NPASS Compound

Structure

NPC78473 OpenBabel07101719252D 34 37 0 0 1 0 0 0 0 0999 V2000 -3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 3.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 3.0032 0.0000 C 0 0 0 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 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 -2.1871 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 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 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -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 1 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 2 0 0 0 0 2 20 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 8 34 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 26 1 0 0 0 0 14 15 1 0 0 0 0 14 22 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 29 1 0 0 0 0 17 31 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 19 32 2 0 0 0 0 21 3 1 6 0 0 0 21 22 1 0 0 0 0 22 29 1 6 0 0 0 23 24 1 0 0 0 0 23 31 1 6 0 0 0 24 28 1 0 0 0 0 25 27 1 0 0 0 0 25 34 1 6 0 0 0 26 28 1 0 0 0 0 26 33 1 6 0 0 0 27 30 1 1 0 0 0 27 31 1 0 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 31 19 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	468.36
Volume:	526.331
LogP:	5.686
LogD:	4.85
LogS:	-5.385
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.262
Synthetic Accessibility Score:	5.332
Fsp3:	0.774
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.856
MDCK Permeability:	1.7209747966262512e-05
Pgp-inhibitor:	0.828
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.945

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.982
Plasma Protein Binding (PPB):	78.40738677978516%
Volume Distribution (VD):	1.79
Pgp-substrate:	11.308211326599121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.487
CYP2C19-inhibitor:	0.045
CYP2C19-substrate:	0.88
CYP2C9-inhibitor:	0.196
CYP2C9-substrate:	0.091
CYP2D6-inhibitor:	0.781
CYP2D6-substrate:	0.639
CYP3A4-inhibitor:	0.958
CYP3A4-substrate:	0.739

ADMET: Excretion

Clearance (CL):	7.87
Half-life (T1/2):	0.058

ADMET: Toxicity

hERG Blockers:	0.487
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.905
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.939
Carcinogencity:	0.186
Eye Corrosion:	0.136
Eye Irritation:	0.081
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC78473

Natural Product ID:	NPC78473
*Common Name:**	(23E)-3Beta-Hydroxy-7Beta-Methoxycucurbita-5,23,25-Trien-19-Al
IUPAC Name:	(3S,7S,8S,9R,10R,13R,14S,17R)-3-hydroxy-7-methoxy-4,4,13,14-tetramethyl-17-[(2R,4E)-6-methylhepta-4,6-dien-2-yl]-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-9-carbaldehyde
Synonyms:
Standard InCHIKey:	WZZAXQGYJDXEDP-UJBPRPQUSA-N
Standard InCHI:	InChI=1S/C31H48O3/c1-20(2)10-9-11-21(3)22-14-15-30(7)27-25(34-8)18-24-23(12-13-26(33)28(24,4)5)31(27,19-32)17-16-29(22,30)6/h9-10,18-19,21-23,25-27,33H,1,11-17H2,2-8H3/b10-9+/t21-,22-,23-,25+,26+,27+,29-,30+,31-/m1/s1
SMILES:	CO[C@H]1C=C2[C@H]([C@]3([C@@H]1[C@]1(C)CC[C@@H]([C@]1(CC3)C)[C@@H](C/C=C/C(=C)C)C)C=O)CC[C@@H](C2(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL252511
PubChem CID:	11167279
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

*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
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17685651]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[18637688]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24836069]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28621938]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Vines	n.a.	n.a.	PMID[32357011]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8182	Momordica charantia	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8182	Momordica charantia	Species	Cucurbitaceae	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
Others	6

Activity Type	# Activity
Cell Line	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[528907]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[528907]
NPT2	Others	Unspecified		Inhibition	=	22.5	%	PMID[528907]
NPT2	Others	Unspecified		Inhibition	=	75.4	%	PMID[528907]
NPT2	Others	Unspecified		Inhibition	=	95.3	%	PMID[528907]
NPT2	Others	Unspecified		Ratio	=	1.6	n.a.	PMID[528907]

☑ 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 NPC78473 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	178
0.1-0.2	975
0.2-0.3	3645
0.3-0.4	9798
0.4-0.5	13050
0.5-0.6	7516
0.6-0.7	5428
0.7-0.8	1945
0.8-0.85	145
0.85-0.9	13
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC126815
0.9457	High Similarity	NPC291634
0.913	High Similarity	NPC292793
0.8602	High Similarity	NPC48010
0.8571	High Similarity	NPC94755
0.8557	High Similarity	NPC103051
0.8556	High Similarity	NPC221758
0.8556	High Similarity	NPC59453
0.8478	Intermediate Similarity	NPC475740
0.8478	Intermediate Similarity	NPC58063
0.8462	Intermediate Similarity	NPC274448
0.8462	Intermediate Similarity	NPC157257
0.8462	Intermediate Similarity	NPC471224
0.8462	Intermediate Similarity	NPC470048
0.8444	Intermediate Similarity	NPC470046
0.8444	Intermediate Similarity	NPC470047
0.8427	Intermediate Similarity	NPC474752
0.8427	Intermediate Similarity	NPC7505
0.8427	Intermediate Similarity	NPC474683
0.8427	Intermediate Similarity	NPC474731
0.8427	Intermediate Similarity	NPC82986
0.8427	Intermediate Similarity	NPC474759
0.8404	Intermediate Similarity	NPC69622
0.84	Intermediate Similarity	NPC36688
0.837	Intermediate Similarity	NPC145879
0.837	Intermediate Similarity	NPC51014
0.837	Intermediate Similarity	NPC474732
0.837	Intermediate Similarity	NPC474778
0.837	Intermediate Similarity	NPC474733
0.837	Intermediate Similarity	NPC31564
0.837	Intermediate Similarity	NPC155011
0.8367	Intermediate Similarity	NPC108368
0.8367	Intermediate Similarity	NPC57079
0.8352	Intermediate Similarity	NPC470077
0.8351	Intermediate Similarity	NPC160056
0.8333	Intermediate Similarity	NPC470049
0.8333	Intermediate Similarity	NPC474690
0.8333	Intermediate Similarity	NPC469406
0.8333	Intermediate Similarity	NPC151519
0.8333	Intermediate Similarity	NPC209662
0.8316	Intermediate Similarity	NPC475806
0.83	Intermediate Similarity	NPC32577
0.83	Intermediate Similarity	NPC155332
0.83	Intermediate Similarity	NPC185530
0.83	Intermediate Similarity	NPC114540
0.8298	Intermediate Similarity	NPC2983
0.8298	Intermediate Similarity	NPC474245
0.8298	Intermediate Similarity	NPC77168
0.8298	Intermediate Similarity	NPC84271
0.8298	Intermediate Similarity	NPC102414
0.8298	Intermediate Similarity	NPC32830
0.8298	Intermediate Similarity	NPC473999
0.8298	Intermediate Similarity	NPC309603
0.8298	Intermediate Similarity	NPC31985
0.8298	Intermediate Similarity	NPC1015
0.828	Intermediate Similarity	NPC142361
0.828	Intermediate Similarity	NPC474684
0.828	Intermediate Similarity	NPC136548
0.828	Intermediate Similarity	NPC149224
0.828	Intermediate Similarity	NPC141292
0.8261	Intermediate Similarity	NPC474083
0.8261	Intermediate Similarity	NPC474218
0.8261	Intermediate Similarity	NPC266511
0.8252	Intermediate Similarity	NPC177064
0.8247	Intermediate Similarity	NPC271195
0.8229	Intermediate Similarity	NPC472942
0.8229	Intermediate Similarity	NPC470224
0.8229	Intermediate Similarity	NPC134826
0.8229	Intermediate Similarity	NPC250575
0.8229	Intermediate Similarity	NPC474736
0.8218	Intermediate Similarity	NPC26478
0.8211	Intermediate Similarity	NPC320026
0.8211	Intermediate Similarity	NPC191684
0.8191	Intermediate Similarity	NPC328313
0.8191	Intermediate Similarity	NPC97884
0.8191	Intermediate Similarity	NPC310752
0.8191	Intermediate Similarity	NPC53911
0.8191	Intermediate Similarity	NPC292491
0.8191	Intermediate Similarity	NPC24816
0.8191	Intermediate Similarity	NPC472220
0.8191	Intermediate Similarity	NPC471722
0.819	Intermediate Similarity	NPC474315
0.8182	Intermediate Similarity	NPC48647
0.8172	Intermediate Similarity	NPC222613
0.8172	Intermediate Similarity	NPC470050
0.8172	Intermediate Similarity	NPC470051
0.8172	Intermediate Similarity	NPC118648
0.8172	Intermediate Similarity	NPC473168
0.8172	Intermediate Similarity	NPC469994
0.8172	Intermediate Similarity	NPC475022
0.8152	Intermediate Similarity	NPC82902
0.8152	Intermediate Similarity	NPC214043
0.8152	Intermediate Similarity	NPC85774
0.8144	Intermediate Similarity	NPC299100
0.8144	Intermediate Similarity	NPC471720
0.8144	Intermediate Similarity	NPC49670
0.8144	Intermediate Similarity	NPC8993
0.8137	Intermediate Similarity	NPC472868
0.8132	Intermediate Similarity	NPC49964
0.8125	Intermediate Similarity	NPC272746
0.8125	Intermediate Similarity	NPC473998
0.8111	Intermediate Similarity	NPC234193
0.8105	Intermediate Similarity	NPC475921
0.8105	Intermediate Similarity	NPC474704
0.8105	Intermediate Similarity	NPC119416
0.8105	Intermediate Similarity	NPC268406
0.8105	Intermediate Similarity	NPC76879
0.8105	Intermediate Similarity	NPC128496
0.8105	Intermediate Similarity	NPC186688
0.8105	Intermediate Similarity	NPC26959
0.81	Intermediate Similarity	NPC201406
0.81	Intermediate Similarity	NPC266955
0.809	Intermediate Similarity	NPC18603
0.809	Intermediate Similarity	NPC307965
0.809	Intermediate Similarity	NPC76931
0.8085	Intermediate Similarity	NPC317590
0.8085	Intermediate Similarity	NPC475772
0.8085	Intermediate Similarity	NPC159046
0.8085	Intermediate Similarity	NPC233836
0.8085	Intermediate Similarity	NPC187376
0.8081	Intermediate Similarity	NPC474938
0.8081	Intermediate Similarity	NPC474785
0.8081	Intermediate Similarity	NPC253826
0.8081	Intermediate Similarity	NPC107243
0.8081	Intermediate Similarity	NPC57416
0.8065	Intermediate Similarity	NPC470574
0.8065	Intermediate Similarity	NPC469948
0.8061	Intermediate Similarity	NPC162001
0.8061	Intermediate Similarity	NPC259286
0.8061	Intermediate Similarity	NPC222845
0.8061	Intermediate Similarity	NPC469599
0.8061	Intermediate Similarity	NPC180950
0.8061	Intermediate Similarity	NPC45324
0.8061	Intermediate Similarity	NPC127063
0.8058	Intermediate Similarity	NPC266570
0.8058	Intermediate Similarity	NPC60681
0.8058	Intermediate Similarity	NPC478052
0.8058	Intermediate Similarity	NPC189863
0.8043	Intermediate Similarity	NPC470558
0.8043	Intermediate Similarity	NPC476082
0.8043	Intermediate Similarity	NPC278648
0.8041	Intermediate Similarity	NPC107674
0.8041	Intermediate Similarity	NPC170220
0.8041	Intermediate Similarity	NPC69454
0.8041	Intermediate Similarity	NPC141497
0.8041	Intermediate Similarity	NPC470375
0.8041	Intermediate Similarity	NPC470376
0.8039	Intermediate Similarity	NPC476237
0.8039	Intermediate Similarity	NPC247957
0.8039	Intermediate Similarity	NPC249187
0.8039	Intermediate Similarity	NPC176883
0.8037	Intermediate Similarity	NPC73050
0.8022	Intermediate Similarity	NPC47761
0.8022	Intermediate Similarity	NPC264245
0.8021	Intermediate Similarity	NPC295668
0.8021	Intermediate Similarity	NPC183283
0.8021	Intermediate Similarity	NPC471896
0.802	Intermediate Similarity	NPC473174
0.802	Intermediate Similarity	NPC115899
0.8	Intermediate Similarity	NPC234617
0.8	Intermediate Similarity	NPC474113
0.8	Intermediate Similarity	NPC28862
0.8	Intermediate Similarity	NPC284828
0.8	Intermediate Similarity	NPC47982
0.8	Intermediate Similarity	NPC109546
0.8	Intermediate Similarity	NPC81306
0.8	Intermediate Similarity	NPC84694
0.8	Intermediate Similarity	NPC124703
0.8	Intermediate Similarity	NPC143182
0.8	Intermediate Similarity	NPC191565
0.8	Intermediate Similarity	NPC206060
0.8	Intermediate Similarity	NPC472483
0.8	Intermediate Similarity	NPC472216
0.8	Intermediate Similarity	NPC173905
0.8	Intermediate Similarity	NPC328539
0.8	Intermediate Similarity	NPC98868
0.8	Intermediate Similarity	NPC477813
0.8	Intermediate Similarity	NPC186810
0.8	Intermediate Similarity	NPC5475
0.8	Intermediate Similarity	NPC193360
0.8	Intermediate Similarity	NPC242864
0.7982	Intermediate Similarity	NPC474518
0.7981	Intermediate Similarity	NPC329048
0.7981	Intermediate Similarity	NPC330011
0.7981	Intermediate Similarity	NPC144459
0.798	Intermediate Similarity	NPC192428
0.798	Intermediate Similarity	NPC301534
0.798	Intermediate Similarity	NPC250757
0.798	Intermediate Similarity	NPC249954
0.7979	Intermediate Similarity	NPC95594
0.7979	Intermediate Similarity	NPC82979
0.7979	Intermediate Similarity	NPC470955
0.7979	Intermediate Similarity	NPC55309
0.7979	Intermediate Similarity	NPC72133
0.7979	Intermediate Similarity	NPC89077
0.7979	Intermediate Similarity	NPC28252
0.7979	Intermediate Similarity	NPC477579
0.7979	Intermediate Similarity	NPC264127
0.7979	Intermediate Similarity	NPC20688
0.7979	Intermediate Similarity	NPC235341

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 NPC78473 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1142
0.2-0.3	3444
0.3-0.4	2903
0.4-0.5	986
0.5-0.6	204
0.6-0.7	183
0.7-0.8	130
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8556	High Similarity	NPD4786	Approved
0.8333	Intermediate Similarity	NPD3667	Approved
0.8172	Intermediate Similarity	NPD3618	Phase 1
0.8125	Intermediate Similarity	NPD6079	Approved
0.8105	Intermediate Similarity	NPD5328	Approved
0.8041	Intermediate Similarity	NPD6399	Phase 3
0.798	Intermediate Similarity	NPD4697	Phase 3
0.7789	Intermediate Similarity	NPD5279	Phase 3
0.7766	Intermediate Similarity	NPD3665	Phase 1
0.7766	Intermediate Similarity	NPD3133	Approved
0.7766	Intermediate Similarity	NPD3666	Approved
0.7753	Intermediate Similarity	NPD7339	Approved
0.7753	Intermediate Similarity	NPD6942	Approved
0.7677	Intermediate Similarity	NPD4202	Approved
0.7658	Intermediate Similarity	NPD7115	Discovery
0.7647	Intermediate Similarity	NPD7638	Approved
0.7624	Intermediate Similarity	NPD5221	Approved
0.7624	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5222	Approved
0.7579	Intermediate Similarity	NPD3668	Phase 3
0.7573	Intermediate Similarity	NPD7640	Approved
0.7573	Intermediate Similarity	NPD7639	Approved
0.7549	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6926	Approved
0.7444	Intermediate Similarity	NPD6924	Approved
0.7429	Intermediate Similarity	NPD5211	Phase 2
0.7416	Intermediate Similarity	NPD7150	Approved
0.7416	Intermediate Similarity	NPD7152	Approved
0.7416	Intermediate Similarity	NPD7151	Approved
0.7404	Intermediate Similarity	NPD5286	Approved
0.7404	Intermediate Similarity	NPD4696	Approved
0.7404	Intermediate Similarity	NPD5285	Approved
0.7379	Intermediate Similarity	NPD4755	Approved
0.7374	Intermediate Similarity	NPD4753	Phase 2
0.7368	Intermediate Similarity	NPD4221	Approved
0.7368	Intermediate Similarity	NPD4223	Phase 3
0.7353	Intermediate Similarity	NPD4629	Approved
0.7353	Intermediate Similarity	NPD5210	Approved
0.734	Intermediate Similarity	NPD7525	Registered
0.7333	Intermediate Similarity	NPD5223	Approved
0.732	Intermediate Similarity	NPD5329	Approved
0.7303	Intermediate Similarity	NPD7143	Approved
0.7303	Intermediate Similarity	NPD7144	Approved
0.729	Intermediate Similarity	NPD5141	Approved
0.7283	Intermediate Similarity	NPD6933	Approved
0.7264	Intermediate Similarity	NPD5224	Approved
0.7264	Intermediate Similarity	NPD5226	Approved
0.7264	Intermediate Similarity	NPD4633	Approved
0.7264	Intermediate Similarity	NPD5225	Approved
0.7248	Intermediate Similarity	NPD6881	Approved
0.7248	Intermediate Similarity	NPD6899	Approved
0.7245	Intermediate Similarity	NPD7334	Approved
0.7245	Intermediate Similarity	NPD6684	Approved
0.7245	Intermediate Similarity	NPD5280	Approved
0.7245	Intermediate Similarity	NPD4694	Approved
0.7245	Intermediate Similarity	NPD7146	Approved
0.7245	Intermediate Similarity	NPD6409	Approved
0.7245	Intermediate Similarity	NPD5330	Approved
0.7245	Intermediate Similarity	NPD7521	Approved
0.7238	Intermediate Similarity	NPD4700	Approved
0.7234	Intermediate Similarity	NPD6929	Approved
0.7228	Intermediate Similarity	NPD8034	Phase 2
0.7228	Intermediate Similarity	NPD5281	Approved
0.7228	Intermediate Similarity	NPD5284	Approved
0.7228	Intermediate Similarity	NPD7515	Phase 2
0.7228	Intermediate Similarity	NPD7637	Suspended
0.7228	Intermediate Similarity	NPD8035	Phase 2
0.7222	Intermediate Similarity	NPD6402	Approved
0.7222	Intermediate Similarity	NPD5739	Approved
0.7222	Intermediate Similarity	NPD7128	Approved
0.7222	Intermediate Similarity	NPD6675	Approved
0.7216	Intermediate Similarity	NPD4197	Approved
0.7212	Intermediate Similarity	NPD6083	Phase 2
0.7212	Intermediate Similarity	NPD6084	Phase 2
0.7207	Intermediate Similarity	NPD6649	Approved
0.7207	Intermediate Similarity	NPD6650	Approved
0.7196	Intermediate Similarity	NPD5175	Approved
0.7196	Intermediate Similarity	NPD5174	Approved
0.7191	Intermediate Similarity	NPD6922	Approved
0.7191	Intermediate Similarity	NPD6923	Approved
0.7182	Intermediate Similarity	NPD6372	Approved
0.7182	Intermediate Similarity	NPD6373	Approved
0.7172	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6931	Approved
0.7158	Intermediate Similarity	NPD6930	Phase 2
0.7158	Intermediate Similarity	NPD7514	Phase 3
0.7156	Intermediate Similarity	NPD5697	Approved
0.7128	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7145	Approved
0.7117	Intermediate Similarity	NPD7290	Approved
0.7117	Intermediate Similarity	NPD6883	Approved
0.7117	Intermediate Similarity	NPD7102	Approved
0.7113	Intermediate Similarity	NPD6695	Phase 3
0.7113	Intermediate Similarity	NPD4788	Approved
0.71	Intermediate Similarity	NPD6903	Approved
0.71	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5737	Approved
0.71	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7320	Approved
0.7091	Intermediate Similarity	NPD6011	Approved
0.7087	Intermediate Similarity	NPD7748	Approved
0.7083	Intermediate Similarity	NPD6902	Approved
0.7071	Intermediate Similarity	NPD4688	Approved
0.7071	Intermediate Similarity	NPD4693	Phase 3
0.7071	Intermediate Similarity	NPD4689	Approved
0.7071	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD5690	Phase 2
0.7071	Intermediate Similarity	NPD4623	Approved
0.7071	Intermediate Similarity	NPD4690	Approved
0.7071	Intermediate Similarity	NPD5205	Approved
0.7071	Intermediate Similarity	NPD4138	Approved
0.7071	Intermediate Similarity	NPD4519	Discontinued
0.7065	Intermediate Similarity	NPD4784	Approved
0.7065	Intermediate Similarity	NPD4785	Approved
0.7059	Intermediate Similarity	NPD6411	Approved
0.7054	Intermediate Similarity	NPD6869	Approved
0.7054	Intermediate Similarity	NPD6617	Approved
0.7054	Intermediate Similarity	NPD6847	Approved
0.7054	Intermediate Similarity	NPD8130	Phase 1
0.7053	Intermediate Similarity	NPD7645	Phase 2
0.7048	Intermediate Similarity	NPD7902	Approved
0.7041	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4754	Approved
0.703	Intermediate Similarity	NPD6051	Approved
0.7027	Intermediate Similarity	NPD6013	Approved
0.7027	Intermediate Similarity	NPD6012	Approved
0.7027	Intermediate Similarity	NPD6014	Approved
0.7021	Intermediate Similarity	NPD5776	Phase 2
0.7021	Intermediate Similarity	NPD6932	Approved
0.7021	Intermediate Similarity	NPD6925	Approved
0.7	Intermediate Similarity	NPD5701	Approved
0.6991	Remote Similarity	NPD8297	Approved
0.6991	Remote Similarity	NPD6882	Approved
0.6989	Remote Similarity	NPD8264	Approved
0.6981	Remote Similarity	NPD5696	Approved
0.6981	Remote Similarity	NPD4225	Approved
0.6979	Remote Similarity	NPD7332	Phase 2
0.697	Remote Similarity	NPD1694	Approved
0.6961	Remote Similarity	NPD5207	Approved
0.6961	Remote Similarity	NPD5785	Approved
0.6947	Remote Similarity	NPD3617	Approved
0.6947	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7632	Discontinued
0.6939	Remote Similarity	NPD5362	Discontinued
0.6937	Remote Similarity	NPD4730	Approved
0.6937	Remote Similarity	NPD5168	Approved
0.6937	Remote Similarity	NPD4729	Approved
0.6931	Remote Similarity	NPD4518	Approved
0.6909	Remote Similarity	NPD4767	Approved
0.6909	Remote Similarity	NPD4768	Approved
0.6903	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6098	Approved
0.6893	Remote Similarity	NPD5693	Phase 1
0.6882	Remote Similarity	NPD4687	Approved
0.6882	Remote Similarity	NPD4058	Approved
0.6882	Remote Similarity	NPD5733	Approved
0.6875	Remote Similarity	NPD4195	Approved
0.6863	Remote Similarity	NPD6101	Approved
0.6863	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7507	Approved
0.6857	Remote Similarity	NPD5695	Phase 3
0.6857	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4243	Approved
0.6848	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7750	Discontinued
0.6832	Remote Similarity	NPD7524	Approved
0.6827	Remote Similarity	NPD5778	Approved
0.6827	Remote Similarity	NPD5779	Approved
0.6814	Remote Similarity	NPD4634	Approved
0.6814	Remote Similarity	NPD5247	Approved
0.6814	Remote Similarity	NPD5135	Approved
0.6814	Remote Similarity	NPD5248	Approved
0.6814	Remote Similarity	NPD5249	Phase 3
0.6814	Remote Similarity	NPD5250	Approved
0.6814	Remote Similarity	NPD5169	Approved
0.6814	Remote Similarity	NPD5251	Approved
0.6814	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6868	Approved
0.6809	Remote Similarity	NPD8039	Approved
0.6804	Remote Similarity	NPD4695	Discontinued
0.6804	Remote Similarity	NPD7509	Discontinued
0.68	Remote Similarity	NPD6893	Approved
0.6796	Remote Similarity	NPD4096	Approved
0.6786	Remote Similarity	NPD5128	Approved
0.6783	Remote Similarity	NPD4632	Approved
0.6762	Remote Similarity	NPD7900	Approved
0.6762	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6404	Discontinued
0.6757	Remote Similarity	NPD6008	Approved
0.6754	Remote Similarity	NPD5217	Approved
0.6754	Remote Similarity	NPD5216	Approved
0.6754	Remote Similarity	NPD5215	Approved
0.6754	Remote Similarity	NPD5127	Approved
0.6739	Remote Similarity	NPD4747	Approved
0.6737	Remote Similarity	NPD6117	Approved
0.6735	Remote Similarity	NPD4139	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