NPASS Compound

Structure

CID121995 OpenBabel06191715472D 31 34 0 0 1 0 0 0 0 0999 V2000 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -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 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 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 4.4152 1.3090 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 5.0029 0.5000 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 0.0000 3.0000 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 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 2 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 0.8660 1.5000 0.0000 C 0 0 2 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 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 -0.5000 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 0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 29 1 0 0 0 0 6 8 1 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 21 1 0 0 0 0 9 30 1 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 11 24 2 0 0 0 0 11 31 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 6 0 0 0 14 30 1 0 0 0 0 15 22 1 0 0 0 0 15 25 2 0 0 0 0 16 17 1 0 0 0 0 16 20 1 6 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 31 1 0 0 0 0 19 23 1 0 0 0 0 19 26 1 0 0 0 0 20 27 2 0 0 0 0 20 29 1 0 0 0 0 21 23 1 0 0 0 0 22 23 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.19
Volume:	429.278
LogP:	1.783
LogD:	1.357
LogS:	-3.565
# Rotatable Bonds:	4
TPSA:	123.27
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	4.989
Fsp3:	0.696
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.004
MDCK Permeability:	6.187400140333921e-05
Pgp-inhibitor:	0.825
Pgp-substrate:	0.435
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.079
30% Bioavailability (F30%):	0.684

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.577
Plasma Protein Binding (PPB):	52.65053176879883%
Volume Distribution (VD):	0.892
Pgp-substrate:	52.010643005371094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.384
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.161
CYP3A4-inhibitor:	0.402
CYP3A4-substrate:	0.454

ADMET: Excretion

Clearance (CL):	5.56
Half-life (T1/2):	0.894

ADMET: Toxicity

hERG Blockers:	0.129
Human Hepatotoxicity (H-HT):	0.757
Drug-inuced Liver Injury (DILI):	0.619
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.618
Maximum Recommended Daily Dose:	0.264
Skin Sensitization:	0.058
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.278

Download Data

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

Natural Product: NPC121995

Natural Product ID:	NPC121995
*Common Name:**	Bonducellpin E
IUPAC Name:	methyl (4aR,5S,6R,6aR,7S,11aS,11bR)-6-acetyloxy-4a,5-dihydroxy-4,4,11b-trimethyl-1-oxo-2,3,5,6,6a,7,11,11a-octahydronaphtho[2,1-f][1]benzofuran-7-carboxylate
Synonyms:	Bonducellpin E
Standard InCHIKey:	ZYLJCUKCYXHXHV-SVBHYKRNSA-N
Standard InCHI:	InChI=1S/C23H30O8/c1-11(24)31-18-17-13(10-14-12(7-9-30-14)16(17)20(27)29-5)22(4)15(25)6-8-21(2,3)23(22,28)19(18)26/h7,9,13,16-19,26,28H,6,8,10H2,1-5H3/t13-,16+,17+,18+,19-,22-,23+/m0/s1
SMILES:	CC(=O)O[C@@H]1[C@@H]2[C@H](Cc3c(cco3)[C@H]2C(=O)OC)[C@@]2(C)C(=O)CCC(C)(C)[C@@]2([C@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252118
PubChem CID:	23642922
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO29844	Caesalpinia bonduc	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[17329887]
NPO29844	Caesalpinia bonduc	Species	Fabaceae	Eukaryota	seed kernels	Amphur Sanamchaikate, Chachoengsao Province, Thailand	2005-JUN	PMID[17848088]
NPO25179	Guilandina bonduc	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26756595]
NPO11853	Eucalyptus froggattii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7886	Eria tomentosa	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13248	Pistacia mexicana	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25179	Guilandina bonduc	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1600.0	nM	PMID[565911]

☑ 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 NPC121995 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	348
0.1-0.2	1299
0.2-0.3	2701
0.3-0.4	5298
0.4-0.5	9849
0.5-0.6	8657
0.6-0.7	6463
0.7-0.8	7340
0.8-0.85	496
0.85-0.9	199
0.9-0.95	30
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9805	High Similarity	NPC18986
0.974	High Similarity	NPC287559
0.9677	High Similarity	NPC68848
0.9615	High Similarity	NPC283209
0.9615	High Similarity	NPC285567
0.9557	High Similarity	NPC270312
0.9554	High Similarity	NPC56358
0.9551	High Similarity	NPC188649
0.949	High Similarity	NPC288602
0.949	High Similarity	NPC88841
0.9484	High Similarity	NPC194499
0.9484	High Similarity	NPC88007
0.9423	High Similarity	NPC140952
0.9419	High Similarity	NPC41880
0.9359	High Similarity	NPC304692
0.9359	High Similarity	NPC195954
0.9359	High Similarity	NPC81405
0.9295	High Similarity	NPC104736
0.9255	High Similarity	NPC296558
0.9245	High Similarity	NPC472773
0.9226	High Similarity	NPC121615
0.9226	High Similarity	NPC294511
0.9221	High Similarity	NPC228842
0.9182	High Similarity	NPC472771
0.9182	High Similarity	NPC79571
0.9177	High Similarity	NPC474611
0.913	High Similarity	NPC475779
0.9119	High Similarity	NPC8389
0.9097	High Similarity	NPC212257
0.9074	High Similarity	NPC472775
0.9074	High Similarity	NPC472774
0.9068	High Similarity	NPC276551
0.9036	High Similarity	NPC472665
0.9032	High Similarity	NPC211625
0.9024	High Similarity	NPC294512
0.9024	High Similarity	NPC475237
0.9024	High Similarity	NPC475641
0.9018	High Similarity	NPC471397
0.9018	High Similarity	NPC160651
0.9012	High Similarity	NPC470875
0.9006	High Similarity	NPC477405
0.9006	High Similarity	NPC292389
0.9006	High Similarity	NPC469338
0.8994	High Similarity	NPC472772
0.8994	High Similarity	NPC7059
0.8987	High Similarity	NPC75310
0.8987	High Similarity	NPC264943
0.8957	High Similarity	NPC472282
0.8957	High Similarity	NPC173516
0.8951	High Similarity	NPC470940
0.8951	High Similarity	NPC469849
0.8944	High Similarity	NPC329938
0.8944	High Similarity	NPC263432
0.8944	High Similarity	NPC200782
0.8944	High Similarity	NPC69028
0.8938	High Similarity	NPC475967
0.8924	High Similarity	NPC114880
0.891	High Similarity	NPC125182
0.891	High Similarity	NPC69647
0.8903	High Similarity	NPC71821
0.8896	High Similarity	NPC277618
0.8896	High Similarity	NPC86800
0.8882	High Similarity	NPC477402
0.8875	High Similarity	NPC167142
0.8875	High Similarity	NPC299038
0.8875	High Similarity	NPC472776
0.8875	High Similarity	NPC472778
0.8875	High Similarity	NPC472777
0.8868	High Similarity	NPC469336
0.8862	High Similarity	NPC56953
0.8862	High Similarity	NPC176413
0.8861	High Similarity	NPC475777
0.8841	High Similarity	NPC473766
0.8841	High Similarity	NPC473753
0.8839	High Similarity	NPC62799
0.8834	High Similarity	NPC472664
0.8834	High Similarity	NPC476857
0.8834	High Similarity	NPC276735
0.8834	High Similarity	NPC476858
0.8834	High Similarity	NPC476856
0.8827	High Similarity	NPC82851
0.8805	High Similarity	NPC178932
0.8788	High Similarity	NPC271235
0.8788	High Similarity	NPC255787
0.8782	High Similarity	NPC255414
0.878	High Similarity	NPC23387
0.8773	High Similarity	NPC39986
0.8773	High Similarity	NPC302369
0.8773	High Similarity	NPC14499
0.8773	High Similarity	NPC134254
0.8773	High Similarity	NPC476035
0.8773	High Similarity	NPC475039
0.8773	High Similarity	NPC476197
0.8765	High Similarity	NPC25255
0.875	High Similarity	NPC92979
0.8742	High Similarity	NPC469503
0.8742	High Similarity	NPC268905
0.8742	High Similarity	NPC476201
0.8742	High Similarity	NPC75906
0.8735	High Similarity	NPC118086
0.8735	High Similarity	NPC470995
0.8727	High Similarity	NPC476861
0.8727	High Similarity	NPC476850
0.8727	High Similarity	NPC476853
0.8726	High Similarity	NPC19747
0.872	High Similarity	NPC470182
0.872	High Similarity	NPC123088
0.872	High Similarity	NPC476860
0.872	High Similarity	NPC271657
0.8718	High Similarity	NPC233763
0.8712	High Similarity	NPC470792
0.8712	High Similarity	NPC470939
0.8712	High Similarity	NPC193798
0.8704	High Similarity	NPC473368
0.8704	High Similarity	NPC477403
0.8704	High Similarity	NPC475226
0.8704	High Similarity	NPC307383
0.8701	High Similarity	NPC263337
0.8696	High Similarity	NPC469485
0.8688	High Similarity	NPC253201
0.8688	High Similarity	NPC302054
0.8688	High Similarity	NPC282445
0.8675	High Similarity	NPC472766
0.8675	High Similarity	NPC472765
0.8675	High Similarity	NPC291742
0.8667	High Similarity	NPC472141
0.8667	High Similarity	NPC308156
0.8667	High Similarity	NPC93172
0.8667	High Similarity	NPC97574
0.8654	High Similarity	NPC5676
0.865	High Similarity	NPC335761
0.865	High Similarity	NPC472653
0.8642	High Similarity	NPC45101
0.8642	High Similarity	NPC469847
0.8642	High Similarity	NPC197137
0.8642	High Similarity	NPC261597
0.8642	High Similarity	NPC249021
0.8642	High Similarity	NPC36655
0.8642	High Similarity	NPC173544
0.8634	High Similarity	NPC476262
0.8634	High Similarity	NPC214541
0.8634	High Similarity	NPC44675
0.8625	High Similarity	NPC472672
0.8623	High Similarity	NPC44602
0.8616	High Similarity	NPC469335
0.8616	High Similarity	NPC477404
0.8616	High Similarity	NPC159927
0.8616	High Similarity	NPC196864
0.8614	High Similarity	NPC472764
0.8614	High Similarity	NPC472651
0.8614	High Similarity	NPC310572
0.8598	High Similarity	NPC5079
0.8598	High Similarity	NPC18347
0.8598	High Similarity	NPC149896
0.8598	High Similarity	NPC207978
0.8589	High Similarity	NPC84349
0.858	High Similarity	NPC471437
0.8571	High Similarity	NPC34421
0.8571	High Similarity	NPC237259
0.8571	High Similarity	NPC285227
0.8571	High Similarity	NPC98206
0.8563	High Similarity	NPC472652
0.8562	High Similarity	NPC18135
0.8555	High Similarity	NPC105395
0.8553	High Similarity	NPC195325
0.8553	High Similarity	NPC472654
0.8545	High Similarity	NPC51568
0.8545	High Similarity	NPC419
0.8545	High Similarity	NPC663
0.8545	High Similarity	NPC234660
0.8545	High Similarity	NPC472139
0.8545	High Similarity	NPC224394
0.8538	High Similarity	NPC11062
0.8537	High Similarity	NPC472299
0.8537	High Similarity	NPC470789
0.8528	High Similarity	NPC470118
0.8528	High Similarity	NPC472283
0.8528	High Similarity	NPC187149
0.8526	High Similarity	NPC243577
0.8526	High Similarity	NPC64568
0.8521	High Similarity	NPC469848
0.8519	High Similarity	NPC141538
0.8519	High Similarity	NPC296807
0.8519	High Similarity	NPC281258
0.8519	High Similarity	NPC35000
0.8519	High Similarity	NPC469850
0.8519	High Similarity	NPC155939
0.8512	High Similarity	NPC302392
0.8512	High Similarity	NPC82602
0.8512	High Similarity	NPC88593
0.8509	High Similarity	NPC33938
0.8506	High Similarity	NPC472663
0.8506	High Similarity	NPC472662
0.8506	High Similarity	NPC202260
0.8503	High Similarity	NPC41689
0.8503	High Similarity	NPC472784
0.85	High Similarity	NPC476122
0.85	High Similarity	NPC470997
0.8494	Intermediate Similarity	NPC27541
0.8494	Intermediate Similarity	NPC261184

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 NPC121995 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	835
0.2-0.3	1730
0.3-0.4	2548
0.4-0.5	2105
0.5-0.6	1103
0.6-0.7	399
0.7-0.8	125
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9048	High Similarity	NPD8434	Phase 2
0.8313	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5761	Phase 2
0.8293	Intermediate Similarity	NPD5760	Phase 2
0.8103	Intermediate Similarity	NPD6764	Approved
0.8103	Intermediate Similarity	NPD6765	Approved
0.8	Intermediate Similarity	NPD4628	Phase 3
0.7939	Intermediate Similarity	NPD3226	Approved
0.7921	Intermediate Similarity	NPD6785	Approved
0.7921	Intermediate Similarity	NPD6784	Approved
0.7898	Intermediate Similarity	NPD6559	Discontinued
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7751	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7819	Suspended
0.7744	Intermediate Similarity	NPD8404	Phase 2
0.7738	Intermediate Similarity	NPD7411	Suspended
0.7719	Intermediate Similarity	NPD7075	Discontinued
0.7716	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7473	Discontinued
0.7702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6801	Discontinued
0.767	Intermediate Similarity	NPD3818	Discontinued
0.7661	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6232	Discontinued
0.763	Intermediate Similarity	NPD5494	Approved
0.7627	Intermediate Similarity	NPD5844	Phase 1
0.7624	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3749	Approved
0.7609	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD920	Approved
0.7602	Intermediate Similarity	NPD3817	Phase 2
0.7602	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1471	Phase 3
0.7586	Intermediate Similarity	NPD8127	Discontinued
0.7574	Intermediate Similarity	NPD4380	Phase 2
0.7545	Intermediate Similarity	NPD6273	Approved
0.7544	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6799	Approved
0.7514	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD5402	Approved
0.7486	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD37	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1934	Approved
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD919	Approved
0.7458	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6166	Phase 2
0.7458	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4967	Phase 2
0.7457	Intermediate Similarity	NPD4966	Approved
0.7457	Intermediate Similarity	NPD3882	Suspended
0.7457	Intermediate Similarity	NPD4965	Approved
0.7396	Intermediate Similarity	NPD5403	Approved
0.7386	Intermediate Similarity	NPD7199	Phase 2
0.7381	Intermediate Similarity	NPD2534	Approved
0.7381	Intermediate Similarity	NPD5401	Approved
0.7381	Intermediate Similarity	NPD2533	Approved
0.7381	Intermediate Similarity	NPD2532	Approved
0.7378	Intermediate Similarity	NPD2346	Discontinued
0.7374	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD3751	Discontinued
0.7371	Intermediate Similarity	NPD6234	Discontinued
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2799	Discontinued
0.7348	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD2801	Approved
0.7317	Intermediate Similarity	NPD2796	Approved
0.731	Intermediate Similarity	NPD7458	Discontinued
0.7303	Intermediate Similarity	NPD3926	Phase 2
0.7297	Intermediate Similarity	NPD8150	Discontinued
0.7294	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD7074	Phase 3
0.7288	Intermediate Similarity	NPD6959	Discontinued
0.7283	Intermediate Similarity	NPD8407	Phase 2
0.7278	Intermediate Similarity	NPD7799	Discontinued
0.7278	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2344	Approved
0.7268	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD7236	Approved
0.7256	Intermediate Similarity	NPD7033	Discontinued
0.7247	Intermediate Similarity	NPD3787	Discontinued
0.7246	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7054	Approved
0.7238	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1549	Phase 2
0.7219	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7435	Discontinued
0.7213	Intermediate Similarity	NPD8368	Discontinued
0.7212	Intermediate Similarity	NPD1551	Phase 2
0.7209	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2313	Discontinued
0.7202	Intermediate Similarity	NPD6190	Approved
0.7198	Intermediate Similarity	NPD7472	Approved
0.7186	Intermediate Similarity	NPD1243	Approved
0.7186	Intermediate Similarity	NPD2800	Approved
0.7182	Intermediate Similarity	NPD7228	Approved
0.7169	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7768	Phase 2
0.7158	Intermediate Similarity	NPD6797	Phase 2
0.7151	Intermediate Similarity	NPD6808	Phase 2
0.7151	Intermediate Similarity	NPD7239	Suspended
0.715	Intermediate Similarity	NPD6778	Approved
0.715	Intermediate Similarity	NPD6782	Approved
0.715	Intermediate Similarity	NPD6779	Approved
0.715	Intermediate Similarity	NPD6781	Approved
0.715	Intermediate Similarity	NPD6776	Approved
0.715	Intermediate Similarity	NPD6777	Approved
0.715	Intermediate Similarity	NPD6780	Approved
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD3750	Approved
0.7126	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7685	Pre-registration
0.712	Intermediate Similarity	NPD7251	Discontinued
0.7118	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1511	Approved
0.7108	Intermediate Similarity	NPD6100	Approved
0.7108	Intermediate Similarity	NPD6099	Approved
0.7101	Intermediate Similarity	NPD2309	Approved
0.7099	Intermediate Similarity	NPD3764	Approved
0.7099	Intermediate Similarity	NPD3268	Approved
0.7091	Intermediate Similarity	NPD7097	Phase 1
0.7081	Intermediate Similarity	NPD7808	Phase 3
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7056	Intermediate Similarity	NPD7229	Phase 3
0.7048	Intermediate Similarity	NPD3748	Approved
0.7048	Intermediate Similarity	NPD1510	Phase 2
0.7045	Intermediate Similarity	NPD8455	Phase 2
0.7041	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7003	Approved
0.7041	Intermediate Similarity	NPD7497	Discontinued
0.7041	Intermediate Similarity	NPD4110	Phase 3
0.7037	Intermediate Similarity	NPD8360	Approved
0.7037	Intermediate Similarity	NPD8435	Approved
0.7037	Intermediate Similarity	NPD8361	Approved
0.7035	Intermediate Similarity	NPD1512	Approved
0.7027	Intermediate Similarity	NPD7240	Approved
0.7025	Intermediate Similarity	NPD1608	Approved
0.7012	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4140	Approved
0.701	Intermediate Similarity	NPD8285	Discontinued
0.7006	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD7874	Approved
0.7	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6798	Discontinued
0.6994	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6832	Phase 2
0.6973	Remote Similarity	NPD5953	Discontinued
0.697	Remote Similarity	NPD447	Suspended
0.6964	Remote Similarity	NPD6002	Phase 3
0.6964	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5762	Approved
0.6964	Remote Similarity	NPD5763	Approved
0.6964	Remote Similarity	NPD6004	Phase 3
0.6964	Remote Similarity	NPD6005	Phase 3
0.6957	Remote Similarity	NPD5647	Approved
0.6954	Remote Similarity	NPD7696	Phase 3
0.6954	Remote Similarity	NPD7698	Approved
0.6954	Remote Similarity	NPD7697	Approved
0.6951	Remote Similarity	NPD6233	Phase 2
0.6951	Remote Similarity	NPD8032	Phase 2
0.695	Remote Similarity	NPD8151	Discontinued
0.6941	Remote Similarity	NPD8166	Discontinued
0.6933	Remote Similarity	NPD7095	Approved
0.6933	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1607	Approved
0.6923	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7870	Phase 2
0.6919	Remote Similarity	NPD8319	Approved
0.6919	Remote Similarity	NPD8320	Phase 1
0.6919	Remote Similarity	NPD7871	Phase 2
0.6909	Remote Similarity	NPD1240	Approved
0.69	Remote Similarity	NPD7701	Phase 2
0.6894	Remote Similarity	NPD3267	Approved
0.6894	Remote Similarity	NPD3266	Approved
0.6893	Remote Similarity	NPD4665	Approved
0.6893	Remote Similarity	NPD4111	Phase 1
0.6891	Remote Similarity	NPD6534	Approved
0.6891	Remote Similarity	NPD6535	Approved
0.689	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2403	Approved
0.6881	Remote Similarity	NPD7801	Approved
0.6872	Remote Similarity	NPD7057	Phase 3
0.6872	Remote Similarity	NPD7058	Phase 2
0.6868	Remote Similarity	NPD5711	Approved
0.6868	Remote Similarity	NPD5710	Approved
0.6867	Remote Similarity	NPD230	Phase 1
0.6852	Remote Similarity	NPD2798	Approved
0.6845	Remote Similarity	NPD4308	Phase 3
0.6842	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD17	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