NPASS Compound

Structure

NPC181327 OpenBabel07101719402D 26 27 0 0 1 0 0 0 0 0999 V2000 0.0000 -2.0000 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 -3.4641 1.0000 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 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 5.8301 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 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 -1.3660 4.0981 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 4.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 13 2 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 6 25 1 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 16 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 15 21 1 0 0 0 0 16 20 1 6 0 0 0 17 22 2 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 20 5 1 6 0 0 0 21 26 1 6 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.19
Volume:	382.792
LogP:	2.56
LogD:	1.807
LogS:	-4.428
# Rotatable Bonds:	7
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.333
Synthetic Accessibility Score:	4.661
Fsp3:	0.524
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.863
MDCK Permeability:	3.065741475438699e-05
Pgp-inhibitor:	0.8
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.034

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	85.10765838623047%
Volume Distribution (VD):	2.051
Pgp-substrate:	8.006357192993164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.229
CYP2C19-substrate:	0.861
CYP2C9-inhibitor:	0.354
CYP2C9-substrate:	0.213
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.528
CYP3A4-substrate:	0.831

ADMET: Excretion

Clearance (CL):	3.952
Half-life (T1/2):	0.897

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.693
Drug-inuced Liver Injury (DILI):	0.149
AMES Toxicity:	0.89
Rat Oral Acute Toxicity:	0.796
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.761
Carcinogencity:	0.908
Eye Corrosion:	0.374
Eye Irritation:	0.173
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC181327

Natural Product ID:	NPC181327
*Common Name:**	Trigonochinene C
IUPAC Name:	methyl 3-[(1R,2R,4aR)-5-ethenyl-4a-hydroperoxy-1,6-dimethyl-7-oxo-2-prop-1-en-2-yl-3,4-dihydro-2H-naphthalen-1-yl]propanoate
Synonyms:	trigonochinene C
Standard InCHIKey:	OONMQCVQEOUVNN-HBGVWJBISA-N
Standard InCHI:	InChI=1S/C21H28O5/c1-7-15-14(4)17(22)12-18-20(5,10-9-19(23)25-6)16(13(2)3)8-11-21(15,18)26-24/h7,12,16,24H,1-2,8-11H2,3-6H3/t16-,20-,21+/m1/s1
SMILES:	COC(=O)CC[C@]1(C)[C@H](CC[C@]2(C1=CC(=O)C(=C2C=C)C)OO)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL477403
PubChem CID:	25019248
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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	=	50.0	ug.mL-1	PMID[456126]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug.mL-1	PMID[456126]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	25.0	ug.mL-1	PMID[456126]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	12.5	ug.mL-1	PMID[456126]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[456126]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[456126]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[456126]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	12.5	ug.mL-1	PMID[456126]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[456126]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	50.0	ug.mL-1	PMID[456126]

☑ 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 NPC181327 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	199
0.1-0.2	1065
0.2-0.3	3880
0.3-0.4	10673
0.4-0.5	13012
0.5-0.6	8038
0.6-0.7	4492
0.7-0.8	1298
0.8-0.85	35
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC36668
0.9524	High Similarity	NPC118011
0.8876	High Similarity	NPC38830
0.8636	High Similarity	NPC284561
0.837	Intermediate Similarity	NPC295347
0.8315	Intermediate Similarity	NPC48107
0.8315	Intermediate Similarity	NPC72397
0.8313	Intermediate Similarity	NPC472300
0.8261	Intermediate Similarity	NPC477130
0.8261	Intermediate Similarity	NPC477129
0.8242	Intermediate Similarity	NPC474018
0.8242	Intermediate Similarity	NPC473986
0.8222	Intermediate Similarity	NPC173042
0.8214	Intermediate Similarity	NPC321514
0.8211	Intermediate Similarity	NPC266955
0.8202	Intermediate Similarity	NPC477228
0.8193	Intermediate Similarity	NPC180886
0.8191	Intermediate Similarity	NPC208094
0.8191	Intermediate Similarity	NPC110937
0.8191	Intermediate Similarity	NPC170131
0.8182	Intermediate Similarity	NPC189311
0.814	Intermediate Similarity	NPC226068
0.8132	Intermediate Similarity	NPC469595
0.8132	Intermediate Similarity	NPC474842
0.8132	Intermediate Similarity	NPC220454
0.8132	Intermediate Similarity	NPC475965
0.8132	Intermediate Similarity	NPC212679
0.8125	Intermediate Similarity	NPC115899
0.8111	Intermediate Similarity	NPC472302
0.8105	Intermediate Similarity	NPC57079
0.8105	Intermediate Similarity	NPC108368
0.8095	Intermediate Similarity	NPC257666
0.8095	Intermediate Similarity	NPC266193
0.809	Intermediate Similarity	NPC220478
0.809	Intermediate Similarity	NPC473226
0.8085	Intermediate Similarity	NPC301534
0.8085	Intermediate Similarity	NPC250757
0.8065	Intermediate Similarity	NPC470697
0.8061	Intermediate Similarity	NPC472868
0.8046	Intermediate Similarity	NPC268122
0.8043	Intermediate Similarity	NPC204341
0.8041	Intermediate Similarity	NPC320447
0.8041	Intermediate Similarity	NPC155332
0.8041	Intermediate Similarity	NPC32577
0.8041	Intermediate Similarity	NPC114540
0.8023	Intermediate Similarity	NPC476809
0.8022	Intermediate Similarity	NPC73995
0.8022	Intermediate Similarity	NPC5509
0.8	Intermediate Similarity	NPC179028
0.8	Intermediate Similarity	NPC275494
0.8	Intermediate Similarity	NPC128644
0.8	Intermediate Similarity	NPC30421
0.8	Intermediate Similarity	NPC84335
0.8	Intermediate Similarity	NPC38530
0.8	Intermediate Similarity	NPC471409
0.8	Intermediate Similarity	NPC74410
0.7979	Intermediate Similarity	NPC209355
0.7979	Intermediate Similarity	NPC171395
0.7978	Intermediate Similarity	NPC474680
0.7976	Intermediate Similarity	NPC899
0.7976	Intermediate Similarity	NPC40353
0.7976	Intermediate Similarity	NPC472305
0.7959	Intermediate Similarity	NPC329345
0.7959	Intermediate Similarity	NPC473283
0.7959	Intermediate Similarity	NPC475050
0.7959	Intermediate Similarity	NPC72151
0.7959	Intermediate Similarity	NPC475526
0.7957	Intermediate Similarity	NPC263780
0.7955	Intermediate Similarity	NPC297398
0.7955	Intermediate Similarity	NPC118423
0.7955	Intermediate Similarity	NPC193198
0.7955	Intermediate Similarity	NPC49019
0.7952	Intermediate Similarity	NPC306928
0.7938	Intermediate Similarity	NPC115862
0.7938	Intermediate Similarity	NPC282524
0.7935	Intermediate Similarity	NPC476437
0.7935	Intermediate Similarity	NPC469372
0.7935	Intermediate Similarity	NPC476369
0.7931	Intermediate Similarity	NPC474955
0.7931	Intermediate Similarity	NPC278459
0.7931	Intermediate Similarity	NPC121984
0.7931	Intermediate Similarity	NPC40228
0.7931	Intermediate Similarity	NPC327002
0.7931	Intermediate Similarity	NPC473420
0.7917	Intermediate Similarity	NPC316598
0.7917	Intermediate Similarity	NPC478056
0.7912	Intermediate Similarity	NPC472870
0.7912	Intermediate Similarity	NPC477128
0.7912	Intermediate Similarity	NPC473229
0.7912	Intermediate Similarity	NPC215831
0.79	Intermediate Similarity	NPC473284
0.79	Intermediate Similarity	NPC329048
0.79	Intermediate Similarity	NPC330011
0.7895	Intermediate Similarity	NPC471153
0.7889	Intermediate Similarity	NPC73038
0.7889	Intermediate Similarity	NPC168248
0.7889	Intermediate Similarity	NPC239685
0.7889	Intermediate Similarity	NPC82979
0.7882	Intermediate Similarity	NPC97377
0.7882	Intermediate Similarity	NPC61952
0.7882	Intermediate Similarity	NPC165711
0.7872	Intermediate Similarity	NPC471078
0.7872	Intermediate Similarity	NPC473280
0.7872	Intermediate Similarity	NPC474690
0.7872	Intermediate Similarity	NPC8993
0.7872	Intermediate Similarity	NPC473435
0.7872	Intermediate Similarity	NPC473431
0.7872	Intermediate Similarity	NPC299100
0.7865	Intermediate Similarity	NPC302360
0.7865	Intermediate Similarity	NPC139566
0.7865	Intermediate Similarity	NPC30486
0.7857	Intermediate Similarity	NPC476346
0.7857	Intermediate Similarity	NPC469606
0.7857	Intermediate Similarity	NPC273005
0.7857	Intermediate Similarity	NPC31058
0.7857	Intermediate Similarity	NPC65650
0.7849	Intermediate Similarity	NPC303697
0.7849	Intermediate Similarity	NPC174167
0.7849	Intermediate Similarity	NPC252433
0.7849	Intermediate Similarity	NPC470036
0.7841	Intermediate Similarity	NPC256112
0.7841	Intermediate Similarity	NPC321289
0.7841	Intermediate Similarity	NPC327969
0.7841	Intermediate Similarity	NPC73882
0.7831	Intermediate Similarity	NPC130016
0.7831	Intermediate Similarity	NPC109576
0.7831	Intermediate Similarity	NPC180015
0.7831	Intermediate Similarity	NPC56747
0.7826	Intermediate Similarity	NPC472676
0.7826	Intermediate Similarity	NPC262043
0.7826	Intermediate Similarity	NPC472688
0.7822	Intermediate Similarity	NPC473482
0.7822	Intermediate Similarity	NPC318363
0.7822	Intermediate Similarity	NPC475418
0.7812	Intermediate Similarity	NPC474785
0.7812	Intermediate Similarity	NPC473456
0.7812	Intermediate Similarity	NPC2049
0.7812	Intermediate Similarity	NPC474938
0.7802	Intermediate Similarity	NPC136948
0.7802	Intermediate Similarity	NPC476409
0.78	Intermediate Similarity	NPC477125
0.7791	Intermediate Similarity	NPC198240
0.7791	Intermediate Similarity	NPC4827
0.7789	Intermediate Similarity	NPC180950
0.7789	Intermediate Similarity	NPC183012
0.7789	Intermediate Similarity	NPC134067
0.7789	Intermediate Similarity	NPC88310
0.7789	Intermediate Similarity	NPC139459
0.7778	Intermediate Similarity	NPC269638
0.7778	Intermediate Similarity	NPC132395
0.7778	Intermediate Similarity	NPC471365
0.7778	Intermediate Similarity	NPC471364
0.7778	Intermediate Similarity	NPC109528
0.7766	Intermediate Similarity	NPC214756
0.7766	Intermediate Similarity	NPC472303
0.7766	Intermediate Similarity	NPC272075
0.7766	Intermediate Similarity	NPC476416
0.7766	Intermediate Similarity	NPC79117
0.7766	Intermediate Similarity	NPC472871
0.7766	Intermediate Similarity	NPC295643
0.7765	Intermediate Similarity	NPC69143
0.7765	Intermediate Similarity	NPC309399
0.7755	Intermediate Similarity	NPC168319
0.7755	Intermediate Similarity	NPC224720
0.7755	Intermediate Similarity	NPC194028
0.7755	Intermediate Similarity	NPC476240
0.7755	Intermediate Similarity	NPC99411
0.7755	Intermediate Similarity	NPC476223
0.7753	Intermediate Similarity	NPC222358
0.7753	Intermediate Similarity	NPC102197
0.7753	Intermediate Similarity	NPC474976
0.7753	Intermediate Similarity	NPC57370
0.7753	Intermediate Similarity	NPC22611
0.7753	Intermediate Similarity	NPC97913
0.7753	Intermediate Similarity	NPC474790
0.7753	Intermediate Similarity	NPC476927
0.7753	Intermediate Similarity	NPC312480
0.7753	Intermediate Similarity	NPC105803
0.7745	Intermediate Similarity	NPC475065
0.7742	Intermediate Similarity	NPC213636
0.7742	Intermediate Similarity	NPC128672
0.7742	Intermediate Similarity	NPC253177
0.7742	Intermediate Similarity	NPC152467
0.7742	Intermediate Similarity	NPC280592
0.7738	Intermediate Similarity	NPC166797
0.7738	Intermediate Similarity	NPC301065
0.7738	Intermediate Similarity	NPC3753
0.7738	Intermediate Similarity	NPC237591
0.7732	Intermediate Similarity	NPC166745
0.7732	Intermediate Similarity	NPC235464
0.7732	Intermediate Similarity	NPC471717
0.7727	Intermediate Similarity	NPC90055
0.7727	Intermediate Similarity	NPC149237
0.7727	Intermediate Similarity	NPC471898
0.7727	Intermediate Similarity	NPC475665
0.7727	Intermediate Similarity	NPC477372
0.7727	Intermediate Similarity	NPC225515
0.7727	Intermediate Similarity	NPC142244
0.7717	Intermediate Similarity	NPC472220
0.7717	Intermediate Similarity	NPC196407

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 NPC181327 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1266
0.2-0.3	3523
0.3-0.4	2633
0.4-0.5	1006
0.5-0.6	315
0.6-0.7	186
0.7-0.8	40
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
0.8	Intermediate Similarity	NPD3573	Approved
0.7849	Intermediate Similarity	NPD5694	Approved
0.7849	Intermediate Similarity	NPD5281	Approved
0.7849	Intermediate Similarity	NPD5284	Approved
0.7742	Intermediate Similarity	NPD5207	Approved
0.7742	Intermediate Similarity	NPD5692	Phase 3
0.7684	Intermediate Similarity	NPD7748	Approved
0.766	Intermediate Similarity	NPD6050	Approved
0.766	Intermediate Similarity	NPD7515	Phase 2
0.764	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1694	Approved
0.7527	Intermediate Similarity	NPD6672	Approved
0.7527	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD4623	Approved
0.75	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD4519	Discontinued
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD7900	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7474	Intermediate Similarity	NPD5693	Phase 1
0.7449	Intermediate Similarity	NPD7902	Approved
0.7447	Intermediate Similarity	NPD6673	Approved
0.7447	Intermediate Similarity	NPD6080	Approved
0.7447	Intermediate Similarity	NPD6904	Approved
0.7423	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5695	Phase 3
0.7416	Intermediate Similarity	NPD4695	Discontinued
0.7396	Intermediate Similarity	NPD6399	Phase 3
0.734	Intermediate Similarity	NPD5208	Approved
0.734	Intermediate Similarity	NPD6903	Approved
0.734	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3618	Phase 1
0.7312	Intermediate Similarity	NPD5280	Approved
0.7312	Intermediate Similarity	NPD4694	Approved
0.7292	Intermediate Similarity	NPD6411	Approved
0.7283	Intermediate Similarity	NPD3668	Phase 3
0.7273	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD6083	Phase 2
0.7253	Intermediate Similarity	NPD4223	Phase 3
0.7253	Intermediate Similarity	NPD3667	Approved
0.7253	Intermediate Similarity	NPD4221	Approved
0.7245	Intermediate Similarity	NPD5654	Approved
0.7241	Intermediate Similarity	NPD8039	Approved
0.7216	Intermediate Similarity	NPD5779	Approved
0.7216	Intermediate Similarity	NPD5778	Approved
0.7212	Intermediate Similarity	NPD5697	Approved
0.72	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD6899	Approved
0.7143	Intermediate Similarity	NPD6001	Approved
0.7143	Intermediate Similarity	NPD6881	Approved
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7128	Intermediate Similarity	NPD6098	Approved
0.7128	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5690	Phase 2
0.7126	Intermediate Similarity	NPD4058	Approved
0.7126	Intermediate Similarity	NPD4687	Approved
0.7115	Intermediate Similarity	NPD7128	Approved
0.7115	Intermediate Similarity	NPD6008	Approved
0.7115	Intermediate Similarity	NPD5739	Approved
0.7115	Intermediate Similarity	NPD6675	Approved
0.7115	Intermediate Similarity	NPD6402	Approved
0.7113	Intermediate Similarity	NPD6079	Approved
0.71	Intermediate Similarity	NPD5959	Approved
0.7097	Intermediate Similarity	NPD3133	Approved
0.7097	Intermediate Similarity	NPD4786	Approved
0.7097	Intermediate Similarity	NPD3666	Approved
0.7097	Intermediate Similarity	NPD3665	Phase 1
0.7097	Intermediate Similarity	NPD4197	Approved
0.7091	Intermediate Similarity	NPD7115	Discovery
0.7083	Intermediate Similarity	NPD5328	Approved
0.7083	Intermediate Similarity	NPD6101	Approved
0.7083	Intermediate Similarity	NPD4753	Phase 2
0.7083	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6013	Approved
0.7075	Intermediate Similarity	NPD6012	Approved
0.7075	Intermediate Similarity	NPD6014	Approved
0.7048	Intermediate Similarity	NPD5701	Approved
0.7041	Intermediate Similarity	NPD4202	Approved
0.7033	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7638	Approved
0.7021	Intermediate Similarity	NPD5329	Approved
0.7021	Intermediate Similarity	NPD1696	Phase 3
0.7009	Intermediate Similarity	NPD6883	Approved
0.7009	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD5222	Approved
0.7	Intermediate Similarity	NPD5221	Approved
0.7	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5211	Phase 2
0.6981	Remote Similarity	NPD7320	Approved
0.6979	Remote Similarity	NPD4518	Approved
0.6961	Remote Similarity	NPD7639	Approved
0.6961	Remote Similarity	NPD5286	Approved
0.6961	Remote Similarity	NPD5285	Approved
0.6961	Remote Similarity	NPD4696	Approved
0.6961	Remote Similarity	NPD7640	Approved
0.6947	Remote Similarity	NPD4693	Phase 3
0.6947	Remote Similarity	NPD4689	Approved
0.6947	Remote Similarity	NPD4690	Approved
0.6947	Remote Similarity	NPD5205	Approved
0.6947	Remote Similarity	NPD4688	Approved
0.6947	Remote Similarity	NPD4138	Approved
0.6944	Remote Similarity	NPD6869	Approved
0.6944	Remote Similarity	NPD6649	Approved
0.6944	Remote Similarity	NPD6847	Approved
0.6944	Remote Similarity	NPD8130	Phase 1
0.6944	Remote Similarity	NPD6650	Approved
0.6944	Remote Similarity	NPD6617	Approved
0.6932	Remote Similarity	NPD5733	Approved
0.6931	Remote Similarity	NPD5173	Approved
0.6931	Remote Similarity	NPD4755	Approved
0.6916	Remote Similarity	NPD6373	Approved
0.6916	Remote Similarity	NPD6372	Approved
0.69	Remote Similarity	NPD5210	Approved
0.69	Remote Similarity	NPD4629	Approved
0.6897	Remote Similarity	NPD5276	Approved
0.6893	Remote Similarity	NPD5223	Approved
0.6889	Remote Similarity	NPD4756	Discovery
0.6881	Remote Similarity	NPD8297	Approved
0.6881	Remote Similarity	NPD6882	Approved
0.6863	Remote Similarity	NPD4225	Approved
0.686	Remote Similarity	NPD4137	Phase 3
0.6857	Remote Similarity	NPD5141	Approved
0.6837	Remote Similarity	NPD4096	Approved
0.6832	Remote Similarity	NPD4697	Phase 3
0.6832	Remote Similarity	NPD7732	Phase 3
0.6827	Remote Similarity	NPD5225	Approved
0.6827	Remote Similarity	NPD5224	Approved
0.6827	Remote Similarity	NPD4633	Approved
0.6827	Remote Similarity	NPD5226	Approved
0.6818	Remote Similarity	NPD4632	Approved
0.6813	Remote Similarity	NPD3617	Approved
0.6796	Remote Similarity	NPD4700	Approved
0.6796	Remote Similarity	NPD6404	Discontinued
0.6789	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4747	Approved
0.6782	Remote Similarity	NPD4691	Approved
0.6762	Remote Similarity	NPD5174	Approved
0.6762	Remote Similarity	NPD5175	Approved
0.6739	Remote Similarity	NPD4195	Approved
0.6702	Remote Similarity	NPD5209	Approved
0.67	Remote Similarity	NPD5133	Approved
0.6667	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6637	Remote Similarity	NPD6317	Approved
0.6637	Remote Similarity	NPD6009	Approved
0.663	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4191	Approved
0.6627	Remote Similarity	NPD4194	Approved
0.6627	Remote Similarity	NPD4193	Approved
0.6627	Remote Similarity	NPD4192	Approved
0.6606	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6052	Approved
0.6604	Remote Similarity	NPD4754	Approved
0.66	Remote Similarity	NPD7637	Suspended
0.6579	Remote Similarity	NPD6314	Approved
0.6579	Remote Similarity	NPD6335	Approved
0.6579	Remote Similarity	NPD6313	Approved
0.6574	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6614	Approved
0.6566	Remote Similarity	NPD6051	Approved
0.6549	Remote Similarity	NPD6274	Approved
0.6549	Remote Similarity	NPD6868	Approved
0.6545	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7100	Approved
0.6522	Remote Similarity	NPD7101	Approved
0.6514	Remote Similarity	NPD4729	Approved
0.6514	Remote Similarity	NPD4730	Approved
0.6512	Remote Similarity	NPD7331	Phase 2
0.6495	Remote Similarity	NPD5363	Approved
0.6495	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4768	Approved
0.6481	Remote Similarity	NPD4767	Approved
0.6476	Remote Similarity	NPD6648	Approved
0.6471	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD6319	Approved
0.6458	Remote Similarity	NPD5362	Discontinued
0.6458	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD8034	Phase 2
0.6436	Remote Similarity	NPD8035	Phase 2
0.6421	Remote Similarity	NPD4139	Approved
0.6421	Remote Similarity	NPD5369	Approved
0.6421	Remote Similarity	NPD4692	Approved
0.641	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5983	Phase 2
0.6408	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD4634	Approved
0.6396	Remote Similarity	NPD5249	Phase 3
0.6396	Remote Similarity	NPD5251	Approved
0.6396	Remote Similarity	NPD5169	Approved
0.6396	Remote Similarity	NPD5247	Approved
0.6396	Remote Similarity	NPD5250	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