NPASS Compound

Structure

NPC471039 OpenBabel07101718322D 26 29 0 0 1 0 0 0 0 0999 V2000 0.8510 -3.7991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2650 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0735 -2.8242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 -1.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8709 -1.0801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6236 -1.0801 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 2.4504 -2.2574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3709 -0.2141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0291 -2.5294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3405 -2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 4 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 18 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 22 1 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 16 1 0 0 0 0 12 23 2 0 0 0 0 13 20 1 0 0 0 0 13 24 1 0 0 0 0 14 25 2 0 0 0 0 14 26 1 0 0 0 0 15 9 1 1 0 0 0 15 16 1 0 0 0 0 17 19 1 0 0 0 0 17 26 1 1 0 0 0 18 20 1 6 0 0 0 18 21 1 0 0 0 0 19 21 1 6 0 0 0 19 22 1 0 0 0 0 20 2 1 6 0 0 0 21 3 1 6 0 0 0 22 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	382.094
LogP:	2.574
LogD:	2.668
LogS:	-4.0
# Rotatable Bonds:	4
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	6.07
Fsp3:	0.818
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.083
MDCK Permeability:	1.6781863450887613e-05
Pgp-inhibitor:	0.083
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.717
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	74.0513687133789%
Volume Distribution (VD):	1.199
Pgp-substrate:	25.71205711364746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.042
CYP2C19-substrate:	0.797
CYP2C9-inhibitor:	0.144
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.117
CYP3A4-inhibitor:	0.826
CYP3A4-substrate:	0.342

ADMET: Excretion

Clearance (CL):	3.433
Half-life (T1/2):	0.739

ADMET: Toxicity

hERG Blockers:	0.331
Human Hepatotoxicity (H-HT):	0.557
Drug-inuced Liver Injury (DILI):	0.113
AMES Toxicity:	0.073
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.938
Carcinogencity:	0.196
Eye Corrosion:	0.334
Eye Irritation:	0.631
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: NPC471039

Natural Product ID:	NPC471039
*Common Name:**	Crotonkinin B
IUPAC Name:	n.a.
Synonyms:	Crotonkinin B
Standard InCHIKey:	IZEWXSNCLIVJKF-HGMIMVGUSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-14(25)26-17-9-15-10-22(11-16(15)12-23)8-5-18-20(2,13-24)6-4-7-21(18,3)19(17)22/h11-12,15,17-19,24H,4-10,13H2,1-3H3/t15-,17-,18+,19-,20+,21+,22-/m1/s1
SMILES:	CC(=O)OC1CC2CC3(C1C4(CCCC(C4CC3)(C)CO)C)C=C2C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2337578
PubChem CID:	71717696
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510600]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18161942]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[19899773]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22085418]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22197145]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	Eukaryota	whole plants	Vietnam	2009-Aug	PMID[23347584]
NPO22879	Croton tonkinensis	Species	Euphorbiaceae	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	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4380.0	nM	PMID[528155]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	3200.0	nM	PMID[528155]

☑ 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 NPC471039 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	196
0.1-0.2	1190
0.2-0.3	4780
0.3-0.4	10777
0.4-0.5	10986
0.5-0.6	6635
0.6-0.7	5384
0.7-0.8	2467
0.8-0.85	259
0.85-0.9	18
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9775	High Similarity	NPC471040
0.9053	High Similarity	NPC471041
0.9022	High Similarity	NPC474185
0.8947	High Similarity	NPC194196
0.8804	High Similarity	NPC328141
0.8776	High Similarity	NPC95585
0.8776	High Similarity	NPC282233
0.8723	High Similarity	NPC269729
0.8632	High Similarity	NPC274417
0.8632	High Similarity	NPC139459
0.8617	High Similarity	NPC79117
0.8587	High Similarity	NPC474925
0.8586	High Similarity	NPC264048
0.8557	High Similarity	NPC471966
0.8539	High Similarity	NPC142683
0.8526	High Similarity	NPC169751
0.8526	High Similarity	NPC272635
0.8469	Intermediate Similarity	NPC35751
0.8469	Intermediate Similarity	NPC201406
0.8469	Intermediate Similarity	NPC117685
0.8454	Intermediate Similarity	NPC473456
0.8438	Intermediate Similarity	NPC317586
0.8438	Intermediate Similarity	NPC279974
0.8438	Intermediate Similarity	NPC139570
0.8438	Intermediate Similarity	NPC470016
0.8421	Intermediate Similarity	NPC170220
0.8421	Intermediate Similarity	NPC294263
0.8421	Intermediate Similarity	NPC272075
0.8421	Intermediate Similarity	NPC141497
0.8421	Intermediate Similarity	NPC107674
0.8421	Intermediate Similarity	NPC214756
0.8421	Intermediate Similarity	NPC295643
0.8404	Intermediate Similarity	NPC85173
0.8404	Intermediate Similarity	NPC471896
0.8404	Intermediate Similarity	NPC126993
0.84	Intermediate Similarity	NPC112009
0.8387	Intermediate Similarity	NPC473229
0.8387	Intermediate Similarity	NPC206060
0.8384	Intermediate Similarity	NPC471412
0.8384	Intermediate Similarity	NPC469327
0.837	Intermediate Similarity	NPC73038
0.837	Intermediate Similarity	NPC325594
0.8367	Intermediate Similarity	NPC114274
0.8351	Intermediate Similarity	NPC61369
0.8351	Intermediate Similarity	NPC219353
0.8351	Intermediate Similarity	NPC469545
0.8351	Intermediate Similarity	NPC5532
0.8333	Intermediate Similarity	NPC166906
0.8333	Intermediate Similarity	NPC159410
0.8333	Intermediate Similarity	NPC74751
0.8333	Intermediate Similarity	NPC240617
0.8333	Intermediate Similarity	NPC471207
0.8316	Intermediate Similarity	NPC250753
0.8316	Intermediate Similarity	NPC158030
0.8316	Intermediate Similarity	NPC86266
0.8316	Intermediate Similarity	NPC65120
0.8316	Intermediate Similarity	NPC230064
0.8316	Intermediate Similarity	NPC145067
0.8316	Intermediate Similarity	NPC212301
0.8316	Intermediate Similarity	NPC110657
0.8316	Intermediate Similarity	NPC476187
0.8316	Intermediate Similarity	NPC4036
0.8316	Intermediate Similarity	NPC233455
0.83	Intermediate Similarity	NPC473163
0.83	Intermediate Similarity	NPC136289
0.8298	Intermediate Similarity	NPC475921
0.8298	Intermediate Similarity	NPC474704
0.8283	Intermediate Similarity	NPC475202
0.8283	Intermediate Similarity	NPC475392
0.8283	Intermediate Similarity	NPC476274
0.8283	Intermediate Similarity	NPC471413
0.8283	Intermediate Similarity	NPC475385
0.828	Intermediate Similarity	NPC142361
0.828	Intermediate Similarity	NPC474684
0.8269	Intermediate Similarity	NPC239097
0.8265	Intermediate Similarity	NPC108078
0.8265	Intermediate Similarity	NPC292133
0.8265	Intermediate Similarity	NPC253826
0.8252	Intermediate Similarity	NPC275539
0.8252	Intermediate Similarity	NPC189075
0.8252	Intermediate Similarity	NPC469844
0.8247	Intermediate Similarity	NPC98639
0.8247	Intermediate Similarity	NPC476174
0.8247	Intermediate Similarity	NPC473170
0.8242	Intermediate Similarity	NPC471037
0.8229	Intermediate Similarity	NPC151722
0.8229	Intermediate Similarity	NPC470224
0.8229	Intermediate Similarity	NPC86368
0.8229	Intermediate Similarity	NPC474436
0.8229	Intermediate Similarity	NPC49776
0.8229	Intermediate Similarity	NPC139692
0.8229	Intermediate Similarity	NPC298554
0.8229	Intermediate Similarity	NPC472871
0.8229	Intermediate Similarity	NPC63118
0.8224	Intermediate Similarity	NPC298278
0.8222	Intermediate Similarity	NPC90055
0.8218	Intermediate Similarity	NPC176883
0.8218	Intermediate Similarity	NPC312900
0.8218	Intermediate Similarity	NPC180204
0.8211	Intermediate Similarity	NPC148414
0.8211	Intermediate Similarity	NPC111585
0.8211	Intermediate Similarity	NPC475965
0.8211	Intermediate Similarity	NPC183283
0.8211	Intermediate Similarity	NPC113989
0.8211	Intermediate Similarity	NPC120840
0.8211	Intermediate Similarity	NPC474842
0.8211	Intermediate Similarity	NPC474728
0.8211	Intermediate Similarity	NPC191684
0.8211	Intermediate Similarity	NPC175628
0.8208	Intermediate Similarity	NPC73050
0.82	Intermediate Similarity	NPC476240
0.82	Intermediate Similarity	NPC118174
0.82	Intermediate Similarity	NPC81530
0.82	Intermediate Similarity	NPC476223
0.82	Intermediate Similarity	NPC224720
0.8191	Intermediate Similarity	NPC246708
0.8191	Intermediate Similarity	NPC104560
0.8191	Intermediate Similarity	NPC182797
0.8191	Intermediate Similarity	NPC52169
0.8191	Intermediate Similarity	NPC474677
0.8191	Intermediate Similarity	NPC472870
0.8191	Intermediate Similarity	NPC328539
0.8191	Intermediate Similarity	NPC40552
0.8182	Intermediate Similarity	NPC260149
0.8182	Intermediate Similarity	NPC58942
0.8182	Intermediate Similarity	NPC57079
0.8182	Intermediate Similarity	NPC478056
0.8182	Intermediate Similarity	NPC108368
0.8182	Intermediate Similarity	NPC471717
0.8182	Intermediate Similarity	NPC119036
0.8173	Intermediate Similarity	NPC41405
0.8172	Intermediate Similarity	NPC471042
0.8163	Intermediate Similarity	NPC329910
0.8163	Intermediate Similarity	NPC29410
0.8163	Intermediate Similarity	NPC328162
0.8163	Intermediate Similarity	NPC96859
0.8163	Intermediate Similarity	NPC151725
0.8163	Intermediate Similarity	NPC305483
0.8163	Intermediate Similarity	NPC192428
0.8163	Intermediate Similarity	NPC106425
0.8163	Intermediate Similarity	NPC98874
0.8163	Intermediate Similarity	NPC471153
0.8163	Intermediate Similarity	NPC200054
0.8163	Intermediate Similarity	NPC122324
0.8163	Intermediate Similarity	NPC328371
0.8163	Intermediate Similarity	NPC29952
0.8163	Intermediate Similarity	NPC327788
0.8163	Intermediate Similarity	NPC301534
0.8163	Intermediate Similarity	NPC250757
0.8155	Intermediate Similarity	NPC44063
0.8155	Intermediate Similarity	NPC475294
0.8155	Intermediate Similarity	NPC110496
0.8152	Intermediate Similarity	NPC248758
0.8152	Intermediate Similarity	NPC470812
0.8144	Intermediate Similarity	NPC474529
0.8144	Intermediate Similarity	NPC184870
0.8144	Intermediate Similarity	NPC222047
0.8144	Intermediate Similarity	NPC209868
0.8144	Intermediate Similarity	NPC49670
0.8137	Intermediate Similarity	NPC255309
0.8137	Intermediate Similarity	NPC235889
0.8125	Intermediate Similarity	NPC168027
0.8125	Intermediate Similarity	NPC60755
0.8125	Intermediate Similarity	NPC272746
0.8125	Intermediate Similarity	NPC470590
0.8125	Intermediate Similarity	NPC285184
0.8125	Intermediate Similarity	NPC185936
0.8125	Intermediate Similarity	NPC218301
0.8125	Intermediate Similarity	NPC77099
0.8125	Intermediate Similarity	NPC26888
0.8125	Intermediate Similarity	NPC189520
0.8119	Intermediate Similarity	NPC162973
0.8105	Intermediate Similarity	NPC30522
0.8105	Intermediate Similarity	NPC121798
0.8105	Intermediate Similarity	NPC263393
0.8105	Intermediate Similarity	NPC143232
0.8105	Intermediate Similarity	NPC130520
0.8105	Intermediate Similarity	NPC119416
0.8105	Intermediate Similarity	NPC290972
0.8105	Intermediate Similarity	NPC470588
0.8105	Intermediate Similarity	NPC86319
0.8105	Intermediate Similarity	NPC61543
0.8105	Intermediate Similarity	NPC225585
0.8105	Intermediate Similarity	NPC25906
0.8105	Intermediate Similarity	NPC198664
0.8105	Intermediate Similarity	NPC59263
0.8105	Intermediate Similarity	NPC293048
0.8105	Intermediate Similarity	NPC174342
0.8105	Intermediate Similarity	NPC234346
0.8105	Intermediate Similarity	NPC64872
0.8105	Intermediate Similarity	NPC127689
0.8105	Intermediate Similarity	NPC275740
0.8105	Intermediate Similarity	NPC477973
0.8105	Intermediate Similarity	NPC270768
0.8105	Intermediate Similarity	NPC184663
0.8105	Intermediate Similarity	NPC469546
0.8105	Intermediate Similarity	NPC474889
0.8105	Intermediate Similarity	NPC274330
0.81	Intermediate Similarity	NPC470074
0.81	Intermediate Similarity	NPC293890

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 NPC471039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	1535
0.2-0.3	3757
0.3-0.4	2436
0.4-0.5	764
0.5-0.6	215
0.6-0.7	163
0.7-0.8	109
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7748	Approved
0.8316	Intermediate Similarity	NPD7515	Phase 2
0.8316	Intermediate Similarity	NPD6079	Approved
0.8298	Intermediate Similarity	NPD5328	Approved
0.8252	Intermediate Similarity	NPD6899	Approved
0.8252	Intermediate Similarity	NPD6881	Approved
0.8235	Intermediate Similarity	NPD7128	Approved
0.8235	Intermediate Similarity	NPD5739	Approved
0.8235	Intermediate Similarity	NPD6675	Approved
0.8235	Intermediate Similarity	NPD6402	Approved
0.8182	Intermediate Similarity	NPD7638	Approved
0.8163	Intermediate Similarity	NPD4697	Phase 3
0.8155	Intermediate Similarity	NPD5697	Approved
0.81	Intermediate Similarity	NPD7639	Approved
0.81	Intermediate Similarity	NPD7640	Approved
0.8095	Intermediate Similarity	NPD6883	Approved
0.8095	Intermediate Similarity	NPD7290	Approved
0.8095	Intermediate Similarity	NPD7102	Approved
0.8081	Intermediate Similarity	NPD7902	Approved
0.8077	Intermediate Similarity	NPD6011	Approved
0.8077	Intermediate Similarity	NPD7320	Approved
0.8019	Intermediate Similarity	NPD6847	Approved
0.8019	Intermediate Similarity	NPD6617	Approved
0.8019	Intermediate Similarity	NPD6650	Approved
0.8019	Intermediate Similarity	NPD6869	Approved
0.8019	Intermediate Similarity	NPD6649	Approved
0.8019	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD6373	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.7981	Intermediate Similarity	NPD5701	Approved
0.798	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD5222	Approved
0.798	Intermediate Similarity	NPD5221	Approved
0.7979	Intermediate Similarity	NPD7146	Approved
0.7979	Intermediate Similarity	NPD7521	Approved
0.7979	Intermediate Similarity	NPD7334	Approved
0.7979	Intermediate Similarity	NPD6409	Approved
0.7979	Intermediate Similarity	NPD3618	Phase 1
0.7979	Intermediate Similarity	NPD6684	Approved
0.7979	Intermediate Similarity	NPD5330	Approved
0.7944	Intermediate Similarity	NPD6882	Approved
0.7944	Intermediate Similarity	NPD8297	Approved
0.79	Intermediate Similarity	NPD6083	Phase 2
0.79	Intermediate Similarity	NPD5173	Approved
0.79	Intermediate Similarity	NPD6084	Phase 2
0.7872	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6399	Phase 3
0.785	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6672	Approved
0.7812	Intermediate Similarity	NPD6903	Approved
0.7812	Intermediate Similarity	NPD5737	Approved
0.7778	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7900	Approved
0.7766	Intermediate Similarity	NPD3133	Approved
0.7766	Intermediate Similarity	NPD3666	Approved
0.7766	Intermediate Similarity	NPD3665	Phase 1
0.7755	Intermediate Similarity	NPD8035	Phase 2
0.7755	Intermediate Similarity	NPD8034	Phase 2
0.7745	Intermediate Similarity	NPD5286	Approved
0.7745	Intermediate Similarity	NPD4696	Approved
0.7745	Intermediate Similarity	NPD5285	Approved
0.7727	Intermediate Similarity	NPD6868	Approved
0.7723	Intermediate Similarity	NPD4755	Approved
0.7708	Intermediate Similarity	NPD3573	Approved
0.767	Intermediate Similarity	NPD5223	Approved
0.7596	Intermediate Similarity	NPD5224	Approved
0.7596	Intermediate Similarity	NPD5225	Approved
0.7596	Intermediate Similarity	NPD5226	Approved
0.7596	Intermediate Similarity	NPD4633	Approved
0.7596	Intermediate Similarity	NPD5211	Phase 2
0.7589	Intermediate Similarity	NPD6335	Approved
0.7579	Intermediate Similarity	NPD4786	Approved
0.7576	Intermediate Similarity	NPD6411	Approved
0.7573	Intermediate Similarity	NPD4700	Approved
0.7568	Intermediate Similarity	NPD6274	Approved
0.7553	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD3667	Approved
0.7545	Intermediate Similarity	NPD4632	Approved
0.7525	Intermediate Similarity	NPD5695	Phase 3
0.7525	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD5175	Approved
0.7524	Intermediate Similarity	NPD5174	Approved
0.7522	Intermediate Similarity	NPD7101	Approved
0.7522	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD6317	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.7476	Intermediate Similarity	NPD5696	Approved
0.7453	Intermediate Similarity	NPD5141	Approved
0.7436	Intermediate Similarity	NPD7507	Approved
0.7434	Intermediate Similarity	NPD6314	Approved
0.7434	Intermediate Similarity	NPD6313	Approved
0.7429	Intermediate Similarity	NPD7632	Discontinued
0.7423	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6008	Approved
0.7374	Intermediate Similarity	NPD6673	Approved
0.7374	Intermediate Similarity	NPD4753	Phase 2
0.7374	Intermediate Similarity	NPD6904	Approved
0.7374	Intermediate Similarity	NPD6080	Approved
0.7374	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6101	Approved
0.7358	Intermediate Similarity	NPD4754	Approved
0.7345	Intermediate Similarity	NPD7115	Discovery
0.7345	Intermediate Similarity	NPD6009	Approved
0.734	Intermediate Similarity	NPD7525	Registered
0.7308	Intermediate Similarity	NPD4225	Approved
0.7304	Intermediate Similarity	NPD6319	Approved
0.7292	Intermediate Similarity	NPD4788	Approved
0.7283	Intermediate Similarity	NPD6117	Approved
0.7265	Intermediate Similarity	NPD7604	Phase 2
0.725	Intermediate Similarity	NPD7319	Approved
0.7248	Intermediate Similarity	NPD4730	Approved
0.7248	Intermediate Similarity	NPD6686	Approved
0.7248	Intermediate Similarity	NPD4729	Approved
0.7248	Intermediate Similarity	NPD5168	Approved
0.7248	Intermediate Similarity	NPD5128	Approved
0.7245	Intermediate Similarity	NPD5279	Phase 3
0.7241	Intermediate Similarity	NPD6909	Approved
0.7241	Intermediate Similarity	NPD6908	Approved
0.7241	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5983	Phase 2
0.7222	Intermediate Similarity	NPD4768	Approved
0.7222	Intermediate Similarity	NPD4767	Approved
0.7204	Intermediate Similarity	NPD6116	Phase 1
0.7203	Intermediate Similarity	NPD7492	Approved
0.72	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4223	Phase 3
0.7188	Intermediate Similarity	NPD4221	Approved
0.7184	Intermediate Similarity	NPD5210	Approved
0.7184	Intermediate Similarity	NPD4629	Approved
0.7167	Intermediate Similarity	NPD7736	Approved
0.7158	Intermediate Similarity	NPD4695	Discontinued
0.7156	Intermediate Similarity	NPD6412	Phase 2
0.7155	Intermediate Similarity	NPD6054	Approved
0.7143	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD6336	Discontinued
0.7143	Intermediate Similarity	NPD5329	Approved
0.7143	Intermediate Similarity	NPD6616	Approved
0.7128	Intermediate Similarity	NPD6114	Approved
0.7128	Intermediate Similarity	NPD6697	Approved
0.7128	Intermediate Similarity	NPD6118	Approved
0.7128	Intermediate Similarity	NPD6115	Approved
0.7117	Intermediate Similarity	NPD5169	Approved
0.7117	Intermediate Similarity	NPD5250	Approved
0.7117	Intermediate Similarity	NPD5251	Approved
0.7117	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4634	Approved
0.7117	Intermediate Similarity	NPD5247	Approved
0.7117	Intermediate Similarity	NPD5248	Approved
0.7117	Intermediate Similarity	NPD5249	Phase 3
0.7117	Intermediate Similarity	NPD5135	Approved
0.7115	Intermediate Similarity	NPD7614	Phase 1
0.71	Intermediate Similarity	NPD5208	Approved
0.7087	Intermediate Similarity	NPD6001	Approved
0.7083	Intermediate Similarity	NPD7078	Approved
0.7071	Intermediate Similarity	NPD6098	Approved
0.7065	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD5284	Approved
0.7059	Intermediate Similarity	NPD6050	Approved
0.7059	Intermediate Similarity	NPD5281	Approved
0.7054	Intermediate Similarity	NPD5217	Approved
0.7054	Intermediate Similarity	NPD5127	Approved
0.7054	Intermediate Similarity	NPD5215	Approved
0.7054	Intermediate Similarity	NPD5216	Approved
0.7053	Intermediate Similarity	NPD7645	Phase 2
0.7041	Intermediate Similarity	NPD3668	Phase 3
0.7041	Intermediate Similarity	NPD4197	Approved
0.7034	Intermediate Similarity	NPD6370	Approved
0.7019	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6435	Approved
0.7009	Intermediate Similarity	NPD6059	Approved
0.699	Remote Similarity	NPD5779	Approved
0.699	Remote Similarity	NPD5778	Approved
0.6975	Remote Similarity	NPD8328	Phase 3
0.6961	Remote Similarity	NPD5692	Phase 3
0.6952	Remote Similarity	NPD7732	Phase 3
0.6949	Remote Similarity	NPD6016	Approved
0.6949	Remote Similarity	NPD6015	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6942	Remote Similarity	NPD8293	Discontinued
0.69	Remote Similarity	NPD4689	Approved
0.69	Remote Similarity	NPD4519	Discontinued
0.69	Remote Similarity	NPD4693	Phase 3
0.69	Remote Similarity	NPD5205	Approved
0.69	Remote Similarity	NPD5690	Phase 2
0.69	Remote Similarity	NPD4688	Approved
0.69	Remote Similarity	NPD4138	Approved
0.69	Remote Similarity	NPD4690	Approved
0.69	Remote Similarity	NPD4623	Approved
0.6893	Remote Similarity	NPD5694	Approved
0.6891	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5167	Approved
0.6842	Remote Similarity	NPD6053	Discontinued
0.6809	Remote Similarity	NPD7339	Approved
0.6809	Remote Similarity	NPD3703	Phase 2

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