NPASS Compound

Structure

CID113425 OpenBabel06191715462D 29 35 0 0 1 0 0 0 0 0999 V2000 0.0799 -3.7813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5058 -2.3800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6182 -1.8670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8094 -1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6177 -4.6679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8077 -3.2676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6513 -0.3049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8091 -4.2014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 -2.8006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9918 -0.9648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4267 -3.2674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4248 -0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6182 -2.8009 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4265 -4.2009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0006 -2.8009 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0005 -1.8669 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4254 -1.3996 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6165 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5525 -0.5461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1348 -2.1071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8094 -3.2679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6166 -1.8666 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2335 -1.8659 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8083 -1.4000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3156 -4.7144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2120 0.1138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7943 -1.4472 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4753 -2.7670 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 4 1 0 0 0 0 3 13 1 0 0 0 0 4 16 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 9 1 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 7 19 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 1 0 0 0 14 25 1 6 0 0 0 15 16 1 0 0 0 0 15 21 1 6 0 0 0 16 24 1 1 0 0 0 17 22 1 6 0 0 0 17 23 1 0 0 0 0 18 24 1 1 0 0 0 18 28 1 0 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 1 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 21 1 1 6 0 0 0 22 24 1 6 0 0 0 23 10 1 6 0 0 0 23 29 1 0 0 0 0 24 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	400.22
Volume:	402.443
LogP:	4.093
LogD:	3.539
LogS:	-5.321
# Rotatable Bonds:	1
TPSA:	71.59
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.54
Synthetic Accessibility Score:	5.719
Fsp3:	0.875
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:	-4.923
MDCK Permeability:	3.9196511352201924e-05
Pgp-inhibitor:	0.501
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.66
30% Bioavailability (F30%):	0.086

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.659
Plasma Protein Binding (PPB):	86.98058319091797%
Volume Distribution (VD):	1.664
Pgp-substrate:	7.34947395324707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.608
CYP2C19-inhibitor:	0.163
CYP2C19-substrate:	0.617
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.909
CYP3A4-substrate:	0.357

ADMET: Excretion

Clearance (CL):	12.14
Half-life (T1/2):	0.287

ADMET: Toxicity

hERG Blockers:	0.579
Human Hepatotoxicity (H-HT):	0.904
Drug-inuced Liver Injury (DILI):	0.447
AMES Toxicity:	0.069
Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.944
Carcinogencity:	0.88
Eye Corrosion:	0.341
Eye Irritation:	0.331
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC113425

Natural Product ID:	NPC113425
*Common Name:**	JZDMFDWKCWMAMI-FVRXVPJRSA-N
IUPAC Name:	n.a.
Synonyms:	20,21-Epoxy-Resibufogenin; 20S,21-Epoxyresibufogenin
Standard InCHIKey:	JZDMFDWKCWMAMI-FVRXVPJRSA-N
Standard InCHI:	InChI=1S/C24H32O5/c1-21-8-5-14(25)11-13(21)3-4-16-15(21)6-9-22(2)17(12-18-24(16,22)28-18)23-10-7-19(26)27-20(23)29-23/h7,10,13-18,20,25H,3-6,8-9,11-12H2,1-2H3/t13-,14+,15+,16-,17+,18-,20-,21+,22-,23+,24-/m1/s1
SMILES:	C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@H](C[C@@H]3[C@]12O3)[C@@]12C=CC(=O)O[C@@H]1O2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485810
PubChem CID:	10453620
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001557] Bufanolides 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
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)99818-1]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	roots	n.a.	n.a.	PMID[10346940]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421725]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575946]
NPO33241	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141860]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165135]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15635246]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730237]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17504571]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21185919]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	twigs and leaves	Yunnan Province, China	2008-OCT	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21954912]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22708620]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7543	Haplopappus venetus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6887	Lytanthus salicinus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	Species	Asteraceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	10.88	ug.mL-1	PMID[448220]
NPT1366	Cell Line	MH60	Mus musculus	IC50	=	1.82	ug.mL-1	PMID[448220]
NPT1366	Cell Line	MH60	Mus musculus	IC50	=	18300.0	nM	PMID[448221]
NPT1366	Cell Line	MH60	Mus musculus	IC50	=	45000.0	nM	PMID[448221]

☑ 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 NPC113425 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	256
0.1-0.2	1874
0.2-0.3	5560
0.3-0.4	12403
0.4-0.5	9492
0.5-0.6	6787
0.6-0.7	4913
0.7-0.8	1329
0.8-0.85	76
0.85-0.9	2
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC232564
0.9533	High Similarity	NPC214005
0.9533	High Similarity	NPC150228
0.8957	High Similarity	NPC115349
0.8929	High Similarity	NPC268213
0.885	High Similarity	NPC290693
0.8673	High Similarity	NPC69576
0.8673	High Similarity	NPC84949
0.8673	High Similarity	NPC31354
0.8673	High Similarity	NPC471633
0.8609	High Similarity	NPC16701
0.8596	High Similarity	NPC5311
0.8596	High Similarity	NPC310341
0.8596	High Similarity	NPC199428
0.8596	High Similarity	NPC99620
0.8596	High Similarity	NPC193382
0.8534	High Similarity	NPC153085
0.8534	High Similarity	NPC29639
0.8534	High Similarity	NPC44899
0.8534	High Similarity	NPC278681
0.8534	High Similarity	NPC213761
0.8534	High Similarity	NPC5883
0.8534	High Similarity	NPC268326
0.8534	High Similarity	NPC304260
0.8534	High Similarity	NPC35171
0.8522	High Similarity	NPC196429
0.8522	High Similarity	NPC244402
0.8522	High Similarity	NPC474418
0.8522	High Similarity	NPC471351
0.8522	High Similarity	NPC84987
0.8522	High Similarity	NPC93883
0.8522	High Similarity	NPC142066
0.8522	High Similarity	NPC157376
0.8522	High Similarity	NPC471354
0.8522	High Similarity	NPC99728
0.8522	High Similarity	NPC152615
0.8522	High Similarity	NPC50305
0.8522	High Similarity	NPC471353
0.8522	High Similarity	NPC473852
0.8522	High Similarity	NPC158344
0.8522	High Similarity	NPC77319
0.8522	High Similarity	NPC157380
0.8522	High Similarity	NPC27507
0.8522	High Similarity	NPC471355
0.8522	High Similarity	NPC87250
0.8522	High Similarity	NPC309034
0.8522	High Similarity	NPC243196
0.8522	High Similarity	NPC203862
0.8522	High Similarity	NPC34390
0.8482	Intermediate Similarity	NPC103491
0.8462	Intermediate Similarity	NPC112936
0.8448	Intermediate Similarity	NPC83287
0.8421	Intermediate Similarity	NPC171126
0.839	Intermediate Similarity	NPC475219
0.839	Intermediate Similarity	NPC231518
0.8376	Intermediate Similarity	NPC32177
0.8376	Intermediate Similarity	NPC55532
0.8376	Intermediate Similarity	NPC30483
0.8376	Intermediate Similarity	NPC292467
0.8376	Intermediate Similarity	NPC470897
0.8376	Intermediate Similarity	NPC329905
0.8376	Intermediate Similarity	NPC236973
0.8376	Intermediate Similarity	NPC469756
0.8362	Intermediate Similarity	NPC185287
0.8319	Intermediate Similarity	NPC193893
0.8305	Intermediate Similarity	NPC474466
0.8305	Intermediate Similarity	NPC475556
0.8305	Intermediate Similarity	NPC257610
0.8305	Intermediate Similarity	NPC475136
0.8305	Intermediate Similarity	NPC475629
0.8305	Intermediate Similarity	NPC135369
0.8305	Intermediate Similarity	NPC72260
0.8291	Intermediate Similarity	NPC472080
0.8291	Intermediate Similarity	NPC218093
0.8246	Intermediate Similarity	NPC470076
0.8235	Intermediate Similarity	NPC173555
0.8235	Intermediate Similarity	NPC475590
0.8235	Intermediate Similarity	NPC474908
0.8235	Intermediate Similarity	NPC475419
0.8235	Intermediate Similarity	NPC120390
0.8235	Intermediate Similarity	NPC314535
0.8235	Intermediate Similarity	NPC40749
0.823	Intermediate Similarity	NPC475030
0.823	Intermediate Similarity	NPC472901
0.822	Intermediate Similarity	NPC291820
0.822	Intermediate Similarity	NPC81222
0.8214	Intermediate Similarity	NPC79298
0.8214	Intermediate Similarity	NPC43063
0.8211	Intermediate Similarity	NPC473593
0.8182	Intermediate Similarity	NPC8374
0.8174	Intermediate Similarity	NPC44537
0.8167	Intermediate Similarity	NPC264336
0.8167	Intermediate Similarity	NPC74259
0.8167	Intermediate Similarity	NPC474423
0.8151	Intermediate Similarity	NPC107607
0.8125	Intermediate Similarity	NPC220217
0.8125	Intermediate Similarity	NPC119855
0.812	Intermediate Similarity	NPC207637
0.8115	Intermediate Similarity	NPC179261
0.8108	Intermediate Similarity	NPC160583
0.8108	Intermediate Similarity	NPC472821
0.8099	Intermediate Similarity	NPC117445
0.8099	Intermediate Similarity	NPC27363
0.8099	Intermediate Similarity	NPC208193
0.8099	Intermediate Similarity	NPC308262
0.8091	Intermediate Similarity	NPC268829
0.8091	Intermediate Similarity	NPC247701
0.8091	Intermediate Similarity	NPC25177
0.8091	Intermediate Similarity	NPC222875
0.8091	Intermediate Similarity	NPC295110
0.8087	Intermediate Similarity	NPC472987
0.8087	Intermediate Similarity	NPC473021
0.8083	Intermediate Similarity	NPC312481
0.8083	Intermediate Similarity	NPC233500
0.808	Intermediate Similarity	NPC231240
0.807	Intermediate Similarity	NPC75389
0.8067	Intermediate Similarity	NPC219656
0.8065	Intermediate Similarity	NPC471407
0.8034	Intermediate Similarity	NPC216665
0.8017	Intermediate Similarity	NPC153700
0.8017	Intermediate Similarity	NPC88326
0.8017	Intermediate Similarity	NPC196130
0.8017	Intermediate Similarity	NPC475354
0.8017	Intermediate Similarity	NPC471082
0.8016	Intermediate Similarity	NPC316915
0.8	Intermediate Similarity	NPC170814
0.8	Intermediate Similarity	NPC12795
0.8	Intermediate Similarity	NPC219285
0.8	Intermediate Similarity	NPC228251
0.8	Intermediate Similarity	NPC470312
0.8	Intermediate Similarity	NPC477971
0.8	Intermediate Similarity	NPC161527
0.8	Intermediate Similarity	NPC20113
0.8	Intermediate Similarity	NPC477972
0.8	Intermediate Similarity	NPC477968
0.7984	Intermediate Similarity	NPC473620
0.7982	Intermediate Similarity	NPC137462
0.7982	Intermediate Similarity	NPC304276
0.7982	Intermediate Similarity	NPC275060
0.7967	Intermediate Similarity	NPC469750
0.7967	Intermediate Similarity	NPC250556
0.7966	Intermediate Similarity	NPC212660
0.7966	Intermediate Similarity	NPC470075
0.7965	Intermediate Similarity	NPC186668
0.7965	Intermediate Similarity	NPC295843
0.7965	Intermediate Similarity	NPC473199
0.7951	Intermediate Similarity	NPC6193
0.7951	Intermediate Similarity	NPC219804
0.7946	Intermediate Similarity	NPC196471
0.7946	Intermediate Similarity	NPC10232
0.7946	Intermediate Similarity	NPC281378
0.7946	Intermediate Similarity	NPC171014
0.7946	Intermediate Similarity	NPC187302
0.7946	Intermediate Similarity	NPC189588
0.7946	Intermediate Similarity	NPC97487
0.7937	Intermediate Similarity	NPC471855
0.7934	Intermediate Similarity	NPC473256
0.7934	Intermediate Similarity	NPC67569
0.7934	Intermediate Similarity	NPC470878
0.7931	Intermediate Similarity	NPC114188
0.792	Intermediate Similarity	NPC476966
0.7917	Intermediate Similarity	NPC475834
0.7917	Intermediate Similarity	NPC474179
0.7913	Intermediate Similarity	NPC206618
0.7903	Intermediate Similarity	NPC240070
0.7903	Intermediate Similarity	NPC146456
0.7903	Intermediate Similarity	NPC469757
0.7903	Intermediate Similarity	NPC179412
0.7903	Intermediate Similarity	NPC298841
0.7903	Intermediate Similarity	NPC329784
0.7903	Intermediate Similarity	NPC287423
0.7903	Intermediate Similarity	NPC42399
0.7903	Intermediate Similarity	NPC117702
0.7903	Intermediate Similarity	NPC471357
0.7903	Intermediate Similarity	NPC471356
0.7895	Intermediate Similarity	NPC33053
0.7895	Intermediate Similarity	NPC472820
0.7886	Intermediate Similarity	NPC241456
0.7886	Intermediate Similarity	NPC469790
0.7886	Intermediate Similarity	NPC32868
0.7881	Intermediate Similarity	NPC43213
0.7876	Intermediate Similarity	NPC470058
0.7876	Intermediate Similarity	NPC470059
0.7876	Intermediate Similarity	NPC470043
0.7876	Intermediate Similarity	NPC470064
0.7876	Intermediate Similarity	NPC470057
0.7876	Intermediate Similarity	NPC470062
0.7876	Intermediate Similarity	NPC470060
0.7876	Intermediate Similarity	NPC165969
0.7876	Intermediate Similarity	NPC470061
0.787	Intermediate Similarity	NPC201725
0.7869	Intermediate Similarity	NPC470265
0.7869	Intermediate Similarity	NPC23786
0.7863	Intermediate Similarity	NPC216595
0.7863	Intermediate Similarity	NPC473125
0.7863	Intermediate Similarity	NPC473567
0.7857	Intermediate Similarity	NPC154452
0.7857	Intermediate Similarity	NPC470972
0.7857	Intermediate Similarity	NPC173347
0.7851	Intermediate Similarity	NPC474370

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 NPC113425 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	1983
0.2-0.3	4118
0.3-0.4	1955
0.4-0.5	459
0.5-0.6	282
0.6-0.7	109
0.7-0.8	22
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8448	Intermediate Similarity	NPD7327	Approved
0.8448	Intermediate Similarity	NPD7328	Approved
0.839	Intermediate Similarity	NPD8033	Approved
0.839	Intermediate Similarity	NPD7503	Approved
0.8376	Intermediate Similarity	NPD7516	Approved
0.8305	Intermediate Similarity	NPD8377	Approved
0.8305	Intermediate Similarity	NPD8294	Approved
0.8235	Intermediate Similarity	NPD8378	Approved
0.8235	Intermediate Similarity	NPD8380	Approved
0.8235	Intermediate Similarity	NPD8379	Approved
0.8235	Intermediate Similarity	NPD8296	Approved
0.8235	Intermediate Similarity	NPD8335	Approved
0.7967	Intermediate Similarity	NPD7507	Approved
0.7778	Intermediate Similarity	NPD7319	Approved
0.7748	Intermediate Similarity	NPD7638	Approved
0.7679	Intermediate Similarity	NPD7640	Approved
0.7679	Intermediate Similarity	NPD7639	Approved
0.7603	Intermediate Similarity	NPD7115	Discovery
0.7559	Intermediate Similarity	NPD7736	Approved
0.7456	Intermediate Similarity	NPD5344	Discontinued
0.7373	Intermediate Similarity	NPD6686	Approved
0.7317	Intermediate Similarity	NPD6009	Approved
0.7311	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6370	Approved
0.7288	Intermediate Similarity	NPD6412	Phase 2
0.7241	Intermediate Similarity	NPD7632	Discontinued
0.7217	Intermediate Similarity	NPD6648	Approved
0.7213	Intermediate Similarity	NPD8133	Approved
0.7188	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6054	Approved
0.7132	Intermediate Similarity	NPD6616	Approved
0.7131	Intermediate Similarity	NPD6882	Approved
0.7107	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7078	Approved
0.7077	Intermediate Similarity	NPD8293	Discontinued
0.7073	Intermediate Similarity	NPD4632	Approved
0.6992	Remote Similarity	NPD8297	Approved
0.6977	Remote Similarity	NPD7604	Phase 2
0.6953	Remote Similarity	NPD6015	Approved
0.6953	Remote Similarity	NPD6016	Approved
0.6942	Remote Similarity	NPD6899	Approved
0.6942	Remote Similarity	NPD6881	Approved
0.6917	Remote Similarity	NPD6008	Approved
0.6901	Remote Similarity	NPD7625	Phase 1
0.6899	Remote Similarity	NPD5988	Approved
0.6875	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD6319	Approved
0.686	Remote Similarity	NPD5697	Approved
0.686	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4225	Approved
0.6829	Remote Similarity	NPD6883	Approved
0.6829	Remote Similarity	NPD7290	Approved
0.6829	Remote Similarity	NPD7102	Approved
0.6822	Remote Similarity	NPD5983	Phase 2
0.6803	Remote Similarity	NPD6011	Approved
0.6777	Remote Similarity	NPD5739	Approved
0.6777	Remote Similarity	NPD7128	Approved
0.6777	Remote Similarity	NPD6402	Approved
0.6777	Remote Similarity	NPD6675	Approved
0.6774	Remote Similarity	NPD8130	Phase 1
0.6774	Remote Similarity	NPD6869	Approved
0.6774	Remote Similarity	NPD6650	Approved
0.6774	Remote Similarity	NPD6649	Approved
0.6774	Remote Similarity	NPD6847	Approved
0.6774	Remote Similarity	NPD6617	Approved
0.6748	Remote Similarity	NPD6012	Approved
0.6748	Remote Similarity	NPD6013	Approved
0.6748	Remote Similarity	NPD6014	Approved
0.6742	Remote Similarity	NPD6336	Discontinued
0.6726	Remote Similarity	NPD6051	Approved
0.672	Remote Similarity	NPD6053	Discontinued
0.6718	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD7320	Approved
0.6613	Remote Similarity	NPD6372	Approved
0.6613	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6373	Approved
0.6591	Remote Similarity	NPD8328	Phase 3
0.6585	Remote Similarity	NPD5701	Approved
0.6565	Remote Similarity	NPD8513	Phase 3
0.6555	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8171	Discontinued
0.6529	Remote Similarity	NPD5211	Phase 2
0.6522	Remote Similarity	NPD7838	Discovery
0.6519	Remote Similarity	NPD6033	Approved
0.6514	Remote Similarity	NPD6928	Phase 2
0.6512	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5285	Approved
0.65	Remote Similarity	NPD5286	Approved
0.65	Remote Similarity	NPD4696	Approved
0.6471	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6084	Phase 2
0.6462	Remote Similarity	NPD6335	Approved
0.6446	Remote Similarity	NPD5223	Approved
0.6446	Remote Similarity	NPD4159	Approved
0.6439	Remote Similarity	NPD8516	Approved
0.6439	Remote Similarity	NPD8515	Approved
0.6439	Remote Similarity	NPD8517	Approved
0.6429	Remote Similarity	NPD4634	Approved
0.6429	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6371	Approved
0.6423	Remote Similarity	NPD5141	Approved
0.6412	Remote Similarity	NPD7101	Approved
0.6412	Remote Similarity	NPD7100	Approved
0.641	Remote Similarity	NPD4202	Approved
0.641	Remote Similarity	NPD6399	Phase 3
0.6404	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD5226	Approved
0.6393	Remote Similarity	NPD5225	Approved
0.6393	Remote Similarity	NPD4633	Approved
0.6393	Remote Similarity	NPD5224	Approved
0.6385	Remote Similarity	NPD6317	Approved
0.6356	Remote Similarity	NPD7748	Approved
0.6348	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5175	Approved
0.6341	Remote Similarity	NPD5174	Approved
0.6336	Remote Similarity	NPD6313	Approved
0.6336	Remote Similarity	NPD6314	Approved
0.6333	Remote Similarity	NPD7902	Approved
0.6333	Remote Similarity	NPD4755	Approved
0.6325	Remote Similarity	NPD7515	Phase 2
0.6325	Remote Similarity	NPD8034	Phase 2
0.6325	Remote Similarity	NPD7637	Suspended
0.6325	Remote Similarity	NPD6079	Approved
0.6325	Remote Similarity	NPD8035	Phase 2
0.6308	Remote Similarity	NPD6274	Approved
0.6303	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.629	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4195	Approved
0.6261	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5785	Approved
0.6239	Remote Similarity	NPD6698	Approved
0.6239	Remote Similarity	NPD46	Approved
0.6235	Remote Similarity	NPD7799	Discontinued
0.623	Remote Similarity	NPD4700	Approved
0.6228	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6695	Phase 3
0.6194	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD5956	Approved
0.6186	Remote Similarity	NPD5693	Phase 1
0.6174	Remote Similarity	NPD5330	Approved
0.6174	Remote Similarity	NPD6684	Approved
0.6174	Remote Similarity	NPD7521	Approved
0.6174	Remote Similarity	NPD7334	Approved
0.6174	Remote Similarity	NPD6409	Approved
0.6174	Remote Similarity	NPD7146	Approved
0.6167	Remote Similarity	NPD5695	Phase 3
0.6154	Remote Similarity	NPD5328	Approved
0.6148	Remote Similarity	NPD5696	Approved
0.6147	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD4730	Approved
0.6142	Remote Similarity	NPD4729	Approved
0.6116	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD5222	Approved
0.6116	Remote Similarity	NPD5221	Approved
0.6102	Remote Similarity	NPD3168	Discontinued
0.6083	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7900	Approved
0.6083	Remote Similarity	NPD6001	Approved
0.608	Remote Similarity	NPD4754	Approved
0.6074	Remote Similarity	NPD6908	Approved
0.6074	Remote Similarity	NPD6909	Approved
0.6068	Remote Similarity	NPD6903	Approved
0.6066	Remote Similarity	NPD5173	Approved
0.6063	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6868	Approved
0.6055	Remote Similarity	NPD6942	Approved
0.6055	Remote Similarity	NPD7339	Approved
0.605	Remote Similarity	NPD5284	Approved
0.605	Remote Similarity	NPD5281	Approved
0.6047	Remote Similarity	NPD5135	Approved
0.6047	Remote Similarity	NPD5247	Approved
0.6047	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6047	Remote Similarity	NPD5251	Approved
0.6047	Remote Similarity	NPD5169	Approved
0.6047	Remote Similarity	NPD5250	Approved
0.6047	Remote Similarity	NPD5249	Phase 3
0.6047	Remote Similarity	NPD5248	Approved
0.6036	Remote Similarity	NPD6697	Approved
0.6036	Remote Similarity	NPD6115	Approved
0.6036	Remote Similarity	NPD6114	Approved
0.6036	Remote Similarity	NPD6118	Approved
0.6034	Remote Similarity	NPD3618	Phase 1
0.6033	Remote Similarity	NPD5210	Approved
0.6033	Remote Similarity	NPD4629	Approved
0.6028	Remote Similarity	NPD7260	Phase 2
0.6026	Remote Similarity	NPD7236	Approved
0.6017	Remote Similarity	NPD6904	Approved
0.6017	Remote Similarity	NPD6673	Approved
0.6017	Remote Similarity	NPD4753	Phase 2
0.6017	Remote Similarity	NPD6080	Approved
0.6016	Remote Similarity	NPD5128	Approved
0.6	Remote Similarity	NPD3666	Approved
0.6	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD5215	Approved
0.6	Remote Similarity	NPD5127	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