NPASS Compound

Structure

NPC87090 OpenBabel07101719132D 26 28 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 -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 -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 -1.8338 0.7983 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 -0.3403 1.5645 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 12 1 0 0 0 0 2 13 1 0 0 0 0 4 15 1 0 0 0 0 5 21 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 9 12 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 13 20 1 0 0 0 0 14 3 1 6 0 0 0 14 19 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 8 1 6 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 10 1 6 0 0 0 17 21 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 6 0 0 0 19 24 1 6 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 22 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.23
Volume:	388.014
LogP:	3.897
LogD:	3.399
LogS:	-4.49
# Rotatable Bonds:	2
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	5.37
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.688
MDCK Permeability:	2.4031200155150145e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.116
Human Intestinal Absorption (HIA):	0.42
20% Bioavailability (F20%):	0.292
30% Bioavailability (F30%):	0.667

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.771
Plasma Protein Binding (PPB):	93.46085357666016%
Volume Distribution (VD):	1.842
Pgp-substrate:	5.796654224395752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.06
CYP1A2-substrate:	0.144
CYP2C19-inhibitor:	0.211
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.224
CYP2C9-substrate:	0.216
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.46

ADMET: Excretion

Clearance (CL):	6.661
Half-life (T1/2):	0.241

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.797
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.834
Maximum Recommended Daily Dose:	0.853
Skin Sensitization:	0.108
Carcinogencity:	0.309
Eye Corrosion:	0.016
Eye Irritation:	0.028
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC87090

Natural Product ID:	NPC87090
*Common Name:**	Jolkinol D
IUPAC Name:	n.a.
Synonyms:	jolkinol D
Standard InCHIKey:	VOSTXBQUXUOFQQ-FTKVYYONSA-N
Standard InCHI:	InChI=1S/C22H32O4/c1-12-7-8-16-17(21(16,5)6)10-13(2)20(25)22(26-15(4)23)11-14(3)19(24)18(22)9-12/h9-10,14,16-19,24H,7-8,11H2,1-6H3/b12-9+,13-10+/t14-,16-,17+,18-,19-,22+/m0/s1
SMILES:	C/C/1=C[C@H]2[C@@H](O)[C@H](C[C@]2(OC(=O)C)C(=O)/C(=C/[C@@H]2[C@H](CC1)C2(C)C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2315610
PubChem CID:	71719801
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]
NPO40127	Euphorbia soongarica	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28590124]
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	13
Others	14

Activity Type	# Activity
Cell Line	7
Individual Protein	6
NON-MOLECULAR	8
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	Ratio IC50	=	0.9	n.a.	PMID[515018]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	99670.0	nM	PMID[515018]
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	=	89870.0	nM	PMID[515018]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	19950.0	nM	PMID[515019]
NPT139	Cell Line	HT-29	Homo sapiens	Ratio IC50	=	0.53	n.a.	PMID[515019]
NPT139	Cell Line	HT-29	Homo sapiens	Ratio IC50	=	0.41	n.a.	PMID[515019]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	25870.0	nM	PMID[515021]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	0.26	n.a.	PMID[515018]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.92	n.a.	PMID[515018]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.79	n.a.	PMID[515018]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10590.0	nM	PMID[515019]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8130.0	nM	PMID[515019]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14330.0	nM	PMID[515019]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14770.0	nM	PMID[515019]
NPT2	Others	Unspecified		Ratio IC50	=	1.03	n.a.	PMID[515019]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	9550.0	nM	PMID[515019]
NPT2	Others	Unspecified		Ratio IC50	=	0.67	n.a.	PMID[515019]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	67260.0	nM	PMID[515019]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	29450.0	nM	PMID[515019]
NPT2	Others	Unspecified		Ratio IC50	=	0.44	n.a.	PMID[515019]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23280.0	nM	PMID[515019]
NPT2	Others	Unspecified		Ratio IC50	=	0.35	n.a.	PMID[515019]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	9.0	%	PMID[515020]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Inhibition	=	14.0	%	PMID[515020]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	66.0	%	PMID[515020]
NPT2	Others	Unspecified		IC50	=	19870.0	nM	PMID[515021]
NPT2	Others	Unspecified		Ratio	=	0.66	n.a.	PMID[515021]

☑ 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 NPC87090 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	229
0.1-0.2	1567
0.2-0.3	6601
0.3-0.4	14041
0.4-0.5	8656
0.5-0.6	6632
0.6-0.7	4189
0.7-0.8	744
0.8-0.85	23
0.85-0.9	1
0.9-0.95	7
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC477356
0.9574	High Similarity	NPC118405
0.9556	High Similarity	NPC477361
0.9556	High Similarity	NPC202824
0.9462	High Similarity	NPC477355
0.9247	High Similarity	NPC477354
0.8925	High Similarity	NPC125180
0.8416	Intermediate Similarity	NPC235889
0.8411	Intermediate Similarity	NPC475305
0.8333	Intermediate Similarity	NPC475401
0.8333	Intermediate Similarity	NPC109414
0.8333	Intermediate Similarity	NPC181265
0.8286	Intermediate Similarity	NPC118860
0.8286	Intermediate Similarity	NPC214797
0.8286	Intermediate Similarity	NPC231589
0.8269	Intermediate Similarity	NPC258543
0.8269	Intermediate Similarity	NPC241927
0.8257	Intermediate Similarity	NPC477092
0.8208	Intermediate Similarity	NPC170487
0.8119	Intermediate Similarity	NPC477950
0.8113	Intermediate Similarity	NPC475495
0.81	Intermediate Similarity	NPC222011
0.8077	Intermediate Similarity	NPC470192
0.8077	Intermediate Similarity	NPC44063
0.8039	Intermediate Similarity	NPC308351
0.8039	Intermediate Similarity	NPC271266
0.8037	Intermediate Similarity	NPC475277
0.8037	Intermediate Similarity	NPC477093
0.8037	Intermediate Similarity	NPC71348
0.8037	Intermediate Similarity	NPC473522
0.8	Intermediate Similarity	NPC69385
0.7982	Intermediate Similarity	NPC270958
0.7963	Intermediate Similarity	NPC202889
0.7944	Intermediate Similarity	NPC43775
0.7925	Intermediate Similarity	NPC304495
0.7925	Intermediate Similarity	NPC2766
0.7921	Intermediate Similarity	NPC470188
0.7889	Intermediate Similarity	NPC276769
0.7885	Intermediate Similarity	NPC310586
0.7885	Intermediate Similarity	NPC137657
0.787	Intermediate Similarity	NPC221144
0.787	Intermediate Similarity	NPC475524
0.787	Intermediate Similarity	NPC100267
0.7864	Intermediate Similarity	NPC78127
0.7864	Intermediate Similarity	NPC105725
0.7864	Intermediate Similarity	NPC471757
0.7864	Intermediate Similarity	NPC15396
0.7857	Intermediate Similarity	NPC221282
0.7838	Intermediate Similarity	NPC118638
0.783	Intermediate Similarity	NPC470269
0.7812	Intermediate Similarity	NPC471738
0.781	Intermediate Similarity	NPC470267
0.7766	Intermediate Similarity	NPC475622
0.7766	Intermediate Similarity	NPC1761
0.7766	Intermediate Similarity	NPC108045
0.7766	Intermediate Similarity	NPC52609
0.7755	Intermediate Similarity	NPC477711
0.7742	Intermediate Similarity	NPC286229
0.7714	Intermediate Similarity	NPC309190
0.7692	Intermediate Similarity	NPC49393
0.7692	Intermediate Similarity	NPC87351
0.7677	Intermediate Similarity	NPC219874
0.767	Intermediate Similarity	NPC476274
0.767	Intermediate Similarity	NPC474720
0.7667	Intermediate Similarity	NPC251435
0.7658	Intermediate Similarity	NPC148458
0.7658	Intermediate Similarity	NPC298278
0.7653	Intermediate Similarity	NPC97032
0.7647	Intermediate Similarity	NPC161493
0.7642	Intermediate Similarity	NPC474101
0.7642	Intermediate Similarity	NPC265127
0.7642	Intermediate Similarity	NPC196528
0.7629	Intermediate Similarity	NPC197333
0.7629	Intermediate Similarity	NPC471739
0.7627	Intermediate Similarity	NPC477363
0.7624	Intermediate Similarity	NPC470974
0.7624	Intermediate Similarity	NPC470978
0.7624	Intermediate Similarity	NPC469599
0.7624	Intermediate Similarity	NPC163228
0.7619	Intermediate Similarity	NPC311612
0.7619	Intermediate Similarity	NPC236390
0.7619	Intermediate Similarity	NPC470839
0.7619	Intermediate Similarity	NPC111323
0.7619	Intermediate Similarity	NPC472755
0.7615	Intermediate Similarity	NPC475937
0.7615	Intermediate Similarity	NPC158523
0.7604	Intermediate Similarity	NPC36350
0.7596	Intermediate Similarity	NPC476270
0.7596	Intermediate Similarity	NPC476240
0.7596	Intermediate Similarity	NPC224720
0.7596	Intermediate Similarity	NPC476223
0.7596	Intermediate Similarity	NPC472753
0.7596	Intermediate Similarity	NPC171759
0.7596	Intermediate Similarity	NPC237190
0.7593	Intermediate Similarity	NPC475941
0.7593	Intermediate Similarity	NPC474901
0.7589	Intermediate Similarity	NPC471854
0.7589	Intermediate Similarity	NPC239273
0.7576	Intermediate Similarity	NPC469368
0.7573	Intermediate Similarity	NPC197386
0.757	Intermediate Similarity	NPC475294
0.7553	Intermediate Similarity	NPC88735
0.7551	Intermediate Similarity	NPC294480
0.7551	Intermediate Similarity	NPC477710
0.7549	Intermediate Similarity	NPC24956
0.7549	Intermediate Similarity	NPC18019
0.7549	Intermediate Similarity	NPC213078
0.7547	Intermediate Similarity	NPC13385
0.7527	Intermediate Similarity	NPC469690
0.7527	Intermediate Similarity	NPC164308
0.7527	Intermediate Similarity	NPC469620
0.7527	Intermediate Similarity	NPC471740
0.7525	Intermediate Similarity	NPC298919
0.7525	Intermediate Similarity	NPC90453
0.7524	Intermediate Similarity	NPC473928
0.7524	Intermediate Similarity	NPC308726
0.7524	Intermediate Similarity	NPC195290
0.7524	Intermediate Similarity	NPC204450
0.7524	Intermediate Similarity	NPC119601
0.7524	Intermediate Similarity	NPC472754
0.7523	Intermediate Similarity	NPC41551
0.7523	Intermediate Similarity	NPC477103
0.7523	Intermediate Similarity	NPC50223
0.7523	Intermediate Similarity	NPC257240
0.7523	Intermediate Similarity	NPC153036
0.7522	Intermediate Similarity	NPC257457
0.7522	Intermediate Similarity	NPC311554
0.75	Intermediate Similarity	NPC475796
0.75	Intermediate Similarity	NPC117604
0.75	Intermediate Similarity	NPC211224
0.75	Intermediate Similarity	NPC90446
0.75	Intermediate Similarity	NPC477370
0.75	Intermediate Similarity	NPC154101
0.75	Intermediate Similarity	NPC144956
0.75	Intermediate Similarity	NPC165287
0.7479	Intermediate Similarity	NPC477366
0.7477	Intermediate Similarity	NPC54737
0.7477	Intermediate Similarity	NPC475661
0.7477	Intermediate Similarity	NPC314244
0.7477	Intermediate Similarity	NPC473488
0.7477	Intermediate Similarity	NPC291643
0.7477	Intermediate Similarity	NPC71889
0.7477	Intermediate Similarity	NPC194100
0.7476	Intermediate Similarity	NPC477949
0.7476	Intermediate Similarity	NPC18509
0.7476	Intermediate Similarity	NPC470834
0.7476	Intermediate Similarity	NPC169205
0.7475	Intermediate Similarity	NPC117405
0.7475	Intermediate Similarity	NPC52198
0.7458	Intermediate Similarity	NPC477362
0.7455	Intermediate Similarity	NPC474871
0.7455	Intermediate Similarity	NPC260786
0.7455	Intermediate Similarity	NPC470281
0.7455	Intermediate Similarity	NPC174471
0.7455	Intermediate Similarity	NPC96739
0.7453	Intermediate Similarity	NPC470310
0.7453	Intermediate Similarity	NPC472747
0.7453	Intermediate Similarity	NPC472750
0.7451	Intermediate Similarity	NPC477438
0.7451	Intermediate Similarity	NPC279313
0.7451	Intermediate Similarity	NPC477437
0.7451	Intermediate Similarity	NPC90121
0.7451	Intermediate Similarity	NPC52044
0.7451	Intermediate Similarity	NPC472469
0.7451	Intermediate Similarity	NPC213698
0.7451	Intermediate Similarity	NPC48803
0.7451	Intermediate Similarity	NPC275960
0.7451	Intermediate Similarity	NPC193645
0.7451	Intermediate Similarity	NPC37408
0.7451	Intermediate Similarity	NPC67584
0.7449	Intermediate Similarity	NPC312215
0.7438	Intermediate Similarity	NPC37968
0.7431	Intermediate Similarity	NPC477102
0.7431	Intermediate Similarity	NPC77089
0.7431	Intermediate Similarity	NPC470257
0.7431	Intermediate Similarity	NPC471400
0.7431	Intermediate Similarity	NPC47951
0.7429	Intermediate Similarity	NPC133907
0.7429	Intermediate Similarity	NPC474327
0.7429	Intermediate Similarity	NPC185141
0.7429	Intermediate Similarity	NPC128733
0.7429	Intermediate Similarity	NPC471767
0.7429	Intermediate Similarity	NPC46998
0.7429	Intermediate Similarity	NPC163372
0.7429	Intermediate Similarity	NPC110443
0.7429	Intermediate Similarity	NPC302537
0.7426	Intermediate Similarity	NPC475488
0.7426	Intermediate Similarity	NPC477435
0.7426	Intermediate Similarity	NPC477436
0.7426	Intermediate Similarity	NPC25750
0.7419	Intermediate Similarity	NPC474056
0.7417	Intermediate Similarity	NPC477365
0.7411	Intermediate Similarity	NPC474872
0.7407	Intermediate Similarity	NPC185
0.7407	Intermediate Similarity	NPC43285
0.7407	Intermediate Similarity	NPC58370
0.7404	Intermediate Similarity	NPC221615
0.7404	Intermediate Similarity	NPC109556
0.7404	Intermediate Similarity	NPC141191
0.74	Intermediate Similarity	NPC123854

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 NPC87090 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	2199
0.2-0.3	3988
0.3-0.4	1870
0.4-0.5	479
0.5-0.6	198
0.6-0.7	146
0.7-0.8	60
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8242	Intermediate Similarity	NPD6435	Approved
0.8173	Intermediate Similarity	NPD6899	Approved
0.8173	Intermediate Similarity	NPD6881	Approved
0.8155	Intermediate Similarity	NPD6675	Approved
0.8155	Intermediate Similarity	NPD7128	Approved
0.8155	Intermediate Similarity	NPD6402	Approved
0.8155	Intermediate Similarity	NPD5739	Approved
0.8113	Intermediate Similarity	NPD6649	Approved
0.8113	Intermediate Similarity	NPD6650	Approved
0.8095	Intermediate Similarity	NPD6372	Approved
0.8095	Intermediate Similarity	NPD6373	Approved
0.8077	Intermediate Similarity	NPD5697	Approved
0.8022	Intermediate Similarity	NPD5368	Approved
0.8019	Intermediate Similarity	NPD7290	Approved
0.8019	Intermediate Similarity	NPD6883	Approved
0.8019	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD6083	Phase 2
0.8	Intermediate Similarity	NPD6084	Phase 2
0.8	Intermediate Similarity	NPD7320	Approved
0.7944	Intermediate Similarity	NPD8130	Phase 1
0.7944	Intermediate Similarity	NPD6869	Approved
0.7944	Intermediate Similarity	NPD6847	Approved
0.7944	Intermediate Similarity	NPD6617	Approved
0.7925	Intermediate Similarity	NPD6014	Approved
0.7925	Intermediate Similarity	NPD6013	Approved
0.7925	Intermediate Similarity	NPD6012	Approved
0.7905	Intermediate Similarity	NPD5701	Approved
0.787	Intermediate Similarity	NPD6882	Approved
0.787	Intermediate Similarity	NPD8297	Approved
0.783	Intermediate Similarity	NPD6011	Approved
0.78	Intermediate Similarity	NPD5695	Phase 3
0.7755	Intermediate Similarity	NPD5785	Approved
0.7745	Intermediate Similarity	NPD5696	Approved
0.7742	Intermediate Similarity	NPD5369	Approved
0.7615	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD5363	Approved
0.7526	Intermediate Similarity	NPD5786	Approved
0.7523	Intermediate Similarity	NPD6371	Approved
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.7476	Intermediate Similarity	NPD4755	Approved
0.7456	Intermediate Similarity	NPD7100	Approved
0.7456	Intermediate Similarity	NPD7101	Approved
0.7451	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4821	Approved
0.7447	Intermediate Similarity	NPD4822	Approved
0.7447	Intermediate Similarity	NPD4820	Approved
0.7447	Intermediate Similarity	NPD4819	Approved
0.7396	Intermediate Similarity	NPD5362	Discontinued
0.7368	Intermediate Similarity	NPD6335	Approved
0.7358	Intermediate Similarity	NPD5224	Approved
0.7358	Intermediate Similarity	NPD5211	Phase 2
0.7358	Intermediate Similarity	NPD5225	Approved
0.7358	Intermediate Similarity	NPD5226	Approved
0.7358	Intermediate Similarity	NPD4633	Approved
0.735	Intermediate Similarity	NPD7604	Phase 2
0.7333	Intermediate Similarity	NPD4700	Approved
0.73	Intermediate Similarity	NPD4753	Phase 2
0.73	Intermediate Similarity	NPD6673	Approved
0.73	Intermediate Similarity	NPD6904	Approved
0.73	Intermediate Similarity	NPD6080	Approved
0.7292	Intermediate Similarity	NPD4269	Approved
0.7292	Intermediate Similarity	NPD4270	Approved
0.729	Intermediate Similarity	NPD5174	Approved
0.729	Intermediate Similarity	NPD5175	Approved
0.7282	Intermediate Similarity	NPD5210	Approved
0.7282	Intermediate Similarity	NPD4629	Approved
0.7281	Intermediate Similarity	NPD6317	Approved
0.7264	Intermediate Similarity	NPD5223	Approved
0.7255	Intermediate Similarity	NPD6399	Phase 3
0.7241	Intermediate Similarity	NPD6319	Approved
0.7234	Intermediate Similarity	NPD4271	Approved
0.7234	Intermediate Similarity	NPD4268	Approved
0.7234	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5141	Approved
0.7217	Intermediate Similarity	NPD6314	Approved
0.7217	Intermediate Similarity	NPD6313	Approved
0.7216	Intermediate Similarity	NPD7154	Phase 3
0.72	Intermediate Similarity	NPD6672	Approved
0.72	Intermediate Similarity	NPD5737	Approved
0.7179	Intermediate Similarity	NPD6908	Approved
0.7179	Intermediate Similarity	NPD6909	Approved
0.7168	Intermediate Similarity	NPD4632	Approved
0.7157	Intermediate Similarity	NPD6050	Approved
0.7156	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.713	Intermediate Similarity	NPD6009	Approved
0.7115	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6054	Approved
0.7091	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4252	Approved
0.7083	Intermediate Similarity	NPD6616	Approved
0.708	Intermediate Similarity	NPD6053	Discontinued
0.7071	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5692	Phase 3
0.7034	Intermediate Similarity	NPD5983	Phase 2
0.7034	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5128	Approved
0.7027	Intermediate Similarity	NPD4729	Approved
0.7027	Intermediate Similarity	NPD4730	Approved
0.7025	Intermediate Similarity	NPD7078	Approved
0.7019	Intermediate Similarity	NPD5282	Discontinued
0.7	Intermediate Similarity	NPD6098	Approved
0.7	Intermediate Similarity	NPD4768	Approved
0.7	Intermediate Similarity	NPD4767	Approved
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.699	Remote Similarity	NPD5693	Phase 1
0.699	Remote Similarity	NPD5281	Approved
0.699	Remote Similarity	NPD5694	Approved
0.699	Remote Similarity	NPD5284	Approved
0.6975	Remote Similarity	NPD6370	Approved
0.6972	Remote Similarity	NPD4754	Approved
0.6967	Remote Similarity	NPD7736	Approved
0.6949	Remote Similarity	NPD6059	Approved
0.6942	Remote Similarity	NPD6336	Discontinued
0.6931	Remote Similarity	NPD4250	Approved
0.6931	Remote Similarity	NPD4251	Approved
0.6903	Remote Similarity	NPD5249	Phase 3
0.6903	Remote Similarity	NPD5250	Approved
0.6903	Remote Similarity	NPD5251	Approved
0.6903	Remote Similarity	NPD4634	Approved
0.6903	Remote Similarity	NPD5248	Approved
0.6903	Remote Similarity	NPD5247	Approved
0.69	Remote Similarity	NPD5329	Approved
0.6897	Remote Similarity	NPD6868	Approved
0.6891	Remote Similarity	NPD6015	Approved
0.6891	Remote Similarity	NPD6016	Approved
0.6887	Remote Similarity	NPD5222	Approved
0.6887	Remote Similarity	NPD4697	Phase 3
0.6887	Remote Similarity	NPD5221	Approved
0.6887	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8293	Discontinued
0.6869	Remote Similarity	NPD5332	Approved
0.6869	Remote Similarity	NPD5331	Approved
0.6863	Remote Similarity	NPD6903	Approved
0.6863	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5215	Approved
0.6842	Remote Similarity	NPD5216	Approved
0.6842	Remote Similarity	NPD5217	Approved
0.6838	Remote Similarity	NPD7115	Discovery
0.6837	Remote Similarity	NPD4790	Discontinued
0.6833	Remote Similarity	NPD5988	Approved
0.6832	Remote Similarity	NPD5279	Phase 3
0.6832	Remote Similarity	NPD5690	Phase 2
0.6832	Remote Similarity	NPD4249	Approved
0.6827	Remote Similarity	NPD6079	Approved
0.6827	Remote Similarity	NPD6411	Approved
0.6822	Remote Similarity	NPD5959	Approved
0.6822	Remote Similarity	NPD5173	Approved
0.68	Remote Similarity	NPD3666	Approved
0.68	Remote Similarity	NPD3665	Phase 1
0.68	Remote Similarity	NPD3133	Approved
0.68	Remote Similarity	NPD4197	Approved
0.6796	Remote Similarity	NPD5328	Approved
0.6796	Remote Similarity	NPD1695	Approved
0.6762	Remote Similarity	NPD4202	Approved
0.6754	Remote Similarity	NPD5135	Approved
0.6754	Remote Similarity	NPD5169	Approved
0.6754	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6698	Approved
0.6731	Remote Similarity	NPD46	Approved
0.6698	Remote Similarity	NPD6001	Approved
0.6696	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6637	Remote Similarity	NPD6614	Approved
0.6637	Remote Similarity	NPD6412	Phase 2
0.6636	Remote Similarity	NPD5654	Approved
0.6635	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6101	Approved
0.6634	Remote Similarity	NPD4786	Approved
0.66	Remote Similarity	NPD5209	Approved
0.66	Remote Similarity	NPD4221	Approved
0.66	Remote Similarity	NPD4223	Phase 3
0.6571	Remote Similarity	NPD5207	Approved
0.6569	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5208	Approved
0.6535	Remote Similarity	NPD4788	Approved
0.6525	Remote Similarity	NPD5167	Approved
0.6514	Remote Similarity	NPD7902	Approved
0.6509	Remote Similarity	NPD7983	Approved
0.6509	Remote Similarity	NPD7637	Suspended
0.6505	Remote Similarity	NPD3618	Phase 1
0.6455	Remote Similarity	NPD7638	Approved
0.6449	Remote Similarity	NPD5778	Approved
0.6449	Remote Similarity	NPD5133	Approved
0.6449	Remote Similarity	NPD5779	Approved
0.6436	Remote Similarity	NPD3667	Approved
0.6429	Remote Similarity	NPD6033	Approved
0.6413	Remote Similarity	NPD7331	Phase 2
0.6408	Remote Similarity	NPD1696	Phase 3
0.64	Remote Similarity	NPD4695	Discontinued

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