NPASS Compound

Structure

CID186191 OpenBabel06191715562D 31 34 0 0 1 0 0 0 0 0999 V2000 -1.4614 5.8901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0016 5.2038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6689 4.1115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2727 3.2223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3763 -2.9580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5319 0.5234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2092 3.4252 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8129 2.5360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6886 -1.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6871 0.9735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6877 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2190 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3754 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6868 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 1.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0334 5.1023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6372 4.2130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 2.4345 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3760 -1.9481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 1.4610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5324 -1.4611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6880 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8441 -0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2193 -1.4606 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5321 -0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9739 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 5.0854 -1.9603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 26 2 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 25 2 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 21 4 1 1 0 0 0 21 23 1 0 0 0 0 22 5 1 1 0 0 0 22 24 1 0 0 0 0 22 27 1 0 0 0 0 23 29 1 6 0 0 0 24 28 1 6 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 6 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.37
Volume:	494.091
LogP:	7.367
LogD:	6.037
LogS:	-6.809
# Rotatable Bonds:	5
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.442
Synthetic Accessibility Score:	4.91
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.759
MDCK Permeability:	1.256355426448863e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.182

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	94.36206817626953%
Volume Distribution (VD):	1.758
Pgp-substrate:	1.9755353927612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.531
CYP2C19-inhibitor:	0.13
CYP2C19-substrate:	0.97
CYP2C9-inhibitor:	0.292
CYP2C9-substrate:	0.275
CYP2D6-inhibitor:	0.258
CYP2D6-substrate:	0.699
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	5.835
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.944
Human Hepatotoxicity (H-HT):	0.447
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.465
Skin Sensitization:	0.965
Carcinogencity:	0.531
Eye Corrosion:	0.446
Eye Irritation:	0.188
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC186191

Natural Product ID:	NPC186191
*Common Name:**	4Alpha,14Alpha-Dimethyl-5Alpha-Ergostan-7,9(11),24(28)-Triene-3Beta-Ol
IUPAC Name:	(3S,4S,5S,10S,13R,14R,17R)-4,10,13,14-tetramethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-1,2,3,4,5,6,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	MQQBTSOGCQNWAX-VSADUBDNSA-N
Standard InCHI:	InChI=1S/C30H48O/c1-19(2)20(3)9-10-21(4)23-13-17-30(8)26-12-11-24-22(5)27(31)15-16-28(24,6)25(26)14-18-29(23,30)7/h12,14,19,21-24,27,31H,3,9-11,13,15-18H2,1-2,4-8H3/t21-,22+,23-,24+,27+,28+,29-,30+/m1/s1
SMILES:	CC(C(=C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CC[C@@H]([C@H]2C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520429
PubChem CID:	5283649
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

*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
NPO11757	Euphorbia chamaesyce	Species	Euphorbiaceae	Eukaryota	whole herb	n.a.	n.a.	PMID[10650087]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[20104880]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342101]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[25895106]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12934	Gynostemma pentaphyllum	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16506	Synotis alata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO918	Dahlia pinnata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11990	Coleostephus myconis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11757	Euphorbia chamaesyce	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4305	Pertusaria wulfenii	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2922	Botryosphaeria berengeriana	Species	Botryosphaeriaceae	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	5

Activity Type	# Activity
Cell Line	1
Others	4

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[503703]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[503703]
NPT2	Others	Unspecified		Activity	=	27.3	%	PMID[503703]
NPT2	Others	Unspecified		Activity	=	74.9	%	PMID[503703]
NPT2	Others	Unspecified		Activity	=	92.4	%	PMID[503703]

☑ 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 NPC186191 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	156
0.1-0.2	1277
0.2-0.3	6767
0.3-0.4	16397
0.4-0.5	8044
0.5-0.6	6028
0.6-0.7	2969
0.7-0.8	855
0.8-0.85	128
0.85-0.9	50
0.9-0.95	17
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC205455
0.9726	High Similarity	NPC318136
0.9722	High Similarity	NPC202642
0.9722	High Similarity	NPC46160
0.9589	High Similarity	NPC214570
0.9583	High Similarity	NPC121744
0.9583	High Similarity	NPC118508
0.9583	High Similarity	NPC322353
0.9474	High Similarity	NPC202389
0.9474	High Similarity	NPC201852
0.9459	High Similarity	NPC275910
0.9452	High Similarity	NPC189883
0.9452	High Similarity	NPC73875
0.9452	High Similarity	NPC470362
0.9342	High Similarity	NPC6707
0.9315	High Similarity	NPC257347
0.9315	High Similarity	NPC141071
0.9315	High Similarity	NPC471723
0.9306	High Similarity	NPC201373
0.9231	High Similarity	NPC231310
0.9221	High Similarity	NPC20853
0.92	High Similarity	NPC76931
0.92	High Similarity	NPC307965
0.92	High Similarity	NPC18603
0.9189	High Similarity	NPC129165
0.9189	High Similarity	NPC237460
0.9189	High Similarity	NPC240604
0.9189	High Similarity	NPC134330
0.9189	High Similarity	NPC300324
0.9079	High Similarity	NPC1319
0.9054	High Similarity	NPC136188
0.9054	High Similarity	NPC134847
0.9054	High Similarity	NPC471468
0.9054	High Similarity	NPC285893
0.9054	High Similarity	NPC22105
0.9054	High Similarity	NPC230301
0.9054	High Similarity	NPC304309
0.9054	High Similarity	NPC28657
0.9054	High Similarity	NPC288035
0.9054	High Similarity	NPC162742
0.8987	High Similarity	NPC238485
0.8974	High Similarity	NPC87489
0.8961	High Similarity	NPC236112
0.8947	High Similarity	NPC302041
0.8947	High Similarity	NPC85346
0.8947	High Similarity	NPC167037
0.8947	High Similarity	NPC285761
0.8947	High Similarity	NPC6978
0.8947	High Similarity	NPC138621
0.8947	High Similarity	NPC65897
0.8947	High Similarity	NPC244385
0.8933	High Similarity	NPC321381
0.8933	High Similarity	NPC107059
0.8933	High Similarity	NPC113733
0.8933	High Similarity	NPC321016
0.8904	High Similarity	NPC110799
0.8889	High Similarity	NPC475772
0.8861	High Similarity	NPC470384
0.8846	High Similarity	NPC474531
0.8831	High Similarity	NPC209430
0.8831	High Similarity	NPC80530
0.8831	High Similarity	NPC30986
0.8831	High Similarity	NPC273410
0.8816	High Similarity	NPC34019
0.8816	High Similarity	NPC318495
0.8816	High Similarity	NPC155986
0.8816	High Similarity	NPC198968
0.8784	High Similarity	NPC474140
0.8784	High Similarity	NPC182717
0.878	High Similarity	NPC470542
0.875	High Similarity	NPC216460
0.8734	High Similarity	NPC470049
0.8734	High Similarity	NPC30166
0.8718	High Similarity	NPC102253
0.8718	High Similarity	NPC13554
0.8718	High Similarity	NPC236237
0.8718	High Similarity	NPC322313
0.8701	High Similarity	NPC72507
0.8701	High Similarity	NPC312328
0.8701	High Similarity	NPC477522
0.8701	High Similarity	NPC474216
0.8701	High Similarity	NPC87604
0.8701	High Similarity	NPC473943
0.8684	High Similarity	NPC106432
0.8684	High Similarity	NPC247325
0.8684	High Similarity	NPC244488
0.8675	High Similarity	NPC84271
0.8675	High Similarity	NPC102414
0.8675	High Similarity	NPC77168
0.8667	High Similarity	NPC469534
0.8667	High Similarity	NPC100334
0.8667	High Similarity	NPC469533
0.8667	High Similarity	NPC469593
0.8659	High Similarity	NPC271967
0.8649	High Similarity	NPC111234
0.8608	High Similarity	NPC470383
0.859	High Similarity	NPC84694
0.859	High Similarity	NPC47982
0.859	High Similarity	NPC28862
0.859	High Similarity	NPC143182
0.859	High Similarity	NPC109546
0.859	High Similarity	NPC328714
0.859	High Similarity	NPC81306
0.8554	High Similarity	NPC2158
0.8554	High Similarity	NPC280556
0.8537	High Similarity	NPC94755
0.8519	High Similarity	NPC478102
0.8519	High Similarity	NPC124172
0.8519	High Similarity	NPC209802
0.8519	High Similarity	NPC474493
0.8519	High Similarity	NPC470077
0.8514	High Similarity	NPC45296
0.85	High Similarity	NPC49964
0.85	High Similarity	NPC296701
0.85	High Similarity	NPC101462
0.85	High Similarity	NPC218616
0.85	High Similarity	NPC248886
0.8493	Intermediate Similarity	NPC208999
0.8493	Intermediate Similarity	NPC160209
0.8481	Intermediate Similarity	NPC164840
0.8481	Intermediate Similarity	NPC241290
0.8481	Intermediate Similarity	NPC22403
0.8481	Intermediate Similarity	NPC209944
0.8481	Intermediate Similarity	NPC234193
0.8481	Intermediate Similarity	NPC26117
0.8471	Intermediate Similarity	NPC212948
0.8462	Intermediate Similarity	NPC477514
0.8442	Intermediate Similarity	NPC27765
0.8442	Intermediate Similarity	NPC30590
0.8442	Intermediate Similarity	NPC290598
0.8442	Intermediate Similarity	NPC96319
0.8442	Intermediate Similarity	NPC122418
0.8442	Intermediate Similarity	NPC120098
0.8442	Intermediate Similarity	NPC265328
0.8434	Intermediate Similarity	NPC159046
0.8434	Intermediate Similarity	NPC233836
0.8434	Intermediate Similarity	NPC187376
0.8421	Intermediate Similarity	NPC91858
0.8421	Intermediate Similarity	NPC145552
0.8421	Intermediate Similarity	NPC477138
0.8421	Intermediate Similarity	NPC243342
0.8421	Intermediate Similarity	NPC192638
0.8421	Intermediate Similarity	NPC5046
0.8421	Intermediate Similarity	NPC329090
0.8421	Intermediate Similarity	NPC62657
0.8421	Intermediate Similarity	NPC25511
0.8421	Intermediate Similarity	NPC254509
0.8421	Intermediate Similarity	NPC49168
0.8421	Intermediate Similarity	NPC27395
0.8421	Intermediate Similarity	NPC196358
0.8415	Intermediate Similarity	NPC318390
0.84	Intermediate Similarity	NPC167706
0.8395	Intermediate Similarity	NPC82538
0.8395	Intermediate Similarity	NPC477818
0.8395	Intermediate Similarity	NPC113978
0.8395	Intermediate Similarity	NPC110778
0.8395	Intermediate Similarity	NPC237795
0.8395	Intermediate Similarity	NPC317458
0.8395	Intermediate Similarity	NPC207013
0.8378	Intermediate Similarity	NPC167272
0.8378	Intermediate Similarity	NPC269877
0.8375	Intermediate Similarity	NPC82986
0.8375	Intermediate Similarity	NPC209620
0.8375	Intermediate Similarity	NPC474752
0.8375	Intermediate Similarity	NPC474759
0.8375	Intermediate Similarity	NPC23852
0.8375	Intermediate Similarity	NPC7505
0.8375	Intermediate Similarity	NPC47761
0.8375	Intermediate Similarity	NPC264245
0.8375	Intermediate Similarity	NPC474683
0.8375	Intermediate Similarity	NPC474731
0.8372	Intermediate Similarity	NPC214697
0.8372	Intermediate Similarity	NPC310013
0.8354	Intermediate Similarity	NPC472463
0.8353	Intermediate Similarity	NPC107189
0.8333	Intermediate Similarity	NPC471722
0.8333	Intermediate Similarity	NPC157996
0.8333	Intermediate Similarity	NPC40394
0.8333	Intermediate Similarity	NPC34177
0.8333	Intermediate Similarity	NPC471798
0.8333	Intermediate Similarity	NPC472805
0.8333	Intermediate Similarity	NPC101475
0.8333	Intermediate Similarity	NPC90979
0.8313	Intermediate Similarity	NPC28252
0.8313	Intermediate Similarity	NPC125399
0.8313	Intermediate Similarity	NPC72133
0.8313	Intermediate Similarity	NPC261266
0.8313	Intermediate Similarity	NPC24277
0.8313	Intermediate Similarity	NPC6391
0.8313	Intermediate Similarity	NPC474970
0.8313	Intermediate Similarity	NPC55309
0.8313	Intermediate Similarity	NPC94462
0.8312	Intermediate Similarity	NPC138374
0.8312	Intermediate Similarity	NPC230704
0.8312	Intermediate Similarity	NPC200243
0.8312	Intermediate Similarity	NPC477923
0.8312	Intermediate Similarity	NPC104387
0.8312	Intermediate Similarity	NPC240235
0.8312	Intermediate Similarity	NPC34700
0.8312	Intermediate Similarity	NPC66566

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 NPC186191 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1563
0.2-0.3	4391
0.3-0.4	2185
0.4-0.5	451
0.5-0.6	186
0.6-0.7	155
0.7-0.8	42
0.8-0.85	13
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9054	High Similarity	NPD7339	Approved
0.9054	High Similarity	NPD6942	Approved
0.8718	High Similarity	NPD7525	Registered
0.8442	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6926	Approved
0.8421	Intermediate Similarity	NPD6924	Approved
0.84	Intermediate Similarity	NPD7150	Approved
0.84	Intermediate Similarity	NPD7152	Approved
0.84	Intermediate Similarity	NPD7151	Approved
0.8378	Intermediate Similarity	NPD6923	Approved
0.8378	Intermediate Similarity	NPD6922	Approved
0.8267	Intermediate Similarity	NPD7144	Approved
0.8267	Intermediate Similarity	NPD7143	Approved
0.8205	Intermediate Similarity	NPD6933	Approved
0.8158	Intermediate Similarity	NPD4243	Approved
0.8125	Intermediate Similarity	NPD7645	Phase 2
0.8072	Intermediate Similarity	NPD4786	Approved
0.8025	Intermediate Similarity	NPD4748	Discontinued
0.8023	Intermediate Similarity	NPD5328	Approved
0.7949	Intermediate Similarity	NPD4785	Approved
0.7949	Intermediate Similarity	NPD4784	Approved
0.7901	Intermediate Similarity	NPD6929	Approved
0.7882	Intermediate Similarity	NPD3618	Phase 1
0.7882	Intermediate Similarity	NPD5279	Phase 3
0.7848	Intermediate Similarity	NPD8264	Approved
0.7841	Intermediate Similarity	NPD6079	Approved
0.7831	Intermediate Similarity	NPD3667	Approved
0.7805	Intermediate Similarity	NPD7509	Discontinued
0.7805	Intermediate Similarity	NPD6931	Approved
0.7805	Intermediate Similarity	NPD6930	Phase 2
0.7654	Intermediate Similarity	NPD5776	Phase 2
0.7654	Intermediate Similarity	NPD6932	Approved
0.7654	Intermediate Similarity	NPD6925	Approved
0.7625	Intermediate Similarity	NPD4190	Phase 3
0.7625	Intermediate Similarity	NPD5275	Approved
0.7586	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD7145	Approved
0.7556	Intermediate Similarity	NPD4202	Approved
0.7529	Intermediate Similarity	NPD6695	Phase 3
0.747	Intermediate Similarity	NPD6683	Phase 2
0.7442	Intermediate Similarity	NPD3666	Approved
0.7442	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3133	Approved
0.7442	Intermediate Similarity	NPD3665	Phase 1
0.7381	Intermediate Similarity	NPD7514	Phase 3
0.7356	Intermediate Similarity	NPD6893	Approved
0.7356	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5222	Approved
0.7312	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD4697	Phase 3
0.7312	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6902	Approved
0.7273	Intermediate Similarity	NPD5280	Approved
0.7273	Intermediate Similarity	NPD4694	Approved
0.7262	Intermediate Similarity	NPD4195	Approved
0.7234	Intermediate Similarity	NPD5173	Approved
0.7234	Intermediate Similarity	NPD4755	Approved
0.7191	Intermediate Similarity	NPD7524	Approved
0.7191	Intermediate Similarity	NPD7750	Discontinued
0.7176	Intermediate Similarity	NPD7332	Phase 2
0.7174	Intermediate Similarity	NPD6399	Phase 3
0.7093	Intermediate Similarity	NPD6898	Phase 1
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7083	Intermediate Similarity	NPD4700	Approved
0.7065	Intermediate Similarity	NPD7515	Phase 2
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7033	Intermediate Similarity	NPD4753	Phase 2
0.7011	Intermediate Similarity	NPD4223	Phase 3
0.7011	Intermediate Similarity	NPD4221	Approved
0.701	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7638	Approved
0.6979	Remote Similarity	NPD5290	Discontinued
0.6966	Remote Similarity	NPD5329	Approved
0.6939	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD5225	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6907	Remote Similarity	NPD7640	Approved
0.6907	Remote Similarity	NPD7639	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6889	Remote Similarity	NPD5690	Phase 2
0.6882	Remote Similarity	NPD5281	Approved
0.6882	Remote Similarity	NPD7087	Discontinued
0.6882	Remote Similarity	NPD5284	Approved
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD4754	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6867	Remote Similarity	NPD5733	Approved
0.6854	Remote Similarity	NPD4197	Approved
0.68	Remote Similarity	NPD5141	Approved
0.6774	Remote Similarity	NPD4096	Approved
0.6765	Remote Similarity	NPD6881	Approved
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6742	Remote Similarity	NPD4788	Approved
0.6737	Remote Similarity	NPD7748	Approved
0.6733	Remote Similarity	NPD4768	Approved
0.6733	Remote Similarity	NPD4767	Approved
0.6707	Remote Similarity	NPD4787	Phase 1
0.6705	Remote Similarity	NPD4139	Approved
0.6705	Remote Similarity	NPD4692	Approved
0.6703	Remote Similarity	NPD7521	Approved
0.6703	Remote Similarity	NPD4689	Approved
0.6703	Remote Similarity	NPD4693	Phase 3
0.6703	Remote Similarity	NPD6684	Approved
0.6703	Remote Similarity	NPD4688	Approved
0.6703	Remote Similarity	NPD5205	Approved
0.6703	Remote Similarity	NPD4690	Approved
0.6703	Remote Similarity	NPD7334	Approved
0.6703	Remote Similarity	NPD6409	Approved
0.6703	Remote Similarity	NPD4138	Approved
0.6703	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7146	Approved
0.6703	Remote Similarity	NPD5330	Approved
0.6702	Remote Similarity	NPD8034	Phase 2
0.6702	Remote Similarity	NPD6411	Approved
0.6702	Remote Similarity	NPD8035	Phase 2
0.6701	Remote Similarity	NPD6083	Phase 2
0.6701	Remote Similarity	NPD6084	Phase 2
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD5210	Approved
0.6667	Remote Similarity	NPD4629	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6632	Remote Similarity	NPD5133	Approved
0.6627	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD5276	Approved
0.6627	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6591	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6571	Remote Similarity	NPD6617	Approved
0.6559	Remote Similarity	NPD4722	Approved
0.6559	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD6903	Approved
0.6559	Remote Similarity	NPD5737	Approved
0.6559	Remote Similarity	NPD4518	Approved
0.6559	Remote Similarity	NPD4723	Approved
0.6559	Remote Similarity	NPD6672	Approved
0.6552	Remote Similarity	NPD3617	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD368	Approved
0.6531	Remote Similarity	NPD7902	Approved
0.6526	Remote Similarity	NPD6050	Approved
0.6526	Remote Similarity	NPD7637	Suspended
0.6512	Remote Similarity	NPD6117	Approved
0.6509	Remote Similarity	NPD6882	Approved
0.6509	Remote Similarity	NPD8297	Approved
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5250	Approved
0.6476	Remote Similarity	NPD5169	Approved
0.6476	Remote Similarity	NPD5247	Approved
0.6476	Remote Similarity	NPD5248	Approved
0.6476	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD5135	Approved
0.6476	Remote Similarity	NPD5249	Phase 3
0.6476	Remote Similarity	NPD5251	Approved
0.6471	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6116	Phase 1
0.6421	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5207	Approved
0.6421	Remote Similarity	NPD7136	Phase 2
0.6421	Remote Similarity	NPD5692	Phase 3
0.6415	Remote Similarity	NPD5215	Approved
0.6415	Remote Similarity	NPD5127	Approved
0.6415	Remote Similarity	NPD5217	Approved
0.6415	Remote Similarity	NPD5216	Approved
0.64	Remote Similarity	NPD342	Phase 1
0.64	Remote Similarity	NPD6404	Discontinued
0.6386	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6118	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