NPASS Compound

Structure

CID239098 OpenBabel06191716042D 23 24 0 0 1 0 0 0 0 0999 V2000 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 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 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 2 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 15 16 1 0 0 0 0 16 19 1 6 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	355.825
LogP:	3.445
LogD:	3.441
LogS:	-4.077
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	4.134
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.326
MDCK Permeability:	1.741811320243869e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.292
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.692
Plasma Protein Binding (PPB):	71.62257385253906%
Volume Distribution (VD):	0.387
Pgp-substrate:	23.093454360961914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.602
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.394
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.152
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	2.584
Half-life (T1/2):	0.66

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.073
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.904
Carcinogencity:	0.068
Eye Corrosion:	0.174
Eye Irritation:	0.818
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC239098

Natural Product ID:	NPC239098
*Common Name:**	Isocupressic Acid
IUPAC Name:	(1S,4aR,5S,8aR)-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:	Isocupressic Acid; Isocupressicacid
Standard InCHIKey:	DOYKMKZYLAAOGH-DOEMEAPXSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h10,16-17,21H,2,5-9,11-13H2,1,3-4H3,(H,22,23)/b14-10+/t16-,17+,19+,20-/m0/s1
SMILES:	C/C(=CCO)/CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511193
PubChem CID:	6438138
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1248/cpb.47.1521]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11000036]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	Leaves and branches	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	leaves	Soorkesh Valley, Gollestan, Iran	n.a.	PMID[15104493]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO32847	fokienia hodginsii	Species	Cupressaceae	Eukaryota	Twigs and Leaves	n.a.	n.a.	PMID[23691952]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32223924]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8951168]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	Brazilian propolis	n.a.	PMID[9677271]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28256	Platycladus orientalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18636	Cupressus macrocarpa	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	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	2
IC50	7
Others	2

Activity Type	# Activity
Cell Line	9
NON-MOLECULAR	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	72.91	ug ml-1	PMID[547009]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[547011]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[547011]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[547011]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[547011]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[547011]
NPT2740	Cell Line	Neutrophils		IC50	=	4800.0	nM	PMID[547012]
NPT2740	Cell Line	Neutrophils		Inhibition	=	78.0	%	PMID[547012]
NPT2740	Cell Line	Neutrophils		Inhibition	=	19.9	%	PMID[547012]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	63.54	ug ml-1	PMID[547009]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	104500.0	nM	PMID[547010]

☑ 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 NPC239098 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	161
0.1-0.2	993
0.2-0.3	4664
0.3-0.4	14390
0.4-0.5	9290
0.5-0.6	6668
0.6-0.7	4629
0.7-0.8	1675
0.8-0.85	166
0.85-0.9	48
0.9-0.95	12
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9103	High Similarity	NPC215893
0.9091	High Similarity	NPC229584
0.9091	High Similarity	NPC14203
0.9067	High Similarity	NPC61952
0.9028	High Similarity	NPC91369
0.8987	High Similarity	NPC194937
0.8987	High Similarity	NPC476038
0.8947	High Similarity	NPC198240
0.8875	High Similarity	NPC283733
0.8846	High Similarity	NPC40228
0.88	High Similarity	NPC476844
0.878	High Similarity	NPC104560
0.8765	High Similarity	NPC322159
0.8765	High Similarity	NPC82979
0.875	High Similarity	NPC165064
0.8701	High Similarity	NPC179028
0.8701	High Similarity	NPC59436
0.8701	High Similarity	NPC269543
0.8701	High Similarity	NPC297996
0.8701	High Similarity	NPC247783
0.8675	High Similarity	NPC281524
0.8667	High Similarity	NPC183503
0.8667	High Similarity	NPC161923
0.8667	High Similarity	NPC103958
0.8667	High Similarity	NPC283908
0.8667	High Similarity	NPC237591
0.8667	High Similarity	NPC18819
0.8667	High Similarity	NPC46610
0.8667	High Similarity	NPC3753
0.8649	High Similarity	NPC72343
0.8649	High Similarity	NPC160817
0.8642	High Similarity	NPC86316
0.8642	High Similarity	NPC106416
0.8611	High Similarity	NPC69649
0.8611	High Similarity	NPC68703
0.859	High Similarity	NPC327674
0.8571	High Similarity	NPC471897
0.8571	High Similarity	NPC232202
0.8571	High Similarity	NPC471899
0.8571	High Similarity	NPC107039
0.8571	High Similarity	NPC74995
0.8553	High Similarity	NPC476795
0.8553	High Similarity	NPC192540
0.8553	High Similarity	NPC279666
0.8537	High Similarity	NPC473226
0.8519	High Similarity	NPC472864
0.8519	High Similarity	NPC19849
0.8519	High Similarity	NPC476412
0.8493	Intermediate Similarity	NPC290445
0.8493	Intermediate Similarity	NPC36616
0.8481	Intermediate Similarity	NPC306095
0.8481	Intermediate Similarity	NPC281880
0.8481	Intermediate Similarity	NPC104545
0.8462	Intermediate Similarity	NPC321514
0.8462	Intermediate Similarity	NPC260385
0.8462	Intermediate Similarity	NPC110094
0.8462	Intermediate Similarity	NPC280654
0.8452	Intermediate Similarity	NPC174342
0.8442	Intermediate Similarity	NPC263582
0.8442	Intermediate Similarity	NPC476601
0.8442	Intermediate Similarity	NPC69143
0.8442	Intermediate Similarity	NPC89294
0.8434	Intermediate Similarity	NPC128644
0.8421	Intermediate Similarity	NPC476046
0.8421	Intermediate Similarity	NPC241854
0.8421	Intermediate Similarity	NPC166797
0.8421	Intermediate Similarity	NPC251970
0.8415	Intermediate Similarity	NPC52628
0.8415	Intermediate Similarity	NPC274724
0.8415	Intermediate Similarity	NPC269638
0.8415	Intermediate Similarity	NPC65661
0.8415	Intermediate Similarity	NPC471224
0.8395	Intermediate Similarity	NPC312480
0.8395	Intermediate Similarity	NPC97913
0.8375	Intermediate Similarity	NPC473420
0.8375	Intermediate Similarity	NPC159148
0.8375	Intermediate Similarity	NPC327002
0.8375	Intermediate Similarity	NPC90055
0.8354	Intermediate Similarity	NPC231431
0.8354	Intermediate Similarity	NPC199595
0.8354	Intermediate Similarity	NPC16394
0.8354	Intermediate Similarity	NPC152061
0.8354	Intermediate Similarity	NPC158846
0.8354	Intermediate Similarity	NPC308038
0.8353	Intermediate Similarity	NPC477782
0.8333	Intermediate Similarity	NPC165711
0.8333	Intermediate Similarity	NPC97377
0.8333	Intermediate Similarity	NPC472870
0.8313	Intermediate Similarity	NPC186975
0.8313	Intermediate Similarity	NPC325594
0.8313	Intermediate Similarity	NPC155011
0.8313	Intermediate Similarity	NPC470955
0.8313	Intermediate Similarity	NPC472869
0.8313	Intermediate Similarity	NPC324063
0.8313	Intermediate Similarity	NPC73038
0.8293	Intermediate Similarity	NPC164577
0.8293	Intermediate Similarity	NPC248758
0.8293	Intermediate Similarity	NPC472865
0.8289	Intermediate Similarity	NPC35656
0.8276	Intermediate Similarity	NPC470957
0.8276	Intermediate Similarity	NPC470958
0.8272	Intermediate Similarity	NPC2524
0.8267	Intermediate Similarity	NPC235586
0.8256	Intermediate Similarity	NPC476187
0.8256	Intermediate Similarity	NPC177037
0.8256	Intermediate Similarity	NPC472814
0.8256	Intermediate Similarity	NPC470113
0.8256	Intermediate Similarity	NPC477783
0.825	Intermediate Similarity	NPC157895
0.825	Intermediate Similarity	NPC477057
0.825	Intermediate Similarity	NPC2482
0.825	Intermediate Similarity	NPC148685
0.825	Intermediate Similarity	NPC37038
0.825	Intermediate Similarity	NPC271104
0.825	Intermediate Similarity	NPC104120
0.8235	Intermediate Similarity	NPC251528
0.8235	Intermediate Similarity	NPC66344
0.8228	Intermediate Similarity	NPC62336
0.8214	Intermediate Similarity	NPC142415
0.8214	Intermediate Similarity	NPC307426
0.8214	Intermediate Similarity	NPC88716
0.8214	Intermediate Similarity	NPC71507
0.8214	Intermediate Similarity	NPC173089
0.8214	Intermediate Similarity	NPC51700
0.8214	Intermediate Similarity	NPC102683
0.8214	Intermediate Similarity	NPC242468
0.8214	Intermediate Similarity	NPC68160
0.8214	Intermediate Similarity	NPC171203
0.8214	Intermediate Similarity	NPC293564
0.8214	Intermediate Similarity	NPC130577
0.8214	Intermediate Similarity	NPC474684
0.8214	Intermediate Similarity	NPC158141
0.8214	Intermediate Similarity	NPC18064
0.8214	Intermediate Similarity	NPC98442
0.8214	Intermediate Similarity	NPC96496
0.8214	Intermediate Similarity	NPC236618
0.8214	Intermediate Similarity	NPC477926
0.8214	Intermediate Similarity	NPC142361
0.8214	Intermediate Similarity	NPC476409
0.8205	Intermediate Similarity	NPC309399
0.8193	Intermediate Similarity	NPC474083
0.8193	Intermediate Similarity	NPC471344
0.8182	Intermediate Similarity	NPC266899
0.8182	Intermediate Similarity	NPC301065
0.8182	Intermediate Similarity	NPC476174
0.8182	Intermediate Similarity	NPC53565
0.8171	Intermediate Similarity	NPC105173
0.8171	Intermediate Similarity	NPC200752
0.8161	Intermediate Similarity	NPC151722
0.8161	Intermediate Similarity	NPC476416
0.8158	Intermediate Similarity	NPC133253
0.8148	Intermediate Similarity	NPC162632
0.8148	Intermediate Similarity	NPC278459
0.8148	Intermediate Similarity	NPC221647
0.8148	Intermediate Similarity	NPC471898
0.8148	Intermediate Similarity	NPC147066
0.8148	Intermediate Similarity	NPC263272
0.8148	Intermediate Similarity	NPC267691
0.8148	Intermediate Similarity	NPC3915
0.8148	Intermediate Similarity	NPC274050
0.8148	Intermediate Similarity	NPC142244
0.814	Intermediate Similarity	NPC51486
0.814	Intermediate Similarity	NPC198818
0.8125	Intermediate Similarity	NPC242767
0.8125	Intermediate Similarity	NPC477371
0.8118	Intermediate Similarity	NPC474511
0.8118	Intermediate Similarity	NPC246708
0.8118	Intermediate Similarity	NPC473242
0.8118	Intermediate Similarity	NPC181225
0.8118	Intermediate Similarity	NPC470629
0.8118	Intermediate Similarity	NPC290690
0.8118	Intermediate Similarity	NPC17733
0.8118	Intermediate Similarity	NPC52169
0.8118	Intermediate Similarity	NPC117122
0.8118	Intermediate Similarity	NPC24816
0.8118	Intermediate Similarity	NPC182797
0.8118	Intermediate Similarity	NPC1753
0.8118	Intermediate Similarity	NPC474512
0.8118	Intermediate Similarity	NPC40552
0.8108	Intermediate Similarity	NPC472875
0.8101	Intermediate Similarity	NPC132542
0.8101	Intermediate Similarity	NPC474433
0.8095	Intermediate Similarity	NPC329692
0.8095	Intermediate Similarity	NPC472986
0.8095	Intermediate Similarity	NPC472985
0.8095	Intermediate Similarity	NPC198761
0.8095	Intermediate Similarity	NPC72638
0.8095	Intermediate Similarity	NPC469994
0.8095	Intermediate Similarity	NPC476104
0.8095	Intermediate Similarity	NPC202394
0.809	Intermediate Similarity	NPC235053
0.809	Intermediate Similarity	NPC301534
0.809	Intermediate Similarity	NPC250757
0.809	Intermediate Similarity	NPC29152
0.8077	Intermediate Similarity	NPC201027
0.8072	Intermediate Similarity	NPC102048
0.8072	Intermediate Similarity	NPC263974
0.8072	Intermediate Similarity	NPC227132
0.8068	Intermediate Similarity	NPC87095
0.8068	Intermediate Similarity	NPC469406

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 NPC239098 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1384
0.2-0.3	3765
0.3-0.4	2515
0.4-0.5	803
0.5-0.6	258
0.6-0.7	240
0.7-0.8	40
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8049	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4786	Approved
0.7841	Intermediate Similarity	NPD7515	Phase 2
0.7831	Intermediate Similarity	NPD3667	Approved
0.7778	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.7647	Intermediate Similarity	NPD3666	Approved
0.7558	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6399	Phase 3
0.7473	Intermediate Similarity	NPD7748	Approved
0.7471	Intermediate Similarity	NPD4623	Approved
0.7471	Intermediate Similarity	NPD7146	Approved
0.7471	Intermediate Similarity	NPD7334	Approved
0.7471	Intermediate Similarity	NPD4519	Discontinued
0.7471	Intermediate Similarity	NPD7521	Approved
0.7471	Intermediate Similarity	NPD6409	Approved
0.7471	Intermediate Similarity	NPD5330	Approved
0.7471	Intermediate Similarity	NPD3618	Phase 1
0.7471	Intermediate Similarity	NPD6684	Approved
0.7447	Intermediate Similarity	NPD7640	Approved
0.7447	Intermediate Similarity	NPD7639	Approved
0.7419	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD6084	Phase 2
0.7416	Intermediate Similarity	NPD5328	Approved
0.7407	Intermediate Similarity	NPD8039	Approved
0.7381	Intermediate Similarity	NPD4695	Discontinued
0.7363	Intermediate Similarity	NPD5779	Approved
0.7363	Intermediate Similarity	NPD5778	Approved
0.734	Intermediate Similarity	NPD7638	Approved
0.7326	Intermediate Similarity	NPD5362	Discontinued
0.7303	Intermediate Similarity	NPD5737	Approved
0.7303	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6672	Approved
0.7303	Intermediate Similarity	NPD6903	Approved
0.7273	Intermediate Similarity	NPD5279	Phase 3
0.7253	Intermediate Similarity	NPD6411	Approved
0.7253	Intermediate Similarity	NPD7637	Suspended
0.7253	Intermediate Similarity	NPD6079	Approved
0.7234	Intermediate Similarity	NPD7902	Approved
0.7222	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.7209	Intermediate Similarity	NPD4221	Approved
0.7209	Intermediate Similarity	NPD4269	Approved
0.7209	Intermediate Similarity	NPD4270	Approved
0.7209	Intermediate Similarity	NPD4223	Phase 3
0.7159	Intermediate Similarity	NPD5329	Approved
0.7158	Intermediate Similarity	NPD4225	Approved
0.7126	Intermediate Similarity	NPD4788	Approved
0.7126	Intermediate Similarity	NPD7154	Phase 3
0.71	Intermediate Similarity	NPD6686	Approved
0.7083	Intermediate Similarity	NPD6404	Discontinued
0.7079	Intermediate Similarity	NPD6098	Approved
0.7073	Intermediate Similarity	NPD6926	Approved
0.7073	Intermediate Similarity	NPD6924	Approved
0.7059	Intermediate Similarity	NPD6929	Approved
0.7045	Intermediate Similarity	NPD4197	Approved
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7033	Intermediate Similarity	NPD6101	Approved
0.7033	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5695	Phase 3
0.6989	Remote Similarity	NPD4202	Approved
0.6988	Remote Similarity	NPD6942	Approved
0.6988	Remote Similarity	NPD7339	Approved
0.6988	Remote Similarity	NPD8264	Approved
0.6979	Remote Similarity	NPD5696	Approved
0.6977	Remote Similarity	NPD4819	Approved
0.6977	Remote Similarity	NPD4252	Approved
0.6977	Remote Similarity	NPD6930	Phase 2
0.6977	Remote Similarity	NPD4822	Approved
0.6977	Remote Similarity	NPD6931	Approved
0.6977	Remote Similarity	NPD4821	Approved
0.6977	Remote Similarity	NPD4820	Approved
0.6966	Remote Similarity	NPD5363	Approved
0.6957	Remote Similarity	NPD5785	Approved
0.6941	Remote Similarity	NPD3617	Approved
0.6941	Remote Similarity	NPD4271	Approved
0.6941	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD4268	Approved
0.6932	Remote Similarity	NPD5332	Approved
0.6932	Remote Similarity	NPD5331	Approved
0.6915	Remote Similarity	NPD7900	Approved
0.6915	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6933	Approved
0.6905	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6897	Remote Similarity	NPD4790	Discontinued
0.6889	Remote Similarity	NPD4693	Phase 3
0.6889	Remote Similarity	NPD4689	Approved
0.6889	Remote Similarity	NPD4688	Approved
0.6889	Remote Similarity	NPD5786	Approved
0.6889	Remote Similarity	NPD4138	Approved
0.6889	Remote Similarity	NPD5205	Approved
0.6889	Remote Similarity	NPD4690	Approved
0.6882	Remote Similarity	NPD8035	Phase 2
0.6882	Remote Similarity	NPD5281	Approved
0.6882	Remote Similarity	NPD8034	Phase 2
0.6882	Remote Similarity	NPD5284	Approved
0.6867	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7645	Phase 2
0.6848	Remote Similarity	NPD6673	Approved
0.6848	Remote Similarity	NPD6904	Approved
0.6848	Remote Similarity	NPD6080	Approved
0.6842	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD5210	Approved
0.6824	Remote Similarity	NPD5776	Phase 2
0.6824	Remote Similarity	NPD6925	Approved
0.6813	Remote Similarity	NPD3573	Approved
0.679	Remote Similarity	NPD6923	Approved
0.679	Remote Similarity	NPD6922	Approved
0.6782	Remote Similarity	NPD7332	Phase 2
0.6782	Remote Similarity	NPD7514	Phase 3
0.6782	Remote Similarity	NPD5368	Approved
0.6782	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7525	Registered
0.6778	Remote Similarity	NPD1694	Approved
0.6771	Remote Similarity	NPD7614	Phase 1
0.6771	Remote Similarity	NPD4697	Phase 3
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6768	Remote Similarity	NPD7632	Discontinued
0.6768	Remote Similarity	NPD5211	Phase 2
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6881	Approved
0.6765	Remote Similarity	NPD6899	Approved
0.6744	Remote Similarity	NPD7145	Approved
0.6742	Remote Similarity	NPD6695	Phase 3
0.6739	Remote Similarity	NPD5208	Approved
0.6729	Remote Similarity	NPD7115	Discovery
0.6712	Remote Similarity	NPD4266	Approved
0.6712	Remote Similarity	NPD3196	Approved
0.6712	Remote Similarity	NPD3194	Approved
0.6712	Remote Similarity	NPD3195	Phase 2
0.6709	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7144	Approved
0.6707	Remote Similarity	NPD7143	Approved
0.6706	Remote Similarity	NPD6117	Approved
0.6705	Remote Similarity	NPD5369	Approved
0.6705	Remote Similarity	NPD6902	Approved
0.6703	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5280	Approved
0.6703	Remote Similarity	NPD5690	Phase 2
0.6703	Remote Similarity	NPD4694	Approved
0.6702	Remote Similarity	NPD5693	Phase 1
0.6701	Remote Similarity	NPD5173	Approved
0.6701	Remote Similarity	NPD4755	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6635	Remote Similarity	NPD6883	Approved
0.6635	Remote Similarity	NPD7102	Approved
0.6635	Remote Similarity	NPD7290	Approved
0.6634	Remote Similarity	NPD5141	Approved
0.663	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6435	Approved
0.6628	Remote Similarity	NPD6116	Phase 1
0.6627	Remote Similarity	NPD7152	Approved
0.6627	Remote Similarity	NPD4243	Approved
0.6627	Remote Similarity	NPD7151	Approved
0.6627	Remote Similarity	NPD7150	Approved
0.6625	Remote Similarity	NPD7331	Phase 2
0.6625	Remote Similarity	NPD4224	Phase 2
0.6623	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD342	Phase 1
0.6602	Remote Similarity	NPD6011	Approved
0.6596	Remote Similarity	NPD46	Approved
0.6596	Remote Similarity	NPD6698	Approved
0.6593	Remote Similarity	NPD6893	Approved
0.6591	Remote Similarity	NPD7509	Discontinued
0.6585	Remote Similarity	NPD4137	Phase 3
0.6582	Remote Similarity	NPD3197	Phase 1
0.6575	Remote Similarity	NPD3172	Approved
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6617	Approved
0.6571	Remote Similarity	NPD6649	Approved
0.6571	Remote Similarity	NPD6869	Approved
0.6571	Remote Similarity	NPD8130	Phase 1
0.6571	Remote Similarity	NPD6650	Approved
0.6571	Remote Similarity	NPD6847	Approved
0.6566	Remote Similarity	NPD5285	Approved
0.6566	Remote Similarity	NPD5286	Approved
0.6566	Remote Similarity	NPD4700	Approved
0.6566	Remote Similarity	NPD4696	Approved
0.6552	Remote Similarity	NPD6115	Approved
0.6552	Remote Similarity	NPD6114	Approved
0.6552	Remote Similarity	NPD6697	Approved
0.6552	Remote Similarity	NPD6118	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD4194	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD4191	Approved
0.6538	Remote Similarity	NPD6013	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