NPASS Compound

Structure

CID304692 OpenBabel06191716112D 25 29 0 0 1 0 0 0 0 0999 V2000 -1.2681 0.3746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7474 -0.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6047 -0.9265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.8219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0218 1.1917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7889 -1.3664 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5570 0.4549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3665 -0.4556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 0.9108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1556 0.9104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5779 -0.0002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1555 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7891 1.3664 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7889 -1.3664 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3667 1.3662 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5780 0.9106 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3668 2.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7889 -0.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7889 -0.4555 0.0000 C 0 0 2 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 1.6190 -1.8457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0330 2.9430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8158 0.4710 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0216 -0.2819 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7892 2.2771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 6 1 0 0 0 0 4 14 1 0 0 0 0 5 7 2 0 0 0 0 5 10 1 0 0 0 0 6 18 1 0 0 0 0 7 24 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 20 1 0 0 0 0 10 12 2 0 0 0 0 11 16 1 0 0 0 0 11 19 1 6 0 0 0 12 24 1 0 0 0 0 13 9 1 6 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 19 1 1 0 0 0 14 21 1 0 0 0 0 15 10 1 6 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 17 22 2 0 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 19 20 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.18
Volume:	347.736
LogP:	2.29
LogD:	2.305
LogS:	-3.749
# Rotatable Bonds:	0
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.705
Synthetic Accessibility Score:	5.128
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.739
MDCK Permeability:	2.215439781139139e-05
Pgp-inhibitor:	0.104
Pgp-substrate:	0.938
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.851
Plasma Protein Binding (PPB):	74.65131378173828%
Volume Distribution (VD):	1.7
Pgp-substrate:	37.626895904541016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.44
CYP2C19-inhibitor:	0.087
CYP2C19-substrate:	0.816
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.223
CYP3A4-inhibitor:	0.378
CYP3A4-substrate:	0.61

ADMET: Excretion

Clearance (CL):	11.157
Half-life (T1/2):	0.112

ADMET: Toxicity

hERG Blockers:	0.706
Human Hepatotoxicity (H-HT):	0.42
Drug-inuced Liver Injury (DILI):	0.249
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.144
Carcinogencity:	0.897
Eye Corrosion:	0.003
Eye Irritation:	0.009
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: NPC304692

Natural Product ID:	NPC304692
*Common Name:**	Caesalmin G
IUPAC Name:	n.a.
Synonyms:	Caesalmin G
Standard InCHIKey:	NSXNSJSUAMXKCX-QQUVXZFBSA-N
Standard InCHI:	InChI=1S/C20H26O5/c1-18(2)6-4-14(21)19(3)11-8-12-10(5-7-24-12)15-16(11)13(25-17(15)22)9-20(18,19)23/h5,7,11,13-16,21,23H,4,6,8-9H2,1-3H3/t11-,13-,14-,15+,16-,19-,20+/m0/s1
SMILES:	O=C1O[C@@H]2[C@H]3[C@H]1c1ccoc1C[C@@H]3[C@@]1([C@](C2)(O)C(C)(C)CC[C@@H]1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465832
PubChem CID:	10936915
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678648]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	Indonesia	n.a.	PMID[15921414]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	seed kernel	n.a.	PMID[15921414]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[23806110]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24303808]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14392	Caesalpinia minax	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
Others	2

Activity Type	# Activity
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT336	Organism	Human parainfluenza virus 3	Human parainfluenza virus 3	IC50	=	14.8	ug.mL-1	PMID[558406]
NPT27	Others	Unspecified		LC50	=	44.7	ug.mL-1	PMID[558406]
NPT27	Others	Unspecified		TI	=	3.0	n.a.	PMID[558406]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10000.0	nM	PMID[558407]

☑ 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 NPC304692 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	329
0.1-0.2	1246
0.2-0.3	2619
0.3-0.4	4733
0.4-0.5	10266
0.5-0.6	9413
0.6-0.7	8772
0.7-0.8	4731
0.8-0.85	341
0.85-0.9	211
0.9-0.95	31
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC104736
0.9737	High Similarity	NPC283209
0.9667	High Similarity	NPC41880
0.9608	High Similarity	NPC285567
0.9463	High Similarity	NPC212257
0.9416	High Similarity	NPC68848
0.9412	High Similarity	NPC140952
0.9359	High Similarity	NPC121995
0.9346	High Similarity	NPC81405
0.9346	High Similarity	NPC194499
0.929	High Similarity	NPC18986
0.9286	High Similarity	NPC474611
0.9226	High Similarity	NPC287559
0.9221	High Similarity	NPC195954
0.9221	High Similarity	NPC88007
0.9172	High Similarity	NPC56358
0.9139	High Similarity	NPC211625
0.9085	High Similarity	NPC294511
0.9085	High Similarity	NPC121615
0.9079	High Similarity	NPC228842
0.906	High Similarity	NPC251865
0.9057	High Similarity	NPC270312
0.9054	High Similarity	NPC263337
0.9051	High Similarity	NPC472664
0.9045	High Similarity	NPC79571
0.9045	High Similarity	NPC188649
0.9026	High Similarity	NPC114880
0.8987	High Similarity	NPC88841
0.8987	High Similarity	NPC288602
0.8981	High Similarity	NPC8389
0.8968	High Similarity	NPC75310
0.8961	High Similarity	NPC75906
0.894	High Similarity	NPC62799
0.8889	High Similarity	NPC475237
0.8889	High Similarity	NPC195325
0.8889	High Similarity	NPC475641
0.8882	High Similarity	NPC216755
0.8882	High Similarity	NPC296558
0.8882	High Similarity	NPC71821
0.8868	High Similarity	NPC476035
0.8868	High Similarity	NPC14499
0.8868	High Similarity	NPC475039
0.8867	High Similarity	NPC243577
0.8861	High Similarity	NPC472299
0.8854	High Similarity	NPC7059
0.8854	High Similarity	NPC472772
0.8851	High Similarity	NPC202260
0.8839	High Similarity	NPC475777
0.8839	High Similarity	NPC268905
0.8839	High Similarity	NPC246164
0.8827	High Similarity	NPC118086
0.8824	High Similarity	NPC19747
0.8808	High Similarity	NPC84479
0.88	High Similarity	NPC121158
0.8797	High Similarity	NPC475967
0.8797	High Similarity	NPC123153
0.8788	High Similarity	NPC472665
0.8782	High Similarity	NPC57998
0.8782	High Similarity	NPC178932
0.8773	High Similarity	NPC294512
0.8766	High Similarity	NPC125182
0.8766	High Similarity	NPC472654
0.8766	High Similarity	NPC69647
0.8758	High Similarity	NPC255414
0.8758	High Similarity	NPC471174
0.8758	High Similarity	NPC277618
0.8758	High Similarity	NPC286038
0.8742	High Similarity	NPC205071
0.8734	High Similarity	NPC299038
0.8726	High Similarity	NPC469336
0.8726	High Similarity	NPC92979
0.8718	High Similarity	NPC469503
0.8716	High Similarity	NPC307401
0.8704	High Similarity	NPC310572
0.8701	High Similarity	NPC66991
0.8696	High Similarity	NPC276735
0.8693	High Similarity	NPC233763
0.8688	High Similarity	NPC470792
0.8688	High Similarity	NPC472771
0.8679	High Similarity	NPC84349
0.8667	High Similarity	NPC67003
0.8667	High Similarity	NPC148374
0.8662	High Similarity	NPC98206
0.8662	High Similarity	NPC282445
0.8662	High Similarity	NPC34421
0.8662	High Similarity	NPC237259
0.8654	High Similarity	NPC272590
0.865	High Similarity	NPC255787
0.8642	High Similarity	NPC308156
0.8642	High Similarity	NPC86800
0.8642	High Similarity	NPC475779
0.8636	High Similarity	NPC250228
0.8636	High Similarity	NPC221809
0.8634	High Similarity	NPC663
0.8634	High Similarity	NPC224394
0.8634	High Similarity	NPC472773
0.8634	High Similarity	NPC419
0.8627	High Similarity	NPC5676
0.8618	High Similarity	NPC64568
0.8618	High Similarity	NPC267632
0.8616	High Similarity	NPC469847
0.8616	High Similarity	NPC249021
0.8616	High Similarity	NPC261597
0.8616	High Similarity	NPC470118
0.8616	High Similarity	NPC472776
0.8616	High Similarity	NPC472778
0.8616	High Similarity	NPC472777
0.8614	High Similarity	NPC176413
0.8614	High Similarity	NPC56953
0.8608	High Similarity	NPC25351
0.8608	High Similarity	NPC141538
0.8608	High Similarity	NPC155939
0.8608	High Similarity	NPC35000
0.8608	High Similarity	NPC296807
0.8608	High Similarity	NPC214541
0.8608	High Similarity	NPC44675
0.86	High Similarity	NPC90953
0.8599	High Similarity	NPC472672
0.8598	High Similarity	NPC88593
0.8598	High Similarity	NPC472660
0.859	High Similarity	NPC196864
0.859	High Similarity	NPC470997
0.859	High Similarity	NPC477404
0.8589	High Similarity	NPC476861
0.8589	High Similarity	NPC472784
0.8589	High Similarity	NPC476850
0.8581	High Similarity	NPC93666
0.858	High Similarity	NPC126984
0.858	High Similarity	NPC27541
0.858	High Similarity	NPC123088
0.858	High Similarity	NPC61967
0.858	High Similarity	NPC62692
0.8571	High Similarity	NPC471003
0.8571	High Similarity	NPC97904
0.8571	High Similarity	NPC346
0.8562	High Similarity	NPC476944
0.8562	High Similarity	NPC475226
0.8562	High Similarity	NPC472823
0.8544	High Similarity	NPC253201
0.8544	High Similarity	NPC44606
0.8544	High Similarity	NPC302054
0.8544	High Similarity	NPC30222
0.8537	High Similarity	NPC291742
0.8537	High Similarity	NPC271235
0.8519	High Similarity	NPC302369
0.8519	High Similarity	NPC134254
0.8519	High Similarity	NPC39986
0.8519	High Similarity	NPC477405
0.8512	High Similarity	NPC11062
0.8509	High Similarity	NPC335761
0.8509	High Similarity	NPC218818
0.8506	High Similarity	NPC41182
0.8506	High Similarity	NPC185456
0.8503	High Similarity	NPC167340
0.85	High Similarity	NPC214495
0.85	High Similarity	NPC36655
0.85	High Similarity	NPC475066
0.85	High Similarity	NPC470119
0.85	High Similarity	NPC197137
0.85	High Similarity	NPC187149
0.8491	Intermediate Similarity	NPC264943
0.8485	Intermediate Similarity	NPC470995
0.8481	Intermediate Similarity	NPC48671
0.8481	Intermediate Similarity	NPC33938
0.8476	Intermediate Similarity	NPC472282
0.8476	Intermediate Similarity	NPC472774
0.8476	Intermediate Similarity	NPC472775
0.8476	Intermediate Similarity	NPC473753
0.8476	Intermediate Similarity	NPC473766
0.8471	Intermediate Similarity	NPC159927
0.8471	Intermediate Similarity	NPC156189
0.8471	Intermediate Similarity	NPC476122
0.8471	Intermediate Similarity	NPC469335
0.8466	Intermediate Similarity	NPC476856
0.8466	Intermediate Similarity	NPC276551
0.8466	Intermediate Similarity	NPC476857
0.8466	Intermediate Similarity	NPC261184
0.8466	Intermediate Similarity	NPC476858
0.8457	Intermediate Similarity	NPC329938
0.8457	Intermediate Similarity	NPC5079
0.8457	Intermediate Similarity	NPC263432
0.8457	Intermediate Similarity	NPC82851
0.8457	Intermediate Similarity	NPC200782
0.8457	Intermediate Similarity	NPC472767
0.8457	Intermediate Similarity	NPC69028
0.8452	Intermediate Similarity	NPC471292
0.8447	Intermediate Similarity	NPC473368
0.8447	Intermediate Similarity	NPC472671
0.8446	Intermediate Similarity	NPC293253
0.8442	Intermediate Similarity	NPC199044
0.8442	Intermediate Similarity	NPC238843
0.8424	Intermediate Similarity	NPC160651
0.8424	Intermediate Similarity	NPC471397
0.8418	Intermediate Similarity	NPC18135
0.8415	Intermediate Similarity	NPC472141
0.8415	Intermediate Similarity	NPC470875
0.8415	Intermediate Similarity	NPC23387
0.8415	Intermediate Similarity	NPC100849
0.8408	Intermediate Similarity	NPC470998
0.8408	Intermediate Similarity	NPC234494

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 NPC304692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	800
0.2-0.3	1636
0.3-0.4	2501
0.4-0.5	2227
0.5-0.6	1203
0.6-0.7	396
0.7-0.8	90
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD8434	Phase 2
0.8491	Intermediate Similarity	NPD5761	Phase 2
0.8491	Intermediate Similarity	NPD5760	Phase 2
0.8284	Intermediate Similarity	NPD6765	Approved
0.8284	Intermediate Similarity	NPD6764	Approved
0.8092	Intermediate Similarity	NPD6784	Approved
0.8092	Intermediate Similarity	NPD6785	Approved
0.8061	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD4628	Phase 3
0.7898	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6273	Approved
0.7791	Intermediate Similarity	NPD3226	Approved
0.7764	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7819	Suspended
0.7679	Intermediate Similarity	NPD3749	Approved
0.7669	Intermediate Similarity	NPD920	Approved
0.759	Intermediate Similarity	NPD7411	Suspended
0.7586	Intermediate Similarity	NPD5844	Phase 1
0.7557	Intermediate Similarity	NPD6559	Discontinued
0.7547	Intermediate Similarity	NPD1471	Phase 3
0.7546	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7236	Approved
0.753	Intermediate Similarity	NPD6599	Discontinued
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4967	Phase 2
0.7515	Intermediate Similarity	NPD4966	Approved
0.7515	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8127	Discontinued
0.7439	Intermediate Similarity	NPD2534	Approved
0.7439	Intermediate Similarity	NPD2533	Approved
0.7439	Intermediate Similarity	NPD2532	Approved
0.7438	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7412	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3750	Approved
0.7384	Intermediate Similarity	NPD5494	Approved
0.7375	Intermediate Similarity	NPD6100	Approved
0.7375	Intermediate Similarity	NPD2796	Approved
0.7375	Intermediate Similarity	NPD6099	Approved
0.7372	Intermediate Similarity	NPD3764	Approved
0.7371	Intermediate Similarity	NPD7473	Discontinued
0.7368	Intermediate Similarity	NPD7075	Discontinued
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.7347	Intermediate Similarity	NPD8404	Phase 2
0.7337	Intermediate Similarity	NPD37	Approved
0.7337	Intermediate Similarity	NPD6801	Discontinued
0.7333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6005	Phase 3
0.7329	Intermediate Similarity	NPD6004	Phase 3
0.7329	Intermediate Similarity	NPD6002	Phase 3
0.7329	Intermediate Similarity	NPD2344	Approved
0.7326	Intermediate Similarity	NPD6234	Discontinued
0.7314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3748	Approved
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7305	Intermediate Similarity	NPD7239	Suspended
0.7303	Intermediate Similarity	NPD1608	Approved
0.7301	Intermediate Similarity	NPD7003	Approved
0.7299	Intermediate Similarity	NPD7229	Phase 3
0.7299	Intermediate Similarity	NPD6232	Discontinued
0.7294	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1549	Phase 2
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4140	Approved
0.7273	Intermediate Similarity	NPD6799	Approved
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7261	Intermediate Similarity	NPD2313	Discontinued
0.7261	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3268	Approved
0.7241	Intermediate Similarity	NPD7199	Phase 2
0.7241	Intermediate Similarity	NPD6959	Discontinued
0.7239	Intermediate Similarity	NPD1243	Approved
0.7239	Intermediate Similarity	NPD2800	Approved
0.7232	Intermediate Similarity	NPD3818	Discontinued
0.7229	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD919	Approved
0.7222	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4380	Phase 2
0.7215	Intermediate Similarity	NPD8032	Phase 2
0.7209	Intermediate Similarity	NPD7768	Phase 2
0.7182	Intermediate Similarity	NPD8313	Approved
0.7182	Intermediate Similarity	NPD8312	Approved
0.7178	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2309	Approved
0.7151	Intermediate Similarity	NPD3817	Phase 2
0.7151	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1934	Approved
0.7135	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD7799	Discontinued
0.7115	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD3882	Suspended
0.7105	Intermediate Similarity	NPD17	Approved
0.7102	Intermediate Similarity	NPD6808	Phase 2
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7099	Intermediate Similarity	NPD1510	Phase 2
0.7091	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3972	Approved
0.7062	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2935	Discontinued
0.7052	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3267	Approved
0.7051	Intermediate Similarity	NPD2797	Approved
0.7051	Intermediate Similarity	NPD3266	Approved
0.7041	Intermediate Similarity	NPD5403	Approved
0.7039	Intermediate Similarity	NPD3751	Discontinued
0.7039	Intermediate Similarity	NPD7177	Discontinued
0.7037	Intermediate Similarity	NPD7097	Phase 1
0.7024	Intermediate Similarity	NPD5401	Approved
0.7022	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6166	Phase 2
0.7022	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7011	Intermediate Similarity	NPD7058	Phase 2
0.7011	Intermediate Similarity	NPD7057	Phase 3
0.6995	Remote Similarity	NPD7497	Discontinued
0.6994	Remote Similarity	NPD2801	Approved
0.6993	Remote Similarity	NPD1778	Approved
0.6988	Remote Similarity	NPD4110	Phase 3
0.6988	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7240	Approved
0.6975	Remote Similarity	NPD1607	Approved
0.6966	Remote Similarity	NPD3926	Phase 2
0.6957	Remote Similarity	NPD4307	Phase 2
0.6957	Remote Similarity	NPD1240	Approved
0.6946	Remote Similarity	NPD6190	Approved
0.6937	Remote Similarity	NPD6798	Discontinued
0.6937	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5953	Discontinued
0.6918	Remote Similarity	NPD6832	Phase 2
0.6914	Remote Similarity	NPD5124	Phase 1
0.6914	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5735	Approved
0.691	Remote Similarity	NPD5710	Approved
0.691	Remote Similarity	NPD3787	Discontinued
0.691	Remote Similarity	NPD5711	Approved
0.6909	Remote Similarity	NPD5762	Approved
0.6909	Remote Similarity	NPD5763	Approved
0.6907	Remote Similarity	NPD7435	Discontinued
0.6906	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2798	Approved
0.6897	Remote Similarity	NPD1465	Phase 2
0.6897	Remote Similarity	NPD8455	Phase 2
0.6894	Remote Similarity	NPD6233	Phase 2
0.6894	Remote Similarity	NPD6663	Approved
0.6886	Remote Similarity	NPD8166	Discontinued
0.6885	Remote Similarity	NPD7685	Pre-registration
0.6883	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8150	Discontinued
0.6879	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1283	Approved
0.6879	Remote Similarity	NPD1876	Approved
0.6875	Remote Similarity	NPD7095	Approved
0.6868	Remote Similarity	NPD7074	Phase 3
0.6865	Remote Similarity	NPD8407	Phase 2
0.6864	Remote Similarity	NPD1511	Approved
0.6863	Remote Similarity	NPD9545	Approved
0.6852	Remote Similarity	NPD2979	Phase 3
0.6848	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD3887	Approved
0.6839	Remote Similarity	NPD6781	Approved
0.6839	Remote Similarity	NPD6778	Approved
0.6839	Remote Similarity	NPD6782	Approved
0.6839	Remote Similarity	NPD6777	Approved
0.6839	Remote Similarity	NPD6776	Approved
0.6839	Remote Similarity	NPD6780	Approved
0.6839	Remote Similarity	NPD6779	Approved
0.6832	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7028	Phase 2
0.6818	Remote Similarity	NPD5585	Approved
0.6813	Remote Similarity	NPD7286	Phase 2
0.6813	Remote Similarity	NPD7054	Approved
0.681	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.681	Remote Similarity	NPD230	Phase 1
0.6809	Remote Similarity	NPD4287	Approved
0.6809	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD8368	Discontinued
0.6788	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD1512	Approved
0.6784	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7472	Approved
0.6772	Remote Similarity	NPD3225	Approved
0.6768	Remote Similarity	NPD6353	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