NPASS Compound

Structure

CID170084 OpenBabel06191715542D 45 50 0 0 1 0 0 0 0 0999 V2000 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1097 -3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 -2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3007 -2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5575 -1.3363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -1.7976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 31 1 0 0 0 0 3 31 1 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 20 1 0 0 0 0 7 9 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 8 16 2 0 0 0 0 9 32 1 0 0 0 0 10 40 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 33 1 0 0 0 0 13 15 1 0 0 0 0 13 41 1 0 0 0 0 14 1 1 1 0 0 0 14 22 1 0 0 0 0 14 42 1 0 0 0 0 15 17 2 0 0 0 0 16 28 1 0 0 0 0 17 32 1 0 0 0 0 18 16 1 6 0 0 0 18 41 1 0 0 0 0 19 12 1 6 0 0 0 19 23 1 0 0 0 0 19 43 1 0 0 0 0 20 31 1 0 0 0 0 20 32 1 6 0 0 0 21 31 1 0 0 0 0 21 44 1 6 0 0 0 22 24 1 0 0 0 0 22 34 1 6 0 0 0 23 25 1 0 0 0 0 23 35 1 1 0 0 0 24 26 1 0 0 0 0 24 36 1 1 0 0 0 25 27 1 0 0 0 0 25 37 1 6 0 0 0 26 29 1 0 0 0 0 26 38 1 1 0 0 0 27 30 1 0 0 0 0 27 45 1 1 0 0 0 28 39 2 0 0 0 0 28 40 1 0 0 0 0 29 42 1 0 0 0 0 29 45 1 6 0 0 0 30 43 1 0 0 0 0 30 44 1 6 0 0 0 32 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	640.31
Volume:	617.053
LogP:	1.687
LogD:	1.923
LogS:	-3.355
# Rotatable Bonds:	6
TPSA:	200.9
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.218
Synthetic Accessibility Score:	5.608
Fsp3:	0.812
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.143
MDCK Permeability:	2.7515419787960127e-05
Pgp-inhibitor:	0.041
Pgp-substrate:	0.976
Human Intestinal Absorption (HIA):	0.927
20% Bioavailability (F20%):	0.188
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.085
Plasma Protein Binding (PPB):	81.82232666015625%
Volume Distribution (VD):	0.372
Pgp-substrate:	14.116704940795898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.292
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.038
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	0.854
Half-life (T1/2):	0.637

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.125
AMES Toxicity:	0.126
Rat Oral Acute Toxicity:	0.5
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.272
Carcinogencity:	0.532
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC170084

Natural Product ID:	NPC170084
*Common Name:**	Alpindenoside A
IUPAC Name:	4-[(2S,6aR,8S,10aS)-8-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-7,7,10a-trimethyl-2,4,5,6,6a,8,9,10-octahydro-1H-benzo[f]isochromen-2-yl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	AEVODBWMGQYTNO-UOXHRDLNSA-N
Standard InCHI:	InChI=1S/C32H48O13/c1-14-22(34)24(36)26(38)29(42-14)45-27-25(37)23(35)19(12-33)43-30(27)44-21-7-9-32(4)17-11-18(16-8-10-40-28(16)39)41-13-15(17)5-6-20(32)31(21,2)3/h8,14,18-27,29-30,33-38H,5-7,9-13H2,1-4H3/t14-,18-,19+,20-,21-,22-,23+,24+,25-,26+,27+,29-,30-,32+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CCC2=C3C[C@H](OC2)C2=CCOC2=O)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL558540
PubChem CID:	25158096
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO26456	Jaborosa leucotricha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517742]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO594	Alpinia densespicata	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555124]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21106458]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	Leaves	n.a.		Database[FooDB]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25803	Strychnos elaeocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26610	Spiraea formosana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10372	Kiggelaria africana	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22353	Lucilia caesar	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7465	Vachellia leucophloea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25768	Senecio ruwenzoriensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26610	Spiraea formosana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13072	Rhamnus formosana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13051	Perymenium jelskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26846	Guettarda noumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24608	Gaertnera morindoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26456	Jaborosa leucotricha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21639	Prunus mahaleb	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26676	Daphne arisanensis	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25854	Tripterospermum lanceolatum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29093	Homalium longifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26208	Brombya platynema	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17771	Senna didymobotrya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26357	Trachyrhamphus serratus	Species	Syngnathidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25732	Trichilia havanensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26481	Astragalus kabadianus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14283	Ponera metallica	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24733	Celastrus dispermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15693	Guadua angustifolia	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26392	Piptadenia colubrina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25996	Stenolobium stans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23410	Potentilla candicans	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25264	Cerbera odollam	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26524	Chondria californica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25582	Aquilegia viridiflora	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26554	Hexagonia speciosa	Species	Carabidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25469	Lupinus luteus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25962	Rhamnus cathartica	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19916	Phenax angustifolius	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25803	Strychnos elaeocarpa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26113	Strychnos wallichiana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25518	Hedychium coronarium	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO594	Alpinia densespicata	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25575	Streptomyces pseudovenezuelae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26816	Clinopodium gracile	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25086	Viburnum betulifolium	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26743	Lippia adoensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26306	Pyrobaculum organotrophum	Species	Thermoproteaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO26079	Asterococcus muratae	Species	Cerococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24829	Gyrostroma missouriense	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23589	Pecten irradians	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24894	Parmelia tinctina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28819	Veronica liwanensis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26643	Cichorium endivia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25393	Coelogyne flavida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25906	Acacia linarioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26175	Spongionella gracilis	Species	Dictyodendrillidae	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
ED50	1
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	34200.0	nM	PMID[534622]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	80.0	%	PMID[534622]
NPT1	Others	Radical scavenging activity		ED50	>	200.0	ug ml-1	PMID[534622]

☑ 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 NPC170084 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	263
0.1-0.2	1515
0.2-0.3	4125
0.3-0.4	6975
0.4-0.5	12091
0.5-0.6	8642
0.6-0.7	5396
0.7-0.8	2844
0.8-0.85	746
0.85-0.9	85
0.9-0.95	13
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476204
0.9558	High Similarity	NPC476150
0.9558	High Similarity	NPC476127
0.9464	High Similarity	NPC474483
0.916	High Similarity	NPC245094
0.9083	High Similarity	NPC476966
0.9016	High Similarity	NPC316915
0.8974	High Similarity	NPC129434
0.8966	High Similarity	NPC232258
0.8934	High Similarity	NPC231240
0.8917	High Similarity	NPC470516
0.8908	High Similarity	NPC318135
0.8889	High Similarity	NPC470312
0.887	High Similarity	NPC44170
0.8852	High Similarity	NPC311178
0.8852	High Similarity	NPC43589
0.8852	High Similarity	NPC477197
0.8852	High Similarity	NPC300655
0.8852	High Similarity	NPC173347
0.8852	High Similarity	NPC222951
0.8843	High Similarity	NPC23020
0.8843	High Similarity	NPC472268
0.8843	High Similarity	NPC472269
0.8843	High Similarity	NPC472270
0.8843	High Similarity	NPC112492
0.8803	High Similarity	NPC470914
0.8803	High Similarity	NPC122971
0.8793	High Similarity	NPC473405
0.878	High Similarity	NPC233223
0.878	High Similarity	NPC475444
0.878	High Similarity	NPC322904
0.878	High Similarity	NPC183816
0.878	High Similarity	NPC324933
0.878	High Similarity	NPC478152
0.878	High Similarity	NPC319719
0.878	High Similarity	NPC196874
0.878	High Similarity	NPC478150
0.878	High Similarity	NPC478153
0.878	High Similarity	NPC475177
0.878	High Similarity	NPC473679
0.8772	High Similarity	NPC80843
0.8772	High Similarity	NPC1046
0.877	High Similarity	NPC477196
0.877	High Similarity	NPC477076
0.877	High Similarity	NPC477079
0.877	High Similarity	NPC470913
0.877	High Similarity	NPC477077
0.875	High Similarity	NPC392
0.875	High Similarity	NPC177524
0.875	High Similarity	NPC219900
0.8718	High Similarity	NPC471548
0.8718	High Similarity	NPC291564
0.871	High Similarity	NPC478151
0.8707	High Similarity	NPC207637
0.8707	High Similarity	NPC268954
0.8699	High Similarity	NPC45346
0.8699	High Similarity	NPC475377
0.8699	High Similarity	NPC475167
0.8699	High Similarity	NPC478065
0.8699	High Similarity	NPC264566
0.8699	High Similarity	NPC134914
0.8699	High Similarity	NPC173435
0.8699	High Similarity	NPC262796
0.8699	High Similarity	NPC478064
0.8699	High Similarity	NPC476074
0.8699	High Similarity	NPC25998
0.8699	High Similarity	NPC172374
0.8699	High Similarity	NPC329993
0.8699	High Similarity	NPC478155
0.8699	High Similarity	NPC301639
0.8696	High Similarity	NPC475208
0.8696	High Similarity	NPC264153
0.8696	High Similarity	NPC251309
0.8696	High Similarity	NPC238935
0.8689	High Similarity	NPC477078
0.8689	High Similarity	NPC45606
0.8689	High Similarity	NPC477194
0.8689	High Similarity	NPC329923
0.8689	High Similarity	NPC477192
0.8689	High Similarity	NPC477075
0.8689	High Similarity	NPC477191
0.8689	High Similarity	NPC311534
0.8689	High Similarity	NPC220838
0.8689	High Similarity	NPC475281
0.8689	High Similarity	NPC477193
0.8684	High Similarity	NPC297208
0.8684	High Similarity	NPC211798
0.8684	High Similarity	NPC30397
0.8684	High Similarity	NPC31839
0.8684	High Similarity	NPC108748
0.8684	High Similarity	NPC473481
0.8684	High Similarity	NPC235841
0.8678	High Similarity	NPC297950
0.8655	High Similarity	NPC202051
0.8632	High Similarity	NPC473968
0.8629	High Similarity	NPC30279
0.8629	High Similarity	NPC476776
0.8629	High Similarity	NPC477195
0.8629	High Similarity	NPC277212
0.8629	High Similarity	NPC473918
0.8629	High Similarity	NPC178264
0.8629	High Similarity	NPC192765
0.8629	High Similarity	NPC71391
0.8629	High Similarity	NPC478154
0.8629	High Similarity	NPC46823
0.8621	High Similarity	NPC110861
0.8621	High Similarity	NPC475486
0.8621	High Similarity	NPC164389
0.8618	High Similarity	NPC9470
0.8618	High Similarity	NPC1314
0.8618	High Similarity	NPC305793
0.8618	High Similarity	NPC280029
0.8618	High Similarity	NPC115656
0.8618	High Similarity	NPC252657
0.8618	High Similarity	NPC107536
0.8618	High Similarity	NPC11577
0.8618	High Similarity	NPC273878
0.8618	High Similarity	NPC252289
0.8618	High Similarity	NPC244296
0.8618	High Similarity	NPC470518
0.8618	High Similarity	NPC97918
0.8618	High Similarity	NPC269484
0.8618	High Similarity	NPC470912
0.8618	High Similarity	NPC82380
0.8618	High Similarity	NPC88311
0.8618	High Similarity	NPC472267
0.8618	High Similarity	NPC141600
0.8618	High Similarity	NPC47995
0.8618	High Similarity	NPC265841
0.8609	High Similarity	NPC471967
0.8609	High Similarity	NPC233003
0.8609	High Similarity	NPC128925
0.8609	High Similarity	NPC48249
0.8609	High Similarity	NPC256798
0.8607	High Similarity	NPC329784
0.8607	High Similarity	NPC240070
0.8607	High Similarity	NPC470780
0.8596	High Similarity	NPC59804
0.8596	High Similarity	NPC242611
0.8596	High Similarity	NPC164194
0.8596	High Similarity	NPC270667
0.8596	High Similarity	NPC475296
0.8596	High Similarity	NPC78046
0.8596	High Similarity	NPC56713
0.8596	High Similarity	NPC136877
0.8596	High Similarity	NPC274507
0.8596	High Similarity	NPC83005
0.8596	High Similarity	NPC269095
0.8596	High Similarity	NPC279554
0.8596	High Similarity	NPC29069
0.8596	High Similarity	NPC174679
0.8596	High Similarity	NPC90856
0.8596	High Similarity	NPC474589
0.8596	High Similarity	NPC127056
0.8584	High Similarity	NPC473483
0.8583	High Similarity	NPC596
0.8571	High Similarity	NPC48692
0.8571	High Similarity	NPC473130
0.856	High Similarity	NPC476779
0.856	High Similarity	NPC116075
0.856	High Similarity	NPC247190
0.856	High Similarity	NPC469749
0.856	High Similarity	NPC225791
0.856	High Similarity	NPC146857
0.856	High Similarity	NPC32793
0.8559	High Similarity	NPC473828
0.8559	High Similarity	NPC470515
0.8559	High Similarity	NPC232237
0.8559	High Similarity	NPC105800
0.8559	High Similarity	NPC473617
0.8548	High Similarity	NPC476775
0.8548	High Similarity	NPC476774
0.8548	High Similarity	NPC271610
0.8548	High Similarity	NPC476780
0.8547	High Similarity	NPC288205
0.8547	High Similarity	NPC476992
0.8547	High Similarity	NPC26626
0.8547	High Similarity	NPC51465
0.8547	High Similarity	NPC291903
0.8547	High Similarity	NPC37134
0.8547	High Similarity	NPC305267
0.8547	High Similarity	NPC75287
0.8534	High Similarity	NPC189884
0.8534	High Similarity	NPC124296
0.8534	High Similarity	NPC75167
0.8534	High Similarity	NPC473159
0.8534	High Similarity	NPC258885
0.8534	High Similarity	NPC47063
0.8534	High Similarity	NPC138334
0.8534	High Similarity	NPC311592
0.8534	High Similarity	NPC204458
0.8522	High Similarity	NPC164419
0.8522	High Similarity	NPC191763
0.8522	High Similarity	NPC179434
0.8509	High Similarity	NPC31522
0.8509	High Similarity	NPC237503
0.8509	High Similarity	NPC476759
0.8509	High Similarity	NPC137917
0.8509	High Similarity	NPC306746
0.8509	High Similarity	NPC167383

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 NPC170084 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	1703
0.2-0.3	3589
0.3-0.4	2302
0.4-0.5	794
0.5-0.6	319
0.6-0.7	163
0.7-0.8	37
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD6686	Approved
0.8361	Intermediate Similarity	NPD8328	Phase 3
0.8347	Intermediate Similarity	NPD8033	Approved
0.8347	Intermediate Similarity	NPD8513	Phase 3
0.832	Intermediate Similarity	NPD7319	Approved
0.8264	Intermediate Similarity	NPD8294	Approved
0.8264	Intermediate Similarity	NPD8377	Approved
0.8226	Intermediate Similarity	NPD7507	Approved
0.8197	Intermediate Similarity	NPD8296	Approved
0.8197	Intermediate Similarity	NPD8516	Approved
0.8197	Intermediate Similarity	NPD8380	Approved
0.8197	Intermediate Similarity	NPD8378	Approved
0.8197	Intermediate Similarity	NPD8335	Approved
0.8197	Intermediate Similarity	NPD8515	Approved
0.8197	Intermediate Similarity	NPD8379	Approved
0.8197	Intermediate Similarity	NPD8517	Approved
0.8167	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD8133	Approved
0.8049	Intermediate Similarity	NPD7503	Approved
0.8034	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7951	Intermediate Similarity	NPD7327	Approved
0.7951	Intermediate Similarity	NPD7328	Approved
0.7886	Intermediate Similarity	NPD7516	Approved
0.7869	Intermediate Similarity	NPD7115	Discovery
0.7863	Intermediate Similarity	NPD6412	Phase 2
0.7674	Intermediate Similarity	NPD7736	Approved
0.7603	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD4225	Approved
0.7462	Intermediate Similarity	NPD8293	Discontinued
0.7422	Intermediate Similarity	NPD6370	Approved
0.7414	Intermediate Similarity	NPD7638	Approved
0.7377	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD7639	Approved
0.735	Intermediate Similarity	NPD7640	Approved
0.7328	Intermediate Similarity	NPD8074	Phase 3
0.7308	Intermediate Similarity	NPD7492	Approved
0.7266	Intermediate Similarity	NPD6319	Approved
0.7266	Intermediate Similarity	NPD6054	Approved
0.7257	Intermediate Similarity	NPD46	Approved
0.7257	Intermediate Similarity	NPD6698	Approved
0.7252	Intermediate Similarity	NPD6616	Approved
0.7217	Intermediate Similarity	NPD7748	Approved
0.7197	Intermediate Similarity	NPD7078	Approved
0.7179	Intermediate Similarity	NPD7902	Approved
0.7132	Intermediate Similarity	NPD6059	Approved
0.7131	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8297	Approved
0.712	Intermediate Similarity	NPD6882	Approved
0.7119	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6016	Approved
0.7077	Intermediate Similarity	NPD6015	Approved
0.7073	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7515	Phase 2
0.7031	Intermediate Similarity	NPD6009	Approved
0.7023	Intermediate Similarity	NPD5988	Approved
0.6992	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7829	Approved
0.697	Remote Similarity	NPD7830	Approved
0.696	Remote Similarity	NPD6371	Approved
0.6929	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7900	Approved
0.6875	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5344	Discontinued
0.685	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD6067	Discontinued
0.681	Remote Similarity	NPD7838	Discovery
0.6803	Remote Similarity	NPD7632	Discontinued
0.68	Remote Similarity	NPD6881	Approved
0.68	Remote Similarity	NPD6899	Approved
0.6774	Remote Similarity	NPD6675	Approved
0.6774	Remote Similarity	NPD6402	Approved
0.6774	Remote Similarity	NPD7128	Approved
0.6774	Remote Similarity	NPD5739	Approved
0.6772	Remote Similarity	NPD6650	Approved
0.6772	Remote Similarity	NPD8130	Phase 1
0.6772	Remote Similarity	NPD6649	Approved
0.6752	Remote Similarity	NPD7983	Approved
0.6752	Remote Similarity	NPD6411	Approved
0.6746	Remote Similarity	NPD6373	Approved
0.6746	Remote Similarity	NPD6372	Approved
0.672	Remote Similarity	NPD5697	Approved
0.6696	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD5779	Approved
0.6695	Remote Similarity	NPD6399	Phase 3
0.6695	Remote Similarity	NPD5778	Approved
0.6694	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD6883	Approved
0.6693	Remote Similarity	NPD4634	Approved
0.6693	Remote Similarity	NPD7290	Approved
0.6693	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD7625	Phase 1
0.6642	Remote Similarity	NPD6033	Approved
0.6642	Remote Similarity	NPD8336	Approved
0.6642	Remote Similarity	NPD8337	Approved
0.6641	Remote Similarity	NPD6869	Approved
0.6641	Remote Similarity	NPD6847	Approved
0.6641	Remote Similarity	NPD6617	Approved
0.6619	Remote Similarity	NPD7260	Phase 2
0.6618	Remote Similarity	NPD8451	Approved
0.6614	Remote Similarity	NPD6014	Approved
0.6614	Remote Similarity	NPD6013	Approved
0.6614	Remote Similarity	NPD6012	Approved
0.6593	Remote Similarity	NPD7604	Phase 2
0.6587	Remote Similarity	NPD5701	Approved
0.6581	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6101	Approved
0.6569	Remote Similarity	NPD8448	Approved
0.6567	Remote Similarity	NPD5983	Phase 2
0.6567	Remote Similarity	NPD6921	Approved
0.6547	Remote Similarity	NPD8392	Approved
0.6547	Remote Similarity	NPD8391	Approved
0.6547	Remote Similarity	NPD8390	Approved
0.6535	Remote Similarity	NPD6011	Approved
0.6522	Remote Similarity	NPD1694	Approved
0.6519	Remote Similarity	NPD8080	Discontinued
0.6515	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6008	Approved
0.6504	Remote Similarity	NPD6648	Approved
0.6503	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6336	Discontinued
0.6475	Remote Similarity	NPD6084	Phase 2
0.6475	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6079	Approved
0.6471	Remote Similarity	NPD8035	Phase 2
0.6471	Remote Similarity	NPD7642	Approved
0.6471	Remote Similarity	NPD8034	Phase 2
0.6466	Remote Similarity	NPD3618	Phase 1
0.6454	Remote Similarity	NPD8338	Approved
0.6446	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD8444	Approved
0.6442	Remote Similarity	NPD7799	Discontinued
0.6441	Remote Similarity	NPD5328	Approved
0.6429	Remote Similarity	NPD6914	Discontinued
0.6423	Remote Similarity	NPD8342	Approved
0.6423	Remote Similarity	NPD8341	Approved
0.6423	Remote Similarity	NPD8340	Approved
0.6423	Remote Similarity	NPD8299	Approved
0.641	Remote Similarity	NPD3573	Approved
0.64	Remote Similarity	NPD5211	Phase 2
0.6393	Remote Similarity	NPD7839	Suspended
0.6387	Remote Similarity	NPD5785	Approved
0.6385	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD5285	Approved
0.6371	Remote Similarity	NPD5286	Approved
0.6371	Remote Similarity	NPD4696	Approved
0.6356	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4755	Approved
0.6338	Remote Similarity	NPD6845	Suspended
0.6333	Remote Similarity	NPD7637	Suspended
0.6325	Remote Similarity	NPD6409	Approved
0.6325	Remote Similarity	NPD5330	Approved
0.6325	Remote Similarity	NPD7146	Approved
0.6325	Remote Similarity	NPD7521	Approved
0.6325	Remote Similarity	NPD6684	Approved
0.6325	Remote Similarity	NPD7334	Approved
0.6324	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6274	Approved
0.6312	Remote Similarity	NPD5956	Approved
0.6311	Remote Similarity	NPD5695	Phase 3
0.6303	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD5141	Approved
0.6296	Remote Similarity	NPD7100	Approved
0.6296	Remote Similarity	NPD7101	Approved
0.6293	Remote Similarity	NPD4786	Approved
0.6281	Remote Similarity	NPD4202	Approved
0.6281	Remote Similarity	NPD8171	Discontinued
0.627	Remote Similarity	NPD5225	Approved
0.627	Remote Similarity	NPD5226	Approved
0.627	Remote Similarity	NPD5224	Approved
0.627	Remote Similarity	NPD4633	Approved
0.6261	Remote Similarity	NPD3667	Approved
0.626	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5222	Approved
0.626	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD8415	Approved
0.624	Remote Similarity	NPD4700	Approved
0.6239	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.623	Remote Similarity	NPD5282	Discontinued
0.6224	Remote Similarity	NPD8449	Approved
0.6222	Remote Similarity	NPD6335	Approved
0.6222	Remote Similarity	NPD7641	Discontinued
0.622	Remote Similarity	NPD5174	Approved
0.622	Remote Similarity	NPD5175	Approved
0.6218	Remote Similarity	NPD5737	Approved
0.6218	Remote Similarity	NPD6672	Approved
0.6218	Remote Similarity	NPD6903	Approved
0.621	Remote Similarity	NPD5173	Approved
0.6194	Remote Similarity	NPD6868	Approved
0.619	Remote Similarity	NPD5223	Approved
0.6186	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD8450	Suspended
0.6167	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.616	Remote Similarity	NPD5696	Approved
0.6154	Remote Similarity	NPD3666	Approved
0.6154	Remote Similarity	NPD3133	Approved
0.6154	Remote Similarity	NPD4730	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