NPASS Compound

Structure

CID202824 OpenBabel06191715592D 29 31 0 0 1 0 0 0 0 0999 V2000 -0.3403 -3.4835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8879 1.7870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5769 0.2355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2755 -0.8359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5251 -0.7897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9279 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9279 -0.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7456 -2.7162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6552 -2.3007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6552 0.3818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8255 0.5644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7557 -2.5738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7456 0.7972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6174 -0.0462 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8429 -1.7374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7210 -0.1953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1958 -1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1958 -0.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2817 -0.9595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2813 -0.9880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7557 0.6549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0619 -0.9595 0.0000 C 0 0 0 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 3.4073 -2.5629 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8338 0.7983 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3403 1.5645 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8458 -1.8135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8041 -0.5945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 23 1 0 0 0 0 7 23 1 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 10 13 2 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 12 15 1 0 0 0 0 12 24 1 0 0 0 0 14 22 1 0 0 0 0 15 3 1 6 0 0 0 15 21 1 0 0 0 0 16 25 2 0 0 0 0 16 28 1 0 0 0 0 17 26 2 0 0 0 0 17 29 1 0 0 0 0 18 9 1 6 0 0 0 18 19 1 0 0 0 0 18 23 1 0 0 0 0 19 11 1 6 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 24 1 6 0 0 0 21 28 1 6 0 0 0 22 24 1 0 0 0 0 22 27 2 0 0 0 0 24 29 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.24
Volume:	428.76
LogP:	4.275
LogD:	4.02
LogS:	-4.451
# Rotatable Bonds:	4
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.506
Synthetic Accessibility Score:	5.137
Fsp3:	0.708
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.789
MDCK Permeability:	2.4046481485129334e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.813
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.874
Plasma Protein Binding (PPB):	86.52497863769531%
Volume Distribution (VD):	2.032
Pgp-substrate:	16.020431518554688%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.341
CYP2C19-substrate:	0.563
CYP2C9-inhibitor:	0.582
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.77
CYP3A4-substrate:	0.44

ADMET: Excretion

Clearance (CL):	3.659
Half-life (T1/2):	0.143

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.949
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.306
Maximum Recommended Daily Dose:	0.521
Skin Sensitization:	0.771
Carcinogencity:	0.088
Eye Corrosion:	0.025
Eye Irritation:	0.034
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC202824

Natural Product ID:	NPC202824
*Common Name:**	Jolkinoate A
IUPAC Name:	n.a.
Synonyms:	jolkinoate A
Standard InCHIKey:	NGGOVTJUPVNNNR-CLHRSZSESA-N
Standard InCHI:	InChI=1S/C24H34O5/c1-13-8-9-18-19(23(18,6)7)11-14(2)22(27)24(29-17(5)26)12-15(3)21(20(24)10-13)28-16(4)25/h10-11,15,18-21H,8-9,12H2,1-7H3/b13-10+,14-11+/t15-,18-,19+,20-,21-,24+/m0/s1
SMILES:	C/C/1=C[C@H]2[C@H]([C@@H](C)C[C@@]2(C(=O)/C(=C/[C@@H]2[C@H](CC1)C2(C)C)/C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2315611
PubChem CID:	53355694
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
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	Zhang County, Gansu Province, China	2002-Sep	PMID[19702283]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21534583]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23691978]
NPO25837	Euphorbia micractina	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	11
Others	9

Activity Type	# Activity
Cell Line	5
Individual Protein	3
NON-MOLECULAR	8
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	Ratio IC50	=	0.6	n.a.	PMID[566624]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	60350.0	nM	PMID[566624]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	38210.0	nM	PMID[566624]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	100000.0	nM	PMID[566625]
NPT139	Cell Line	HT-29	Homo sapiens	Ratio IC50	=	0.94	n.a.	PMID[566625]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	0.18	n.a.	PMID[566624]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	33.76	n.a.	PMID[566624]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	1.16	n.a.	PMID[566624]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	94360.0	nM	PMID[566625]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[566625]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	27310.0	nM	PMID[566625]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21250.0	nM	PMID[566625]
NPT2	Others	Unspecified		Ratio IC50	=	0.78	n.a.	PMID[566625]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4180.0	nM	PMID[566625]
NPT2	Others	Unspecified		Ratio IC50	=	0.15	n.a.	PMID[566625]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47080.0	nM	PMID[566625]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	19450.0	nM	PMID[566625]
NPT2	Others	Unspecified		Ratio IC50	=	0.41	n.a.	PMID[566625]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	21150.0	nM	PMID[566625]
NPT2	Others	Unspecified		Ratio IC50	=	0.45	n.a.	PMID[566625]

☑ 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 NPC202824 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	248
0.1-0.2	1856
0.2-0.3	7909
0.3-0.4	14496
0.4-0.5	8313
0.5-0.6	6262
0.6-0.7	3172
0.7-0.8	404
0.8-0.85	22
0.85-0.9	2
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477361
0.9663	High Similarity	NPC477354
0.9556	High Similarity	NPC87090
0.9247	High Similarity	NPC477356
0.9239	High Similarity	NPC477355
0.9149	High Similarity	NPC118405
0.8495	Intermediate Similarity	NPC125180
0.8431	Intermediate Similarity	NPC475495
0.84	Intermediate Similarity	NPC470192
0.8367	Intermediate Similarity	NPC308351
0.8367	Intermediate Similarity	NPC271266
0.835	Intermediate Similarity	NPC477093
0.835	Intermediate Similarity	NPC475277
0.835	Intermediate Similarity	NPC473522
0.8247	Intermediate Similarity	NPC470188
0.8191	Intermediate Similarity	NPC221282
0.8182	Intermediate Similarity	NPC471757
0.8182	Intermediate Similarity	NPC105725
0.8182	Intermediate Similarity	NPC78127
0.8137	Intermediate Similarity	NPC470269
0.8119	Intermediate Similarity	NPC470267
0.8111	Intermediate Similarity	NPC475622
0.8111	Intermediate Similarity	NPC108045
0.809	Intermediate Similarity	NPC286229
0.8037	Intermediate Similarity	NPC475305
0.802	Intermediate Similarity	NPC235889
0.8	Intermediate Similarity	NPC49393
0.7963	Intermediate Similarity	NPC475401
0.7957	Intermediate Similarity	NPC471739
0.7941	Intermediate Similarity	NPC181265
0.7938	Intermediate Similarity	NPC470978
0.7938	Intermediate Similarity	NPC470974
0.7917	Intermediate Similarity	NPC109414
0.7905	Intermediate Similarity	NPC231589
0.7905	Intermediate Similarity	NPC214797
0.7905	Intermediate Similarity	NPC118860
0.789	Intermediate Similarity	NPC477092
0.7885	Intermediate Similarity	NPC258543
0.7885	Intermediate Similarity	NPC241927
0.7865	Intermediate Similarity	NPC469620
0.7865	Intermediate Similarity	NPC471740
0.7865	Intermediate Similarity	NPC469690
0.783	Intermediate Similarity	NPC170487
0.7826	Intermediate Similarity	NPC475796
0.7767	Intermediate Similarity	NPC291643
0.7753	Intermediate Similarity	NPC474056
0.7727	Intermediate Similarity	NPC226242
0.7723	Intermediate Similarity	NPC477950
0.7723	Intermediate Similarity	NPC471767
0.77	Intermediate Similarity	NPC222011
0.7692	Intermediate Similarity	NPC44063
0.7684	Intermediate Similarity	NPC475902
0.7667	Intermediate Similarity	NPC622
0.7667	Intermediate Similarity	NPC276647
0.7664	Intermediate Similarity	NPC71348
0.766	Intermediate Similarity	NPC469676
0.7647	Intermediate Similarity	NPC250594
0.7615	Intermediate Similarity	NPC270958
0.7604	Intermediate Similarity	NPC305039
0.7604	Intermediate Similarity	NPC474679
0.76	Intermediate Similarity	NPC69385
0.7593	Intermediate Similarity	NPC202889
0.7582	Intermediate Similarity	NPC304795
0.7576	Intermediate Similarity	NPC474490
0.757	Intermediate Similarity	NPC43775
0.7547	Intermediate Similarity	NPC471934
0.7547	Intermediate Similarity	NPC304495
0.7547	Intermediate Similarity	NPC2766
0.7527	Intermediate Similarity	NPC474703
0.7526	Intermediate Similarity	NPC329857
0.7526	Intermediate Similarity	NPC471818
0.7526	Intermediate Similarity	NPC469718
0.7525	Intermediate Similarity	NPC54843
0.7525	Intermediate Similarity	NPC176845
0.75	Intermediate Similarity	NPC221144
0.75	Intermediate Similarity	NPC167049
0.75	Intermediate Similarity	NPC121036
0.75	Intermediate Similarity	NPC137657
0.75	Intermediate Similarity	NPC100267
0.75	Intermediate Similarity	NPC471325
0.75	Intermediate Similarity	NPC469691
0.75	Intermediate Similarity	NPC475524
0.75	Intermediate Similarity	NPC169843
0.75	Intermediate Similarity	NPC472674
0.75	Intermediate Similarity	NPC310586
0.75	Intermediate Similarity	NPC255580
0.75	Intermediate Similarity	NPC39411
0.7477	Intermediate Similarity	NPC118638
0.7476	Intermediate Similarity	NPC15396
0.7475	Intermediate Similarity	NPC294266
0.7475	Intermediate Similarity	NPC476596
0.7474	Intermediate Similarity	NPC70422
0.7474	Intermediate Similarity	NPC474045
0.7474	Intermediate Similarity	NPC104961
0.7474	Intermediate Similarity	NPC70555
0.7474	Intermediate Similarity	NPC261253
0.7449	Intermediate Similarity	NPC150978
0.7449	Intermediate Similarity	NPC123177
0.7449	Intermediate Similarity	NPC74103
0.7449	Intermediate Similarity	NPC70595
0.7449	Intermediate Similarity	NPC20713
0.7449	Intermediate Similarity	NPC290651
0.7444	Intermediate Similarity	NPC276769
0.7416	Intermediate Similarity	NPC251435
0.7416	Intermediate Similarity	NPC469669
0.7416	Intermediate Similarity	NPC469678
0.7416	Intermediate Similarity	NPC475771
0.7414	Intermediate Similarity	NPC8990
0.7404	Intermediate Similarity	NPC470839
0.74	Intermediate Similarity	NPC163228
0.7396	Intermediate Similarity	NPC471738
0.7396	Intermediate Similarity	NPC197333
0.7386	Intermediate Similarity	NPC92909
0.7386	Intermediate Similarity	NPC107783
0.7374	Intermediate Similarity	NPC476598
0.7374	Intermediate Similarity	NPC476597
0.7353	Intermediate Similarity	NPC252295
0.735	Intermediate Similarity	NPC477369
0.7347	Intermediate Similarity	NPC477711
0.7347	Intermediate Similarity	NPC253144
0.734	Intermediate Similarity	NPC54468
0.734	Intermediate Similarity	NPC473629
0.734	Intermediate Similarity	NPC1761
0.734	Intermediate Similarity	NPC52609
0.7339	Intermediate Similarity	NPC471933
0.7333	Intermediate Similarity	NPC309190
0.7333	Intermediate Similarity	NPC13385
0.7327	Intermediate Similarity	NPC476275
0.7327	Intermediate Similarity	NPC213078
0.732	Intermediate Similarity	NPC475906
0.732	Intermediate Similarity	NPC469628
0.732	Intermediate Similarity	NPC471047
0.732	Intermediate Similarity	NPC469631
0.732	Intermediate Similarity	NPC469653
0.7315	Intermediate Similarity	NPC477103
0.7312	Intermediate Similarity	NPC141810
0.7308	Intermediate Similarity	NPC87351
0.73	Intermediate Similarity	NPC90453
0.73	Intermediate Similarity	NPC148463
0.7297	Intermediate Similarity	NPC298278
0.7297	Intermediate Similarity	NPC148458
0.7292	Intermediate Similarity	NPC472863
0.7292	Intermediate Similarity	NPC238593
0.7292	Intermediate Similarity	NPC195640
0.7292	Intermediate Similarity	NPC107787
0.729	Intermediate Similarity	NPC117604
0.7288	Intermediate Similarity	NPC477363
0.7283	Intermediate Similarity	NPC617
0.7283	Intermediate Similarity	NPC178277
0.7282	Intermediate Similarity	NPC476274
0.7282	Intermediate Similarity	NPC474720
0.7273	Intermediate Similarity	NPC191339
0.7273	Intermediate Similarity	NPC284185
0.7273	Intermediate Similarity	NPC218301
0.7273	Intermediate Similarity	NPC286341
0.7273	Intermediate Similarity	NPC219874
0.7265	Intermediate Similarity	NPC477362
0.7264	Intermediate Similarity	NPC314244
0.7264	Intermediate Similarity	NPC475571
0.7264	Intermediate Similarity	NPC196528
0.7264	Intermediate Similarity	NPC474101
0.7264	Intermediate Similarity	NPC265127
0.7263	Intermediate Similarity	NPC115786
0.7263	Intermediate Similarity	NPC90446
0.7255	Intermediate Similarity	NPC161493
0.7255	Intermediate Similarity	NPC226986
0.7255	Intermediate Similarity	NPC23680
0.7255	Intermediate Similarity	NPC216904
0.7255	Intermediate Similarity	NPC470834
0.7253	Intermediate Similarity	NPC186109
0.7248	Intermediate Similarity	NPC158523
0.7248	Intermediate Similarity	NPC474871
0.7248	Intermediate Similarity	NPC475937
0.7248	Intermediate Similarity	NPC96739
0.7248	Intermediate Similarity	NPC174471
0.7248	Intermediate Similarity	NPC260786
0.7245	Intermediate Similarity	NPC283409
0.7245	Intermediate Similarity	NPC472872
0.7245	Intermediate Similarity	NPC97032
0.7245	Intermediate Similarity	NPC166919
0.7241	Intermediate Similarity	NPC22301
0.7238	Intermediate Similarity	NPC111323
0.7238	Intermediate Similarity	NPC472755
0.7238	Intermediate Similarity	NPC311612
0.7238	Intermediate Similarity	NPC236390
0.7234	Intermediate Similarity	NPC35556
0.7232	Intermediate Similarity	NPC471854
0.7232	Intermediate Similarity	NPC239273
0.7228	Intermediate Similarity	NPC474947
0.7228	Intermediate Similarity	NPC67584
0.7228	Intermediate Similarity	NPC469599
0.7228	Intermediate Similarity	NPC33473
0.7222	Intermediate Similarity	NPC477102
0.7222	Intermediate Similarity	NPC474901
0.7222	Intermediate Similarity	NPC475941
0.7216	Intermediate Similarity	NPC24728
0.7212	Intermediate Similarity	NPC237190
0.7212	Intermediate Similarity	NPC224720
0.7212	Intermediate Similarity	NPC476240
0.7212	Intermediate Similarity	NPC473384

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 NPC202824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	2445
0.2-0.3	4082
0.3-0.4	1631
0.4-0.5	412
0.5-0.6	171
0.6-0.7	135
0.7-0.8	47
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7802	Intermediate Similarity	NPD6435	Approved
0.7788	Intermediate Similarity	NPD6899	Approved
0.7788	Intermediate Similarity	NPD6881	Approved
0.7767	Intermediate Similarity	NPD5739	Approved
0.7767	Intermediate Similarity	NPD6675	Approved
0.7767	Intermediate Similarity	NPD7128	Approved
0.7767	Intermediate Similarity	NPD6402	Approved
0.7736	Intermediate Similarity	NPD6649	Approved
0.7736	Intermediate Similarity	NPD6650	Approved
0.7714	Intermediate Similarity	NPD6372	Approved
0.7714	Intermediate Similarity	NPD6373	Approved
0.7692	Intermediate Similarity	NPD5697	Approved
0.7642	Intermediate Similarity	NPD7102	Approved
0.7642	Intermediate Similarity	NPD6883	Approved
0.7642	Intermediate Similarity	NPD7290	Approved
0.7619	Intermediate Similarity	NPD7320	Approved
0.7604	Intermediate Similarity	NPD6673	Approved
0.7604	Intermediate Similarity	NPD6080	Approved
0.7604	Intermediate Similarity	NPD6904	Approved
0.76	Intermediate Similarity	NPD6083	Phase 2
0.76	Intermediate Similarity	NPD6084	Phase 2
0.7582	Intermediate Similarity	NPD5368	Approved
0.7576	Intermediate Similarity	NPD5695	Phase 3
0.757	Intermediate Similarity	NPD6847	Approved
0.757	Intermediate Similarity	NPD6869	Approved
0.757	Intermediate Similarity	NPD6617	Approved
0.757	Intermediate Similarity	NPD8130	Phase 1
0.7547	Intermediate Similarity	NPD6012	Approved
0.7547	Intermediate Similarity	NPD6013	Approved
0.7547	Intermediate Similarity	NPD6014	Approved
0.7525	Intermediate Similarity	NPD5696	Approved
0.7524	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD5737	Approved
0.75	Intermediate Similarity	NPD6672	Approved
0.75	Intermediate Similarity	NPD8297	Approved
0.7453	Intermediate Similarity	NPD6011	Approved
0.7449	Intermediate Similarity	NPD6050	Approved
0.7429	Intermediate Similarity	NPD6008	Approved
0.74	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5785	Approved
0.7347	Intermediate Similarity	NPD5692	Phase 3
0.7312	Intermediate Similarity	NPD5369	Approved
0.7292	Intermediate Similarity	NPD6098	Approved
0.7292	Intermediate Similarity	NPD7146	Approved
0.7292	Intermediate Similarity	NPD6409	Approved
0.7292	Intermediate Similarity	NPD6684	Approved
0.7292	Intermediate Similarity	NPD5330	Approved
0.7292	Intermediate Similarity	NPD7521	Approved
0.7292	Intermediate Similarity	NPD7334	Approved
0.7273	Intermediate Similarity	NPD5693	Phase 1
0.7273	Intermediate Similarity	NPD5694	Approved
0.7248	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD5363	Approved
0.7156	Intermediate Similarity	NPD6371	Approved
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6274	Approved
0.7115	Intermediate Similarity	NPD5286	Approved
0.7115	Intermediate Similarity	NPD5285	Approved
0.7115	Intermediate Similarity	NPD4696	Approved
0.7113	Intermediate Similarity	NPD5786	Approved
0.7105	Intermediate Similarity	NPD7101	Approved
0.7105	Intermediate Similarity	NPD7100	Approved
0.7087	Intermediate Similarity	NPD4755	Approved
0.7087	Intermediate Similarity	NPD5959	Approved
0.7071	Intermediate Similarity	NPD1695	Approved
0.7059	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6399	Phase 3
0.7021	Intermediate Similarity	NPD4820	Approved
0.7021	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4822	Approved
0.7021	Intermediate Similarity	NPD4821	Approved
0.7021	Intermediate Similarity	NPD4819	Approved
0.7018	Intermediate Similarity	NPD6335	Approved
0.7009	Intermediate Similarity	NPD7604	Phase 2
0.6981	Remote Similarity	NPD5224	Approved
0.6981	Remote Similarity	NPD5225	Approved
0.6981	Remote Similarity	NPD5211	Phase 2
0.6981	Remote Similarity	NPD4633	Approved
0.6981	Remote Similarity	NPD5226	Approved
0.6979	Remote Similarity	NPD5362	Discontinued
0.6961	Remote Similarity	NPD6001	Approved
0.6952	Remote Similarity	NPD4700	Approved
0.693	Remote Similarity	NPD6317	Approved
0.6916	Remote Similarity	NPD5174	Approved
0.6916	Remote Similarity	NPD5175	Approved
0.69	Remote Similarity	NPD4753	Phase 2
0.6897	Remote Similarity	NPD6319	Approved
0.6893	Remote Similarity	NPD5654	Approved
0.6893	Remote Similarity	NPD4629	Approved
0.6893	Remote Similarity	NPD5210	Approved
0.6887	Remote Similarity	NPD5223	Approved
0.6881	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6614	Approved
0.6875	Remote Similarity	NPD4269	Approved
0.6875	Remote Similarity	NPD4270	Approved
0.6875	Remote Similarity	NPD5209	Approved
0.687	Remote Similarity	NPD6313	Approved
0.687	Remote Similarity	NPD6314	Approved
0.6852	Remote Similarity	NPD5141	Approved
0.6838	Remote Similarity	NPD6908	Approved
0.6838	Remote Similarity	NPD6909	Approved
0.6837	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5207	Approved
0.6814	Remote Similarity	NPD4632	Approved
0.6809	Remote Similarity	NPD4268	Approved
0.6809	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4271	Approved
0.6807	Remote Similarity	NPD7492	Approved
0.6804	Remote Similarity	NPD7154	Phase 3
0.68	Remote Similarity	NPD5208	Approved
0.6796	Remote Similarity	NPD5282	Discontinued
0.6783	Remote Similarity	NPD6009	Approved
0.6765	Remote Similarity	NPD5281	Approved
0.6765	Remote Similarity	NPD5284	Approved
0.6752	Remote Similarity	NPD6054	Approved
0.675	Remote Similarity	NPD6616	Approved
0.6726	Remote Similarity	NPD6053	Discontinued
0.6695	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5983	Phase 2
0.6694	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD4252	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4729	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6636	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD4767	Approved
0.6612	Remote Similarity	NPD6336	Discontinued
0.661	Remote Similarity	NPD6059	Approved
0.6606	Remote Similarity	NPD4754	Approved
0.66	Remote Similarity	NPD5690	Phase 2
0.6566	Remote Similarity	NPD4197	Approved
0.6557	Remote Similarity	NPD8293	Discontinued
0.6555	Remote Similarity	NPD6016	Approved
0.6555	Remote Similarity	NPD6015	Approved
0.6552	Remote Similarity	NPD6868	Approved
0.6549	Remote Similarity	NPD4634	Approved
0.6549	Remote Similarity	NPD5251	Approved
0.6549	Remote Similarity	NPD5249	Phase 3
0.6549	Remote Similarity	NPD5248	Approved
0.6549	Remote Similarity	NPD5250	Approved
0.6549	Remote Similarity	NPD5247	Approved
0.6535	Remote Similarity	NPD4250	Approved
0.6535	Remote Similarity	NPD4251	Approved
0.6531	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5222	Approved
0.6509	Remote Similarity	NPD5221	Approved
0.6509	Remote Similarity	NPD4697	Phase 3
0.65	Remote Similarity	NPD1694	Approved
0.65	Remote Similarity	NPD5988	Approved
0.6496	Remote Similarity	NPD7115	Discovery
0.6491	Remote Similarity	NPD5217	Approved
0.6491	Remote Similarity	NPD5215	Approved
0.6491	Remote Similarity	NPD5216	Approved
0.6476	Remote Similarity	NPD7900	Approved
0.6476	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5331	Approved
0.6465	Remote Similarity	NPD5332	Approved
0.6455	Remote Similarity	NPD6052	Approved
0.6449	Remote Similarity	NPD5173	Approved
0.6442	Remote Similarity	NPD6411	Approved
0.6442	Remote Similarity	NPD6079	Approved
0.6436	Remote Similarity	NPD4694	Approved
0.6436	Remote Similarity	NPD4249	Approved
0.6436	Remote Similarity	NPD5279	Phase 3
0.6436	Remote Similarity	NPD5280	Approved
0.6429	Remote Similarity	NPD4790	Discontinued
0.6408	Remote Similarity	NPD5328	Approved
0.6404	Remote Similarity	NPD5169	Approved
0.6404	Remote Similarity	NPD5135	Approved
0.6404	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3666	Approved
0.64	Remote Similarity	NPD3665	Phase 1
0.64	Remote Similarity	NPD3133	Approved
0.6381	Remote Similarity	NPD4202	Approved
0.6373	Remote Similarity	NPD3573	Approved
0.6364	Remote Similarity	NPD4223	Phase 3
0.6364	Remote Similarity	NPD4221	Approved
0.6348	Remote Similarity	NPD5127	Approved
0.6346	Remote Similarity	NPD46	Approved
0.6346	Remote Similarity	NPD6698	Approved
0.6296	Remote Similarity	NPD7902	Approved
0.6283	Remote Similarity	NPD6412	Phase 2
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6051	Approved
0.6238	Remote Similarity	NPD4786	Approved
0.6226	Remote Similarity	NPD5133	Approved
0.6186	Remote Similarity	NPD5167	Approved
0.6168	Remote Similarity	NPD7748	Approved
0.6162	Remote Similarity	NPD4695	Discontinued
0.6154	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7331	Phase 2
0.6154	Remote Similarity	NPD4518	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