote Similarity	NPD6882	Approved
0.6961	Remote Similarity	NPD4202	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6923	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5222	Approved
0.6923	Remote Similarity	NPD5221	Approved
0.6916	Remote Similarity	NPD5211	Phase 2
0.6897	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5286	Approved
0.6887	Remote Similarity	NPD4696	Approved
0.6887	Remote Similarity	NPD5285	Approved
0.6875	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD4623	Approved
0.6869	Remote Similarity	NPD5279	Phase 3
0.6869	Remote Similarity	NPD4519	Discontinued
0.6869	Remote Similarity	NPD6098	Approved
0.6857	Remote Similarity	NPD4755	Approved
0.6857	Remote Similarity	NPD5173	Approved
0.6837	Remote Similarity	NPD3666	Approved
0.6837	Remote Similarity	NPD3133	Approved
0.6837	Remote Similarity	NPD4786	Approved
0.6837	Remote Similarity	NPD3665	Phase 1
0.6822	Remote Similarity	NPD5223	Approved
0.6822	Remote Similarity	NPD5344	Discontinued
0.6789	Remote Similarity	NPD5141	Approved
0.6771	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD4695	Discontinued
0.6768	Remote Similarity	NPD1696	Phase 3
0.6765	Remote Similarity	NPD46	Approved
0.6765	Remote Similarity	NPD6698	Approved
0.6765	Remote Similarity	NPD5785	Approved
0.6762	Remote Similarity	NPD4697	Phase 3
0.6759	Remote Similarity	NPD5224	Approved
0.6759	Remote Similarity	NPD5226	Approved
0.6759	Remote Similarity	NPD5225	Approved
0.6759	Remote Similarity	NPD4633	Approved
0.6759	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD4632	Approved
0.6729	Remote Similarity	NPD4700	Approved
0.6724	Remote Similarity	NPD6317	Approved
0.67	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4694	Approved
0.67	Remote Similarity	NPD5280	Approved
0.6697	Remote Similarity	NPD5174	Approved
0.6697	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4058	Approved
0.6638	Remote Similarity	NPD6868	Approved
0.6638	Remote Similarity	NPD6274	Approved
0.6633	Remote Similarity	NPD4221	Approved
0.6633	Remote Similarity	NPD4223	Phase 3
0.661	Remote Similarity	NPD7101	Approved
0.661	Remote Similarity	NPD7100	Approved
0.6607	Remote Similarity	NPD6686	Approved
0.6602	Remote Similarity	NPD7838	Discovery
0.6591	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6009	Approved
0.6555	Remote Similarity	NPD6319	Approved
0.6545	Remote Similarity	NPD4754	Approved
0.6538	Remote Similarity	NPD8035	Phase 2
0.6538	Remote Similarity	NPD8034	Phase 2
0.6538	Remote Similarity	NPD7637	Suspended
0.6535	Remote Similarity	NPD5690	Phase 2
0.6529	Remote Similarity	NPD7604	Phase 2
0.6522	Remote Similarity	NPD6053	Discontinued
0.6509	Remote Similarity	NPD4629	Approved
0.6509	Remote Similarity	NPD5210	Approved
0.6505	Remote Similarity	NPD1695	Approved
0.65	Remote Similarity	NPD5983	Phase 2
0.65	Remote Similarity	NPD4197	Approved
0.65	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5733	Approved
0.6466	Remote Similarity	NPD6858	Approved
0.6466	Remote Similarity	NPD7094	Approved
0.646	Remote Similarity	NPD4729	Approved
0.646	Remote Similarity	NPD4730	Approved
0.646	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5276	Approved
0.6449	Remote Similarity	NPD7732	Phase 3
0.6436	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5329	Approved
0.6429	Remote Similarity	NPD7260	Phase 2
0.6429	Remote Similarity	NPD4767	Approved
0.6429	Remote Similarity	NPD4768	Approved
0.6423	Remote Similarity	NPD7507	Approved
0.6421	Remote Similarity	NPD8264	Approved
0.6413	Remote Similarity	NPD4137	Phase 3
0.6408	Remote Similarity	NPD4518	Approved
0.6396	Remote Similarity	NPD6052	Approved
0.6392	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4688	Approved
0.6373	Remote Similarity	NPD4690	Approved
0.6373	Remote Similarity	NPD5205	Approved
0.6373	Remote Similarity	NPD4138	Approved
0.6373	Remote Similarity	NPD4689	Approved
0.6373	Remote Similarity	NPD4693	Phase 3
0.6372	Remote Similarity	NPD6614	Approved
0.6364	Remote Similarity	NPD7503	Approved
0.6364	Remote Similarity	NPD6909	Approved
0.6364	Remote Similarity	NPD6908	Approved
0.6348	Remote Similarity	NPD5250	Approved
0.6348	Remote Similarity	NPD5251	Approved
0.6348	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD5249	Phase 3
0.6348	Remote Similarity	NPD5248	Approved
0.6348	Remote Similarity	NPD5247	Approved
0.6348	Remote Similarity	NPD4634	Approved
0.6348	Remote Similarity	NPD5169	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