NPASS Compound

Structure

CID295843 OpenBabel06191716102D 29 33 0 0 1 0 0 0 0 0999 V2000 0.8132 2.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7177 0.9917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1021 -0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5314 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0701 -0.1994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5308 3.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6873 2.9226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3749 1.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8433 1.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9259 1.3755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5300 0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5314 1.4616 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3746 2.9221 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6871 -0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0005 1.9484 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4660 0.6898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8433 0.4869 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 4.2407 3.4221 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0005 2.9484 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4340 0.7916 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8939 1.4773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 23 1 0 0 0 0 3 6 2 0 0 0 0 3 14 1 0 0 0 0 4 5 1 0 0 0 0 4 15 1 0 0 0 0 5 18 1 0 0 0 0 6 20 1 0 0 0 0 7 9 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 22 1 0 0 0 0 10 24 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 19 1 0 0 0 0 12 23 1 0 0 0 0 13 14 2 0 0 0 0 13 29 1 0 0 0 0 14 17 1 0 0 0 0 15 22 1 1 0 0 0 16 25 1 6 0 0 0 17 23 1 6 0 0 0 18 21 1 0 0 0 0 18 24 1 1 0 0 0 19 21 1 0 0 0 0 19 26 1 1 0 0 0 20 27 2 0 0 0 0 20 29 1 0 0 0 0 21 22 1 6 0 0 0 22 1 1 6 0 0 0 23 24 1 6 0 0 0 24 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.24
Volume:	416.92
LogP:	2.564
LogD:	2.356
LogS:	-3.943
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	4.625
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.909
MDCK Permeability:	1.4324431504064705e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288
Plasma Protein Binding (PPB):	89.59502410888672%
Volume Distribution (VD):	0.855
Pgp-substrate:	9.806159019470215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.65
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.672
CYP2C9-inhibitor:	0.148
CYP2C9-substrate:	0.17
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.248
CYP3A4-inhibitor:	0.716
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	9.623
Half-life (T1/2):	0.327

ADMET: Toxicity

hERG Blockers:	0.308
Human Hepatotoxicity (H-HT):	0.368
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.888
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.478
Carcinogencity:	0.703
Eye Corrosion:	0.027
Eye Irritation:	0.067
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC295843

Natural Product ID:	NPC295843
*Common Name:**	Gamabufotalin
IUPAC Name:	5-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3,11,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
Synonyms:	Gamabufotalin
Standard InCHIKey:	FMTLOAVOGWSPEF-KJRPADTMSA-N
Standard InCHI:	InChI=1S/C24H34O5/c1-22-9-7-16(25)11-15(22)4-5-18-21(22)19(26)12-23(2)17(8-10-24(18,23)28)14-3-6-20(27)29-13-14/h3,6,13,15-19,21,25-26,28H,4-5,7-12H2,1-2H3/t15-,16+,17-,18-,19-,21-,22+,23-,24+/m1/s1
SMILES:	C[C@]12CC[C@@H](C[C@H]1CC[C@@H]1[C@@H]2[C@@H](C[C@]2(C)[C@H](CC[C@]12O)c1ccc(=O)oc1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465318
PubChem CID:	259803
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]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21185919]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	twigs and leaves	Yunnan Province, China	2008-OCT	PMID[21954912]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	twig	n.a.	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]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	venom	n.a.	n.a.	PMID[24050254]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26722868]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28256122]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21528	Equisetum arvense	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31404	Bufo melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21528	Equisetum arvense	Species	Equisetaceae	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]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21528	Equisetum arvense	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	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]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	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]
NPO31404	Bufo melanostictus	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5177	Lecanora conizaeoides	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9576	Bufo bufo	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12952	Cabucala madagascariensis	Species	Apocynaceae	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]
NPO2498	Kochia trichophylla	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12735	Halimeda macroloba	Species	Halimedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12012	Saururus cernuus	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO223	Rhaponticum carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21528	Equisetum arvense	Species	Equisetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9398	Cortinarius rubellus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11981	Bufo gargarizans	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19205	Buxus sempervirens	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6011	Pleurotus citrinopileatus	Species	Pleurotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11885	Dysoxylum lenticellatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21463	Aruncus dioicus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7884	Centaurea amara	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11515	Streptomyces plumbeus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO664	Potentilla multifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2917	Artemisia oranensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26231	Vicia villosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12250	Strychnos fendleri	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4797	Gavia immer	Species	Gaviidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7543	Haplopappus venetus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3983	Piper futokadsura	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10672	Vitex megapotamica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10043	Phebalium ozothamnoides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8733	Duttaphrynus melanostictus	Species	Bufonidae	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	5

Activity Type	# Activity
Cell Line	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.75	ug.mL-1	PMID[574008]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	0.014	ug.mL-1	PMID[574008]
NPT1366	Cell Line	MH60	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[574008]
NPT2	Others	Unspecified		IC50	=	0.00023	ug.mL-1	PMID[574007]
NPT2	Others	Unspecified		IC50	=	0.0008	ug.mL-1	PMID[574007]

☑ 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 NPC295843 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	353
0.1-0.2	1401
0.2-0.3	2692
0.3-0.4	5074
0.4-0.5	10173
0.5-0.6	10233
0.6-0.7	10081
0.7-0.8	2330
0.8-0.85	255
0.85-0.9	51
0.9-0.95	29
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC171014
0.9604	High Similarity	NPC12795
0.96	High Similarity	NPC275060
0.9505	High Similarity	NPC75389
0.95	High Similarity	NPC43063
0.95	High Similarity	NPC79298
0.9406	High Similarity	NPC137462
0.9406	High Similarity	NPC304276
0.9231	High Similarity	NPC44537
0.9223	High Similarity	NPC103491
0.9143	High Similarity	NPC241977
0.9143	High Similarity	NPC171126
0.9135	High Similarity	NPC183603
0.9038	High Similarity	NPC16270
0.8962	High Similarity	NPC154815
0.8962	High Similarity	NPC73050
0.8922	High Similarity	NPC165969
0.8889	High Similarity	NPC185287
0.8889	High Similarity	NPC157380
0.8868	High Similarity	NPC247760
0.8835	High Similarity	NPC189863
0.8818	High Similarity	NPC41123
0.8818	High Similarity	NPC257610
0.8818	High Similarity	NPC145074
0.8818	High Similarity	NPC114939
0.8807	High Similarity	NPC16701
0.8727	High Similarity	NPC278681
0.8727	High Similarity	NPC35171
0.8727	High Similarity	NPC213761
0.8649	High Similarity	NPC112936
0.8641	High Similarity	NPC160583
0.8636	High Similarity	NPC146786
0.8482	Intermediate Similarity	NPC184555
0.8476	Intermediate Similarity	NPC266570
0.8447	Intermediate Similarity	NPC25177
0.8447	Intermediate Similarity	NPC247701
0.8447	Intermediate Similarity	NPC222875
0.8447	Intermediate Similarity	NPC268829
0.8447	Intermediate Similarity	NPC295110
0.8416	Intermediate Similarity	NPC299654
0.8407	Intermediate Similarity	NPC312481
0.84	Intermediate Similarity	NPC201725
0.8333	Intermediate Similarity	NPC231751
0.8302	Intermediate Similarity	NPC119855
0.8302	Intermediate Similarity	NPC220217
0.8286	Intermediate Similarity	NPC97487
0.8286	Intermediate Similarity	NPC297617
0.8286	Intermediate Similarity	NPC196471
0.8286	Intermediate Similarity	NPC10232
0.8286	Intermediate Similarity	NPC472821
0.8286	Intermediate Similarity	NPC189588
0.8286	Intermediate Similarity	NPC187302
0.8261	Intermediate Similarity	NPC6193
0.8261	Intermediate Similarity	NPC55602
0.8257	Intermediate Similarity	NPC255401
0.8257	Intermediate Similarity	NPC284162
0.8252	Intermediate Similarity	NPC108368
0.8252	Intermediate Similarity	NPC181147
0.8252	Intermediate Similarity	NPC278673
0.8252	Intermediate Similarity	NPC218107
0.8252	Intermediate Similarity	NPC57079
0.8252	Intermediate Similarity	NPC92275
0.8235	Intermediate Similarity	NPC190713
0.8235	Intermediate Similarity	NPC16967
0.822	Intermediate Similarity	NPC221414
0.8218	Intermediate Similarity	NPC191521
0.8155	Intermediate Similarity	NPC99726
0.8131	Intermediate Similarity	NPC186668
0.812	Intermediate Similarity	NPC159499
0.8119	Intermediate Similarity	NPC214697
0.8119	Intermediate Similarity	NPC476304
0.8113	Intermediate Similarity	NPC112009
0.81	Intermediate Similarity	NPC302280
0.8095	Intermediate Similarity	NPC168319
0.8095	Intermediate Similarity	NPC194028
0.8091	Intermediate Similarity	NPC262083
0.8091	Intermediate Similarity	NPC471484
0.8073	Intermediate Similarity	NPC475030
0.8039	Intermediate Similarity	NPC476186
0.8039	Intermediate Similarity	NPC105490
0.8037	Intermediate Similarity	NPC272632
0.8037	Intermediate Similarity	NPC200861
0.8037	Intermediate Similarity	NPC472822
0.8034	Intermediate Similarity	NPC233041
0.802	Intermediate Similarity	NPC212948
0.802	Intermediate Similarity	NPC110923
0.802	Intermediate Similarity	NPC74296
0.8	Intermediate Similarity	NPC472240
0.8	Intermediate Similarity	NPC262858
0.8	Intermediate Similarity	NPC473647
0.8	Intermediate Similarity	NPC238850
0.8	Intermediate Similarity	NPC201406
0.8	Intermediate Similarity	NPC251680
0.8	Intermediate Similarity	NPC472826
0.7981	Intermediate Similarity	NPC210337
0.7981	Intermediate Similarity	NPC141401
0.7966	Intermediate Similarity	NPC179261
0.7965	Intermediate Similarity	NPC232564
0.7965	Intermediate Similarity	NPC113425
0.7963	Intermediate Similarity	NPC471206
0.7951	Intermediate Similarity	NPC248703
0.7944	Intermediate Similarity	NPC183570
0.7944	Intermediate Similarity	NPC180204
0.7941	Intermediate Similarity	NPC162615
0.7941	Intermediate Similarity	NPC205034
0.7941	Intermediate Similarity	NPC7349
0.7941	Intermediate Similarity	NPC38232
0.7941	Intermediate Similarity	NPC152778
0.7938	Intermediate Similarity	NPC470558
0.7928	Intermediate Similarity	NPC474315
0.7928	Intermediate Similarity	NPC470076
0.7921	Intermediate Similarity	NPC310479
0.79	Intermediate Similarity	NPC473879
0.79	Intermediate Similarity	NPC471952
0.7885	Intermediate Similarity	NPC253115
0.7885	Intermediate Similarity	NPC88009
0.7885	Intermediate Similarity	NPC195366
0.7885	Intermediate Similarity	NPC114743
0.7885	Intermediate Similarity	NPC301534
0.7885	Intermediate Similarity	NPC250757
0.7885	Intermediate Similarity	NPC304899
0.7876	Intermediate Similarity	NPC84949
0.7876	Intermediate Similarity	NPC31354
0.7876	Intermediate Similarity	NPC471633
0.7876	Intermediate Similarity	NPC69576
0.7864	Intermediate Similarity	NPC279410
0.7864	Intermediate Similarity	NPC119562
0.7863	Intermediate Similarity	NPC196130
0.7857	Intermediate Similarity	NPC470077
0.785	Intermediate Similarity	NPC32577
0.785	Intermediate Similarity	NPC155332
0.785	Intermediate Similarity	NPC114540
0.7845	Intermediate Similarity	NPC474370
0.7843	Intermediate Similarity	NPC177641
0.7843	Intermediate Similarity	NPC329842
0.783	Intermediate Similarity	NPC227865
0.783	Intermediate Similarity	NPC473510
0.783	Intermediate Similarity	NPC230546
0.783	Intermediate Similarity	NPC290802
0.7826	Intermediate Similarity	NPC83287
0.7822	Intermediate Similarity	NPC146554
0.781	Intermediate Similarity	NPC51499
0.781	Intermediate Similarity	NPC253826
0.7807	Intermediate Similarity	NPC5311
0.7807	Intermediate Similarity	NPC193382
0.7807	Intermediate Similarity	NPC199428
0.7807	Intermediate Similarity	NPC310341
0.7807	Intermediate Similarity	NPC99620
0.7798	Intermediate Similarity	NPC472818
0.7798	Intermediate Similarity	NPC34768
0.7798	Intermediate Similarity	NPC81630
0.7788	Intermediate Similarity	NPC276110
0.7788	Intermediate Similarity	NPC122056
0.7788	Intermediate Similarity	NPC474909
0.7778	Intermediate Similarity	NPC85742
0.7778	Intermediate Similarity	NPC45897
0.7778	Intermediate Similarity	NPC474013
0.7778	Intermediate Similarity	NPC280566
0.7778	Intermediate Similarity	NPC233500
0.7778	Intermediate Similarity	NPC318390
0.7778	Intermediate Similarity	NPC109528
0.7759	Intermediate Similarity	NPC219656
0.7759	Intermediate Similarity	NPC264954
0.7757	Intermediate Similarity	NPC11974
0.7757	Intermediate Similarity	NPC473160
0.7757	Intermediate Similarity	NPC282524
0.7748	Intermediate Similarity	NPC228477
0.7748	Intermediate Similarity	NPC137911
0.7745	Intermediate Similarity	NPC273199
0.7745	Intermediate Similarity	NPC78973
0.7745	Intermediate Similarity	NPC182136
0.7745	Intermediate Similarity	NPC221111
0.7745	Intermediate Similarity	NPC280149
0.7739	Intermediate Similarity	NPC471355
0.7739	Intermediate Similarity	NPC87250
0.7739	Intermediate Similarity	NPC93883
0.7739	Intermediate Similarity	NPC84987
0.7739	Intermediate Similarity	NPC158344
0.7739	Intermediate Similarity	NPC244402
0.7739	Intermediate Similarity	NPC473852
0.7739	Intermediate Similarity	NPC27507
0.7739	Intermediate Similarity	NPC474418
0.7739	Intermediate Similarity	NPC243196
0.7739	Intermediate Similarity	NPC142066
0.7739	Intermediate Similarity	NPC471351
0.7739	Intermediate Similarity	NPC309034
0.7739	Intermediate Similarity	NPC34390
0.7739	Intermediate Similarity	NPC157376
0.7739	Intermediate Similarity	NPC471354
0.7739	Intermediate Similarity	NPC196429
0.7739	Intermediate Similarity	NPC290693
0.7739	Intermediate Similarity	NPC77319
0.7739	Intermediate Similarity	NPC152615
0.7739	Intermediate Similarity	NPC99728
0.7739	Intermediate Similarity	NPC50305
0.7739	Intermediate Similarity	NPC471353
0.7736	Intermediate Similarity	NPC325229
0.7736	Intermediate Similarity	NPC275086
0.7736	Intermediate Similarity	NPC98868
0.7736	Intermediate Similarity	NPC186810

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 NPC295843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	865
0.2-0.3	1591
0.3-0.4	2559
0.4-0.5	2238
0.5-0.6	1153
0.6-0.7	393
0.7-0.8	40
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8246	Intermediate Similarity	NPD7503	Approved
0.8077	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7639	Approved
0.7826	Intermediate Similarity	NPD7327	Approved
0.7826	Intermediate Similarity	NPD7328	Approved
0.7759	Intermediate Similarity	NPD7516	Approved
0.7658	Intermediate Similarity	NPD6881	Approved
0.7658	Intermediate Similarity	NPD6899	Approved
0.7629	Intermediate Similarity	NPD7525	Registered
0.7586	Intermediate Similarity	NPD7115	Discovery
0.7568	Intermediate Similarity	NPD5697	Approved
0.7542	Intermediate Similarity	NPD8377	Approved
0.7542	Intermediate Similarity	NPD8294	Approved
0.7522	Intermediate Similarity	NPD7102	Approved
0.7522	Intermediate Similarity	NPD7290	Approved
0.7522	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.7479	Intermediate Similarity	NPD8380	Approved
0.7479	Intermediate Similarity	NPD8335	Approved
0.7479	Intermediate Similarity	NPD8379	Approved
0.7479	Intermediate Similarity	NPD8378	Approved
0.7479	Intermediate Similarity	NPD8033	Approved
0.7479	Intermediate Similarity	NPD8296	Approved
0.7477	Intermediate Similarity	NPD5739	Approved
0.7477	Intermediate Similarity	NPD6675	Approved
0.7477	Intermediate Similarity	NPD7128	Approved
0.7477	Intermediate Similarity	NPD6402	Approved
0.7476	Intermediate Similarity	NPD6051	Approved
0.7456	Intermediate Similarity	NPD8130	Phase 1
0.7456	Intermediate Similarity	NPD6617	Approved
0.7456	Intermediate Similarity	NPD6650	Approved
0.7456	Intermediate Similarity	NPD6869	Approved
0.7456	Intermediate Similarity	NPD6649	Approved
0.7456	Intermediate Similarity	NPD6847	Approved
0.7434	Intermediate Similarity	NPD6013	Approved
0.7434	Intermediate Similarity	NPD6012	Approved
0.7434	Intermediate Similarity	NPD6014	Approved
0.7391	Intermediate Similarity	NPD6882	Approved
0.7391	Intermediate Similarity	NPD8297	Approved
0.7364	Intermediate Similarity	NPD7632	Discontinued
0.7364	Intermediate Similarity	NPD5211	Phase 2
0.7345	Intermediate Similarity	NPD7320	Approved
0.7339	Intermediate Similarity	NPD5285	Approved
0.7339	Intermediate Similarity	NPD5286	Approved
0.7339	Intermediate Similarity	NPD4696	Approved
0.7281	Intermediate Similarity	NPD6373	Approved
0.7281	Intermediate Similarity	NPD6372	Approved
0.7273	Intermediate Similarity	NPD5223	Approved
0.7264	Intermediate Similarity	NPD4202	Approved
0.7257	Intermediate Similarity	NPD5701	Approved
0.7236	Intermediate Similarity	NPD7507	Approved
0.7232	Intermediate Similarity	NPD5141	Approved
0.7207	Intermediate Similarity	NPD5224	Approved
0.7207	Intermediate Similarity	NPD5225	Approved
0.7207	Intermediate Similarity	NPD4633	Approved
0.7207	Intermediate Similarity	NPD5226	Approved
0.7179	Intermediate Similarity	NPD4632	Approved
0.7172	Intermediate Similarity	NPD4195	Approved
0.717	Intermediate Similarity	NPD7515	Phase 2
0.717	Intermediate Similarity	NPD5284	Approved
0.717	Intermediate Similarity	NPD6079	Approved
0.717	Intermediate Similarity	NPD5281	Approved
0.7156	Intermediate Similarity	NPD6083	Phase 2
0.7156	Intermediate Similarity	NPD4755	Approved
0.7156	Intermediate Similarity	NPD6084	Phase 2
0.7155	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD5174	Approved
0.7094	Intermediate Similarity	NPD6053	Discontinued
0.7091	Intermediate Similarity	NPD4225	Approved
0.7087	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6335	Approved
0.7063	Intermediate Similarity	NPD7319	Approved
0.7048	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7748	Approved
0.7027	Intermediate Similarity	NPD4700	Approved
0.7025	Intermediate Similarity	NPD7100	Approved
0.7025	Intermediate Similarity	NPD7101	Approved
0.7009	Intermediate Similarity	NPD8035	Phase 2
0.7009	Intermediate Similarity	NPD8034	Phase 2
0.7	Intermediate Similarity	NPD6009	Approved
0.7	Intermediate Similarity	NPD7902	Approved
0.7	Intermediate Similarity	NPD6317	Approved
0.6981	Remote Similarity	NPD5328	Approved
0.6944	Remote Similarity	NPD6399	Phase 3
0.6942	Remote Similarity	NPD6314	Approved
0.6942	Remote Similarity	NPD6313	Approved
0.6917	Remote Similarity	NPD6274	Approved
0.6909	Remote Similarity	NPD5221	Approved
0.6909	Remote Similarity	NPD5222	Approved
0.6909	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4730	Approved
0.6897	Remote Similarity	NPD4729	Approved
0.6893	Remote Similarity	NPD4788	Approved
0.6875	Remote Similarity	NPD6648	Approved
0.6869	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7334	Approved
0.6857	Remote Similarity	NPD7146	Approved
0.6857	Remote Similarity	NPD6409	Approved
0.6857	Remote Similarity	NPD5330	Approved
0.6857	Remote Similarity	NPD6684	Approved
0.6857	Remote Similarity	NPD3618	Phase 1
0.6857	Remote Similarity	NPD7521	Approved
0.6852	Remote Similarity	NPD7637	Suspended
0.6852	Remote Similarity	NPD5693	Phase 1
0.685	Remote Similarity	NPD7736	Approved
0.6847	Remote Similarity	NPD5173	Approved
0.6842	Remote Similarity	NPD4754	Approved
0.6837	Remote Similarity	NPD6926	Approved
0.6837	Remote Similarity	NPD6924	Approved
0.6832	Remote Similarity	NPD7645	Phase 2
0.6829	Remote Similarity	NPD6319	Approved
0.6827	Remote Similarity	NPD3665	Phase 1
0.6827	Remote Similarity	NPD3133	Approved
0.6827	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD3666	Approved
0.6822	Remote Similarity	NPD4753	Phase 2
0.6818	Remote Similarity	NPD5695	Phase 3
0.6818	Remote Similarity	NPD5210	Approved
0.6818	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4629	Approved
0.6814	Remote Similarity	NPD5344	Discontinued
0.68	Remote Similarity	NPD7604	Phase 2
0.6792	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5696	Approved
0.678	Remote Similarity	NPD5169	Approved
0.678	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5248	Approved
0.678	Remote Similarity	NPD5247	Approved
0.678	Remote Similarity	NPD5251	Approved
0.678	Remote Similarity	NPD4634	Approved
0.678	Remote Similarity	NPD5249	Phase 3
0.678	Remote Similarity	NPD5135	Approved
0.678	Remote Similarity	NPD5250	Approved
0.6774	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5983	Phase 2
0.6768	Remote Similarity	NPD6942	Approved
0.6768	Remote Similarity	NPD7339	Approved
0.6759	Remote Similarity	NPD5785	Approved
0.6752	Remote Similarity	NPD5128	Approved
0.6746	Remote Similarity	NPD7492	Approved
0.6731	Remote Similarity	NPD6695	Phase 3
0.6729	Remote Similarity	NPD6903	Approved
0.6727	Remote Similarity	NPD7900	Approved
0.6727	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4767	Approved
0.6724	Remote Similarity	NPD6008	Approved
0.6724	Remote Similarity	NPD4768	Approved
0.6723	Remote Similarity	NPD5215	Approved
0.6723	Remote Similarity	NPD5127	Approved
0.6723	Remote Similarity	NPD5217	Approved
0.6723	Remote Similarity	NPD5216	Approved
0.67	Remote Similarity	NPD6933	Approved
0.6697	Remote Similarity	NPD5694	Approved
0.6697	Remote Similarity	NPD6050	Approved
0.6695	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD6054	Approved
0.6693	Remote Similarity	NPD6616	Approved
0.6693	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6643	Remote Similarity	NPD7236	Approved
0.6641	Remote Similarity	NPD7078	Approved
0.664	Remote Similarity	NPD6909	Approved
0.664	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD6868	Approved
0.6635	Remote Similarity	NPD4221	Approved
0.6635	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4223	Phase 3
0.6633	Remote Similarity	NPD7150	Approved
0.6633	Remote Similarity	NPD7152	Approved
0.6633	Remote Similarity	NPD7151	Approved
0.6633	Remote Similarity	NPD4243	Approved
0.661	Remote Similarity	NPD6686	Approved
0.6607	Remote Similarity	NPD4697	Phase 3
0.6606	Remote Similarity	NPD5692	Phase 3
0.6606	Remote Similarity	NPD5207	Approved
0.6604	Remote Similarity	NPD5329	Approved
0.6604	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6931	Approved
0.6602	Remote Similarity	NPD6930	Phase 2
0.6602	Remote Similarity	NPD7514	Phase 3
0.6602	Remote Similarity	NPD7509	Discontinued
0.6587	Remote Similarity	NPD6370	Approved
0.6574	Remote Similarity	NPD5737	Approved
0.6574	Remote Similarity	NPD6672	Approved
0.6569	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5167	Approved
0.6542	Remote Similarity	NPD5280	Approved
0.6542	Remote Similarity	NPD5279	Phase 3
0.6542	Remote Similarity	NPD5690	Phase 2
0.6542	Remote Similarity	NPD4694	Approved
0.6542	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7143	Approved
0.6531	Remote Similarity	NPD7144	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