NPASS Compound

Structure

CID152615 OpenBabel06191715522D 38 43 0 0 1 0 0 0 0 0999 V2000 -4.8415 -0.1075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8003 -2.4147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6905 -0.9760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9501 -1.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4913 -0.4795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4908 -3.3553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6598 0.9582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 -1.9176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6606 -2.8763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 -1.4381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6609 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8299 1.4374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9689 -1.3082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3215 -1.9174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7300 -2.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1309 0.2332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1377 -1.0190 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4899 -0.4786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4913 -1.4384 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3212 -2.8758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6604 0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3713 -2.1298 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8305 -1.4384 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9059 -1.1091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7925 -2.6428 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0751 -1.2183 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6609 -1.9179 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8299 -0.4792 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8304 -0.4795 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6178 -1.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7164 -0.5061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8304 1.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 0.4886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3088 -2.3291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0060 -0.1564 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4964 -1.7313 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1512 -3.3550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 28 1 0 0 0 0 4 35 1 0 0 0 0 5 11 1 0 0 0 0 5 19 1 0 0 0 0 6 9 1 0 0 0 0 6 20 1 0 0 0 0 7 12 1 0 0 0 0 7 21 1 0 0 0 0 8 10 1 0 0 0 0 8 23 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 29 1 0 0 0 0 12 30 1 0 0 0 0 13 18 2 0 0 0 0 13 24 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 36 1 0 0 0 0 17 1 1 1 0 0 0 17 26 1 0 0 0 0 17 37 1 0 0 0 0 18 21 1 0 0 0 0 19 27 1 1 0 0 0 20 38 1 6 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 35 1 1 0 0 0 23 27 1 6 0 0 0 23 29 1 0 0 0 0 24 31 2 0 0 0 0 24 36 1 0 0 0 0 25 37 1 0 0 0 0 25 38 1 1 0 0 0 26 32 1 1 0 0 0 27 2 1 6 0 0 0 28 30 1 6 0 0 0 29 30 1 1 0 0 0 29 33 1 0 0 0 0 30 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.32
Volume:	541.146
LogP:	3.539
LogD:	3.049
LogS:	-4.034
# Rotatable Bonds:	4
TPSA:	121.75
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.423
Synthetic Accessibility Score:	5.412
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
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:	-5.43
MDCK Permeability:	1.8103952243109234e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.787
30% Bioavailability (F30%):	0.545

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	96.81742095947266%
Volume Distribution (VD):	1.047
Pgp-substrate:	3.546501636505127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.58
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.193
CYP3A4-inhibitor:	0.474
CYP3A4-substrate:	0.677

ADMET: Excretion

Clearance (CL):	6.705
Half-life (T1/2):	0.266

ADMET: Toxicity

hERG Blockers:	0.59
Human Hepatotoxicity (H-HT):	0.372
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.039
Rat Oral Acute Toxicity:	0.809
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.467
Carcinogencity:	0.142
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC152615

Natural Product ID:	NPC152615
*Common Name:**	3Beta-O-(Beta-D-Diginosyl)-8,14-Dihydroxy-5Beta,14Beta-Card-20(22)-Dienolide
IUPAC Name:	3-[(3S,5R,8S,9R,10S,13R,14R,17R)-8,14-dihydroxy-3-[(2R,4R,5S,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
Synonyms:
Standard InCHIKey:	UZWLNBWIIKVXSW-QFUJVLJYSA-N
Standard InCHI:	InChI=1S/C30H46O8/c1-17-26(32)22(35-4)15-25(37-17)38-20-6-9-27(2)19(14-20)5-11-29(33)23(27)8-10-28(3)21(7-12-30(28,29)34)18-13-24(31)36-16-18/h13,17,19-23,25-26,32-34H,5-12,14-16H2,1-4H3/t17-,19-,20+,21-,22-,23-,25+,26+,27+,28-,29+,30-/m1/s1
SMILES:	C[C@@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@]3([C@@H]2CC[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)O)C1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL229260
PubChem CID:	44425148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11277760]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6520	Myrica multiflora	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8840	Ptilidium ciliare	Species	Ptilidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5591	Fucus spiralis	Species	Fucaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5980	Eria subsessilis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20132	Scutellaria seleriana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3146	Ammodendron conollyi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2518	Crinum kirkii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO715	Teucrium pestalozzae	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4253	Viguiera annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8472	Knightia deplanchei	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1308	Veronica pectinata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15583	Tripodanthus acutifolius	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1071	Parerythropodium fulvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO351	Cirsium dipsacolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8585	Verpa digitaliformis	Species	Morchellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5197	Streptomyces eurythermus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6377	Cocculus diversifolius	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1607	Croton rhamnifolius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2342	Cytisus scoparius	Species	Fabaceae	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	6
Others	3

Activity Type	# Activity
Cell Line	5
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	1600000.0	nM	PMID[520394]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	4700000.0	nM	PMID[520394]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5900.0	nM	PMID[520394]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6000.0	nM	PMID[520394]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[520394]
NPT27	Others	Unspecified		IC50	=	9400000.0	nM	PMID[520394]
NPT2	Others	Unspecified		Activity	=	112.0	%	PMID[520394]
NPT2	Others	Unspecified		Activity	=	107.0	%	PMID[520394]

☑ 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 NPC152615 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	246
0.1-0.2	1718
0.2-0.3	5052
0.3-0.4	10880
0.4-0.5	10292
0.5-0.6	6512
0.6-0.7	4555
0.7-0.8	2703
0.8-0.85	448
0.85-0.9	152
0.9-0.95	82
0.95-1	57

Similarity Score	Similarity Level	Natural Product ID
0.9907	High Similarity	NPC99620
0.9907	High Similarity	NPC199428
0.9907	High Similarity	NPC193382
0.9907	High Similarity	NPC5311
0.9907	High Similarity	NPC310341
0.9817	High Similarity	NPC329905
0.9815	High Similarity	NPC471353
0.9815	High Similarity	NPC50305
0.9815	High Similarity	NPC471354
0.9815	High Similarity	NPC244402
0.9815	High Similarity	NPC158344
0.9815	High Similarity	NPC142066
0.9815	High Similarity	NPC93883
0.9815	High Similarity	NPC27507
0.9815	High Similarity	NPC34390
0.9815	High Similarity	NPC471355
0.9815	High Similarity	NPC309034
0.9815	High Similarity	NPC474418
0.9815	High Similarity	NPC157376
0.9815	High Similarity	NPC473852
0.9815	High Similarity	NPC87250
0.9815	High Similarity	NPC471351
0.9815	High Similarity	NPC243196
0.9815	High Similarity	NPC196429
0.9815	High Similarity	NPC84987
0.9815	High Similarity	NPC77319
0.9815	High Similarity	NPC99728
0.9813	High Similarity	NPC31354
0.9813	High Similarity	NPC471633
0.9813	High Similarity	NPC69576
0.9813	High Similarity	NPC84949
0.9727	High Similarity	NPC475136
0.9727	High Similarity	NPC474466
0.9725	High Similarity	NPC83287
0.9636	High Similarity	NPC44899
0.9636	High Similarity	NPC292467
0.9636	High Similarity	NPC5883
0.9636	High Similarity	NPC304260
0.9636	High Similarity	NPC30483
0.9636	High Similarity	NPC469756
0.9636	High Similarity	NPC29639
0.9636	High Similarity	NPC32177
0.9636	High Similarity	NPC236973
0.9636	High Similarity	NPC55532
0.9636	High Similarity	NPC470897
0.9633	High Similarity	NPC203862
0.9633	High Similarity	NPC290693
0.955	High Similarity	NPC475556
0.955	High Similarity	NPC72260
0.955	High Similarity	NPC475629
0.9464	High Similarity	NPC475590
0.9464	High Similarity	NPC231518
0.9464	High Similarity	NPC475419
0.9464	High Similarity	NPC474908
0.9464	High Similarity	NPC314535
0.9464	High Similarity	NPC120390
0.9464	High Similarity	NPC40749
0.9464	High Similarity	NPC173555
0.9464	High Similarity	NPC475219
0.9381	High Similarity	NPC115349
0.9381	High Similarity	NPC264336
0.9381	High Similarity	NPC74259
0.9381	High Similarity	NPC474423
0.9381	High Similarity	NPC193893
0.9369	High Similarity	NPC218093
0.9298	High Similarity	NPC117445
0.9298	High Similarity	NPC208193
0.9298	High Similarity	NPC308262
0.9298	High Similarity	NPC27363
0.9286	High Similarity	NPC291820
0.9286	High Similarity	NPC81222
0.9204	High Similarity	NPC107607
0.9167	High Similarity	NPC475030
0.9138	High Similarity	NPC469750
0.9138	High Similarity	NPC250556
0.9115	High Similarity	NPC153085
0.9115	High Similarity	NPC268326
0.906	High Similarity	NPC329784
0.906	High Similarity	NPC469757
0.906	High Similarity	NPC117702
0.906	High Similarity	NPC179412
0.906	High Similarity	NPC240070
0.906	High Similarity	NPC471357
0.906	High Similarity	NPC146456
0.906	High Similarity	NPC471356
0.9035	High Similarity	NPC470312
0.8992	High Similarity	NPC159338
0.8992	High Similarity	NPC16569
0.8992	High Similarity	NPC253456
0.8917	High Similarity	NPC93416
0.8917	High Similarity	NPC19124
0.8917	High Similarity	NPC42670
0.8908	High Similarity	NPC471361
0.8908	High Similarity	NPC471358
0.8908	High Similarity	NPC10823
0.8908	High Similarity	NPC469752
0.8908	High Similarity	NPC471360
0.8908	High Similarity	NPC180079
0.8908	High Similarity	NPC91
0.8908	High Similarity	NPC125077
0.8908	High Similarity	NPC471359
0.8908	High Similarity	NPC284406
0.8908	High Similarity	NPC329986
0.8908	High Similarity	NPC251866
0.8908	High Similarity	NPC471352
0.8908	High Similarity	NPC86159
0.8908	High Similarity	NPC70542
0.8908	High Similarity	NPC469753
0.8908	High Similarity	NPC276838
0.8908	High Similarity	NPC232785
0.8908	High Similarity	NPC89514
0.8908	High Similarity	NPC469754
0.8908	High Similarity	NPC219085
0.8908	High Similarity	NPC9499
0.8908	High Similarity	NPC197707
0.8908	High Similarity	NPC188234
0.8908	High Similarity	NPC17896
0.8908	High Similarity	NPC469755
0.8908	High Similarity	NPC6108
0.8908	High Similarity	NPC140092
0.8908	High Similarity	NPC469751
0.8889	High Similarity	NPC186668
0.8889	High Similarity	NPC473199
0.8879	High Similarity	NPC472821
0.8879	High Similarity	NPC281378
0.887	High Similarity	NPC135369
0.8843	High Similarity	NPC225385
0.8843	High Similarity	NPC157817
0.8843	High Similarity	NPC298783
0.8843	High Similarity	NPC104585
0.8843	High Similarity	NPC477709
0.8843	High Similarity	NPC476221
0.8839	High Similarity	NPC144068
0.8824	High Similarity	NPC311534
0.8818	High Similarity	NPC296761
0.8818	High Similarity	NPC51925
0.8818	High Similarity	NPC154085
0.8818	High Similarity	NPC125361
0.8818	High Similarity	NPC473570
0.8818	High Similarity	NPC43976
0.8807	High Similarity	NPC472820
0.8739	High Similarity	NPC177047
0.8727	High Similarity	NPC472988
0.8727	High Similarity	NPC38217
0.8716	High Similarity	NPC119855
0.8716	High Similarity	NPC220217
0.8716	High Similarity	NPC472818
0.8716	High Similarity	NPC51719
0.8704	High Similarity	NPC196471
0.8704	High Similarity	NPC189588
0.8704	High Similarity	NPC187302
0.8704	High Similarity	NPC10232
0.8704	High Similarity	NPC97487
0.8704	High Similarity	NPC160583
0.8692	High Similarity	NPC25177
0.8692	High Similarity	NPC295110
0.8692	High Similarity	NPC247701
0.8692	High Similarity	NPC222875
0.8692	High Similarity	NPC268829
0.8689	High Similarity	NPC32793
0.8689	High Similarity	NPC469749
0.8689	High Similarity	NPC116075
0.8689	High Similarity	NPC247190
0.8689	High Similarity	NPC146857
0.8689	High Similarity	NPC142756
0.8684	High Similarity	NPC207637
0.8661	High Similarity	NPC114188
0.8661	High Similarity	NPC65167
0.8649	High Similarity	NPC472901
0.8649	High Similarity	NPC206618
0.8649	High Similarity	NPC257853
0.8636	High Similarity	NPC122816
0.8636	High Similarity	NPC471205
0.8636	High Similarity	NPC234160
0.8632	High Similarity	NPC233500
0.8624	High Similarity	NPC472819
0.8621	High Similarity	NPC219656
0.8618	High Similarity	NPC329636
0.8611	High Similarity	NPC121423
0.8609	High Similarity	NPC476690
0.8609	High Similarity	NPC100048
0.8609	High Similarity	NPC20979
0.8596	High Similarity	NPC477580
0.8595	High Similarity	NPC471407
0.8584	High Similarity	NPC473567
0.8584	High Similarity	NPC475354
0.8584	High Similarity	NPC216595
0.8571	High Similarity	NPC170974
0.8571	High Similarity	NPC191439
0.8571	High Similarity	NPC103627
0.8559	High Similarity	NPC196130
0.8559	High Similarity	NPC471082
0.8559	High Similarity	NPC473517
0.8559	High Similarity	NPC38948
0.8548	High Similarity	NPC194716
0.8547	High Similarity	NPC257610
0.8545	High Similarity	NPC472900
0.8545	High Similarity	NPC472899
0.8545	High Similarity	NPC472898
0.8545	High Similarity	NPC85670

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 NPC152615 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	1821
0.2-0.3	4087
0.3-0.4	2003
0.4-0.5	555
0.5-0.6	265
0.6-0.7	166
0.7-0.8	25
0.8-0.85	1
0.85-0.9	1
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9817	High Similarity	NPD7516	Approved
0.9725	High Similarity	NPD7328	Approved
0.9725	High Similarity	NPD7327	Approved
0.955	High Similarity	NPD8294	Approved
0.955	High Similarity	NPD8377	Approved
0.9464	High Similarity	NPD8378	Approved
0.9464	High Similarity	NPD8380	Approved
0.9464	High Similarity	NPD8296	Approved
0.9464	High Similarity	NPD8033	Approved
0.9464	High Similarity	NPD8335	Approved
0.9464	High Similarity	NPD8379	Approved
0.9138	High Similarity	NPD7507	Approved
0.8908	High Similarity	NPD7319	Approved
0.8793	High Similarity	NPD7503	Approved
0.823	Intermediate Similarity	NPD6686	Approved
0.8034	Intermediate Similarity	NPD8133	Approved
0.8	Intermediate Similarity	NPD7638	Approved
0.7982	Intermediate Similarity	NPD6412	Phase 2
0.7928	Intermediate Similarity	NPD7640	Approved
0.7928	Intermediate Similarity	NPD7639	Approved
0.7852	Intermediate Similarity	NPD7625	Phase 1
0.7778	Intermediate Similarity	NPD7736	Approved
0.7559	Intermediate Similarity	NPD8293	Discontinued
0.752	Intermediate Similarity	NPD6370	Approved
0.7402	Intermediate Similarity	NPD7492	Approved
0.7395	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6054	Approved
0.736	Intermediate Similarity	NPD6059	Approved
0.7355	Intermediate Similarity	NPD6882	Approved
0.7344	Intermediate Similarity	NPD6616	Approved
0.7328	Intermediate Similarity	NPD7632	Discontinued
0.7323	Intermediate Similarity	NPD8328	Phase 3
0.7287	Intermediate Similarity	NPD7078	Approved
0.7258	Intermediate Similarity	NPD6009	Approved
0.7258	Intermediate Similarity	NPD7115	Discovery
0.7232	Intermediate Similarity	NPD8171	Discontinued
0.7222	Intermediate Similarity	NPD6319	Approved
0.7213	Intermediate Similarity	NPD8297	Approved
0.719	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7320	Approved
0.7165	Intermediate Similarity	NPD6016	Approved
0.7165	Intermediate Similarity	NPD6015	Approved
0.7154	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7109	Intermediate Similarity	NPD5988	Approved
0.7107	Intermediate Similarity	NPD6372	Approved
0.7107	Intermediate Similarity	NPD6373	Approved
0.7094	Intermediate Similarity	NPD5344	Discontinued
0.7069	Intermediate Similarity	NPD4225	Approved
0.7054	Intermediate Similarity	NPD6067	Discontinued
0.7025	Intermediate Similarity	NPD6881	Approved
0.7025	Intermediate Similarity	NPD6899	Approved
0.6992	Remote Similarity	NPD6650	Approved
0.6992	Remote Similarity	NPD6649	Approved
0.6984	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6051	Approved
0.6942	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5701	Approved
0.6942	Remote Similarity	NPD5697	Approved
0.6935	Remote Similarity	NPD6053	Discontinued
0.6917	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7525	Registered
0.6911	Remote Similarity	NPD7102	Approved
0.6911	Remote Similarity	NPD6883	Approved
0.6911	Remote Similarity	NPD7290	Approved
0.6899	Remote Similarity	NPD8513	Phase 3
0.6899	Remote Similarity	NPD8515	Approved
0.6899	Remote Similarity	NPD8517	Approved
0.6899	Remote Similarity	NPD8516	Approved
0.686	Remote Similarity	NPD6008	Approved
0.6855	Remote Similarity	NPD8130	Phase 1
0.6855	Remote Similarity	NPD6617	Approved
0.6855	Remote Similarity	NPD6869	Approved
0.6855	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD6033	Approved
0.6838	Remote Similarity	NPD6084	Phase 2
0.6838	Remote Similarity	NPD6083	Phase 2
0.6829	Remote Similarity	NPD6013	Approved
0.6829	Remote Similarity	NPD6014	Approved
0.6829	Remote Similarity	NPD6012	Approved
0.6794	Remote Similarity	NPD7604	Phase 2
0.6786	Remote Similarity	NPD7524	Approved
0.6769	Remote Similarity	NPD5983	Phase 2
0.6759	Remote Similarity	NPD6928	Phase 2
0.6748	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6011	Approved
0.6723	Remote Similarity	NPD6648	Approved
0.672	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD4755	Approved
0.6692	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD8449	Approved
0.664	Remote Similarity	NPD4634	Approved
0.6639	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD4202	Approved
0.6612	Remote Similarity	NPD5211	Phase 2
0.6609	Remote Similarity	NPD6698	Approved
0.6609	Remote Similarity	NPD46	Approved
0.6594	Remote Similarity	NPD8450	Suspended
0.6587	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD5286	Approved
0.6583	Remote Similarity	NPD5285	Approved
0.6583	Remote Similarity	NPD4700	Approved
0.6583	Remote Similarity	NPD4696	Approved
0.6581	Remote Similarity	NPD7748	Approved
0.6579	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7902	Approved
0.6552	Remote Similarity	NPD7515	Phase 2
0.6552	Remote Similarity	NPD8035	Phase 2
0.6552	Remote Similarity	NPD8034	Phase 2
0.6532	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD4159	Approved
0.6525	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5695	Phase 3
0.6518	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6274	Approved
0.6508	Remote Similarity	NPD6371	Approved
0.6504	Remote Similarity	NPD5141	Approved
0.65	Remote Similarity	NPD5696	Approved
0.6496	Remote Similarity	NPD6399	Phase 3
0.6491	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7101	Approved
0.6489	Remote Similarity	NPD7100	Approved
0.6475	Remote Similarity	NPD5226	Approved
0.6475	Remote Similarity	NPD5225	Approved
0.6475	Remote Similarity	NPD4633	Approved
0.6475	Remote Similarity	NPD5224	Approved
0.6466	Remote Similarity	NPD7838	Discovery
0.646	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4768	Approved
0.6452	Remote Similarity	NPD4767	Approved
0.6435	Remote Similarity	NPD6903	Approved
0.6429	Remote Similarity	NPD6695	Phase 3
0.6423	Remote Similarity	NPD5175	Approved
0.6423	Remote Similarity	NPD5174	Approved
0.6412	Remote Similarity	NPD6335	Approved
0.641	Remote Similarity	NPD5693	Phase 1
0.641	Remote Similarity	NPD7637	Suspended
0.6404	Remote Similarity	NPD7334	Approved
0.6404	Remote Similarity	NPD6684	Approved
0.6404	Remote Similarity	NPD7146	Approved
0.6404	Remote Similarity	NPD6409	Approved
0.6404	Remote Similarity	NPD7521	Approved
0.6404	Remote Similarity	NPD5330	Approved
0.6398	Remote Similarity	NPD7799	Discontinued
0.6393	Remote Similarity	NPD5223	Approved
0.6391	Remote Similarity	NPD6909	Approved
0.6391	Remote Similarity	NPD6908	Approved
0.6379	Remote Similarity	NPD4753	Phase 2
0.6379	Remote Similarity	NPD5328	Approved
0.6377	Remote Similarity	NPD5956	Approved
0.6364	Remote Similarity	NPD7645	Phase 2
0.6349	Remote Similarity	NPD4729	Approved
0.6349	Remote Similarity	NPD4730	Approved
0.6336	Remote Similarity	NPD6317	Approved
0.6316	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD7900	Approved
0.629	Remote Similarity	NPD4754	Approved
0.6288	Remote Similarity	NPD6313	Approved
0.6288	Remote Similarity	NPD6314	Approved
0.6277	Remote Similarity	NPD8074	Phase 3
0.6271	Remote Similarity	NPD6079	Approved
0.6269	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD6921	Approved
0.6261	Remote Similarity	NPD3618	Phase 1
0.625	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD5250	Approved
0.625	Remote Similarity	NPD5247	Approved
0.625	Remote Similarity	NPD5248	Approved
0.625	Remote Similarity	NPD5249	Phase 3
0.6239	Remote Similarity	NPD6673	Approved
0.6239	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6904	Approved
0.6239	Remote Similarity	NPD6080	Approved
0.6228	Remote Similarity	NPD3666	Approved
0.6228	Remote Similarity	NPD3665	Phase 1
0.6228	Remote Similarity	NPD3133	Approved
0.622	Remote Similarity	NPD5128	Approved
0.6216	Remote Similarity	NPD4195	Approved
0.6207	Remote Similarity	NPD7750	Discontinued
0.6195	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.617	Remote Similarity	NPD8338	Approved
0.6167	Remote Similarity	NPD6001	Approved
0.6161	Remote Similarity	NPD6931	Approved
0.6161	Remote Similarity	NPD6930	Phase 2
0.6154	Remote Similarity	NPD6672	Approved
0.6154	Remote Similarity	NPD5737	Approved
0.6147	Remote Similarity	NPD7339	Approved
0.6147	Remote Similarity	NPD6942	Approved
0.6136	Remote Similarity	NPD6940	Discontinued
0.6134	Remote Similarity	NPD5281	Approved
0.6134	Remote Similarity	NPD5284	Approved
0.6116	Remote Similarity	NPD4629	Approved
0.6116	Remote Similarity	NPD5210	Approved
0.6115	Remote Similarity	NPD8336	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