NPASS Compound

Structure

CID270312 OpenBabel06191716072D 34 37 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 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 0.8660 -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 0.8660 1.5000 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 0.0000 1.0000 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 -0.8660 -3.5000 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 -3.0000 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 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 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 0.8660 -1.5000 0.0000 C 0 0 1 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 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 2.5981 2.5000 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 4.4152 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 23 1 0 0 0 0 5 23 1 0 0 0 0 6 24 1 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 25 1 0 0 0 0 10 31 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 26 2 0 0 0 0 12 32 1 0 0 0 0 13 27 2 0 0 0 0 13 33 1 0 0 0 0 14 28 2 0 0 0 0 14 34 1 0 0 0 0 15 7 1 1 0 0 0 15 17 1 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 24 1 6 0 0 0 18 31 1 0 0 0 0 19 29 2 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 32 1 1 0 0 0 21 23 1 0 0 0 0 21 33 1 1 0 0 0 22 24 1 1 0 0 0 22 34 1 0 0 0 0 23 25 1 0 0 0 0 24 25 1 6 0 0 0 25 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.2
Volume:	470.024
LogP:	2.679
LogD:	2.253
LogS:	-4.548
# Rotatable Bonds:	6
TPSA:	129.34
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	4.919
Fsp3:	0.68
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:	-5.129
MDCK Permeability:	3.504686173982918e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.497
20% Bioavailability (F20%):	0.196
30% Bioavailability (F30%):	0.942

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.471
Plasma Protein Binding (PPB):	71.89019012451172%
Volume Distribution (VD):	1.341
Pgp-substrate:	24.392370223999023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.199
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.143
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.288
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.89
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.624
CYP3A4-substrate:	0.411

ADMET: Excretion

Clearance (CL):	2.714
Half-life (T1/2):	0.402

ADMET: Toxicity

hERG Blockers:	0.674
Human Hepatotoxicity (H-HT):	0.785
Drug-inuced Liver Injury (DILI):	0.84
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.817
Maximum Recommended Daily Dose:	0.257
Skin Sensitization:	0.227
Carcinogencity:	0.219
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC270312

Natural Product ID:	NPC270312
*Common Name:**	3-O-Acetylnorcaesalpinin A
IUPAC Name:	[(1R,2S,3S,4aR,6aR,11aS,11bS)-1,3-diacetyloxy-4a-hydroxy-4,4,11b-trimethyl-7-oxo-1,2,3,5,6,6a,11,11a-octahydronaphtho[2,1-f][1]benzofuran-2-yl] acetate
Synonyms:
Standard InCHIKey:	SJZIFWGVHGVKAH-AVZLBZSXSA-N
Standard InCHI:	InChI=1S/C25H32O9/c1-12(26)32-20-21(33-13(2)27)23(4,5)25(30)9-7-15-17(24(25,6)22(20)34-14(3)28)11-18-16(19(15)29)8-10-31-18/h8,10,15,17,20-22,30H,7,9,11H2,1-6H3/t15-,17+,20+,21-,22+,24+,25-/m1/s1
SMILES:	CC(=O)O[C@H]1[C@H](C(C)(C)[C@@]2(CC[C@@H]3[C@H](Cc4c(cco4)C3=O)[C@@]2(C)[C@H]1OC(=O)C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465810
PubChem CID:	11248550
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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	=	2000.0	nM	PMID[505543]

☑ 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 NPC270312 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	364
0.1-0.2	1432
0.2-0.3	2903
0.3-0.4	5948
0.4-0.5	10782
0.5-0.6	7733
0.6-0.7	6122
0.7-0.8	6834
0.8-0.85	432
0.85-0.9	118
0.9-0.95	24
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9871	High Similarity	NPC56358
0.9557	High Similarity	NPC121995
0.9548	High Similarity	NPC81405
0.949	High Similarity	NPC188649
0.949	High Similarity	NPC68848
0.9487	High Similarity	NPC140952
0.943	High Similarity	NPC288602
0.943	High Similarity	NPC88841
0.9427	High Similarity	NPC287559
0.9423	High Similarity	NPC195954
0.9367	High Similarity	NPC18986
0.9359	High Similarity	NPC41880
0.9308	High Similarity	NPC285567
0.9299	High Similarity	NPC88007
0.9202	High Similarity	NPC294512
0.9187	High Similarity	NPC283209
0.9177	High Similarity	NPC194499
0.913	High Similarity	NPC276735
0.9114	High Similarity	NPC104736
0.9096	High Similarity	NPC472665
0.908	High Similarity	NPC296558
0.9074	High Similarity	NPC86800
0.9057	High Similarity	NPC304692
0.9038	High Similarity	NPC212257
0.9036	High Similarity	NPC176413
0.9036	High Similarity	NPC56953
0.9012	High Similarity	NPC472664
0.9006	High Similarity	NPC472771
0.9	High Similarity	NPC474611
0.8951	High Similarity	NPC472773
0.8944	High Similarity	NPC8389
0.8924	High Similarity	NPC294511
0.8924	High Similarity	NPC121615
0.8917	High Similarity	NPC228842
0.8903	High Similarity	NPC233763
0.8902	High Similarity	NPC472775
0.8902	High Similarity	NPC472774
0.8889	High Similarity	NPC79571
0.8855	High Similarity	NPC475237
0.8855	High Similarity	NPC475641
0.8854	High Similarity	NPC211625
0.8848	High Similarity	NPC291742
0.8848	High Similarity	NPC160651
0.8846	High Similarity	NPC71821
0.8846	High Similarity	NPC255414
0.8841	High Similarity	NPC475779
0.8834	High Similarity	NPC14499
0.8834	High Similarity	NPC475039
0.8834	High Similarity	NPC292389
0.8834	High Similarity	NPC469338
0.8834	High Similarity	NPC476035
0.882	High Similarity	NPC167142
0.882	High Similarity	NPC7059
0.882	High Similarity	NPC472772
0.8812	High Similarity	NPC264943
0.8788	High Similarity	NPC473753
0.8788	High Similarity	NPC473766
0.8788	High Similarity	NPC173516
0.878	High Similarity	NPC476857
0.878	High Similarity	NPC469849
0.878	High Similarity	NPC276551
0.878	High Similarity	NPC470940
0.878	High Similarity	NPC476856
0.878	High Similarity	NPC476858
0.8773	High Similarity	NPC329938
0.8773	High Similarity	NPC82851
0.8773	High Similarity	NPC200782
0.8773	High Similarity	NPC263432
0.8735	High Similarity	NPC471397
0.8734	High Similarity	NPC125182
0.8734	High Similarity	NPC69647
0.8727	High Similarity	NPC277618
0.8727	High Similarity	NPC470875
0.8727	High Similarity	NPC308156
0.872	High Similarity	NPC476197
0.872	High Similarity	NPC477405
0.8712	High Similarity	NPC25255
0.8696	High Similarity	NPC75310
0.8696	High Similarity	NPC476262
0.8696	High Similarity	NPC469336
0.8688	High Similarity	NPC476201
0.8675	High Similarity	NPC476850
0.8675	High Similarity	NPC476853
0.8675	High Similarity	NPC472282
0.8675	High Similarity	NPC476861
0.8667	High Similarity	NPC476860
0.8662	High Similarity	NPC62799
0.8659	High Similarity	NPC69028
0.8659	High Similarity	NPC470939
0.8659	High Similarity	NPC193798
0.865	High Similarity	NPC477403
0.8634	High Similarity	NPC178932
0.8634	High Similarity	NPC114880
0.8634	High Similarity	NPC282445
0.8614	High Similarity	NPC23387
0.8614	High Similarity	NPC472141
0.8606	High Similarity	NPC134254
0.8606	High Similarity	NPC39986
0.8606	High Similarity	NPC302369
0.8598	High Similarity	NPC477402
0.8598	High Similarity	NPC472653
0.8589	High Similarity	NPC472778
0.8589	High Similarity	NPC299038
0.8589	High Similarity	NPC469847
0.8589	High Similarity	NPC249021
0.8589	High Similarity	NPC472776
0.8589	High Similarity	NPC472777
0.8571	High Similarity	NPC118086
0.8571	High Similarity	NPC44602
0.8571	High Similarity	NPC475777
0.8571	High Similarity	NPC469503
0.8571	High Similarity	NPC88593
0.8571	High Similarity	NPC268905
0.8562	High Similarity	NPC476122
0.8562	High Similarity	NPC469335
0.8562	High Similarity	NPC196864
0.8562	High Similarity	NPC159927
0.8562	High Similarity	NPC477404
0.8554	High Similarity	NPC123088
0.8554	High Similarity	NPC470182
0.8553	High Similarity	NPC19747
0.8545	High Similarity	NPC471166
0.8545	High Similarity	NPC471167
0.8537	High Similarity	NPC475226
0.8537	High Similarity	NPC473368
0.8537	High Similarity	NPC475967
0.8528	High Similarity	NPC469485
0.8526	High Similarity	NPC263337
0.8526	High Similarity	NPC121158
0.8512	High Similarity	NPC271235
0.8512	High Similarity	NPC255787
0.8509	High Similarity	NPC18135
0.8503	High Similarity	NPC93172
0.8503	High Similarity	NPC97574
0.8494	Intermediate Similarity	NPC472139
0.8494	Intermediate Similarity	NPC51568
0.8494	Intermediate Similarity	NPC224394
0.8494	Intermediate Similarity	NPC419
0.8494	Intermediate Similarity	NPC663
0.8494	Intermediate Similarity	NPC471168
0.8494	Intermediate Similarity	NPC234660
0.8491	Intermediate Similarity	NPC224418
0.8485	Intermediate Similarity	NPC333139
0.8485	Intermediate Similarity	NPC191828
0.8485	Intermediate Similarity	NPC335761
0.8481	Intermediate Similarity	NPC5676
0.8476	Intermediate Similarity	NPC472283
0.8476	Intermediate Similarity	NPC470118
0.8476	Intermediate Similarity	NPC173544
0.8471	Intermediate Similarity	NPC469848
0.8466	Intermediate Similarity	NPC469850
0.8466	Intermediate Similarity	NPC92979
0.8462	Intermediate Similarity	NPC470995
0.8462	Intermediate Similarity	NPC302392
0.8457	Intermediate Similarity	NPC472672
0.8457	Intermediate Similarity	NPC75906
0.8452	Intermediate Similarity	NPC472764
0.8443	Intermediate Similarity	NPC271657
0.8443	Intermediate Similarity	NPC126984
0.8443	Intermediate Similarity	NPC27541
0.8443	Intermediate Similarity	NPC62692
0.8443	Intermediate Similarity	NPC61967
0.8434	Intermediate Similarity	NPC5079
0.8434	Intermediate Similarity	NPC472668
0.8434	Intermediate Similarity	NPC470792
0.8434	Intermediate Similarity	NPC18347
0.8434	Intermediate Similarity	NPC149896
0.8424	Intermediate Similarity	NPC237155
0.8424	Intermediate Similarity	NPC473473
0.8424	Intermediate Similarity	NPC123153
0.8424	Intermediate Similarity	NPC307383
0.8424	Intermediate Similarity	NPC475295
0.8421	Intermediate Similarity	NPC118128
0.8418	Intermediate Similarity	NPC251865
0.8415	Intermediate Similarity	NPC107646
0.8412	Intermediate Similarity	NPC285227
0.8405	Intermediate Similarity	NPC302054
0.8405	Intermediate Similarity	NPC30222
0.8405	Intermediate Similarity	NPC253201
0.8402	Intermediate Similarity	NPC472765
0.8402	Intermediate Similarity	NPC472766
0.84	Intermediate Similarity	NPC105395
0.8385	Intermediate Similarity	NPC472654
0.8383	Intermediate Similarity	NPC469846
0.8383	Intermediate Similarity	NPC472669
0.8373	Intermediate Similarity	NPC472299
0.8373	Intermediate Similarity	NPC475381
0.8372	Intermediate Similarity	NPC167340
0.8364	Intermediate Similarity	NPC261597
0.8364	Intermediate Similarity	NPC286722
0.8364	Intermediate Similarity	NPC36655
0.8364	Intermediate Similarity	NPC1408
0.8364	Intermediate Similarity	NPC246841
0.8364	Intermediate Similarity	NPC197137
0.8364	Intermediate Similarity	NPC45101
0.8354	Intermediate Similarity	NPC44675
0.8354	Intermediate Similarity	NPC281258
0.8354	Intermediate Similarity	NPC179170
0.8354	Intermediate Similarity	NPC35000
0.8354	Intermediate Similarity	NPC214541

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 NPC270312 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	306
0.1-0.2	894
0.2-0.3	1838
0.3-0.4	2575
0.4-0.5	2121
0.5-0.6	983
0.6-0.7	324
0.7-0.8	108
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8882	High Similarity	NPD8434	Phase 2
0.8485	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5760	Phase 2
0.8133	Intermediate Similarity	NPD5761	Phase 2
0.7892	Intermediate Similarity	NPD3226	Approved
0.7853	Intermediate Similarity	NPD6765	Approved
0.7853	Intermediate Similarity	NPD6764	Approved
0.7811	Intermediate Similarity	NPD7819	Suspended
0.7771	Intermediate Similarity	NPD7473	Discontinued
0.7706	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7411	Suspended
0.7688	Intermediate Similarity	NPD5494	Approved
0.768	Intermediate Similarity	NPD6785	Approved
0.768	Intermediate Similarity	NPD6784	Approved
0.7674	Intermediate Similarity	NPD7075	Discontinued
0.7665	Intermediate Similarity	NPD920	Approved
0.7661	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD1471	Phase 3
0.7654	Intermediate Similarity	NPD6559	Discontinued
0.7633	Intermediate Similarity	NPD6599	Discontinued
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7614	Intermediate Similarity	NPD8404	Phase 2
0.76	Intermediate Similarity	NPD6232	Discontinued
0.7582	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3749	Approved
0.7568	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6801	Discontinued
0.7543	Intermediate Similarity	NPD1247	Approved
0.7528	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5844	Phase 1
0.7457	Intermediate Similarity	NPD3817	Phase 2
0.7443	Intermediate Similarity	NPD8127	Discontinued
0.744	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD3818	Discontinued
0.7429	Intermediate Similarity	NPD919	Approved
0.7416	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6799	Approved
0.7377	Intermediate Similarity	NPD8313	Approved
0.7377	Intermediate Similarity	NPD8312	Approved
0.736	Intermediate Similarity	NPD3926	Phase 2
0.7356	Intermediate Similarity	NPD5402	Approved
0.7349	Intermediate Similarity	NPD2800	Approved
0.7345	Intermediate Similarity	NPD6959	Discontinued
0.7341	Intermediate Similarity	NPD1934	Approved
0.7337	Intermediate Similarity	NPD2532	Approved
0.7337	Intermediate Similarity	NPD2534	Approved
0.7337	Intermediate Similarity	NPD2533	Approved
0.7333	Intermediate Similarity	NPD2344	Approved
0.7333	Intermediate Similarity	NPD2346	Discontinued
0.7326	Intermediate Similarity	NPD4380	Phase 2
0.7321	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2799	Discontinued
0.7314	Intermediate Similarity	NPD3882	Suspended
0.7299	Intermediate Similarity	NPD2801	Approved
0.7294	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD2796	Approved
0.7273	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7458	Discontinued
0.7258	Intermediate Similarity	NPD8150	Discontinued
0.7241	Intermediate Similarity	NPD37	Approved
0.7235	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6166	Phase 2
0.7222	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4966	Approved
0.7216	Intermediate Similarity	NPD4967	Phase 2
0.7216	Intermediate Similarity	NPD4965	Approved
0.7216	Intermediate Similarity	NPD7768	Phase 2
0.7207	Intermediate Similarity	NPD6808	Phase 2
0.7202	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1549	Phase 2
0.7179	Intermediate Similarity	NPD7435	Discontinued
0.7169	Intermediate Similarity	NPD1551	Phase 2
0.716	Intermediate Similarity	NPD2313	Discontinued
0.716	Intermediate Similarity	NPD2309	Approved
0.7158	Intermediate Similarity	NPD7074	Phase 3
0.7151	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5403	Approved
0.7151	Intermediate Similarity	NPD8407	Phase 2
0.7143	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD7799	Discontinued
0.7143	Intermediate Similarity	NPD1243	Approved
0.7135	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6234	Discontinued
0.7135	Intermediate Similarity	NPD5401	Approved
0.7126	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7236	Approved
0.7104	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7054	Approved
0.7083	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD8368	Discontinued
0.7066	Intermediate Similarity	NPD6100	Approved
0.7066	Intermediate Similarity	NPD6099	Approved
0.7066	Intermediate Similarity	NPD2935	Discontinued
0.7065	Intermediate Similarity	NPD7472	Approved
0.7062	Intermediate Similarity	NPD8285	Discontinued
0.7056	Intermediate Similarity	NPD7199	Phase 2
0.7048	Intermediate Similarity	NPD7097	Phase 1
0.7037	Intermediate Similarity	NPD6832	Phase 2
0.7027	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6782	Approved
0.7026	Intermediate Similarity	NPD6776	Approved
0.7026	Intermediate Similarity	NPD6781	Approved
0.7026	Intermediate Similarity	NPD6780	Approved
0.7026	Intermediate Similarity	NPD6778	Approved
0.7026	Intermediate Similarity	NPD6777	Approved
0.7026	Intermediate Similarity	NPD6779	Approved
0.7017	Intermediate Similarity	NPD3787	Discontinued
0.7017	Intermediate Similarity	NPD7229	Phase 3
0.7011	Intermediate Similarity	NPD7239	Suspended
0.7006	Intermediate Similarity	NPD1465	Phase 2
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.7006	Intermediate Similarity	NPD1510	Phase 2
0.7005	Intermediate Similarity	NPD7497	Discontinued
0.7005	Intermediate Similarity	NPD7696	Phase 3
0.7005	Intermediate Similarity	NPD7698	Approved
0.7005	Intermediate Similarity	NPD7697	Approved
0.7	Intermediate Similarity	NPD3750	Approved
0.6989	Remote Similarity	NPD7251	Discontinued
0.6988	Remote Similarity	NPD6651	Approved
0.6978	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1511	Approved
0.6971	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7870	Phase 2
0.697	Remote Similarity	NPD7871	Phase 2
0.6965	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7874	Approved
0.6959	Remote Similarity	NPD6190	Approved
0.6957	Remote Similarity	NPD7228	Approved
0.6952	Remote Similarity	NPD7808	Phase 3
0.6951	Remote Similarity	NPD3764	Approved
0.6951	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3268	Approved
0.6951	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.694	Remote Similarity	NPD2403	Approved
0.6935	Remote Similarity	NPD6797	Phase 2
0.6935	Remote Similarity	NPD5953	Discontinued
0.6928	Remote Similarity	NPD6355	Discontinued
0.6928	Remote Similarity	NPD447	Suspended
0.6919	Remote Similarity	NPD7286	Phase 2
0.6911	Remote Similarity	NPD8360	Approved
0.6911	Remote Similarity	NPD8435	Approved
0.6911	Remote Similarity	NPD8361	Approved
0.6909	Remote Similarity	NPD8032	Phase 2
0.6905	Remote Similarity	NPD3748	Approved
0.6901	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7003	Approved
0.6901	Remote Similarity	NPD4110	Phase 3
0.6898	Remote Similarity	NPD7685	Pre-registration
0.6897	Remote Similarity	NPD1512	Approved
0.6897	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD1607	Approved
0.6875	Remote Similarity	NPD1608	Approved
0.6867	Remote Similarity	NPD1240	Approved
0.6866	Remote Similarity	NPD7701	Phase 2
0.6847	Remote Similarity	NPD7801	Approved
0.6832	Remote Similarity	NPD8151	Discontinued
0.6831	Remote Similarity	NPD5710	Approved
0.6831	Remote Similarity	NPD5711	Approved
0.6816	Remote Similarity	NPD8455	Phase 2
0.681	Remote Similarity	NPD2798	Approved
0.6809	Remote Similarity	NPD7240	Approved
0.6807	Remote Similarity	NPD6233	Phase 2
0.6802	Remote Similarity	NPD8166	Discontinued
0.68	Remote Similarity	NPD8319	Approved
0.68	Remote Similarity	NPD8320	Phase 1
0.6794	Remote Similarity	NPD7907	Approved
0.6788	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7095	Approved
0.6784	Remote Similarity	NPD6823	Phase 2
0.677	Remote Similarity	NPD3972	Approved
0.6769	Remote Similarity	NPD6534	Approved
0.6769	Remote Similarity	NPD6535	Approved
0.6768	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD4140	Approved
0.6765	Remote Similarity	NPD7783	Phase 2
0.6765	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6279	Approved
0.676	Remote Similarity	NPD6280	Approved
0.6751	Remote Similarity	NPD7700	Phase 2
0.6751	Remote Similarity	NPD7699	Phase 2
0.6748	Remote Similarity	NPD3266	Approved
0.6748	Remote Similarity	NPD3267	Approved
0.6747	Remote Similarity	NPD6798	Discontinued
0.6736	Remote Similarity	NPD4287	Approved
0.6726	Remote Similarity	NPD1933	Approved
0.6726	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5763	Approved
0.6725	Remote Similarity	NPD6003	Clinical (unspecified phase)

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