NPASS Compound

Structure

CID156348 OpenBabel06191715522D 36 39 0 0 1 0 0 0 0 0999 V2000 -3.1656 4.3264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0320 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0320 2.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9474 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 3.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5135 2.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 3.6479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9474 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0483 -0.1614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4084 -1.8556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0264 0.0466 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3866 -1.6476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -0.8460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7611 -1.3203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 3.4254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1659 0.9010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1659 1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7393 -1.1124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5135 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6956 -0.6966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 1.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0920 -0.5772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2999 0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2999 2.4010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3093 0.2318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 0.9010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0975 -0.6817 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.2954 -0.6235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6737 -0.4887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3479 -1.5245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2999 3.4010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2874 0.4397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 19 2 0 0 0 0 4 6 1 0 0 0 0 4 8 1 0 0 0 0 5 7 1 0 0 0 0 5 9 2 0 0 0 0 6 17 1 0 0 0 0 7 17 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 20 2 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 25 1 0 0 0 0 16 20 1 0 0 0 0 17 1 1 1 0 0 0 18 2 1 1 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 21 31 1 6 0 0 0 22 32 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 1 0 0 0 24 16 1 6 0 0 0 24 26 1 0 0 0 0 24 30 1 0 0 0 0 25 33 2 0 0 0 0 25 36 1 0 0 0 0 26 29 1 1 0 0 0 27 34 1 6 0 0 0 28 30 2 0 0 0 0 28 35 1 0 0 0 0 29 28 1 1 0 0 0 29 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	495.26
Volume:	518.561
LogP:	3.09
LogD:	3.005
LogS:	-4.591
# Rotatable Bonds:	2
TPSA:	112.93
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	5.641
Fsp3:	0.552
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:	-4.976
MDCK Permeability:	3.98181400669273e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.968
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.77
Plasma Protein Binding (PPB):	74.70645904541016%
Volume Distribution (VD):	0.888
Pgp-substrate:	15.378607749938965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.522
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.625
CYP2C9-substrate:	0.517
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.369
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	10.509
Half-life (T1/2):	0.42

ADMET: Toxicity

hERG Blockers:	0.196
Human Hepatotoxicity (H-HT):	0.363
Drug-inuced Liver Injury (DILI):	0.393
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.869
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.205
Carcinogencity:	0.66
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC156348

Natural Product ID:	NPC156348
*Common Name:**	Cytochalasin Z5
IUPAC Name:	n.a.
Synonyms:	Cytochalasin Z5
Standard InCHIKey:	AJMKPZXRIKVSAQ-LFOGIAMQSA-N
Standard InCHI:	InChI=1S/C29H37NO6/c1-17-6-4-8-21(31)14-15-25(33)36-29-23(9-5-7-17)27(34)19(3)18(2)26(29)24(30-28(29)35)16-20-10-12-22(32)13-11-20/h5,9-15,17-18,21,23-24,26-27,31-32,34H,3-4,6-8,16H2,1-2H3,(H,30,35)/b9-5+,15-14+/t17-,18-,21-,23+,24+,26+,27-,29-/m1/s1
SMILES:	C[C@@H]1CCC[C@@H](O)/C=C/C(=O)O[C@@]23[C@@H](/C=C/C1)[C@H](O)C(=C)[C@H]([C@H]3[C@@H](N=C2O)Cc1ccc(cc1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512971
PubChem CID:	21574192
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001821] Cytochalasans

*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]
NPO21471.1	Boeremia exigua var. heteromorpha	Varieties	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695792]
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]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	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]
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[TCMID]
NPO2747	Hypericum triquetrifolium	Species	Hypericaceae	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]
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]
NPO3664	Mesembryanthemum anatomicum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2342	Cytisus scoparius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13325	Plantago lanceolata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4082	Ophiarthrum elegans	Species	Ophiocomidae	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]
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]
NPO21471.1	Boeremia exigua var. heteromorpha	Varieties	Didymellaceae	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]
NPO7097	Rhynchosporium orthosporum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6776	Trifolium apertum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6974	Solanum racemigerum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2361	Aconitum brevicalcaratum	Species	Ranunculaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT140	Organism	Artemia	Artemia	Activity	=	21.0	%	PMID[517937]

☑ 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 NPC156348 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	195
0.1-0.2	927
0.2-0.3	2307
0.3-0.4	6943
0.4-0.5	11170
0.5-0.6	12273
0.6-0.7	8609
0.7-0.8	249
0.8-0.85	10
0.85-0.9	9
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC15506
0.9184	High Similarity	NPC31171
0.9184	High Similarity	NPC237240
0.9	High Similarity	NPC201692
0.8867	High Similarity	NPC173934
0.8784	High Similarity	NPC108852
0.8784	High Similarity	NPC261709
0.8784	High Similarity	NPC111586
0.865	High Similarity	NPC477115
0.8255	Intermediate Similarity	NPC90693
0.8255	Intermediate Similarity	NPC64897
0.8163	Intermediate Similarity	NPC295478
0.805	Intermediate Similarity	NPC4108
0.8026	Intermediate Similarity	NPC175870
0.8013	Intermediate Similarity	NPC262216
0.7987	Intermediate Similarity	NPC239770
0.7911	Intermediate Similarity	NPC313414
0.7905	Intermediate Similarity	NPC278097
0.7898	Intermediate Similarity	NPC49565
0.7778	Intermediate Similarity	NPC228511
0.7727	Intermediate Similarity	NPC113325
0.7727	Intermediate Similarity	NPC279045
0.7714	Intermediate Similarity	NPC474607
0.767	Intermediate Similarity	NPC474650
0.7651	Intermediate Similarity	NPC476194
0.7625	Intermediate Similarity	NPC204644
0.7593	Intermediate Similarity	NPC320734
0.7557	Intermediate Similarity	NPC475794
0.7547	Intermediate Similarity	NPC470617
0.7547	Intermediate Similarity	NPC470616
0.7546	Intermediate Similarity	NPC476744
0.7532	Intermediate Similarity	NPC42423
0.7514	Intermediate Similarity	NPC477816
0.7485	Intermediate Similarity	NPC476743
0.7484	Intermediate Similarity	NPC469360
0.7484	Intermediate Similarity	NPC116742
0.7484	Intermediate Similarity	NPC139243
0.7483	Intermediate Similarity	NPC10154
0.7483	Intermediate Similarity	NPC474532
0.7483	Intermediate Similarity	NPC265413
0.7468	Intermediate Similarity	NPC322526
0.7452	Intermediate Similarity	NPC6570
0.7452	Intermediate Similarity	NPC64205
0.7421	Intermediate Similarity	NPC197921
0.7414	Intermediate Similarity	NPC474953
0.741	Intermediate Similarity	NPC476741
0.7405	Intermediate Similarity	NPC473055
0.7405	Intermediate Similarity	NPC473052
0.7394	Intermediate Similarity	NPC182119
0.7375	Intermediate Similarity	NPC91953
0.7362	Intermediate Similarity	NPC26045
0.736	Intermediate Similarity	NPC32154
0.7358	Intermediate Similarity	NPC471201
0.7349	Intermediate Similarity	NPC476742
0.7348	Intermediate Similarity	NPC474661
0.7348	Intermediate Similarity	NPC475919
0.7345	Intermediate Similarity	NPC241704
0.7337	Intermediate Similarity	NPC471203
0.7337	Intermediate Similarity	NPC235460
0.7321	Intermediate Similarity	NPC207675
0.7321	Intermediate Similarity	NPC212699
0.7321	Intermediate Similarity	NPC217801
0.7317	Intermediate Similarity	NPC163898
0.7316	Intermediate Similarity	NPC475768
0.7301	Intermediate Similarity	NPC235557
0.7299	Intermediate Similarity	NPC304846
0.7283	Intermediate Similarity	NPC54125
0.7283	Intermediate Similarity	NPC89199
0.7273	Intermediate Similarity	NPC88378
0.7273	Intermediate Similarity	NPC211713
0.7273	Intermediate Similarity	NPC61181
0.7262	Intermediate Similarity	NPC275027
0.7261	Intermediate Similarity	NPC478255
0.7261	Intermediate Similarity	NPC328070
0.7256	Intermediate Similarity	NPC25491
0.7256	Intermediate Similarity	NPC96447
0.7255	Intermediate Similarity	NPC472414
0.7251	Intermediate Similarity	NPC329837
0.725	Intermediate Similarity	NPC471283
0.7244	Intermediate Similarity	NPC288290
0.7237	Intermediate Similarity	NPC327070
0.7233	Intermediate Similarity	NPC11266
0.7232	Intermediate Similarity	NPC110374
0.7232	Intermediate Similarity	NPC474051
0.7232	Intermediate Similarity	NPC289743
0.7226	Intermediate Similarity	NPC71271
0.7226	Intermediate Similarity	NPC103533
0.7222	Intermediate Similarity	NPC271494
0.7222	Intermediate Similarity	NPC155192
0.7222	Intermediate Similarity	NPC473591
0.7216	Intermediate Similarity	NPC471165
0.7212	Intermediate Similarity	NPC132771
0.7208	Intermediate Similarity	NPC475933
0.7208	Intermediate Similarity	NPC470158
0.7197	Intermediate Similarity	NPC45191
0.7195	Intermediate Similarity	NPC252133
0.7195	Intermediate Similarity	NPC186296
0.7195	Intermediate Similarity	NPC310621
0.7193	Intermediate Similarity	NPC195766
0.7193	Intermediate Similarity	NPC206736
0.7191	Intermediate Similarity	NPC203005
0.7188	Intermediate Similarity	NPC182217
0.7188	Intermediate Similarity	NPC233350
0.7188	Intermediate Similarity	NPC70680
0.7179	Intermediate Similarity	NPC93632
0.7178	Intermediate Similarity	NPC159387
0.7178	Intermediate Similarity	NPC137501
0.7178	Intermediate Similarity	NPC154262
0.7178	Intermediate Similarity	NPC304110
0.7178	Intermediate Similarity	NPC7518
0.7178	Intermediate Similarity	NPC27518
0.7171	Intermediate Similarity	NPC474862
0.717	Intermediate Similarity	NPC185777
0.7161	Intermediate Similarity	NPC476971
0.7161	Intermediate Similarity	NPC476972
0.716	Intermediate Similarity	NPC77310
0.716	Intermediate Similarity	NPC182249
0.716	Intermediate Similarity	NPC151946
0.716	Intermediate Similarity	NPC171134
0.716	Intermediate Similarity	NPC76032
0.716	Intermediate Similarity	NPC132723
0.716	Intermediate Similarity	NPC321638
0.716	Intermediate Similarity	NPC472547
0.716	Intermediate Similarity	NPC328273
0.716	Intermediate Similarity	NPC321184
0.7159	Intermediate Similarity	NPC182257
0.7158	Intermediate Similarity	NPC327699
0.7152	Intermediate Similarity	NPC251062
0.7152	Intermediate Similarity	NPC184464
0.7152	Intermediate Similarity	NPC235294
0.7152	Intermediate Similarity	NPC471824
0.7152	Intermediate Similarity	NPC46137
0.7151	Intermediate Similarity	NPC1291
0.7151	Intermediate Similarity	NPC115343
0.7151	Intermediate Similarity	NPC69360
0.7143	Intermediate Similarity	NPC39549
0.7143	Intermediate Similarity	NPC329717
0.7143	Intermediate Similarity	NPC471988
0.7143	Intermediate Similarity	NPC470733
0.7143	Intermediate Similarity	NPC38099
0.7143	Intermediate Similarity	NPC476699
0.7143	Intermediate Similarity	NPC275839
0.7143	Intermediate Similarity	NPC90984
0.7143	Intermediate Similarity	NPC198741
0.7143	Intermediate Similarity	NPC26954
0.7143	Intermediate Similarity	NPC471872
0.7143	Intermediate Similarity	NPC154485
0.7134	Intermediate Similarity	NPC30174
0.7134	Intermediate Similarity	NPC86257
0.7134	Intermediate Similarity	NPC67467
0.7134	Intermediate Similarity	NPC35212
0.7126	Intermediate Similarity	NPC472937
0.7126	Intermediate Similarity	NPC470330
0.7126	Intermediate Similarity	NPC269668
0.7126	Intermediate Similarity	NPC472938
0.7126	Intermediate Similarity	NPC472936
0.7125	Intermediate Similarity	NPC135127
0.7125	Intermediate Similarity	NPC67247
0.7125	Intermediate Similarity	NPC208725
0.7125	Intermediate Similarity	NPC68517
0.7124	Intermediate Similarity	NPC325301
0.7115	Intermediate Similarity	NPC173150
0.7115	Intermediate Similarity	NPC58061
0.7115	Intermediate Similarity	NPC288416
0.7115	Intermediate Similarity	NPC106677
0.7115	Intermediate Similarity	NPC471881
0.7115	Intermediate Similarity	NPC35288
0.7115	Intermediate Similarity	NPC471882
0.7115	Intermediate Similarity	NPC66331
0.7115	Intermediate Similarity	NPC156692
0.7115	Intermediate Similarity	NPC45224
0.7111	Intermediate Similarity	NPC475345
0.711	Intermediate Similarity	NPC202839
0.711	Intermediate Similarity	NPC66678
0.7108	Intermediate Similarity	NPC469701
0.7101	Intermediate Similarity	NPC470619
0.7101	Intermediate Similarity	NPC145527
0.7101	Intermediate Similarity	NPC267469
0.7101	Intermediate Similarity	NPC116292
0.7101	Intermediate Similarity	NPC87630
0.7101	Intermediate Similarity	NPC179128
0.7101	Intermediate Similarity	NPC470916
0.7101	Intermediate Similarity	NPC208785
0.7101	Intermediate Similarity	NPC470618
0.7099	Intermediate Similarity	NPC216940
0.7099	Intermediate Similarity	NPC155963
0.7099	Intermediate Similarity	NPC475482
0.7099	Intermediate Similarity	NPC22676
0.7099	Intermediate Similarity	NPC198621
0.7099	Intermediate Similarity	NPC281780
0.7097	Intermediate Similarity	NPC94499
0.7097	Intermediate Similarity	NPC45821
0.7097	Intermediate Similarity	NPC476970
0.7095	Intermediate Similarity	NPC329969
0.7095	Intermediate Similarity	NPC187678
0.7083	Intermediate Similarity	NPC477483
0.7083	Intermediate Similarity	NPC81835
0.7083	Intermediate Similarity	NPC102934
0.7083	Intermediate Similarity	NPC236166
0.7083	Intermediate Similarity	NPC252402

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 NPC156348 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	518
0.2-0.3	982
0.3-0.4	2118
0.4-0.5	2832
0.5-0.6	1797
0.6-0.7	737
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9184	High Similarity	NPD7274	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2238	Phase 2
0.7256	Intermediate Similarity	NPD6667	Approved
0.7256	Intermediate Similarity	NPD6666	Approved
0.7241	Intermediate Similarity	NPD7315	Approved
0.7239	Intermediate Similarity	NPD3400	Discontinued
0.7225	Intermediate Similarity	NPD4666	Phase 3
0.7219	Intermediate Similarity	NPD6072	Discontinued
0.7168	Intermediate Similarity	NPD5709	Phase 3
0.7135	Intermediate Similarity	NPD5772	Approved
0.7135	Intermediate Similarity	NPD5773	Approved
0.7126	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7526	Approved
0.7126	Intermediate Similarity	NPD52	Approved
0.7101	Intermediate Similarity	NPD3455	Phase 2
0.7101	Intermediate Similarity	NPD4005	Discontinued
0.7099	Intermediate Similarity	NPD2161	Phase 2
0.709	Intermediate Similarity	NPD7565	Approved
0.7055	Intermediate Similarity	NPD1375	Discontinued
0.7055	Intermediate Similarity	NPD7266	Discontinued
0.7039	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7311	Approved
0.7033	Intermediate Similarity	NPD7313	Approved
0.7033	Intermediate Similarity	NPD7312	Approved
0.7033	Intermediate Similarity	NPD7310	Approved
0.7031	Intermediate Similarity	NPD7497	Discontinued
0.7029	Intermediate Similarity	NPD6746	Phase 2
0.7025	Intermediate Similarity	NPD3136	Phase 2
0.7011	Intermediate Similarity	NPD4663	Approved
0.7006	Intermediate Similarity	NPD2970	Approved
0.7006	Intermediate Similarity	NPD2969	Approved
0.7	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5557	Phase 1
0.6995	Remote Similarity	NPD7309	Approved
0.6983	Remote Similarity	NPD3909	Discontinued
0.6973	Remote Similarity	NPD7906	Approved
0.6973	Remote Similarity	NPD6841	Approved
0.6973	Remote Similarity	NPD6843	Phase 3
0.6973	Remote Similarity	NPD6842	Approved
0.6966	Remote Similarity	NPD2489	Approved
0.6966	Remote Similarity	NPD27	Approved
0.6966	Remote Similarity	NPD4481	Phase 3
0.6964	Remote Similarity	NPD3536	Discontinued
0.6961	Remote Similarity	NPD7007	Discovery
0.6951	Remote Similarity	NPD7978	Discontinued
0.6951	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD3051	Approved
0.694	Remote Similarity	NPD4578	Approved
0.694	Remote Similarity	NPD4577	Approved
0.694	Remote Similarity	NPD5035	Approved
0.6937	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8360	Approved
0.6935	Remote Similarity	NPD8361	Approved
0.6928	Remote Similarity	NPD6331	Phase 2
0.6919	Remote Similarity	NPD5090	Approved
0.6919	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5089	Approved
0.6909	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4357	Discontinued
0.6902	Remote Similarity	NPD8407	Phase 2
0.6895	Remote Similarity	NPD8485	Approved
0.6885	Remote Similarity	NPD7549	Discontinued
0.6879	Remote Similarity	NPD4433	Discontinued
0.6879	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4103	Phase 2
0.6868	Remote Similarity	NPD3823	Discontinued
0.6866	Remote Similarity	NPD8404	Phase 2
0.6864	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5763	Approved
0.6848	Remote Similarity	NPD5762	Approved
0.6845	Remote Similarity	NPD8435	Approved
0.6839	Remote Similarity	NPD7972	Discontinued
0.6832	Remote Similarity	NPD6405	Approved
0.6832	Remote Similarity	NPD6407	Approved
0.6831	Remote Similarity	NPD8368	Discontinued
0.6829	Remote Similarity	NPD1753	Discontinued
0.6828	Remote Similarity	NPD8150	Discontinued
0.6828	Remote Similarity	NPD5037	Approved
0.6828	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5038	Approved
0.6821	Remote Similarity	NPD8319	Approved
0.6821	Remote Similarity	NPD6385	Approved
0.6821	Remote Similarity	NPD6386	Approved
0.6821	Remote Similarity	NPD8320	Phase 1
0.6818	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7874	Approved
0.681	Remote Similarity	NPD2568	Approved
0.6804	Remote Similarity	NPD6823	Phase 2
0.68	Remote Similarity	NPD2229	Approved
0.68	Remote Similarity	NPD2234	Approved
0.68	Remote Similarity	NPD2228	Approved
0.6795	Remote Similarity	NPD2230	Approved
0.6795	Remote Similarity	NPD2233	Approved
0.6795	Remote Similarity	NPD2232	Approved
0.679	Remote Similarity	NPD6346	Approved
0.679	Remote Similarity	NPD4060	Phase 1
0.6788	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD9570	Approved
0.6786	Remote Similarity	NPD6190	Approved
0.6784	Remote Similarity	NPD7801	Approved
0.6774	Remote Similarity	NPD5036	Approved
0.6768	Remote Similarity	NPD3553	Approved
0.6768	Remote Similarity	NPD3554	Approved
0.6768	Remote Similarity	NPD3555	Approved
0.6768	Remote Similarity	NPD3552	Approved
0.6766	Remote Similarity	NPD4236	Phase 3
0.6766	Remote Similarity	NPD4237	Approved
0.6765	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD9622	Approved
0.6752	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD4659	Approved
0.6744	Remote Similarity	NPD3687	Approved
0.6744	Remote Similarity	NPD3686	Approved
0.6743	Remote Similarity	NPD2977	Approved
0.6743	Remote Similarity	NPD2978	Approved
0.6743	Remote Similarity	NPD5929	Approved
0.6728	Remote Similarity	NPD2674	Phase 3
0.6727	Remote Similarity	NPD4108	Discontinued
0.6726	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8166	Discontinued
0.6726	Remote Similarity	NPD4628	Phase 3
0.6725	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD4055	Discovery
0.672	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.671	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.671	Remote Similarity	NPD2668	Approved
0.671	Remote Similarity	NPD2667	Approved
0.6707	Remote Similarity	NPD2157	Approved
0.6703	Remote Similarity	NPD5026	Approved
0.6703	Remote Similarity	NPD5028	Approved
0.6703	Remote Similarity	NPD4955	Approved
0.6703	Remote Similarity	NPD4954	Approved
0.6703	Remote Similarity	NPD5034	Approved
0.6703	Remote Similarity	NPD5032	Approved
0.6703	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD36	Approved
0.6687	Remote Similarity	NPD5736	Approved
0.6686	Remote Similarity	NPD3692	Discontinued
0.6686	Remote Similarity	NPD2677	Approved
0.6685	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8151	Discontinued
0.6667	Remote Similarity	NPD6502	Phase 2
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD3144	Approved
0.6667	Remote Similarity	NPD42	Phase 2
0.6667	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6042	Phase 2
0.6667	Remote Similarity	NPD4678	Approved
0.6667	Remote Similarity	NPD7827	Phase 1
0.6667	Remote Similarity	NPD3145	Approved
0.6667	Remote Similarity	NPD4675	Approved
0.6667	Remote Similarity	NPD4123	Phase 3
0.6667	Remote Similarity	NPD2494	Approved
0.6667	Remote Similarity	NPD2493	Approved
0.6667	Remote Similarity	NPD5617	Suspended
0.665	Remote Similarity	NPD7047	Phase 3
0.665	Remote Similarity	NPD4582	Approved
0.665	Remote Similarity	NPD4583	Approved
0.6649	Remote Similarity	NPD7038	Approved
0.6649	Remote Similarity	NPD7039	Approved
0.6649	Remote Similarity	NPD5039	Approved
0.6649	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5030	Phase 2
0.6648	Remote Similarity	NPD7089	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3656	Approved
0.6646	Remote Similarity	NPD555	Phase 2
0.6646	Remote Similarity	NPD1669	Approved
0.663	Remote Similarity	NPD4956	Approved
0.6629	Remote Similarity	NPD3453	Discontinued
0.6628	Remote Similarity	NPD2675	Approved
0.6628	Remote Similarity	NPD2676	Approved
0.6626	Remote Similarity	NPD839	Approved
0.6626	Remote Similarity	NPD1132	Approved
0.6626	Remote Similarity	NPD1136	Approved
0.6626	Remote Similarity	NPD1130	Approved
0.6626	Remote Similarity	NPD7477	Discontinued
0.6626	Remote Similarity	NPD840	Approved
0.6625	Remote Similarity	NPD2194	Approved
0.6625	Remote Similarity	NPD2195	Approved
0.6624	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD7999	Approved
0.6615	Remote Similarity	NPD6535	Approved
0.6615	Remote Similarity	NPD6534	Approved
0.6614	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD8127	Discontinued
0.661	Remote Similarity	NPD2563	Approved
0.661	Remote Similarity	NPD2560	Approved
0.6607	Remote Similarity	NPD2424	Discontinued
0.6606	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD817	Approved
0.6606	Remote Similarity	NPD823	Approved
0.6606	Remote Similarity	NPD5314	Approved
0.6605	Remote Similarity	NPD3027	Phase 3
0.6601	Remote Similarity	NPD7930	Approved
0.6599	Remote Similarity	NPD4002	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