NPASS Compound

Structure

CID25833 OpenBabel06191715352D 25 28 0 0 1 0 0 0 0 0999 V2000 -3.4158 -0.0982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3296 -0.0983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9129 -2.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8842 -2.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7973 -2.6514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2826 -1.8106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4564 -0.1296 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3692 -0.1291 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4273 -0.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3406 -0.1290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4562 -1.8117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4270 -1.8113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9709 -0.9709 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3698 -1.8111 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3412 -1.8109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8840 -0.9699 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7978 -0.9701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9126 -0.9700 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8264 -0.9702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2979 -0.1041 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9709 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9709 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9709 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3 4 1 0 0 0 0 3 12 2 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 16 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 18 1 0 0 0 0 13 24 1 6 0 0 0 14 4 1 1 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 19 1 6 0 0 0 16 18 1 6 0 0 0 17 19 1 0 0 0 0 17 20 2 0 0 0 0 18 1 1 6 0 0 0 19 2 1 6 0 0 0 21 25 1 0 0 0 0 22 25 2 0 0 0 0 23 25 2 0 0 0 0 24 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.17
Volume:	360.142
LogP:	1.793
LogD:	1.811
LogS:	-1.887
# Rotatable Bonds:	2
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.594
Synthetic Accessibility Score:	4.154
Fsp3:	0.842
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.743
MDCK Permeability:	1.5186060409178026e-05
Pgp-inhibitor:	0.229
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.192
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.356
Plasma Protein Binding (PPB):	90.54691314697266%
Volume Distribution (VD):	0.702
Pgp-substrate:	2.7136893272399902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.773
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.343
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.082

ADMET: Excretion

Clearance (CL):	6.331
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.582
Drug-inuced Liver Injury (DILI):	0.222
AMES Toxicity:	0.866
Rat Oral Acute Toxicity:	0.248
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.937
Carcinogencity:	0.937
Eye Corrosion:	0.677
Eye Irritation:	0.621
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC25833

Natural Product ID:	NPC25833
*Common Name:**	Prasterone Sulfuric Acid
IUPAC Name:	[(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] hydrogen sulfate
Synonyms:
Standard InCHIKey:	CZWCKYRVOZZJNM-USOAJAOKSA-N
Standard InCHI:	InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1
SMILES:	C[C@]12CC[C@@H](CC1=CC[C@H]1[C@@H]3CCC(=O)[C@@]3(C)CC[C@H]21)OS(=O)(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL259898
PubChem CID:	12594
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001692] Sulfated steroids

*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

☑ 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
EC50	1
IC50	3
Others	22

Activity Type	# Activity
Individual Protein	23
ORGANISM	1
Others	1
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1731	Individual Protein	Steryl-sulfatase	Homo sapiens	Km	=	1700.0	nM	PMID[515277]
NPT1731	Individual Protein	Steryl-sulfatase	Homo sapiens	Km	=	19000.0	nM	PMID[515277]
NPT612	Individual Protein	Canalicular multispecific organic anion transporter 1	Homo sapiens	Activity	=	395.0	%	PMID[515279]
NPT1472	Individual Protein	Solute carrier family 22 member 11	Homo sapiens	Km	=	630.0	nM	PMID[515281]
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	Km	=	1900.0	nM	PMID[515282]
NPT1736	Individual Protein	ATP-binding cassette sub-family C member 11	Homo sapiens	Km	=	13000.0	nM	PMID[515283]
NPT1736	Individual Protein	ATP-binding cassette sub-family C member 11	Homo sapiens	Activity	=	196.0	%	PMID[515283]
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	Activity	=	34.0	%	PMID[515292]
NPT1422	Individual Protein	ATP-binding cassette sub-family G member 2	Homo sapiens	Activity	=	50.0	%	PMID[515293]
NPT1631	Individual Protein	Solute carrier organic anion transporter family member 1A5	Rattus norvegicus	Km	=	162000.0	nM	PMID[515295]
NPT305	Individual Protein	Solute carrier organic anion transporter family member 1A4	Rattus norvegicus	Km	=	17000.0	nM	PMID[515296]
NPT1742	Individual Protein	Solute carrier organic anion transporter family member 1B2	Rattus norvegicus	Km	=	5300.0	nM	PMID[515295]
NPT1594	Individual Protein	Multidrug resistance-associated protein 1	Homo sapiens	Km	=	5000.0	nM	PMID[515282]
NPT1733	Individual Protein	Solute carrier organic anion transporter family member 1A2	Homo sapiens	Km	=	6600.0	nM	PMID[515299]
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	IC50	=	3000.0	nM	PMID[515282]
NPT2742	Individual Protein	Aldehyde oxidase	Homo sapiens	IC50	>	100000.0	nM	PMID[515307]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	EC50	=	127000.0	nM	PMID[515278]
NPT745	Individual Protein	G-protein coupled bile acid receptor 1	Homo sapiens	Efficacy	=	83.0	%	PMID[515278]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Km	=	21500.0	nM	PMID[515297]
NPT752	Individual Protein	Solute carrier organic anion transporter family member 1A1	Rattus norvegicus	Km	=	5000.0	nM	PMID[515298]
NPT750	Individual Protein	Solute carrier organic anion transporter family member 1A3	Rattus norvegicus	Km	=	7600.0	nM	PMID[515300]
NPT24822	SINGLE PROTEIN	Solute carrier organic anion transporter family member 1A1	Mus musculus	Km	=	8200.0	nM	PMID[515301]
NPT750	Individual Protein	Solute carrier organic anion transporter family member 1A3	Rattus norvegicus	Km	=	8500.0	nM	PMID[515300]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Km	>	30000.0	nM	PMID[515297]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Hit score	=	0.1405	n.a.	PMID[515306]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[515307]

☑ 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 NPC25833 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	164
0.1-0.2	1245
0.2-0.3	5657
0.3-0.4	16463
0.4-0.5	7036
0.5-0.6	6501
0.6-0.7	4083
0.7-0.8	1430
0.8-0.85	91
0.85-0.9	24
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC328351
0.9012	High Similarity	NPC151519
0.8795	High Similarity	NPC221758
0.8795	High Similarity	NPC59453
0.8636	High Similarity	NPC475255
0.8588	High Similarity	NPC474733
0.8588	High Similarity	NPC31564
0.8588	High Similarity	NPC474732
0.8588	High Similarity	NPC145879
0.8588	High Similarity	NPC474778
0.8588	High Similarity	NPC20688
0.8588	High Similarity	NPC51014
0.8506	High Similarity	NPC1015
0.8506	High Similarity	NPC31985
0.8506	High Similarity	NPC32830
0.8506	High Similarity	NPC474245
0.8488	Intermediate Similarity	NPC475740
0.8488	Intermediate Similarity	NPC58063
0.8391	Intermediate Similarity	NPC328313
0.8372	Intermediate Similarity	NPC155011
0.8353	Intermediate Similarity	NPC85774
0.8353	Intermediate Similarity	NPC214043
0.8353	Intermediate Similarity	NPC329043
0.8353	Intermediate Similarity	NPC58841
0.8353	Intermediate Similarity	NPC161423
0.8353	Intermediate Similarity	NPC227064
0.8353	Intermediate Similarity	NPC321187
0.8353	Intermediate Similarity	NPC82902
0.8295	Intermediate Similarity	NPC268406
0.8295	Intermediate Similarity	NPC76879
0.8295	Intermediate Similarity	NPC186688
0.8295	Intermediate Similarity	NPC26959
0.8293	Intermediate Similarity	NPC475337
0.8276	Intermediate Similarity	NPC317590
0.8276	Intermediate Similarity	NPC90652
0.8256	Intermediate Similarity	NPC474218
0.8256	Intermediate Similarity	NPC469948
0.8256	Intermediate Similarity	NPC478127
0.8256	Intermediate Similarity	NPC471224
0.8256	Intermediate Similarity	NPC470574
0.8235	Intermediate Similarity	NPC470046
0.8235	Intermediate Similarity	NPC470047
0.8235	Intermediate Similarity	NPC476082
0.8235	Intermediate Similarity	NPC278648
0.8222	Intermediate Similarity	NPC478129
0.8214	Intermediate Similarity	NPC14151
0.8202	Intermediate Similarity	NPC48010
0.8182	Intermediate Similarity	NPC470417
0.8182	Intermediate Similarity	NPC471722
0.8182	Intermediate Similarity	NPC328539
0.8182	Intermediate Similarity	NPC53911
0.8161	Intermediate Similarity	NPC264127
0.8161	Intermediate Similarity	NPC327115
0.8161	Intermediate Similarity	NPC475022
0.8161	Intermediate Similarity	NPC469994
0.8161	Intermediate Similarity	NPC222613
0.8161	Intermediate Similarity	NPC118648
0.814	Intermediate Similarity	NPC473246
0.814	Intermediate Similarity	NPC472265
0.814	Intermediate Similarity	NPC237712
0.814	Intermediate Similarity	NPC180834
0.8132	Intermediate Similarity	NPC196485
0.8132	Intermediate Similarity	NPC245972
0.8118	Intermediate Similarity	NPC212083
0.8111	Intermediate Similarity	NPC473998
0.8111	Intermediate Similarity	NPC168027
0.8111	Intermediate Similarity	NPC185936
0.8095	Intermediate Similarity	NPC2482
0.8095	Intermediate Similarity	NPC472478
0.809	Intermediate Similarity	NPC119416
0.809	Intermediate Similarity	NPC309603
0.809	Intermediate Similarity	NPC475921
0.809	Intermediate Similarity	NPC477943
0.809	Intermediate Similarity	NPC474704
0.809	Intermediate Similarity	NPC473999
0.8068	Intermediate Similarity	NPC472482
0.8068	Intermediate Similarity	NPC96496
0.8068	Intermediate Similarity	NPC472481
0.8068	Intermediate Similarity	NPC472484
0.8068	Intermediate Similarity	NPC474684
0.8068	Intermediate Similarity	NPC142361
0.8046	Intermediate Similarity	NPC474083
0.8046	Intermediate Similarity	NPC323765
0.8046	Intermediate Similarity	NPC202868
0.8046	Intermediate Similarity	NPC197823
0.8043	Intermediate Similarity	NPC469599
0.8022	Intermediate Similarity	NPC109305
0.8	Intermediate Similarity	NPC121984
0.8	Intermediate Similarity	NPC471896
0.8	Intermediate Similarity	NPC136150
0.8	Intermediate Similarity	NPC171441
0.8	Intermediate Similarity	NPC147066
0.8	Intermediate Similarity	NPC473534
0.8	Intermediate Similarity	NPC320026
0.8	Intermediate Similarity	NPC126642
0.7978	Intermediate Similarity	NPC97884
0.7978	Intermediate Similarity	NPC193360
0.7978	Intermediate Similarity	NPC472483
0.7978	Intermediate Similarity	NPC472220
0.7978	Intermediate Similarity	NPC242864
0.7976	Intermediate Similarity	NPC215843
0.7976	Intermediate Similarity	NPC476177
0.7957	Intermediate Similarity	NPC9487
0.7955	Intermediate Similarity	NPC470051
0.7955	Intermediate Similarity	NPC473168
0.7955	Intermediate Similarity	NPC72133
0.7955	Intermediate Similarity	NPC94755
0.7955	Intermediate Similarity	NPC94666
0.7955	Intermediate Similarity	NPC195640
0.7955	Intermediate Similarity	NPC470050
0.7935	Intermediate Similarity	NPC111015
0.7935	Intermediate Similarity	NPC8993
0.7935	Intermediate Similarity	NPC292793
0.7931	Intermediate Similarity	NPC33913
0.7931	Intermediate Similarity	NPC472480
0.7912	Intermediate Similarity	NPC110657
0.7912	Intermediate Similarity	NPC475806
0.7912	Intermediate Similarity	NPC131872
0.7912	Intermediate Similarity	NPC155304
0.7912	Intermediate Similarity	NPC272746
0.7912	Intermediate Similarity	NPC212301
0.7912	Intermediate Similarity	NPC86266
0.7912	Intermediate Similarity	NPC189520
0.7912	Intermediate Similarity	NPC26888
0.7912	Intermediate Similarity	NPC154101
0.7907	Intermediate Similarity	NPC48362
0.7907	Intermediate Similarity	NPC193347
0.7907	Intermediate Similarity	NPC310989
0.7907	Intermediate Similarity	NPC163236
0.7907	Intermediate Similarity	NPC260956
0.7889	Intermediate Similarity	NPC474570
0.7889	Intermediate Similarity	NPC310010
0.7889	Intermediate Similarity	NPC2983
0.7889	Intermediate Similarity	NPC469319
0.7889	Intermediate Similarity	NPC271974
0.7889	Intermediate Similarity	NPC247312
0.7889	Intermediate Similarity	NPC326627
0.7889	Intermediate Similarity	NPC86319
0.7889	Intermediate Similarity	NPC229871
0.7889	Intermediate Similarity	NPC275740
0.7872	Intermediate Similarity	NPC108078
0.7872	Intermediate Similarity	NPC190554
0.7865	Intermediate Similarity	NPC187376
0.7865	Intermediate Similarity	NPC136548
0.7865	Intermediate Similarity	NPC233836
0.7865	Intermediate Similarity	NPC141292
0.7865	Intermediate Similarity	NPC73064
0.7865	Intermediate Similarity	NPC93778
0.7865	Intermediate Similarity	NPC159046
0.7857	Intermediate Similarity	NPC82635
0.7849	Intermediate Similarity	NPC473170
0.7849	Intermediate Similarity	NPC127063
0.7849	Intermediate Similarity	NPC472485
0.7841	Intermediate Similarity	NPC470223
0.7841	Intermediate Similarity	NPC133954
0.7841	Intermediate Similarity	NPC470048
0.7831	Intermediate Similarity	NPC96319
0.7831	Intermediate Similarity	NPC107059
0.7831	Intermediate Similarity	NPC321016
0.7831	Intermediate Similarity	NPC321381
0.7826	Intermediate Similarity	NPC470376
0.7826	Intermediate Similarity	NPC170220
0.7826	Intermediate Similarity	NPC12722
0.7826	Intermediate Similarity	NPC107674
0.7826	Intermediate Similarity	NPC472942
0.7826	Intermediate Similarity	NPC474736
0.7826	Intermediate Similarity	NPC470375
0.7826	Intermediate Similarity	NPC141497
0.7802	Intermediate Similarity	NPC69622
0.7802	Intermediate Similarity	NPC148414
0.7802	Intermediate Similarity	NPC126993
0.7802	Intermediate Similarity	NPC175628
0.7802	Intermediate Similarity	NPC191684
0.7802	Intermediate Similarity	NPC85173
0.7802	Intermediate Similarity	NPC111585
0.7791	Intermediate Similarity	NPC3915
0.7791	Intermediate Similarity	NPC201912
0.7791	Intermediate Similarity	NPC473420
0.7791	Intermediate Similarity	NPC38350
0.7789	Intermediate Similarity	NPC114274
0.7778	Intermediate Similarity	NPC44181
0.7778	Intermediate Similarity	NPC310752
0.7778	Intermediate Similarity	NPC143767
0.7778	Intermediate Similarity	NPC131470
0.7778	Intermediate Similarity	NPC474677
0.7778	Intermediate Similarity	NPC28227
0.7778	Intermediate Similarity	NPC471724
0.7778	Intermediate Similarity	NPC292491
0.7766	Intermediate Similarity	NPC192428
0.7765	Intermediate Similarity	NPC44083
0.7765	Intermediate Similarity	NPC472490
0.7765	Intermediate Similarity	NPC474113
0.7765	Intermediate Similarity	NPC477371
0.7765	Intermediate Similarity	NPC153987
0.7753	Intermediate Similarity	NPC213412
0.7753	Intermediate Similarity	NPC73038
0.7753	Intermediate Similarity	NPC89077
0.7753	Intermediate Similarity	NPC475862
0.7753	Intermediate Similarity	NPC470955
0.7753	Intermediate Similarity	NPC28252

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 NPC25833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1415
0.2-0.3	4276
0.3-0.4	2355
0.4-0.5	509
0.5-0.6	161
0.6-0.7	163
0.7-0.8	111
0.8-0.85	13
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3668	Phase 3
0.9012	High Similarity	NPD3667	Approved
0.8795	High Similarity	NPD4786	Approved
0.8372	Intermediate Similarity	NPD3618	Phase 1
0.8353	Intermediate Similarity	NPD3666	Approved
0.8353	Intermediate Similarity	NPD3133	Approved
0.8353	Intermediate Similarity	NPD3665	Phase 1
0.8222	Intermediate Similarity	NPD6399	Phase 3
0.809	Intermediate Similarity	NPD5328	Approved
0.7955	Intermediate Similarity	NPD6409	Approved
0.7955	Intermediate Similarity	NPD6684	Approved
0.7955	Intermediate Similarity	NPD5330	Approved
0.7955	Intermediate Similarity	NPD7146	Approved
0.7955	Intermediate Similarity	NPD7521	Approved
0.7955	Intermediate Similarity	NPD7334	Approved
0.7912	Intermediate Similarity	NPD6079	Approved
0.7907	Intermediate Similarity	NPD4223	Phase 3
0.7907	Intermediate Similarity	NPD4221	Approved
0.7889	Intermediate Similarity	NPD4753	Phase 2
0.7831	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4202	Approved
0.7778	Intermediate Similarity	NPD6903	Approved
0.7778	Intermediate Similarity	NPD6672	Approved
0.7778	Intermediate Similarity	NPD5737	Approved
0.7778	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD5222	Approved
0.7766	Intermediate Similarity	NPD4697	Phase 3
0.7766	Intermediate Similarity	NPD5221	Approved
0.7753	Intermediate Similarity	NPD5279	Phase 3
0.775	Intermediate Similarity	NPD4137	Phase 3
0.7727	Intermediate Similarity	NPD4197	Approved
0.7711	Intermediate Similarity	NPD7339	Approved
0.7711	Intermediate Similarity	NPD6942	Approved
0.7684	Intermediate Similarity	NPD4755	Approved
0.7684	Intermediate Similarity	NPD5173	Approved
0.7674	Intermediate Similarity	NPD4695	Discontinued
0.7654	Intermediate Similarity	NPD4691	Approved
0.7654	Intermediate Similarity	NPD4747	Approved
0.7647	Intermediate Similarity	NPD3617	Approved
0.764	Intermediate Similarity	NPD5329	Approved
0.7625	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4688	Approved
0.7556	Intermediate Similarity	NPD4138	Approved
0.7556	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD4689	Approved
0.7556	Intermediate Similarity	NPD4690	Approved
0.7556	Intermediate Similarity	NPD4693	Phase 3
0.7556	Intermediate Similarity	NPD5205	Approved
0.7527	Intermediate Similarity	NPD7515	Phase 2
0.7526	Intermediate Similarity	NPD5286	Approved
0.7526	Intermediate Similarity	NPD4700	Approved
0.7526	Intermediate Similarity	NPD4696	Approved
0.7526	Intermediate Similarity	NPD5285	Approved
0.7475	Intermediate Similarity	NPD4754	Approved
0.7474	Intermediate Similarity	NPD4629	Approved
0.7474	Intermediate Similarity	NPD5210	Approved
0.7449	Intermediate Similarity	NPD5223	Approved
0.7381	Intermediate Similarity	NPD4058	Approved
0.7374	Intermediate Similarity	NPD5225	Approved
0.7374	Intermediate Similarity	NPD5226	Approved
0.7374	Intermediate Similarity	NPD5224	Approved
0.7374	Intermediate Similarity	NPD4633	Approved
0.7374	Intermediate Similarity	NPD5211	Phase 2
0.7368	Intermediate Similarity	NPD7748	Approved
0.7363	Intermediate Similarity	NPD5280	Approved
0.7363	Intermediate Similarity	NPD4694	Approved
0.7363	Intermediate Similarity	NPD6098	Approved
0.7363	Intermediate Similarity	NPD5690	Phase 2
0.732	Intermediate Similarity	NPD6084	Phase 2
0.732	Intermediate Similarity	NPD6083	Phase 2
0.7312	Intermediate Similarity	NPD6904	Approved
0.7312	Intermediate Similarity	NPD6080	Approved
0.7312	Intermediate Similarity	NPD6673	Approved
0.73	Intermediate Similarity	NPD5175	Approved
0.73	Intermediate Similarity	NPD5174	Approved
0.7292	Intermediate Similarity	NPD5695	Phase 3
0.7273	Intermediate Similarity	NPD7525	Registered
0.7253	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5696	Approved
0.7228	Intermediate Similarity	NPD5141	Approved
0.7222	Intermediate Similarity	NPD4788	Approved
0.7204	Intermediate Similarity	NPD5208	Approved
0.7191	Intermediate Similarity	NPD4692	Approved
0.7191	Intermediate Similarity	NPD4139	Approved
0.7188	Intermediate Similarity	NPD7900	Approved
0.7188	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4687	Approved
0.7176	Intermediate Similarity	NPD5733	Approved
0.7174	Intermediate Similarity	NPD4623	Approved
0.7174	Intermediate Similarity	NPD4519	Discontinued
0.7159	Intermediate Similarity	NPD4195	Approved
0.7158	Intermediate Similarity	NPD5693	Phase 1
0.7158	Intermediate Similarity	NPD5284	Approved
0.7158	Intermediate Similarity	NPD5281	Approved
0.7157	Intermediate Similarity	NPD7128	Approved
0.7157	Intermediate Similarity	NPD4767	Approved
0.7157	Intermediate Similarity	NPD4768	Approved
0.7157	Intermediate Similarity	NPD6008	Approved
0.7157	Intermediate Similarity	NPD5739	Approved
0.7157	Intermediate Similarity	NPD6675	Approved
0.7157	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD5276	Approved
0.7113	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5697	Approved
0.7087	Intermediate Similarity	NPD5701	Approved
0.7053	Intermediate Similarity	NPD5692	Phase 3
0.7048	Intermediate Similarity	NPD5135	Approved
0.7048	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6899	Approved
0.7019	Intermediate Similarity	NPD6881	Approved
0.7019	Intermediate Similarity	NPD4729	Approved
0.7019	Intermediate Similarity	NPD4730	Approved
0.7019	Intermediate Similarity	NPD6011	Approved
0.7019	Intermediate Similarity	NPD5128	Approved
0.7019	Intermediate Similarity	NPD5168	Approved
0.7019	Intermediate Similarity	NPD7320	Approved
0.6981	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD8035	Phase 2
0.6979	Remote Similarity	NPD6050	Approved
0.6979	Remote Similarity	NPD8034	Phase 2
0.6979	Remote Similarity	NPD5694	Approved
0.6977	Remote Similarity	NPD4785	Approved
0.6977	Remote Similarity	NPD4784	Approved
0.6977	Remote Similarity	NPD6926	Approved
0.6977	Remote Similarity	NPD6924	Approved
0.6952	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD6012	Approved
0.6952	Remote Similarity	NPD6373	Approved
0.6952	Remote Similarity	NPD6014	Approved
0.6952	Remote Similarity	NPD6372	Approved
0.6947	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4243	Approved
0.6941	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6412	Phase 2
0.6915	Remote Similarity	NPD3573	Approved
0.6915	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3698	Phase 2
0.69	Remote Similarity	NPD7638	Approved
0.6887	Remote Similarity	NPD4634	Approved
0.6887	Remote Similarity	NPD5250	Approved
0.6887	Remote Similarity	NPD5247	Approved
0.6887	Remote Similarity	NPD5169	Approved
0.6887	Remote Similarity	NPD7102	Approved
0.6887	Remote Similarity	NPD5249	Phase 3
0.6887	Remote Similarity	NPD7290	Approved
0.6887	Remote Similarity	NPD5248	Approved
0.6887	Remote Similarity	NPD6883	Approved
0.6887	Remote Similarity	NPD5251	Approved
0.6875	Remote Similarity	NPD5207	Approved
0.6875	Remote Similarity	NPD4096	Approved
0.6842	Remote Similarity	NPD4518	Approved
0.6837	Remote Similarity	NPD6001	Approved
0.6832	Remote Similarity	NPD7640	Approved
0.6832	Remote Similarity	NPD7639	Approved
0.6829	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4245	Approved
0.6824	Remote Similarity	NPD4244	Approved
0.6822	Remote Similarity	NPD8130	Phase 1
0.6822	Remote Similarity	NPD5127	Approved
0.6822	Remote Similarity	NPD5215	Approved
0.6822	Remote Similarity	NPD6617	Approved
0.6822	Remote Similarity	NPD5216	Approved
0.6822	Remote Similarity	NPD6869	Approved
0.6822	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD5217	Approved
0.6822	Remote Similarity	NPD6649	Approved
0.6822	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6933	Approved
0.6778	Remote Similarity	NPD7645	Phase 2
0.6771	Remote Similarity	NPD6051	Approved
0.6759	Remote Similarity	NPD6882	Approved
0.6759	Remote Similarity	NPD8297	Approved
0.6744	Remote Similarity	NPD7152	Approved
0.6744	Remote Similarity	NPD7151	Approved
0.6744	Remote Similarity	NPD7150	Approved
0.6735	Remote Similarity	NPD5133	Approved
0.6733	Remote Similarity	NPD5290	Discontinued
0.6706	Remote Similarity	NPD6923	Approved
0.6706	Remote Similarity	NPD6922	Approved
0.6705	Remote Similarity	NPD3703	Phase 2
0.6705	Remote Similarity	NPD5275	Approved
0.6705	Remote Similarity	NPD4190	Phase 3
0.6703	Remote Similarity	NPD4748	Discontinued
0.6699	Remote Similarity	NPD5091	Approved
0.6697	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5364	Discontinued
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6317	Approved
0.6636	Remote Similarity	NPD5167	Approved
0.6635	Remote Similarity	NPD6052	Approved
0.6633	Remote Similarity	NPD6411	Approved
0.6629	Remote Similarity	NPD6117	Approved
0.6628	Remote Similarity	NPD4789	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