NPASS Compound

Structure

CID81405 OpenBabel06191715422D 30 33 0 0 1 0 0 0 0 0999 V2000 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 0.0000 2.0000 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 -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 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 -2.5981 -1.5000 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 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 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 21 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 23 1 0 0 0 0 9 28 1 0 0 0 0 10 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 12 24 2 0 0 0 0 12 29 1 0 0 0 0 13 25 2 0 0 0 0 13 30 1 0 0 0 0 14 6 1 1 0 0 0 14 16 1 0 0 0 0 14 20 1 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 22 1 6 0 0 0 17 28 1 0 0 0 0 18 21 1 0 0 0 0 18 29 1 1 0 0 0 19 22 1 1 0 0 0 19 30 1 0 0 0 0 20 26 2 0 0 0 0 21 23 1 0 0 0 0 22 23 1 6 0 0 0 23 27 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.2
Volume:	420.488
LogP:	2.775
LogD:	2.368
LogS:	-4.304
# Rotatable Bonds:	4
TPSA:	103.04
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	4.778
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:	-4.843
MDCK Permeability:	3.980445762863383e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.128

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.315
Plasma Protein Binding (PPB):	82.35176086425781%
Volume Distribution (VD):	1.222
Pgp-substrate:	22.189863204956055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.26
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.379
CYP2C19-substrate:	0.241
CYP2C9-inhibitor:	0.637
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.514
CYP3A4-substrate:	0.476

ADMET: Excretion

Clearance (CL):	3.731
Half-life (T1/2):	0.139

ADMET: Toxicity

hERG Blockers:	0.864
Human Hepatotoxicity (H-HT):	0.631
Drug-inuced Liver Injury (DILI):	0.795
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.243
Carcinogencity:	0.767
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC81405

Natural Product ID:	NPC81405
*Common Name:**	Norcaesalpinin B
IUPAC Name:	[(1S,3R,4aR,6aR,11aS,11bS)-1-acetyloxy-4a-hydroxy-4,4,11b-trimethyl-7-oxo-1,2,3,5,6,6a,11,11a-octahydronaphtho[2,1-f][1]benzofuran-3-yl] acetate
Synonyms:
Standard InCHIKey:	MPFACQITBMQUJJ-PQIIFOIOSA-N
Standard InCHI:	InChI=1S/C23H30O7/c1-12(24)29-18-11-19(30-13(2)25)22(5)16-10-17-15(7-9-28-17)20(26)14(16)6-8-23(22,27)21(18,3)4/h7,9,14,16,18-19,27H,6,8,10-11H2,1-5H3/t14-,16+,18-,19+,22+,23-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]([C@]2(C)[C@H]3Cc4c(cco4)C(=O)[C@@H]3CC[C@]2(C1(C)C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464366
PubChem CID:	10895033
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
NPO1064	Caesalpinia bonducella	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0040-4039(01)89961-5]
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]
NPO1064	Caesalpinia bonducella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	=	260.0	nM	PMID[538563]

☑ 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 NPC81405 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	342
0.1-0.2	1401
0.2-0.3	2782
0.3-0.4	5795
0.4-0.5	11137
0.5-0.6	8298
0.6-0.7	6484
0.7-0.8	5919
0.8-0.85	400
0.85-0.9	109
0.9-0.95	24
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC140952
0.9673	High Similarity	NPC56358
0.9548	High Similarity	NPC270312
0.9416	High Similarity	NPC18986
0.9408	High Similarity	NPC104736
0.9408	High Similarity	NPC41880
0.9359	High Similarity	NPC121995
0.9351	High Similarity	NPC287559
0.9346	High Similarity	NPC304692
0.9333	High Similarity	NPC212257
0.9324	High Similarity	NPC233763
0.9295	High Similarity	NPC472664
0.9167	High Similarity	NPC188649
0.9167	High Similarity	NPC68848
0.9161	High Similarity	NPC474611
0.9139	High Similarity	NPC211625
0.9108	High Similarity	NPC285567
0.9108	High Similarity	NPC283209
0.9108	High Similarity	NPC88841
0.9108	High Similarity	NPC288602
0.9018	High Similarity	NPC472665
0.8974	High Similarity	NPC88007
0.8974	High Similarity	NPC195954
0.8974	High Similarity	NPC194499
0.8968	High Similarity	NPC75310
0.8954	High Similarity	NPC228842
0.894	High Similarity	NPC62799
0.8926	High Similarity	NPC263337
0.8903	High Similarity	NPC114880
0.8882	High Similarity	NPC296558
0.8861	High Similarity	NPC8389
0.8854	High Similarity	NPC472772
0.8839	High Similarity	NPC475777
0.8839	High Similarity	NPC121615
0.8839	High Similarity	NPC294511
0.8824	High Similarity	NPC19747
0.8805	High Similarity	NPC79571
0.8797	High Similarity	NPC123153
0.8782	High Similarity	NPC178932
0.8773	High Similarity	NPC294512
0.8758	High Similarity	NPC224418
0.8758	High Similarity	NPC71821
0.8734	High Similarity	NPC7059
0.8726	High Similarity	NPC179170
0.8726	High Similarity	NPC469336
0.8725	High Similarity	NPC202260
0.8718	High Similarity	NPC75906
0.871	High Similarity	NPC196864
0.871	High Similarity	NPC477404
0.8696	High Similarity	NPC276735
0.8688	High Similarity	NPC472771
0.8667	High Similarity	NPC148374
0.8662	High Similarity	NPC282445
0.8654	High Similarity	NPC144010
0.8642	High Similarity	NPC86800
0.8642	High Similarity	NPC475779
0.8642	High Similarity	NPC277618
0.8634	High Similarity	NPC663
0.8634	High Similarity	NPC224394
0.8634	High Similarity	NPC472773
0.8625	High Similarity	NPC472299
0.8618	High Similarity	NPC243577
0.8616	High Similarity	NPC249021
0.8614	High Similarity	NPC176413
0.8614	High Similarity	NPC56953
0.8608	High Similarity	NPC264943
0.8608	High Similarity	NPC472786
0.8608	High Similarity	NPC88958
0.8599	High Similarity	NPC246164
0.8599	High Similarity	NPC469503
0.8599	High Similarity	NPC145830
0.8591	High Similarity	NPC307401
0.859	High Similarity	NPC159927
0.859	High Similarity	NPC469335
0.8589	High Similarity	NPC473766
0.8589	High Similarity	NPC473753
0.8571	High Similarity	NPC263432
0.8571	High Similarity	NPC329938
0.8562	High Similarity	NPC251865
0.8562	High Similarity	NPC84479
0.8562	High Similarity	NPC473368
0.8553	High Similarity	NPC121158
0.8545	High Similarity	NPC475237
0.8545	High Similarity	NPC475641
0.8544	High Similarity	NPC30222
0.8537	High Similarity	NPC160651
0.8535	High Similarity	NPC272590
0.8528	High Similarity	NPC308156
0.8526	High Similarity	NPC472654
0.8526	High Similarity	NPC195325
0.8523	High Similarity	NPC46896
0.8519	High Similarity	NPC477405
0.8519	High Similarity	NPC469338
0.8519	High Similarity	NPC419
0.8519	High Similarity	NPC292389
0.8516	High Similarity	NPC255414
0.8516	High Similarity	NPC216755
0.8516	High Similarity	NPC286038
0.8509	High Similarity	NPC25255
0.8503	High Similarity	NPC167340
0.85	High Similarity	NPC167142
0.85	High Similarity	NPC221992
0.85	High Similarity	NPC299038
0.8497	Intermediate Similarity	NPC205071
0.8497	Intermediate Similarity	NPC103134
0.8497	Intermediate Similarity	NPC64568
0.8497	Intermediate Similarity	NPC267632
0.8491	Intermediate Similarity	NPC35000
0.8491	Intermediate Similarity	NPC469850
0.8491	Intermediate Similarity	NPC25351
0.8485	Intermediate Similarity	NPC44602
0.8476	Intermediate Similarity	NPC472784
0.8476	Intermediate Similarity	NPC136641
0.8476	Intermediate Similarity	NPC472282
0.8476	Intermediate Similarity	NPC472774
0.8476	Intermediate Similarity	NPC173516
0.8476	Intermediate Similarity	NPC472775
0.8471	Intermediate Similarity	NPC476122
0.8467	Intermediate Similarity	NPC42400
0.8466	Intermediate Similarity	NPC469849
0.8466	Intermediate Similarity	NPC476856
0.8466	Intermediate Similarity	NPC276551
0.8466	Intermediate Similarity	NPC470940
0.8466	Intermediate Similarity	NPC476857
0.8466	Intermediate Similarity	NPC476858
0.8466	Intermediate Similarity	NPC476860
0.8462	Intermediate Similarity	NPC66991
0.8457	Intermediate Similarity	NPC193798
0.8457	Intermediate Similarity	NPC470939
0.8457	Intermediate Similarity	NPC82851
0.8457	Intermediate Similarity	NPC69028
0.8452	Intermediate Similarity	NPC97904
0.8447	Intermediate Similarity	NPC475967
0.8447	Intermediate Similarity	NPC299094
0.8447	Intermediate Similarity	NPC10051
0.8447	Intermediate Similarity	NPC477403
0.8442	Intermediate Similarity	NPC476944
0.8431	Intermediate Similarity	NPC52412
0.8428	Intermediate Similarity	NPC57998
0.8428	Intermediate Similarity	NPC10429
0.8424	Intermediate Similarity	NPC471397
0.8424	Intermediate Similarity	NPC255787
0.8424	Intermediate Similarity	NPC291742
0.8424	Intermediate Similarity	NPC125465
0.8421	Intermediate Similarity	NPC18904
0.8415	Intermediate Similarity	NPC470875
0.8415	Intermediate Similarity	NPC23387
0.8415	Intermediate Similarity	NPC100849
0.8408	Intermediate Similarity	NPC125182
0.8408	Intermediate Similarity	NPC69647
0.8405	Intermediate Similarity	NPC39986
0.8405	Intermediate Similarity	NPC475039
0.8405	Intermediate Similarity	NPC476197
0.8405	Intermediate Similarity	NPC476035
0.8405	Intermediate Similarity	NPC14499
0.8405	Intermediate Similarity	NPC302369
0.8405	Intermediate Similarity	NPC134254
0.8402	Intermediate Similarity	NPC295914
0.8402	Intermediate Similarity	NPC472661
0.8397	Intermediate Similarity	NPC281398
0.8397	Intermediate Similarity	NPC471174
0.8397	Intermediate Similarity	NPC221809
0.8395	Intermediate Similarity	NPC477402
0.8395	Intermediate Similarity	NPC335761
0.8395	Intermediate Similarity	NPC333139
0.8387	Intermediate Similarity	NPC41182
0.8385	Intermediate Similarity	NPC261597
0.8375	Intermediate Similarity	NPC44675
0.8375	Intermediate Similarity	NPC92979
0.8375	Intermediate Similarity	NPC214541
0.8373	Intermediate Similarity	NPC472660
0.8373	Intermediate Similarity	NPC302392
0.8365	Intermediate Similarity	NPC476201
0.8365	Intermediate Similarity	NPC268905
0.8364	Intermediate Similarity	NPC476850
0.8364	Intermediate Similarity	NPC476861
0.8364	Intermediate Similarity	NPC476853
0.8354	Intermediate Similarity	NPC123088
0.8354	Intermediate Similarity	NPC156189
0.8354	Intermediate Similarity	NPC472298
0.8344	Intermediate Similarity	NPC472767
0.8344	Intermediate Similarity	NPC197596
0.8344	Intermediate Similarity	NPC5079
0.8344	Intermediate Similarity	NPC200782
0.8333	Intermediate Similarity	NPC158525
0.8333	Intermediate Similarity	NPC346
0.8333	Intermediate Similarity	NPC262198
0.8333	Intermediate Similarity	NPC472823
0.8323	Intermediate Similarity	NPC238843
0.8323	Intermediate Similarity	NPC107646
0.8323	Intermediate Similarity	NPC474542
0.8323	Intermediate Similarity	NPC263265
0.8323	Intermediate Similarity	NPC60973
0.8323	Intermediate Similarity	NPC142113
0.8323	Intermediate Similarity	NPC199044
0.8323	Intermediate Similarity	NPC469485
0.8322	Intermediate Similarity	NPC293253
0.8313	Intermediate Similarity	NPC44606
0.8301	Intermediate Similarity	NPC67003
0.8293	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 NPC81405 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	885
0.2-0.3	1725
0.3-0.4	2559
0.4-0.5	2146
0.5-0.6	1079
0.6-0.7	350
0.7-0.8	105
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8471	Intermediate Similarity	NPD8434	Phase 2
0.8395	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD5760	Phase 2
0.8261	Intermediate Similarity	NPD5761	Phase 2
0.8012	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD1471	Phase 3
0.7927	Intermediate Similarity	NPD7819	Suspended
0.7914	Intermediate Similarity	NPD7411	Suspended
0.7898	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3749	Approved
0.7888	Intermediate Similarity	NPD920	Approved
0.7861	Intermediate Similarity	NPD6764	Approved
0.7861	Intermediate Similarity	NPD6765	Approved
0.7771	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD6599	Discontinued
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6785	Approved
0.7684	Intermediate Similarity	NPD6784	Approved
0.7658	Intermediate Similarity	NPD2344	Approved
0.7654	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD2799	Discontinued
0.764	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6273	Approved
0.7595	Intermediate Similarity	NPD2796	Approved
0.7574	Intermediate Similarity	NPD7075	Discontinued
0.7562	Intermediate Similarity	NPD2800	Approved
0.7557	Intermediate Similarity	NPD6559	Discontinued
0.7547	Intermediate Similarity	NPD2346	Discontinued
0.7546	Intermediate Similarity	NPD2534	Approved
0.7546	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2532	Approved
0.7546	Intermediate Similarity	NPD2533	Approved
0.7545	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD6808	Phase 2
0.7485	Intermediate Similarity	NPD6799	Approved
0.7485	Intermediate Similarity	NPD5494	Approved
0.7484	Intermediate Similarity	NPD1551	Phase 2
0.7471	Intermediate Similarity	NPD7473	Discontinued
0.7469	Intermediate Similarity	NPD2309	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.7442	Intermediate Similarity	NPD6959	Discontinued
0.7439	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD919	Approved
0.7412	Intermediate Similarity	NPD7768	Phase 2
0.7407	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6232	Discontinued
0.7396	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7341	Intermediate Similarity	NPD1247	Approved
0.7312	Intermediate Similarity	NPD1510	Phase 2
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.731	Intermediate Similarity	NPD3882	Suspended
0.7301	Intermediate Similarity	NPD3750	Approved
0.7288	Intermediate Similarity	NPD5844	Phase 1
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6100	Approved
0.7267	Intermediate Similarity	NPD6099	Approved
0.7262	Intermediate Similarity	NPD7458	Discontinued
0.7262	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD3764	Approved
0.7261	Intermediate Similarity	NPD3268	Approved
0.7259	Intermediate Similarity	NPD8404	Phase 2
0.7257	Intermediate Similarity	NPD3926	Phase 2
0.7251	Intermediate Similarity	NPD3817	Phase 2
0.7235	Intermediate Similarity	NPD1934	Approved
0.7232	Intermediate Similarity	NPD3818	Discontinued
0.7219	Intermediate Similarity	NPD4380	Phase 2
0.7212	Intermediate Similarity	NPD7236	Approved
0.7209	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD3748	Approved
0.7198	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7003	Approved
0.7195	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1608	Approved
0.7188	Intermediate Similarity	NPD1607	Approved
0.7182	Intermediate Similarity	NPD8313	Approved
0.7182	Intermediate Similarity	NPD8312	Approved
0.717	Intermediate Similarity	NPD1240	Approved
0.7168	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2935	Discontinued
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD5403	Approved
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7126	Intermediate Similarity	NPD5401	Approved
0.7115	Intermediate Similarity	NPD2798	Approved
0.7111	Intermediate Similarity	NPD5953	Discontinued
0.7107	Intermediate Similarity	NPD8032	Phase 2
0.7102	Intermediate Similarity	NPD7229	Phase 3
0.7093	Intermediate Similarity	NPD2801	Approved
0.7081	Intermediate Similarity	NPD6651	Approved
0.7078	Intermediate Similarity	NPD3972	Approved
0.7063	Intermediate Similarity	NPD4140	Approved
0.7051	Intermediate Similarity	NPD3267	Approved
0.7051	Intermediate Similarity	NPD3266	Approved
0.7044	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6279	Approved
0.7035	Intermediate Similarity	NPD37	Approved
0.7035	Intermediate Similarity	NPD6280	Approved
0.7022	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6166	Phase 2
0.7013	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4965	Approved
0.7011	Intermediate Similarity	NPD4967	Phase 2
0.7011	Intermediate Similarity	NPD4966	Approved
0.7006	Intermediate Similarity	NPD5711	Approved
0.7006	Intermediate Similarity	NPD5710	Approved
0.7	Intermediate Similarity	NPD7239	Suspended
0.7	Intermediate Similarity	NPD7286	Phase 2
0.6994	Remote Similarity	NPD4308	Phase 3
0.6994	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD17	Approved
0.6989	Remote Similarity	NPD4287	Approved
0.6968	Remote Similarity	NPD9717	Approved
0.6964	Remote Similarity	NPD1511	Approved
0.6964	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2296	Approved
0.6949	Remote Similarity	NPD7199	Phase 2
0.6944	Remote Similarity	NPD7799	Discontinued
0.6944	Remote Similarity	NPD3751	Discontinued
0.6944	Remote Similarity	NPD7177	Discontinued
0.6943	Remote Similarity	NPD1203	Approved
0.6943	Remote Similarity	NPD2797	Approved
0.6943	Remote Similarity	NPD1470	Approved
0.694	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6234	Discontinued
0.6914	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6355	Discontinued
0.6909	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6004	Phase 3
0.6909	Remote Similarity	NPD6005	Phase 3
0.6909	Remote Similarity	NPD6002	Phase 3
0.6907	Remote Similarity	NPD7435	Discontinued
0.6906	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4110	Phase 3
0.6886	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1778	Approved
0.6882	Remote Similarity	NPD1512	Approved
0.6882	Remote Similarity	NPD8150	Discontinued
0.6879	Remote Similarity	NPD1876	Approved
0.6875	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8285	Discontinued
0.6872	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7074	Phase 3
0.6852	Remote Similarity	NPD4307	Phase 2
0.6848	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6781	Approved
0.6839	Remote Similarity	NPD6780	Approved
0.6839	Remote Similarity	NPD6778	Approved
0.6839	Remote Similarity	NPD6782	Approved
0.6839	Remote Similarity	NPD6776	Approved
0.6839	Remote Similarity	NPD6779	Approved
0.6839	Remote Similarity	NPD6777	Approved
0.6833	Remote Similarity	NPD2403	Approved
0.6832	Remote Similarity	NPD411	Approved
0.6832	Remote Similarity	NPD6798	Discontinued
0.6831	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7097	Phase 1
0.6816	Remote Similarity	NPD3787	Discontinued
0.6813	Remote Similarity	NPD7054	Approved
0.681	Remote Similarity	NPD447	Suspended
0.68	Remote Similarity	NPD1465	Phase 2
0.6786	Remote Similarity	NPD8166	Discontinued
0.6782	Remote Similarity	NPD5889	Approved
0.6782	Remote Similarity	NPD5890	Approved
0.6776	Remote Similarity	NPD7472	Approved
0.6774	Remote Similarity	NPD8407	Phase 2
0.6772	Remote Similarity	NPD1283	Approved
0.677	Remote Similarity	NPD7095	Approved
0.6753	Remote Similarity	NPD9545	Approved
0.6747	Remote Similarity	NPD5405	Approved
0.6747	Remote Similarity	NPD5408	Approved
0.6747	Remote Similarity	NPD5404	Approved
0.6747	Remote Similarity	NPD5406	Approved
0.6746	Remote Similarity	NPD3887	Approved
0.6739	Remote Similarity	NPD6797	Phase 2
0.6735	Remote Similarity	NPD7698	Approved
0.6735	Remote Similarity	NPD7697	Approved
0.6735	Remote Similarity	NPD7696	Phase 3
0.6735	Remote Similarity	NPD7497	Discontinued
0.6724	Remote Similarity	NPD6585	Discontinued
0.6723	Remote Similarity	NPD7057	Phase 3
0.6723	Remote Similarity	NPD7058	Phase 2
0.6707	Remote Similarity	NPD1933	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