NPASS Compound

Structure

CID41880 OpenBabel06191715372D 33 36 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 0.8660 -3.5000 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 1.7321 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 1.0000 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 1.7321 -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 1 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 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 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 2.5981 -3.5000 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 -0.8660 0.5000 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 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 30 1 0 0 0 0 7 9 1 0 0 0 0 7 19 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 23 1 0 0 0 0 10 31 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 25 1 0 0 0 0 13 26 2 0 0 0 0 13 32 1 0 0 0 0 14 27 2 0 0 0 0 14 33 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 16 24 1 6 0 0 0 17 31 1 0 0 0 0 18 21 1 0 0 0 0 18 32 1 6 0 0 0 19 24 1 1 0 0 0 19 33 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 6 0 0 0 22 28 2 0 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 24 25 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	462.23
Volume:	463.87
LogP:	2.836
LogD:	2.462
LogS:	-4.007
# Rotatable Bonds:	6
TPSA:	112.27
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	4.945
Fsp3:	0.72
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:	-4.929
MDCK Permeability:	4.1848994442261755e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.783
Plasma Protein Binding (PPB):	62.49406433105469%
Volume Distribution (VD):	1.858
Pgp-substrate:	35.746551513671875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.097
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.755
CYP2C9-inhibitor:	0.075
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.146
CYP3A4-inhibitor:	0.548
CYP3A4-substrate:	0.663

ADMET: Excretion

Clearance (CL):	6.296
Half-life (T1/2):	0.138

ADMET: Toxicity

hERG Blockers:	0.874
Human Hepatotoxicity (H-HT):	0.637
Drug-inuced Liver Injury (DILI):	0.818
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.867
Maximum Recommended Daily Dose:	0.727
Skin Sensitization:	0.18
Carcinogencity:	0.341
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC41880

Natural Product ID:	NPC41880
*Common Name:**	Acetoxybonducellpin C
IUPAC Name:	methyl (1S,4aR,6S,6aR,7S,11aS,11bS)-1,6-diacetyloxy-4a-hydroxy-4,4,11b-trimethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-7-carboxylate
Synonyms:	Acetoxybonducellpin C
Standard InCHIKey:	VWWBNOKRESJKKB-QKLQQXTASA-N
Standard InCHI:	InChI=1S/C25H34O8/c1-13(26)32-18-12-25(29)23(3,4)9-7-19(33-14(2)27)24(25,5)16-11-17-15(8-10-31-17)20(21(16)18)22(28)30-6/h8,10,16,18-21,29H,7,9,11-12H2,1-6H3/t16-,18-,19-,20+,21-,24-,25+/m0/s1
SMILES:	COC(=O)[C@@H]1c2ccoc2C[C@H]2[C@H]1[C@@H](OC(=O)C)C[C@@]1([C@]2(C)[C@H](CCC1(C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463938
PubChem CID:	10742713
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
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]
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]

☑ 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	=	600.0	nM	PMID[465965]

☑ 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 NPC41880 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	335
0.1-0.2	1302
0.2-0.3	2585
0.3-0.4	5092
0.4-0.5	10340
0.5-0.6	8692
0.6-0.7	7615
0.7-0.8	6141
0.8-0.85	387
0.85-0.9	159
0.9-0.95	38
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9735	High Similarity	NPC68848
0.9732	High Similarity	NPC104736
0.9667	High Similarity	NPC304692
0.966	High Similarity	NPC212257
0.9542	High Similarity	NPC285567
0.9536	High Similarity	NPC195954
0.9536	High Similarity	NPC88007
0.9419	High Similarity	NPC121995
0.9416	High Similarity	NPC283209
0.9408	High Similarity	NPC81405
0.9408	High Similarity	NPC194499
0.9359	High Similarity	NPC270312
0.9351	High Similarity	NPC188649
0.9346	High Similarity	NPC474611
0.9346	High Similarity	NPC140952
0.929	High Similarity	NPC288602
0.929	High Similarity	NPC88841
0.9286	High Similarity	NPC287559
0.9231	High Similarity	NPC56358
0.9226	High Similarity	NPC18986
0.92	High Similarity	NPC211625
0.9161	High Similarity	NPC8389
0.9145	High Similarity	NPC121615
0.9145	High Similarity	NPC294511
0.9139	High Similarity	NPC228842
0.9116	High Similarity	NPC263337
0.9103	High Similarity	NPC79571
0.9067	High Similarity	NPC71821
0.9057	High Similarity	NPC296558
0.9032	High Similarity	NPC7059
0.9032	High Similarity	NPC472772
0.9	High Similarity	NPC62799
0.8986	High Similarity	NPC121158
0.8961	High Similarity	NPC114880
0.8961	High Similarity	NPC282445
0.894	High Similarity	NPC255414
0.8931	High Similarity	NPC277618
0.8924	High Similarity	NPC476035
0.8924	High Similarity	NPC14499
0.8924	High Similarity	NPC475039
0.8912	High Similarity	NPC202260
0.891	High Similarity	NPC249021
0.8903	High Similarity	NPC75310
0.8903	High Similarity	NPC469336
0.8896	High Similarity	NPC246164
0.8896	High Similarity	NPC469503
0.8882	High Similarity	NPC19747
0.8868	High Similarity	NPC472664
0.8867	High Similarity	NPC251865
0.8861	High Similarity	NPC472771
0.8854	High Similarity	NPC123153
0.8839	High Similarity	NPC178932
0.8827	High Similarity	NPC475237
0.8827	High Similarity	NPC475641
0.8827	High Similarity	NPC294512
0.8824	High Similarity	NPC125182
0.8824	High Similarity	NPC69647
0.882	High Similarity	NPC291742
0.8816	High Similarity	NPC216755
0.8812	High Similarity	NPC475779
0.8805	High Similarity	NPC472773
0.88	High Similarity	NPC243577
0.8797	High Similarity	NPC472299
0.8782	High Similarity	NPC264943
0.8776	High Similarity	NPC307401
0.8774	High Similarity	NPC475777
0.8766	High Similarity	NPC476122
0.8766	High Similarity	NPC159927
0.8766	High Similarity	NPC469335
0.8766	High Similarity	NPC196864
0.8766	High Similarity	NPC477404
0.8765	High Similarity	NPC118086
0.8758	High Similarity	NPC473753
0.8758	High Similarity	NPC473766
0.875	High Similarity	NPC233763
0.875	High Similarity	NPC276735
0.8742	High Similarity	NPC329938
0.8742	High Similarity	NPC82851
0.8725	High Similarity	NPC67003
0.8725	High Similarity	NPC148374
0.8718	High Similarity	NPC30222
0.871	High Similarity	NPC272590
0.8704	High Similarity	NPC160651
0.8701	High Similarity	NPC472654
0.8696	High Similarity	NPC308156
0.8696	High Similarity	NPC86800
0.8693	High Similarity	NPC286038
0.8693	High Similarity	NPC471174
0.8688	High Similarity	NPC469338
0.8688	High Similarity	NPC224394
0.8688	High Similarity	NPC477405
0.8688	High Similarity	NPC663
0.8688	High Similarity	NPC39986
0.8688	High Similarity	NPC292389
0.8688	High Similarity	NPC134254
0.8688	High Similarity	NPC302369
0.8684	High Similarity	NPC5676
0.8679	High Similarity	NPC25255
0.8671	High Similarity	NPC469847
0.8671	High Similarity	NPC470118
0.8671	High Similarity	NPC167142
0.8667	High Similarity	NPC56953
0.8667	High Similarity	NPC176413
0.8662	High Similarity	NPC92979
0.8662	High Similarity	NPC25351
0.8662	High Similarity	NPC469850
0.8662	High Similarity	NPC35000
0.8654	High Similarity	NPC476201
0.8654	High Similarity	NPC75906
0.8654	High Similarity	NPC472672
0.8654	High Similarity	NPC268905
0.865	High Similarity	NPC88593
0.8645	High Similarity	NPC156189
0.8642	High Similarity	NPC472774
0.8642	High Similarity	NPC472282
0.8642	High Similarity	NPC472775
0.8642	High Similarity	NPC173516
0.8636	High Similarity	NPC66991
0.8634	High Similarity	NPC27541
0.8634	High Similarity	NPC469849
0.8634	High Similarity	NPC476856
0.8634	High Similarity	NPC61967
0.8634	High Similarity	NPC476858
0.8634	High Similarity	NPC476857
0.8634	High Similarity	NPC126984
0.8634	High Similarity	NPC62692
0.8634	High Similarity	NPC276551
0.8634	High Similarity	NPC470940
0.8625	High Similarity	NPC263432
0.8625	High Similarity	NPC200782
0.8625	High Similarity	NPC193798
0.8625	High Similarity	NPC470939
0.8625	High Similarity	NPC470792
0.8625	High Similarity	NPC69028
0.8618	High Similarity	NPC84479
0.8616	High Similarity	NPC477403
0.8614	High Similarity	NPC472665
0.8599	High Similarity	NPC253201
0.8599	High Similarity	NPC302054
0.8589	High Similarity	NPC255787
0.8589	High Similarity	NPC471397
0.8581	High Similarity	NPC195325
0.858	High Similarity	NPC470875
0.8571	High Similarity	NPC470941
0.8571	High Similarity	NPC165218
0.8571	High Similarity	NPC221809
0.8571	High Similarity	NPC419
0.8571	High Similarity	NPC476197
0.8562	High Similarity	NPC472653
0.8562	High Similarity	NPC41182
0.8562	High Similarity	NPC335761
0.8562	High Similarity	NPC477402
0.8554	High Similarity	NPC167340
0.8553	High Similarity	NPC472776
0.8553	High Similarity	NPC472777
0.8553	High Similarity	NPC64568
0.8553	High Similarity	NPC299038
0.8553	High Similarity	NPC472778
0.8553	High Similarity	NPC205071
0.8544	High Similarity	NPC476262
0.8537	High Similarity	NPC302392
0.8535	High Similarity	NPC48671
0.8528	High Similarity	NPC476853
0.8528	High Similarity	NPC476861
0.8528	High Similarity	NPC310572
0.8528	High Similarity	NPC476850
0.8526	High Similarity	NPC470997
0.8523	High Similarity	NPC310043
0.8519	High Similarity	NPC476860
0.8519	High Similarity	NPC123088
0.8519	High Similarity	NPC470182
0.8516	High Similarity	NPC93666
0.8509	High Similarity	NPC472767
0.8509	High Similarity	NPC471003
0.8509	High Similarity	NPC5079
0.8506	High Similarity	NPC471292
0.8506	High Similarity	NPC97904
0.8503	High Similarity	NPC293253
0.85	High Similarity	NPC475226
0.85	High Similarity	NPC307383
0.85	High Similarity	NPC473368
0.85	High Similarity	NPC475967
0.85	High Similarity	NPC84349
0.8497	Intermediate Similarity	NPC238843
0.8497	Intermediate Similarity	NPC476944
0.8497	Intermediate Similarity	NPC199044
0.8491	Intermediate Similarity	NPC469485
0.8491	Intermediate Similarity	NPC107646
0.8481	Intermediate Similarity	NPC98206
0.8481	Intermediate Similarity	NPC57998
0.8481	Intermediate Similarity	NPC34421
0.8481	Intermediate Similarity	NPC44606
0.8481	Intermediate Similarity	NPC237259
0.8476	Intermediate Similarity	NPC271235
0.8471	Intermediate Similarity	NPC18135
0.8466	Intermediate Similarity	NPC472141
0.8466	Intermediate Similarity	NPC23387
0.8462	Intermediate Similarity	NPC470790
0.8462	Intermediate Similarity	NPC470791
0.8457	Intermediate Similarity	NPC234660

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 NPC41880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	287
0.1-0.2	842
0.2-0.3	1563
0.3-0.4	2515
0.4-0.5	2181
0.5-0.6	1224
0.6-0.7	419
0.7-0.8	113
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8743	High Similarity	NPD8434	Phase 2
0.8428	Intermediate Similarity	NPD5761	Phase 2
0.8428	Intermediate Similarity	NPD5760	Phase 2
0.8118	Intermediate Similarity	NPD6765	Approved
0.8118	Intermediate Similarity	NPD6764	Approved
0.811	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7819	Suspended
0.795	Intermediate Similarity	NPD3226	Approved
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6785	Approved
0.7931	Intermediate Similarity	NPD6784	Approved
0.7898	Intermediate Similarity	NPD4628	Phase 3
0.7764	Intermediate Similarity	NPD6273	Approved
0.7744	Intermediate Similarity	NPD7411	Suspended
0.7725	Intermediate Similarity	NPD3749	Approved
0.7716	Intermediate Similarity	NPD920	Approved
0.7711	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7075	Discontinued
0.7616	Intermediate Similarity	NPD7473	Discontinued
0.76	Intermediate Similarity	NPD6559	Discontinued
0.7595	Intermediate Similarity	NPD1471	Phase 3
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD8127	Discontinued
0.7578	Intermediate Similarity	NPD7236	Approved
0.7576	Intermediate Similarity	NPD6599	Discontinued
0.756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6100	Approved
0.7532	Intermediate Similarity	NPD6099	Approved
0.7529	Intermediate Similarity	NPD5844	Phase 1
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.7485	Intermediate Similarity	NPD2532	Approved
0.7485	Intermediate Similarity	NPD2533	Approved
0.7485	Intermediate Similarity	NPD2534	Approved
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7474	Intermediate Similarity	NPD8404	Phase 2
0.7471	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7457	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7239	Suspended
0.7453	Intermediate Similarity	NPD3750	Approved
0.7442	Intermediate Similarity	NPD7229	Phase 3
0.7442	Intermediate Similarity	NPD6232	Discontinued
0.7427	Intermediate Similarity	NPD5494	Approved
0.7421	Intermediate Similarity	NPD2796	Approved
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3764	Approved
0.7418	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD6959	Discontinued
0.7381	Intermediate Similarity	NPD6801	Discontinued
0.7381	Intermediate Similarity	NPD37	Approved
0.7378	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2344	Approved
0.7372	Intermediate Similarity	NPD8032	Phase 2
0.7358	Intermediate Similarity	NPD3748	Approved
0.7353	Intermediate Similarity	NPD4965	Approved
0.7353	Intermediate Similarity	NPD4966	Approved
0.7353	Intermediate Similarity	NPD7768	Phase 2
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7351	Intermediate Similarity	NPD1608	Approved
0.7346	Intermediate Similarity	NPD7003	Approved
0.7337	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1549	Phase 2
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7317	Intermediate Similarity	NPD6799	Approved
0.7312	Intermediate Similarity	NPD1551	Phase 2
0.7308	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD2313	Discontinued
0.7296	Intermediate Similarity	NPD7097	Phase 1
0.7294	Intermediate Similarity	NPD3817	Phase 2
0.7289	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2800	Approved
0.7284	Intermediate Similarity	NPD1243	Approved
0.7273	Intermediate Similarity	NPD3818	Discontinued
0.7267	Intermediate Similarity	NPD919	Approved
0.7267	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4380	Phase 2
0.725	Intermediate Similarity	NPD7033	Discontinued
0.7222	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4140	Approved
0.7209	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD2309	Approved
0.7193	Intermediate Similarity	NPD5402	Approved
0.7184	Intermediate Similarity	NPD7199	Phase 2
0.7184	Intermediate Similarity	NPD1247	Approved
0.7179	Intermediate Similarity	NPD6832	Phase 2
0.7176	Intermediate Similarity	NPD1934	Approved
0.7175	Intermediate Similarity	NPD7799	Discontinued
0.717	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD6004	Phase 3
0.716	Intermediate Similarity	NPD6002	Phase 3
0.716	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6005	Phase 3
0.7152	Intermediate Similarity	NPD17	Approved
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD3882	Suspended
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD6808	Phase 2
0.7124	Intermediate Similarity	NPD3972	Approved
0.7108	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3926	Phase 2
0.7102	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2935	Discontinued
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7097	Intermediate Similarity	NPD2797	Approved
0.7093	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5403	Approved
0.7079	Intermediate Similarity	NPD7177	Discontinued
0.7079	Intermediate Similarity	NPD7228	Approved
0.7066	Intermediate Similarity	NPD5401	Approved
0.7062	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6166	Phase 2
0.7062	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5953	Discontinued
0.7052	Intermediate Similarity	NPD7057	Phase 3
0.7052	Intermediate Similarity	NPD7058	Phase 2
0.7039	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1778	Approved
0.7035	Intermediate Similarity	NPD8455	Phase 2
0.7035	Intermediate Similarity	NPD2801	Approved
0.7035	Intermediate Similarity	NPD1465	Phase 2
0.7031	Intermediate Similarity	NPD7435	Discontinued
0.7031	Intermediate Similarity	NPD7497	Discontinued
0.703	Intermediate Similarity	NPD4110	Phase 3
0.703	Intermediate Similarity	NPD8166	Discontinued
0.703	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7095	Approved
0.7025	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1607	Approved
0.7018	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7685	Pre-registration
0.7011	Intermediate Similarity	NPD8150	Discontinued
0.7	Intermediate Similarity	NPD7074	Phase 3
0.7	Intermediate Similarity	NPD1240	Approved
0.7	Intermediate Similarity	NPD4307	Phase 2
0.6995	Remote Similarity	NPD8407	Phase 2
0.6988	Remote Similarity	NPD6190	Approved
0.6983	Remote Similarity	NPD3751	Discontinued
0.6981	Remote Similarity	NPD6798	Discontinued
0.6981	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5763	Approved
0.6951	Remote Similarity	NPD5762	Approved
0.6949	Remote Similarity	NPD5711	Approved
0.6949	Remote Similarity	NPD5710	Approved
0.6944	Remote Similarity	NPD7054	Approved
0.6944	Remote Similarity	NPD7286	Phase 2
0.6943	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2798	Approved
0.6937	Remote Similarity	NPD6663	Approved
0.6937	Remote Similarity	NPD6233	Phase 2
0.6928	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8368	Discontinued
0.6923	Remote Similarity	NPD1283	Approved
0.6923	Remote Similarity	NPD1876	Approved
0.6923	Remote Similarity	NPD7240	Approved
0.6923	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6651	Approved
0.6911	Remote Similarity	NPD8285	Discontinued
0.6908	Remote Similarity	NPD9545	Approved
0.6906	Remote Similarity	NPD7472	Approved
0.6905	Remote Similarity	NPD1511	Approved
0.6899	Remote Similarity	NPD5736	Approved
0.6894	Remote Similarity	NPD2979	Phase 3
0.689	Remote Similarity	NPD2438	Suspended
0.6886	Remote Similarity	NPD3887	Approved
0.6885	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6778	Approved
0.6875	Remote Similarity	NPD6779	Approved
0.6875	Remote Similarity	NPD6781	Approved
0.6875	Remote Similarity	NPD6776	Approved
0.6875	Remote Similarity	NPD6777	Approved
0.6875	Remote Similarity	NPD6782	Approved
0.6875	Remote Similarity	NPD6780	Approved
0.6875	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5585	Approved
0.6859	Remote Similarity	NPD5327	Phase 3
0.6856	Remote Similarity	NPD7696	Phase 3
0.6856	Remote Similarity	NPD7698	Approved
0.6856	Remote Similarity	NPD7697	Approved
0.6854	Remote Similarity	NPD3787	Discontinued
0.6852	Remote Similarity	NPD5735	Approved
0.6852	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD5124	Phase 1
0.6852	Remote Similarity	NPD230	Phase 1

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