NPASS Compound

Structure

CID195954 OpenBabel06191715582D 34 37 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 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 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 -2.5981 -1.5000 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 1 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 0.0000 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 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 13 2 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 9 18 1 0 0 0 0 10 26 1 0 0 0 0 11 31 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 27 2 0 0 0 0 14 32 1 0 0 0 0 15 28 2 0 0 0 0 15 33 1 0 0 0 0 16 29 2 0 0 0 0 16 34 1 0 0 0 0 17 8 1 1 0 0 0 17 19 1 0 0 0 0 18 20 2 0 0 0 0 19 25 1 6 0 0 0 20 31 1 0 0 0 0 21 22 1 0 0 0 0 21 23 1 0 0 0 0 21 32 1 1 0 0 0 22 24 1 0 0 0 0 22 33 1 1 0 0 0 23 25 1 1 0 0 0 23 34 1 0 0 0 0 24 26 1 0 0 0 0 25 26 1 6 0 0 0 26 30 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.23
Volume:	478.529
LogP:	3.24
LogD:	2.591
LogS:	-4.301
# 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:	0.524
Synthetic Accessibility Score:	5.021
Fsp3:	0.654
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:	-5.089
MDCK Permeability:	3.0000072001712397e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.388
20% Bioavailability (F20%):	0.819
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.246
Plasma Protein Binding (PPB):	78.69375610351562%
Volume Distribution (VD):	2.391
Pgp-substrate:	22.32061004638672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.292
CYP1A2-substrate:	0.043
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.342
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.916
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.663
CYP3A4-substrate:	0.374

ADMET: Excretion

Clearance (CL):	3.025
Half-life (T1/2):	0.355

ADMET: Toxicity

hERG Blockers:	0.831
Human Hepatotoxicity (H-HT):	0.737
Drug-inuced Liver Injury (DILI):	0.842
AMES Toxicity:	0.053
Rat Oral Acute Toxicity:	0.854
Maximum Recommended Daily Dose:	0.254
Skin Sensitization:	0.274
Carcinogencity:	0.175
Eye Corrosion:	0.005
Eye Irritation:	0.01
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC195954

Natural Product ID:	NPC195954
*Common Name:**	14(17)-Dehydrocaesalpin F
IUPAC Name:	[(1R,2S,3S,4aR,6aR,11aS,11bS)-1,3-diacetyloxy-4a-hydroxy-4,4,11b-trimethyl-7-methylidene-1,2,3,5,6,6a,11,11a-octahydronaphtho[2,1-f][1]benzofuran-2-yl] acetate
Synonyms:	14(17)-Dehydrocaesalpin F
Standard InCHIKey:	PPFRBUXKYCVYTK-GIPIGPSXSA-N
Standard InCHI:	InChI=1S/C26H34O8/c1-13-17-8-10-26(30)24(5,6)22(33-15(3)28)21(32-14(2)27)23(34-16(4)29)25(26,7)19(17)12-20-18(13)9-11-31-20/h9,11,17,19,21-23,30H,1,8,10,12H2,2-7H3/t17-,19-,21-,22+,23-,25-,26+/m0/s1
SMILES:	C=C1[C@@H]2CC[C@]3(C(C)(C)[C@@H]([C@@H]([C@@H]([C@]3(C)[C@H]2Cc2c1cco2)OC(=O)C)OC(=O)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517030
PubChem CID:	44584000
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]
NPO25179	Guilandina bonduc	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26756595]
NPO26402	Caesalpinia crista	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
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	=	200.0	nM	PMID[536378]

☑ 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 NPC195954 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	332
0.1-0.2	1268
0.2-0.3	2605
0.3-0.4	5033
0.4-0.5	9898
0.5-0.6	8539
0.6-0.7	7106
0.7-0.8	7190
0.8-0.85	512
0.85-0.9	153
0.9-0.95	53
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC88007
0.9733	High Similarity	NPC194499
0.9671	High Similarity	NPC68848
0.9595	High Similarity	NPC212257
0.9542	High Similarity	NPC188649
0.9536	High Similarity	NPC41880
0.9481	High Similarity	NPC285567
0.9481	High Similarity	NPC288602
0.9481	High Similarity	NPC88841
0.9477	High Similarity	NPC8389
0.9467	High Similarity	NPC294511
0.9467	High Similarity	NPC121615
0.9463	High Similarity	NPC228842
0.9423	High Similarity	NPC270312
0.9416	High Similarity	NPC79571
0.9392	High Similarity	NPC71821
0.9392	High Similarity	NPC255414
0.9359	High Similarity	NPC121995
0.9355	High Similarity	NPC283209
0.9346	High Similarity	NPC7059
0.9295	High Similarity	NPC56358
0.929	High Similarity	NPC18986
0.9281	High Similarity	NPC104736
0.9267	High Similarity	NPC69647
0.9267	High Similarity	NPC125182
0.9241	High Similarity	NPC291742
0.9241	High Similarity	NPC296558
0.9236	High Similarity	NPC277618
0.9231	High Similarity	NPC475039
0.9231	High Similarity	NPC14499
0.9231	High Similarity	NPC476035
0.9226	High Similarity	NPC287559
0.9221	High Similarity	NPC304692
0.9161	High Similarity	NPC474611
0.9114	High Similarity	NPC308156
0.9062	High Similarity	NPC118086
0.9054	High Similarity	NPC263337
0.9054	High Similarity	NPC121158
0.9013	High Similarity	NPC211625
0.9006	High Similarity	NPC294512
0.9006	High Similarity	NPC475641
0.9006	High Similarity	NPC475237
0.9	High Similarity	NPC5676
0.8974	High Similarity	NPC81405
0.8961	High Similarity	NPC472672
0.8961	High Similarity	NPC268905
0.8944	High Similarity	NPC88593
0.8931	High Similarity	NPC27541
0.8931	High Similarity	NPC62692
0.8931	High Similarity	NPC276735
0.8931	High Similarity	NPC126984
0.8931	High Similarity	NPC61967
0.8924	High Similarity	NPC82851
0.8924	High Similarity	NPC200782
0.8924	High Similarity	NPC472771
0.8917	High Similarity	NPC140952
0.8903	High Similarity	NPC253201
0.8903	High Similarity	NPC302054
0.8882	High Similarity	NPC255787
0.8875	High Similarity	NPC86800
0.8868	High Similarity	NPC472773
0.8851	High Similarity	NPC202260
0.8846	High Similarity	NPC476262
0.8841	High Similarity	NPC56953
0.8841	High Similarity	NPC176413
0.8839	High Similarity	NPC476201
0.882	High Similarity	NPC472774
0.882	High Similarity	NPC310572
0.882	High Similarity	NPC472775
0.8808	High Similarity	NPC251865
0.8805	High Similarity	NPC470792
0.8797	High Similarity	NPC123153
0.8792	High Similarity	NPC67003
0.8782	High Similarity	NPC34421
0.8782	High Similarity	NPC114880
0.8782	High Similarity	NPC282445
0.8782	High Similarity	NPC237259
0.8782	High Similarity	NPC98206
0.8765	High Similarity	NPC160651
0.8758	High Similarity	NPC475779
0.8758	High Similarity	NPC216755
0.8758	High Similarity	NPC472141
0.875	High Similarity	NPC302369
0.875	High Similarity	NPC469338
0.875	High Similarity	NPC39986
0.875	High Similarity	NPC292389
0.875	High Similarity	NPC134254
0.8742	High Similarity	NPC472653
0.8735	High Similarity	NPC11062
0.8734	High Similarity	NPC1408
0.8734	High Similarity	NPC249021
0.8734	High Similarity	NPC472772
0.8734	High Similarity	NPC475066
0.8734	High Similarity	NPC470118
0.8734	High Similarity	NPC472777
0.8734	High Similarity	NPC214495
0.8734	High Similarity	NPC472776
0.8734	High Similarity	NPC299038
0.8734	High Similarity	NPC246841
0.8734	High Similarity	NPC472778
0.8734	High Similarity	NPC470119
0.8734	High Similarity	NPC167142
0.8726	High Similarity	NPC264943
0.8718	High Similarity	NPC246164
0.8718	High Similarity	NPC469503
0.8716	High Similarity	NPC307401
0.871	High Similarity	NPC476122
0.8704	High Similarity	NPC173516
0.8704	High Similarity	NPC473766
0.8704	High Similarity	NPC41689
0.8704	High Similarity	NPC473753
0.8701	High Similarity	NPC19747
0.8696	High Similarity	NPC476858
0.8696	High Similarity	NPC476857
0.8696	High Similarity	NPC470940
0.8696	High Similarity	NPC469849
0.8696	High Similarity	NPC476856
0.8696	High Similarity	NPC276551
0.8696	High Similarity	NPC470182
0.8693	High Similarity	NPC62799
0.8688	High Similarity	NPC329938
0.8688	High Similarity	NPC471003
0.8679	High Similarity	NPC84349
0.8679	High Similarity	NPC475226
0.8679	High Similarity	NPC472671
0.8679	High Similarity	NPC475967
0.8654	High Similarity	NPC18135
0.865	High Similarity	NPC271235
0.865	High Similarity	NPC471397
0.8642	High Similarity	NPC93172
0.8642	High Similarity	NPC97574
0.8642	High Similarity	NPC470875
0.8636	High Similarity	NPC471174
0.8636	High Similarity	NPC286038
0.8634	High Similarity	NPC476197
0.8634	High Similarity	NPC472139
0.8634	High Similarity	NPC477405
0.8634	High Similarity	NPC51568
0.8634	High Similarity	NPC234660
0.8625	High Similarity	NPC472299
0.8625	High Similarity	NPC25255
0.8625	High Similarity	NPC335761
0.8618	High Similarity	NPC243577
0.8616	High Similarity	NPC469847
0.8608	High Similarity	NPC141538
0.8608	High Similarity	NPC469336
0.8608	High Similarity	NPC296807
0.8608	High Similarity	NPC75310
0.8608	High Similarity	NPC155939
0.8608	High Similarity	NPC92979
0.86	High Similarity	NPC171207
0.86	High Similarity	NPC97667
0.86	High Similarity	NPC90614
0.8599	High Similarity	NPC33938
0.8599	High Similarity	NPC182427
0.8599	High Similarity	NPC29695
0.8599	High Similarity	NPC322546
0.8599	High Similarity	NPC308205
0.8598	High Similarity	NPC470995
0.8598	High Similarity	NPC302392
0.859	High Similarity	NPC470997
0.8589	High Similarity	NPC476853
0.8589	High Similarity	NPC472282
0.8589	High Similarity	NPC476861
0.8589	High Similarity	NPC476850
0.8581	High Similarity	NPC66991
0.858	High Similarity	NPC476860
0.858	High Similarity	NPC271657
0.8571	High Similarity	NPC5079
0.8571	High Similarity	NPC263432
0.8571	High Similarity	NPC472668
0.8571	High Similarity	NPC470939
0.8571	High Similarity	NPC471166
0.8571	High Similarity	NPC471167
0.8571	High Similarity	NPC193798
0.8571	High Similarity	NPC18347
0.8571	High Similarity	NPC69028
0.8571	High Similarity	NPC149896
0.8563	High Similarity	NPC472665
0.8562	High Similarity	NPC473473
0.8562	High Similarity	NPC477403
0.8562	High Similarity	NPC307383
0.8562	High Similarity	NPC475295
0.8553	High Similarity	NPC107646
0.8544	High Similarity	NPC178932
0.8544	High Similarity	NPC30222
0.8543	High Similarity	NPC118080
0.8543	High Similarity	NPC27377
0.8543	High Similarity	NPC87448
0.8543	High Similarity	NPC16912
0.8543	High Similarity	NPC97947
0.8543	High Similarity	NPC148374
0.8543	High Similarity	NPC41481
0.8543	High Similarity	NPC291599
0.8543	High Similarity	NPC472576
0.8535	High Similarity	NPC119252
0.8528	High Similarity	NPC23387
0.8526	High Similarity	NPC471001
0.8526	High Similarity	NPC472654
0.8526	High Similarity	NPC234494

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC195954 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	813
0.2-0.3	1598
0.3-0.4	2514
0.4-0.5	2156
0.5-0.6	1195
0.6-0.7	460
0.7-0.8	121
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
0.8802	High Similarity	NPD8434	Phase 2
0.8261	Intermediate Similarity	NPD5760	Phase 2
0.8261	Intermediate Similarity	NPD5761	Phase 2
0.8176	Intermediate Similarity	NPD6765	Approved
0.8176	Intermediate Similarity	NPD6764	Approved
0.8077	Intermediate Similarity	NPD4628	Phase 3
0.7989	Intermediate Similarity	NPD6784	Approved
0.7989	Intermediate Similarity	NPD6785	Approved
0.7952	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7819	Suspended
0.7895	Intermediate Similarity	NPD5844	Phase 1
0.7886	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD8127	Discontinued
0.7818	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7075	Discontinued
0.7771	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6559	Discontinued
0.7744	Intermediate Similarity	NPD6599	Discontinued
0.7725	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6273	Approved
0.7692	Intermediate Similarity	NPD5494	Approved
0.7683	Intermediate Similarity	NPD7458	Discontinued
0.7674	Intermediate Similarity	NPD7473	Discontinued
0.7654	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD8404	Phase 2
0.759	Intermediate Similarity	NPD7411	Suspended
0.7576	Intermediate Similarity	NPD3226	Approved
0.7574	Intermediate Similarity	NPD3749	Approved
0.7561	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD920	Approved
0.756	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD3817	Phase 2
0.7545	Intermediate Similarity	NPD6801	Discontinued
0.7545	Intermediate Similarity	NPD37	Approved
0.7531	Intermediate Similarity	NPD7236	Approved
0.7529	Intermediate Similarity	NPD919	Approved
0.7515	Intermediate Similarity	NPD4967	Phase 2
0.7515	Intermediate Similarity	NPD4966	Approved
0.7515	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6799	Approved
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7473	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7199	Phase 2
0.744	Intermediate Similarity	NPD1934	Approved
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3818	Discontinued
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7425	Intermediate Similarity	NPD4380	Phase 2
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7239	Suspended
0.7407	Intermediate Similarity	NPD3750	Approved
0.7378	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2796	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7374	Intermediate Similarity	NPD8312	Approved
0.7372	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD7497	Discontinued
0.7353	Intermediate Similarity	NPD5402	Approved
0.7342	Intermediate Similarity	NPD6355	Discontinued
0.7341	Intermediate Similarity	NPD1247	Approved
0.7341	Intermediate Similarity	NPD6959	Discontinued
0.7333	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2534	Approved
0.7333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2533	Approved
0.733	Intermediate Similarity	NPD7799	Discontinued
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7325	Intermediate Similarity	NPD8032	Phase 2
0.7314	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6166	Phase 2
0.7314	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3748	Approved
0.7312	Intermediate Similarity	NPD2799	Discontinued
0.731	Intermediate Similarity	NPD3882	Suspended
0.731	Intermediate Similarity	NPD7768	Phase 2
0.7303	Intermediate Similarity	NPD1608	Approved
0.7303	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4110	Phase 3
0.7301	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7003	Approved
0.7299	Intermediate Similarity	NPD7229	Phase 3
0.7294	Intermediate Similarity	NPD2801	Approved
0.7289	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1549	Phase 2
0.7268	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1551	Phase 2
0.7261	Intermediate Similarity	NPD3764	Approved
0.7256	Intermediate Similarity	NPD6190	Approved
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.725	Intermediate Similarity	NPD7097	Phase 1
0.7247	Intermediate Similarity	NPD7074	Phase 3
0.7246	Intermediate Similarity	NPD5403	Approved
0.7239	Intermediate Similarity	NPD1243	Approved
0.7238	Intermediate Similarity	NPD8407	Phase 2
0.7232	Intermediate Similarity	NPD7228	Approved
0.7229	Intermediate Similarity	NPD5401	Approved
0.7222	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1471	Phase 3
0.7215	Intermediate Similarity	NPD6233	Phase 2
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7197	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8166	Discontinued
0.7193	Intermediate Similarity	NPD1465	Phase 2
0.7193	Intermediate Similarity	NPD8455	Phase 2
0.7191	Intermediate Similarity	NPD7054	Approved
0.7191	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4140	Approved
0.7167	Intermediate Similarity	NPD7685	Pre-registration
0.7167	Intermediate Similarity	NPD8368	Discontinued
0.716	Intermediate Similarity	NPD2935	Discontinued
0.7159	Intermediate Similarity	NPD3926	Phase 2
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7151	Intermediate Similarity	NPD7472	Approved
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2800	Approved
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7127	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2344	Approved
0.7117	Intermediate Similarity	NPD5762	Approved
0.7117	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6004	Phase 3
0.7117	Intermediate Similarity	NPD6005	Phase 3
0.7117	Intermediate Similarity	NPD5763	Approved
0.7117	Intermediate Similarity	NPD6002	Phase 3
0.7105	Intermediate Similarity	NPD17	Approved
0.7102	Intermediate Similarity	NPD3787	Discontinued
0.7099	Intermediate Similarity	NPD1510	Phase 2
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7083	Intermediate Similarity	NPD7435	Discontinued
0.7078	Intermediate Similarity	NPD3972	Approved
0.7072	Intermediate Similarity	NPD7251	Discontinued
0.7072	Intermediate Similarity	NPD7240	Approved
0.7066	Intermediate Similarity	NPD1511	Approved
0.7055	Intermediate Similarity	NPD2438	Suspended
0.7052	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD2797	Approved
0.7048	Intermediate Similarity	NPD3887	Approved
0.7044	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7177	Discontinued
0.7033	Intermediate Similarity	NPD7808	Phase 3
0.7018	Intermediate Similarity	NPD7028	Phase 2
0.7017	Intermediate Similarity	NPD6797	Phase 2
0.7016	Intermediate Similarity	NPD4107	Approved
0.7011	Intermediate Similarity	NPD7058	Phase 2
0.7011	Intermediate Similarity	NPD7057	Phase 3
0.7	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1778	Approved
0.6989	Remote Similarity	NPD8361	Approved
0.6989	Remote Similarity	NPD8360	Approved
0.6989	Remote Similarity	NPD8435	Approved
0.6982	Remote Similarity	NPD1512	Approved
0.6975	Remote Similarity	NPD1607	Approved
0.6957	Remote Similarity	NPD4307	Phase 2
0.6957	Remote Similarity	NPD1240	Approved
0.6946	Remote Similarity	NPD2354	Approved
0.6946	Remote Similarity	NPD2309	Approved
0.6943	Remote Similarity	NPD3266	Approved
0.6943	Remote Similarity	NPD3267	Approved
0.6927	Remote Similarity	NPD6777	Approved
0.6927	Remote Similarity	NPD6779	Approved
0.6927	Remote Similarity	NPD6782	Approved
0.6927	Remote Similarity	NPD6776	Approved
0.6927	Remote Similarity	NPD6781	Approved
0.6927	Remote Similarity	NPD6778	Approved
0.6927	Remote Similarity	NPD6780	Approved
0.6914	Remote Similarity	NPD447	Suspended
0.6914	Remote Similarity	NPD230	Phase 1
0.6914	Remote Similarity	NPD5735	Approved
0.6907	Remote Similarity	NPD7697	Approved
0.6907	Remote Similarity	NPD7696	Phase 3
0.6907	Remote Similarity	NPD7698	Approved
0.6899	Remote Similarity	NPD2798	Approved
0.6899	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6663	Approved
0.6891	Remote Similarity	NPD4482	Phase 3
0.6882	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6385	Approved
0.6879	Remote Similarity	NPD1283	Approved
0.6879	Remote Similarity	NPD6386	Approved
0.6872	Remote Similarity	NPD7871	Phase 2
0.6872	Remote Similarity	NPD7870	Phase 2
0.6871	Remote Similarity	NPD6653	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