NPASS Compound

Structure

NPC118011 OpenBabel07101719522D 25 26 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 -0.0000 1.0000 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 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 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.2
Volume:	374.001
LogP:	3.001
LogD:	2.536
LogS:	-4.662
# Rotatable Bonds:	6
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.61
Synthetic Accessibility Score:	4.501
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:	-4.798
MDCK Permeability:	2.873556877602823e-05
Pgp-inhibitor:	0.967
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	81.50557708740234%
Volume Distribution (VD):	1.976
Pgp-substrate:	11.192339897155762%

ADMET: Metabolism

CYP1A2-inhibitor:	0.192
CYP1A2-substrate:	0.772
CYP2C19-inhibitor:	0.661
CYP2C19-substrate:	0.845
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.132
CYP2D6-inhibitor:	0.065
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.706
CYP3A4-substrate:	0.879

ADMET: Excretion

Clearance (CL):	4.063
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.385
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.893
Skin Sensitization:	0.814
Carcinogencity:	0.834
Eye Corrosion:	0.054
Eye Irritation:	0.082
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC118011

Natural Product ID:	NPC118011
*Common Name:**	Trigonochinene B
IUPAC Name:	methyl 3-[(1R,2R,4aR)-5-ethenyl-4a-hydroxy-1,6-dimethyl-7-oxo-2-prop-1-en-2-yl-3,4-dihydro-2H-naphthalen-1-yl]propanoate
Synonyms:	trigonochinene B
Standard InCHIKey:	ZFLNGJFWUHGMKC-HBGVWJBISA-N
Standard InCHI:	InChI=1S/C21H28O4/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)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)O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515632
PubChem CID:	25019247
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	=	12.5	ug.mL-1	PMID[519109]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	25.0	ug.mL-1	PMID[519109]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	50.0	ug.mL-1	PMID[519109]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	50.0	ug.mL-1	PMID[519109]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	50.0	ug.mL-1	PMID[519109]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[519109]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	50.0	ug.mL-1	PMID[519109]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	50.0	ug.mL-1	PMID[519109]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	50.0	ug.mL-1	PMID[519109]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[519109]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	50.0	ug.mL-1	PMID[519109]

☑ 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 NPC118011 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	183
0.1-0.2	938
0.2-0.3	3522
0.3-0.4	8551
0.4-0.5	14024
0.5-0.6	8302
0.6-0.7	4970
0.7-0.8	2065
0.8-0.85	119
0.85-0.9	20
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC36668
0.9524	High Similarity	NPC181327
0.875	High Similarity	NPC72397
0.875	High Similarity	NPC48107
0.8681	High Similarity	NPC38830
0.8667	High Similarity	NPC474018
0.8667	High Similarity	NPC473986
0.8617	High Similarity	NPC266955
0.8602	High Similarity	NPC170131
0.8602	High Similarity	NPC208094
0.8587	High Similarity	NPC295347
0.8554	High Similarity	NPC266193
0.8554	High Similarity	NPC257666
0.8526	High Similarity	NPC115899
0.8523	High Similarity	NPC473226
0.8495	Intermediate Similarity	NPC301534
0.8495	Intermediate Similarity	NPC250757
0.8462	Intermediate Similarity	NPC204341
0.8454	Intermediate Similarity	NPC472868
0.8452	Intermediate Similarity	NPC275494
0.8452	Intermediate Similarity	NPC471409
0.8452	Intermediate Similarity	NPC179028
0.8452	Intermediate Similarity	NPC321514
0.8444	Intermediate Similarity	NPC284561
0.8434	Intermediate Similarity	NPC472305
0.8434	Intermediate Similarity	NPC180886
0.8427	Intermediate Similarity	NPC128644
0.8391	Intermediate Similarity	NPC49019
0.8351	Intermediate Similarity	NPC475050
0.8351	Intermediate Similarity	NPC72151
0.8333	Intermediate Similarity	NPC61952
0.8333	Intermediate Similarity	NPC282524
0.8333	Intermediate Similarity	NPC97377
0.8333	Intermediate Similarity	NPC115862
0.8333	Intermediate Similarity	NPC472870
0.8316	Intermediate Similarity	NPC108368
0.8316	Intermediate Similarity	NPC57079
0.8316	Intermediate Similarity	NPC316598
0.8316	Intermediate Similarity	NPC478056
0.8315	Intermediate Similarity	NPC239685
0.8315	Intermediate Similarity	NPC82979
0.8295	Intermediate Similarity	NPC302360
0.8283	Intermediate Similarity	NPC473284
0.828	Intermediate Similarity	NPC299100
0.828	Intermediate Similarity	NPC474690
0.8261	Intermediate Similarity	NPC252433
0.8256	Intermediate Similarity	NPC476809
0.8247	Intermediate Similarity	NPC155332
0.8247	Intermediate Similarity	NPC114540
0.8247	Intermediate Similarity	NPC32577
0.8247	Intermediate Similarity	NPC320447
0.8242	Intermediate Similarity	NPC472676
0.8242	Intermediate Similarity	NPC472688
0.8242	Intermediate Similarity	NPC5509
0.8242	Intermediate Similarity	NPC262043
0.8235	Intermediate Similarity	NPC198240
0.8235	Intermediate Similarity	NPC74410
0.8222	Intermediate Similarity	NPC136948
0.8222	Intermediate Similarity	NPC476409
0.8211	Intermediate Similarity	NPC474938
0.8211	Intermediate Similarity	NPC474785
0.8202	Intermediate Similarity	NPC269638
0.8202	Intermediate Similarity	NPC109528
0.8202	Intermediate Similarity	NPC474680
0.8191	Intermediate Similarity	NPC209355
0.8191	Intermediate Similarity	NPC171395
0.8191	Intermediate Similarity	NPC134067
0.8191	Intermediate Similarity	NPC180950
0.8182	Intermediate Similarity	NPC476927
0.8182	Intermediate Similarity	NPC57370
0.8182	Intermediate Similarity	NPC97913
0.8182	Intermediate Similarity	NPC297398
0.8172	Intermediate Similarity	NPC472871
0.8172	Intermediate Similarity	NPC263780
0.8172	Intermediate Similarity	NPC476416
0.8172	Intermediate Similarity	NPC472303
0.8163	Intermediate Similarity	NPC475526
0.8163	Intermediate Similarity	NPC329345
0.8163	Intermediate Similarity	NPC473283
0.8161	Intermediate Similarity	NPC121984
0.8161	Intermediate Similarity	NPC473420
0.8161	Intermediate Similarity	NPC40228
0.8161	Intermediate Similarity	NPC278459
0.8161	Intermediate Similarity	NPC226068
0.8161	Intermediate Similarity	NPC327002
0.8152	Intermediate Similarity	NPC476437
0.8152	Intermediate Similarity	NPC476369
0.8144	Intermediate Similarity	NPC99411
0.8144	Intermediate Similarity	NPC224720
0.8144	Intermediate Similarity	NPC476240
0.8144	Intermediate Similarity	NPC476223
0.814	Intermediate Similarity	NPC170394
0.814	Intermediate Similarity	NPC308038
0.8132	Intermediate Similarity	NPC229612
0.8132	Intermediate Similarity	NPC473229
0.8132	Intermediate Similarity	NPC7280
0.8132	Intermediate Similarity	NPC104560
0.8125	Intermediate Similarity	NPC235464
0.8125	Intermediate Similarity	NPC471717
0.8125	Intermediate Similarity	NPC166745
0.8118	Intermediate Similarity	NPC34110
0.8118	Intermediate Similarity	NPC165711
0.8118	Intermediate Similarity	NPC472300
0.8111	Intermediate Similarity	NPC322159
0.8111	Intermediate Similarity	NPC472869
0.8111	Intermediate Similarity	NPC73038
0.8111	Intermediate Similarity	NPC202394
0.8111	Intermediate Similarity	NPC472974
0.8105	Intermediate Similarity	NPC471153
0.81	Intermediate Similarity	NPC330011
0.81	Intermediate Similarity	NPC329048
0.8095	Intermediate Similarity	NPC476795
0.8095	Intermediate Similarity	NPC476346
0.809	Intermediate Similarity	NPC472865
0.809	Intermediate Similarity	NPC164577
0.8085	Intermediate Similarity	NPC477129
0.8085	Intermediate Similarity	NPC477130
0.8085	Intermediate Similarity	NPC469406
0.8085	Intermediate Similarity	NPC8993
0.8081	Intermediate Similarity	NPC118911
0.8072	Intermediate Similarity	NPC180015
0.8072	Intermediate Similarity	NPC130016
0.8072	Intermediate Similarity	NPC109576
0.8072	Intermediate Similarity	NPC247586
0.8072	Intermediate Similarity	NPC56747
0.8068	Intermediate Similarity	NPC256112
0.8068	Intermediate Similarity	NPC2524
0.8068	Intermediate Similarity	NPC469799
0.8068	Intermediate Similarity	NPC469806
0.8068	Intermediate Similarity	NPC73882
0.8068	Intermediate Similarity	NPC93590
0.8065	Intermediate Similarity	NPC475806
0.8065	Intermediate Similarity	NPC289479
0.8065	Intermediate Similarity	NPC470036
0.8065	Intermediate Similarity	NPC174167
0.8065	Intermediate Similarity	NPC116726
0.8065	Intermediate Similarity	NPC303697
0.8061	Intermediate Similarity	NPC273005
0.8061	Intermediate Similarity	NPC31058
0.8061	Intermediate Similarity	NPC469606
0.8046	Intermediate Similarity	NPC160582
0.8043	Intermediate Similarity	NPC472983
0.8043	Intermediate Similarity	NPC173042
0.8043	Intermediate Similarity	NPC66344
0.8043	Intermediate Similarity	NPC474918
0.8041	Intermediate Similarity	NPC476274
0.8023	Intermediate Similarity	NPC169095
0.8022	Intermediate Similarity	NPC477228
0.8022	Intermediate Similarity	NPC471792
0.8022	Intermediate Similarity	NPC312561
0.8021	Intermediate Similarity	NPC474343
0.8021	Intermediate Similarity	NPC253826
0.8021	Intermediate Similarity	NPC110937
0.8021	Intermediate Similarity	NPC473456
0.8021	Intermediate Similarity	NPC99726
0.8021	Intermediate Similarity	NPC320306
0.8021	Intermediate Similarity	NPC254496
0.802	Intermediate Similarity	NPC475418
0.802	Intermediate Similarity	NPC473482
0.802	Intermediate Similarity	NPC318363
0.8	Intermediate Similarity	NPC69143
0.8	Intermediate Similarity	NPC7629
0.8	Intermediate Similarity	NPC53565
0.8	Intermediate Similarity	NPC151622
0.8	Intermediate Similarity	NPC477125
0.8	Intermediate Similarity	NPC183012
0.8	Intermediate Similarity	NPC309399
0.8	Intermediate Similarity	NPC139459
0.8	Intermediate Similarity	NPC263582
0.8	Intermediate Similarity	NPC189311
0.8	Intermediate Similarity	NPC88310
0.798	Intermediate Similarity	NPC478057
0.798	Intermediate Similarity	NPC95899
0.7979	Intermediate Similarity	NPC242069
0.7979	Intermediate Similarity	NPC295643
0.7979	Intermediate Similarity	NPC131840
0.7979	Intermediate Similarity	NPC272075
0.7979	Intermediate Similarity	NPC214756
0.7978	Intermediate Similarity	NPC310470
0.7978	Intermediate Similarity	NPC279639
0.7978	Intermediate Similarity	NPC312480
0.7978	Intermediate Similarity	NPC105803
0.7978	Intermediate Similarity	NPC102197
0.7978	Intermediate Similarity	NPC3856
0.7976	Intermediate Similarity	NPC237591
0.7976	Intermediate Similarity	NPC3753
0.7976	Intermediate Similarity	NPC301065
0.7961	Intermediate Similarity	NPC474315
0.7959	Intermediate Similarity	NPC81530
0.7959	Intermediate Similarity	NPC118174
0.7959	Intermediate Similarity	NPC472643
0.7959	Intermediate Similarity	NPC97435
0.7957	Intermediate Similarity	NPC474842
0.7957	Intermediate Similarity	NPC472866
0.7957	Intermediate Similarity	NPC475965
0.7957	Intermediate Similarity	NPC134321
0.7957	Intermediate Similarity	NPC232426
0.7957	Intermediate Similarity	NPC232202
0.7957	Intermediate Similarity	NPC281942
0.7957	Intermediate Similarity	NPC182136

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 NPC118011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1197
0.2-0.3	3281
0.3-0.4	2755
0.4-0.5	1149
0.5-0.6	335
0.6-0.7	208
0.7-0.8	62
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
0.8065	Intermediate Similarity	NPD5281	Approved
0.8065	Intermediate Similarity	NPD5284	Approved
0.7912	Intermediate Similarity	NPD4519	Discontinued
0.7912	Intermediate Similarity	NPD4623	Approved
0.7895	Intermediate Similarity	NPD7748	Approved
0.7872	Intermediate Similarity	NPD7515	Phase 2
0.7849	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3573	Approved
0.7684	Intermediate Similarity	NPD5694	Approved
0.7653	Intermediate Similarity	NPD7902	Approved
0.764	Intermediate Similarity	NPD4695	Discontinued
0.7629	Intermediate Similarity	NPD5695	Phase 3
0.7604	Intermediate Similarity	NPD5778	Approved
0.7604	Intermediate Similarity	NPD5779	Approved
0.7604	Intermediate Similarity	NPD6399	Phase 3
0.7579	Intermediate Similarity	NPD5692	Phase 3
0.7579	Intermediate Similarity	NPD5207	Approved
0.7527	Intermediate Similarity	NPD5280	Approved
0.7527	Intermediate Similarity	NPD4694	Approved
0.7527	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD6050	Approved
0.75	Intermediate Similarity	NPD6411	Approved
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7473	Intermediate Similarity	NPD3667	Approved
0.7473	Intermediate Similarity	NPD4221	Approved
0.7473	Intermediate Similarity	NPD4223	Phase 3
0.7473	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD7115	Discovery
0.7419	Intermediate Similarity	NPD1696	Phase 3
0.7419	Intermediate Similarity	NPD1694	Approved
0.7404	Intermediate Similarity	NPD5697	Approved
0.74	Intermediate Similarity	NPD5696	Approved
0.7368	Intermediate Similarity	NPD6672	Approved
0.7368	Intermediate Similarity	NPD5737	Approved
0.7353	Intermediate Similarity	NPD5211	Phase 2
0.7347	Intermediate Similarity	NPD7900	Approved
0.7347	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD5690	Phase 2
0.734	Intermediate Similarity	NPD5279	Phase 3
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.734	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7146	Approved
0.7333	Intermediate Similarity	NPD6881	Approved
0.7333	Intermediate Similarity	NPD6899	Approved
0.7333	Intermediate Similarity	NPD6011	Approved
0.7327	Intermediate Similarity	NPD7639	Approved
0.7327	Intermediate Similarity	NPD7640	Approved
0.732	Intermediate Similarity	NPD6079	Approved
0.732	Intermediate Similarity	NPD5693	Phase 1
0.7312	Intermediate Similarity	NPD3133	Approved
0.7312	Intermediate Similarity	NPD3665	Phase 1
0.7312	Intermediate Similarity	NPD3666	Approved
0.7312	Intermediate Similarity	NPD4197	Approved
0.7312	Intermediate Similarity	NPD4786	Approved
0.7308	Intermediate Similarity	NPD7128	Approved
0.7308	Intermediate Similarity	NPD6675	Approved
0.7308	Intermediate Similarity	NPD6402	Approved
0.7308	Intermediate Similarity	NPD5739	Approved
0.7303	Intermediate Similarity	NPD4756	Discovery
0.7292	Intermediate Similarity	NPD6904	Approved
0.7292	Intermediate Similarity	NPD6673	Approved
0.7292	Intermediate Similarity	NPD6101	Approved
0.7292	Intermediate Similarity	NPD4753	Phase 2
0.7292	Intermediate Similarity	NPD5328	Approved
0.7292	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6080	Approved
0.7273	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD6012	Approved
0.7264	Intermediate Similarity	NPD6014	Approved
0.7264	Intermediate Similarity	NPD6013	Approved
0.7253	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD4202	Approved
0.7238	Intermediate Similarity	NPD5701	Approved
0.7234	Intermediate Similarity	NPD5329	Approved
0.7228	Intermediate Similarity	NPD7638	Approved
0.7228	Intermediate Similarity	NPD4225	Approved
0.7212	Intermediate Similarity	NPD5141	Approved
0.72	Intermediate Similarity	NPD5222	Approved
0.72	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5221	Approved
0.7196	Intermediate Similarity	NPD7290	Approved
0.7196	Intermediate Similarity	NPD7102	Approved
0.7196	Intermediate Similarity	NPD6883	Approved
0.7188	Intermediate Similarity	NPD5208	Approved
0.7188	Intermediate Similarity	NPD6903	Approved
0.7188	Intermediate Similarity	NPD4518	Approved
0.7188	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7320	Approved
0.7158	Intermediate Similarity	NPD4693	Phase 3
0.7158	Intermediate Similarity	NPD4690	Approved
0.7158	Intermediate Similarity	NPD4138	Approved
0.7158	Intermediate Similarity	NPD5205	Approved
0.7158	Intermediate Similarity	NPD4688	Approved
0.7158	Intermediate Similarity	NPD4689	Approved
0.7157	Intermediate Similarity	NPD5285	Approved
0.7157	Intermediate Similarity	NPD6404	Discontinued
0.7157	Intermediate Similarity	NPD5286	Approved
0.7157	Intermediate Similarity	NPD4696	Approved
0.713	Intermediate Similarity	NPD6869	Approved
0.713	Intermediate Similarity	NPD6617	Approved
0.713	Intermediate Similarity	NPD6847	Approved
0.713	Intermediate Similarity	NPD8130	Phase 1
0.713	Intermediate Similarity	NPD6649	Approved
0.713	Intermediate Similarity	NPD6650	Approved
0.7129	Intermediate Similarity	NPD5173	Approved
0.7129	Intermediate Similarity	NPD4755	Approved
0.7128	Intermediate Similarity	NPD3668	Phase 3
0.7103	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD6373	Approved
0.71	Intermediate Similarity	NPD4629	Approved
0.71	Intermediate Similarity	NPD5654	Approved
0.71	Intermediate Similarity	NPD5210	Approved
0.7087	Intermediate Similarity	NPD5223	Approved
0.7079	Intermediate Similarity	NPD8039	Approved
0.7079	Intermediate Similarity	NPD8264	Approved
0.7064	Intermediate Similarity	NPD6882	Approved
0.7064	Intermediate Similarity	NPD8297	Approved
0.7041	Intermediate Similarity	NPD5785	Approved
0.7041	Intermediate Similarity	NPD4096	Approved
0.7033	Intermediate Similarity	NPD3617	Approved
0.7033	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4697	Phase 3
0.7019	Intermediate Similarity	NPD5225	Approved
0.7019	Intermediate Similarity	NPD5226	Approved
0.7019	Intermediate Similarity	NPD4633	Approved
0.7019	Intermediate Similarity	NPD5224	Approved
0.7	Intermediate Similarity	NPD6001	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.699	Remote Similarity	NPD4700	Approved
0.6981	Remote Similarity	NPD6008	Approved
0.6979	Remote Similarity	NPD6098	Approved
0.6972	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7637	Suspended
0.6966	Remote Similarity	NPD4687	Approved
0.6966	Remote Similarity	NPD4058	Approved
0.6961	Remote Similarity	NPD5959	Approved
0.6957	Remote Similarity	NPD4195	Approved
0.6952	Remote Similarity	NPD5174	Approved
0.6952	Remote Similarity	NPD5175	Approved
0.69	Remote Similarity	NPD5133	Approved
0.6875	Remote Similarity	NPD5363	Approved
0.6867	Remote Similarity	NPD4193	Approved
0.6867	Remote Similarity	NPD4192	Approved
0.6867	Remote Similarity	NPD4194	Approved
0.6867	Remote Similarity	NPD4191	Approved
0.6863	Remote Similarity	NPD7614	Phase 1
0.6842	Remote Similarity	NPD5362	Discontinued
0.6814	Remote Similarity	NPD6009	Approved
0.6814	Remote Similarity	NPD6317	Approved
0.6792	Remote Similarity	NPD4754	Approved
0.6789	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5733	Approved
0.6754	Remote Similarity	NPD6314	Approved
0.6754	Remote Similarity	NPD6335	Approved
0.6754	Remote Similarity	NPD6313	Approved
0.6744	Remote Similarity	NPD7331	Phase 2
0.6742	Remote Similarity	NPD5276	Approved
0.6737	Remote Similarity	NPD4270	Approved
0.6737	Remote Similarity	NPD4269	Approved
0.6727	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6868	Approved
0.6726	Remote Similarity	NPD6274	Approved
0.6705	Remote Similarity	NPD4137	Phase 3
0.6701	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7732	Phase 3
0.6698	Remote Similarity	NPD7632	Discontinued
0.6697	Remote Similarity	NPD4730	Approved
0.6697	Remote Similarity	NPD4729	Approved
0.6696	Remote Similarity	NPD7100	Approved
0.6696	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD6648	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD6319	Approved
0.6634	Remote Similarity	NPD8035	Phase 2
0.6634	Remote Similarity	NPD8034	Phase 2
0.6633	Remote Similarity	NPD5786	Approved
0.6632	Remote Similarity	NPD4139	Approved
0.6632	Remote Similarity	NPD5369	Approved
0.6632	Remote Similarity	NPD4692	Approved
0.6629	Remote Similarity	NPD4691	Approved
0.6629	Remote Similarity	NPD4747	Approved
0.6628	Remote Similarity	NPD7341	Phase 2
0.6602	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5983	Phase 2
0.6577	Remote Similarity	NPD4634	Approved
0.6577	Remote Similarity	NPD5250	Approved
0.6577	Remote Similarity	NPD5249	Phase 3
0.6577	Remote Similarity	NPD5169	Approved
0.6577	Remote Similarity	NPD5248	Approved
0.6577	Remote Similarity	NPD5251	Approved
0.6577	Remote Similarity	NPD5247	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