NPASS Compound

Structure

CID80150 OpenBabel06191715422D 28 28 0 0 1 0 0 0 0 0999 V2000 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.8660 -1.5000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 2 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 -2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 14 1 0 0 0 0 6 14 2 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 18 2 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 15 3 1 1 0 0 0 15 17 1 0 0 0 0 15 21 1 0 0 0 0 16 4 1 6 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 5 1 6 0 0 0 17 28 1 0 0 0 0 19 23 2 3 0 0 0 19 24 1 0 0 0 0 20 22 1 1 0 0 0 20 23 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	387.2
Volume:	414.368
LogP:	4.039
LogD:	2.803
LogS:	-3.893
# Rotatable Bonds:	11
TPSA:	93.03
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	4.014
Fsp3:	0.455
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:	-4.989
MDCK Permeability:	3.3648087992332876e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	99.0870132446289%
Volume Distribution (VD):	0.243
Pgp-substrate:	1.8226832151412964%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.4
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.835
CYP2C9-inhibitor:	0.531
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.074
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	0.992
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.818
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.194
Carcinogencity:	0.048
Eye Corrosion:	0.004
Eye Irritation:	0.03
Respiratory Toxicity:	0.146

Download Data

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

Natural Product: NPC80150

Natural Product ID:	NPC80150
*Common Name:**	Jomthonic Acid A
IUPAC Name:	(2R,3R)-2-methyl-3-[(2S,3R)-2-[[(2E,4E)-4-methylhexa-2,4-dienoyl]amino]-3-phenylbutanoyl]oxybutanoic acid
Synonyms:	Jomthonic Acid A
Standard InCHIKey:	VVPVXDHEFAYPAR-ZZSCLJTRSA-N
Standard InCHI:	InChI=1S/C22H29NO5/c1-6-14(2)12-13-19(24)23-20(16(4)18-10-8-7-9-11-18)22(27)28-17(5)15(3)21(25)26/h6-13,15-17,20H,1-5H3,(H,23,24)(H,25,26)/b13-12+,14-6+/t15-,16-,17-,20+/m1/s1
SMILES:	C/C=C(C)/C=C/C(=N[C@@H]([C@H](C)c1ccccc1)C(=O)O[C@H](C)[C@@H](C)C(=O)O)O
Synthetic Gene Cluster:	BGC0001457;
ChEMBL Identifier:	CHEMBL2047367
PubChem CID:	59051357
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides

*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
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344559]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10344578]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10348041]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10604756]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10695669]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10724004]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10994816]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11099231]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11132958]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11374972]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11473415]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14738393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Australian	n.a.	PMID[15497950]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15813185]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15844966]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15974616]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16180833]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1666120]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16724845]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16830891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16872146]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17125235]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17315965]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17551212]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17608531]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17844998]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17887721]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17917237]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18044841]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Indonesian	n.a.	PMID[18081255]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18205372]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	Northwest Territories, Canada	1995	PMID[18327911]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18666798]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18776684]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19007176]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19129624]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19191549]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19856955]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19883065]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20092333]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20545334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20836523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028889]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21028891]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21090727]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21314175]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21639131]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21728289]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21751787]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21807523]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21873059]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	latex	n.a.	PMID[21879726]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[22145663]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22574670]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22583058]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22591466]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22758660]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22775474]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23387796]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23662937]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24592993]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24754815]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24878306]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24964393]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25211234]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25455147]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25495422]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25537064]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25918793]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25934225]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26035239]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26465675]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26798949]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26905826]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31013087]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31298537]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31894983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[32298122]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8501018]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[8784423]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8931733]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8982334]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031666]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9031676]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066767]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9066768]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9186568]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9531983]
NPO30376	Streptomyces sp.	Species	Streptomycetaceae	Bacteria	n.a.	mycelium	n.a.	PMID[9711246]

☑ 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	1
MIC	3
Others	1

Activity Type	# Activity
Cell Line	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[526263]
NPT2	Others	Unspecified		Activity	=	80.0	%	PMID[526263]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	50.0	ug.mL-1	PMID[526263]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	50.0	ug.mL-1	PMID[526263]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	50.0	ug.mL-1	PMID[526263]

☑ 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 NPC80150 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	98
0.1-0.2	491
0.2-0.3	1910
0.3-0.4	6898
0.4-0.5	21914
0.5-0.6	9785
0.6-0.7	1319
0.7-0.8	256
0.8-0.85	13
0.85-0.9	8
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9145	High Similarity	NPC190663
0.8992	High Similarity	NPC160493
0.8974	High Similarity	NPC310467
0.8889	High Similarity	NPC169328
0.8512	High Similarity	NPC478016
0.8512	High Similarity	NPC478015
0.8512	High Similarity	NPC478014
0.8361	Intermediate Similarity	NPC477061
0.8361	Intermediate Similarity	NPC45777
0.8347	Intermediate Similarity	NPC237420
0.832	Intermediate Similarity	NPC4974
0.8305	Intermediate Similarity	NPC273814
0.8268	Intermediate Similarity	NPC296712
0.8214	Intermediate Similarity	NPC12730
0.8	Intermediate Similarity	NPC474584
0.7951	Intermediate Similarity	NPC197470
0.7951	Intermediate Similarity	NPC188010
0.7907	Intermediate Similarity	NPC210950
0.7907	Intermediate Similarity	NPC199738
0.7903	Intermediate Similarity	NPC314992
0.7891	Intermediate Similarity	NPC47667
0.7874	Intermediate Similarity	NPC35996
0.7845	Intermediate Similarity	NPC164859
0.7797	Intermediate Similarity	NPC327481
0.7797	Intermediate Similarity	NPC191215
0.7797	Intermediate Similarity	NPC274089
0.7795	Intermediate Similarity	NPC169485
0.7795	Intermediate Similarity	NPC84281
0.7795	Intermediate Similarity	NPC213126
0.7795	Intermediate Similarity	NPC317474
0.7795	Intermediate Similarity	NPC474862
0.7795	Intermediate Similarity	NPC291027
0.7778	Intermediate Similarity	NPC476183
0.7742	Intermediate Similarity	NPC2265
0.7737	Intermediate Similarity	NPC91953
0.7717	Intermediate Similarity	NPC476184
0.7717	Intermediate Similarity	NPC476281
0.7704	Intermediate Similarity	NPC6570
0.7698	Intermediate Similarity	NPC319950
0.7686	Intermediate Similarity	NPC319579
0.7669	Intermediate Similarity	NPC246913
0.7664	Intermediate Similarity	NPC197921
0.7652	Intermediate Similarity	NPC69496
0.7652	Intermediate Similarity	NPC478147
0.7634	Intermediate Similarity	NPC476353
0.7623	Intermediate Similarity	NPC329011
0.7612	Intermediate Similarity	NPC245836
0.7612	Intermediate Similarity	NPC233910
0.7612	Intermediate Similarity	NPC470392
0.7609	Intermediate Similarity	NPC161069
0.7597	Intermediate Similarity	NPC476278
0.7591	Intermediate Similarity	NPC307357
0.7591	Intermediate Similarity	NPC268841
0.7591	Intermediate Similarity	NPC46098
0.7576	Intermediate Similarity	NPC116057
0.7576	Intermediate Similarity	NPC472413
0.7554	Intermediate Similarity	NPC476978
0.7541	Intermediate Similarity	NPC323007
0.7538	Intermediate Similarity	NPC476241
0.7538	Intermediate Similarity	NPC476260
0.7537	Intermediate Similarity	NPC45191
0.7536	Intermediate Similarity	NPC263493
0.7536	Intermediate Similarity	NPC269398
0.7521	Intermediate Similarity	NPC182549
0.7521	Intermediate Similarity	NPC114741
0.7519	Intermediate Similarity	NPC142577
0.7518	Intermediate Similarity	NPC135121
0.7518	Intermediate Similarity	NPC473052
0.7518	Intermediate Similarity	NPC473055
0.75	Intermediate Similarity	NPC313867
0.75	Intermediate Similarity	NPC5620
0.75	Intermediate Similarity	NPC316008
0.7482	Intermediate Similarity	NPC469360
0.7482	Intermediate Similarity	NPC139326
0.7481	Intermediate Similarity	NPC476179
0.7481	Intermediate Similarity	NPC476125
0.7481	Intermediate Similarity	NPC328070
0.7479	Intermediate Similarity	NPC88267
0.7479	Intermediate Similarity	NPC194390
0.7479	Intermediate Similarity	NPC224610
0.7479	Intermediate Similarity	NPC113326
0.7464	Intermediate Similarity	NPC322526
0.7463	Intermediate Similarity	NPC183722
0.7462	Intermediate Similarity	NPC472415
0.7447	Intermediate Similarity	NPC314358
0.7445	Intermediate Similarity	NPC68865
0.7429	Intermediate Similarity	NPC315283
0.7429	Intermediate Similarity	NPC314388
0.7414	Intermediate Similarity	NPC10781
0.7414	Intermediate Similarity	NPC293628
0.7414	Intermediate Similarity	NPC122493
0.7407	Intermediate Similarity	NPC246079
0.7395	Intermediate Similarity	NPC471317
0.7394	Intermediate Similarity	NPC138775
0.7394	Intermediate Similarity	NPC145113
0.7391	Intermediate Similarity	NPC58674
0.7385	Intermediate Similarity	NPC27581
0.7376	Intermediate Similarity	NPC201244
0.7376	Intermediate Similarity	NPC477217
0.735	Intermediate Similarity	NPC322598
0.7348	Intermediate Similarity	NPC472414
0.7338	Intermediate Similarity	NPC163392
0.7338	Intermediate Similarity	NPC239762
0.7338	Intermediate Similarity	NPC471201
0.7333	Intermediate Similarity	NPC19136
0.7328	Intermediate Similarity	NPC25565
0.7319	Intermediate Similarity	NPC208725
0.7319	Intermediate Similarity	NPC471265
0.7319	Intermediate Similarity	NPC471264
0.731	Intermediate Similarity	NPC470274
0.731	Intermediate Similarity	NPC162104
0.7299	Intermediate Similarity	NPC64897
0.7299	Intermediate Similarity	NPC90693
0.7292	Intermediate Similarity	NPC129666
0.7286	Intermediate Similarity	NPC239770
0.7286	Intermediate Similarity	NPC469426
0.7286	Intermediate Similarity	NPC469427
0.7273	Intermediate Similarity	NPC67043
0.7273	Intermediate Similarity	NPC329761
0.7273	Intermediate Similarity	NPC321670
0.7273	Intermediate Similarity	NPC225648
0.7266	Intermediate Similarity	NPC92784
0.7266	Intermediate Similarity	NPC98424
0.7266	Intermediate Similarity	NPC470884
0.7266	Intermediate Similarity	NPC476133
0.7266	Intermediate Similarity	NPC178662
0.7265	Intermediate Similarity	NPC324569
0.7265	Intermediate Similarity	NPC473501
0.7265	Intermediate Similarity	NPC475439
0.7259	Intermediate Similarity	NPC325651
0.7254	Intermediate Similarity	NPC209509
0.7241	Intermediate Similarity	NPC7817
0.7241	Intermediate Similarity	NPC475168
0.7239	Intermediate Similarity	NPC319766
0.7234	Intermediate Similarity	NPC57976
0.7234	Intermediate Similarity	NPC176226
0.7227	Intermediate Similarity	NPC469457
0.7226	Intermediate Similarity	NPC244866
0.7222	Intermediate Similarity	NPC474544
0.7222	Intermediate Similarity	NPC1986
0.7203	Intermediate Similarity	NPC81026
0.7194	Intermediate Similarity	NPC127741
0.7185	Intermediate Similarity	NPC71271
0.7174	Intermediate Similarity	NPC248283
0.7172	Intermediate Similarity	NPC2501
0.7168	Intermediate Similarity	NPC325441
0.7167	Intermediate Similarity	NPC318154
0.7164	Intermediate Similarity	NPC65310
0.7164	Intermediate Similarity	NPC477937
0.7153	Intermediate Similarity	NPC326966
0.7143	Intermediate Similarity	NPC473341
0.7133	Intermediate Similarity	NPC266741
0.7131	Intermediate Similarity	NPC211551
0.7119	Intermediate Similarity	NPC477767
0.7113	Intermediate Similarity	NPC197682
0.7111	Intermediate Similarity	NPC152850
0.7111	Intermediate Similarity	NPC239990
0.7111	Intermediate Similarity	NPC71933
0.7111	Intermediate Similarity	NPC89923
0.7111	Intermediate Similarity	NPC105114
0.7103	Intermediate Similarity	NPC105717
0.7095	Intermediate Similarity	NPC470902
0.7095	Intermediate Similarity	NPC39431
0.7094	Intermediate Similarity	NPC206764
0.7094	Intermediate Similarity	NPC161972
0.7094	Intermediate Similarity	NPC303045
0.7092	Intermediate Similarity	NPC476259
0.709	Intermediate Similarity	NPC474847
0.7087	Intermediate Similarity	NPC276949
0.7087	Intermediate Similarity	NPC35850
0.7083	Intermediate Similarity	NPC262216
0.7071	Intermediate Similarity	NPC6913
0.7068	Intermediate Similarity	NPC6975
0.7059	Intermediate Similarity	NPC81092
0.7059	Intermediate Similarity	NPC469666
0.7059	Intermediate Similarity	NPC271475
0.7059	Intermediate Similarity	NPC103605
0.7055	Intermediate Similarity	NPC132771
0.7043	Intermediate Similarity	NPC258627
0.7042	Intermediate Similarity	NPC168113
0.7037	Intermediate Similarity	NPC136453
0.7034	Intermediate Similarity	NPC3371
0.7031	Intermediate Similarity	NPC33742
0.7029	Intermediate Similarity	NPC42423
0.7027	Intermediate Similarity	NPC122590
0.7027	Intermediate Similarity	NPC472761
0.7016	Intermediate Similarity	NPC20485
0.7	Intermediate Similarity	NPC279045
0.7	Intermediate Similarity	NPC314835
0.7	Intermediate Similarity	NPC470545
0.7	Intermediate Similarity	NPC113325
0.6993	Remote Similarity	NPC111586
0.6993	Remote Similarity	NPC471052
0.6993	Remote Similarity	NPC108852
0.6993	Remote Similarity	NPC471053
0.6993	Remote Similarity	NPC471051
0.6993	Remote Similarity	NPC261709
0.6992	Remote Similarity	NPC252878
0.6974	Remote Similarity	NPC476194
0.697	Remote Similarity	NPC474223

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 NPC80150 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	92
0.1-0.2	337
0.2-0.3	775
0.3-0.4	2100
0.4-0.5	3235
0.5-0.6	2030
0.6-0.7	482
0.7-0.8	95
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8291	Intermediate Similarity	NPD3642	Approved
0.8291	Intermediate Similarity	NPD3644	Approved
0.8291	Intermediate Similarity	NPD3643	Approved
0.813	Intermediate Similarity	NPD5981	Approved
0.8	Intermediate Similarity	NPD4738	Phase 2
0.7951	Intermediate Similarity	NPD1348	Approved
0.7934	Intermediate Similarity	NPD2652	Approved
0.7934	Intermediate Similarity	NPD2650	Approved
0.7903	Intermediate Similarity	NPD2218	Phase 2
0.7903	Intermediate Similarity	NPD2217	Approved
0.7795	Intermediate Similarity	NPD4216	Approved
0.7795	Intermediate Similarity	NPD4217	Approved
0.7795	Intermediate Similarity	NPD2612	Approved
0.7795	Intermediate Similarity	NPD2608	Approved
0.7795	Intermediate Similarity	NPD4218	Approved
0.7795	Intermediate Similarity	NPD2610	Approved
0.7795	Intermediate Similarity	NPD4215	Approved
0.7795	Intermediate Similarity	NPD2609	Approved
0.7795	Intermediate Similarity	NPD3132	Approved
0.7795	Intermediate Similarity	NPD2611	Approved
0.7795	Intermediate Similarity	NPD3131	Approved
0.7734	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD4209	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD2613	Approved
0.7612	Intermediate Similarity	NPD3616	Approved
0.7612	Intermediate Similarity	NPD4746	Phase 3
0.7612	Intermediate Similarity	NPD3615	Approved
0.7612	Intermediate Similarity	NPD2570	Approved
0.7612	Intermediate Similarity	NPD2572	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD3088	Approved
0.7612	Intermediate Similarity	NPD2573	Approved
0.7612	Intermediate Similarity	NPD3089	Approved
0.7612	Intermediate Similarity	NPD3087	Approved
0.7612	Intermediate Similarity	NPD2566	Approved
0.7612	Intermediate Similarity	NPD2574	Discontinued
0.7612	Intermediate Similarity	NPD4745	Approved
0.7612	Intermediate Similarity	NPD2571	Approved
0.7612	Intermediate Similarity	NPD3090	Approved
0.7612	Intermediate Similarity	NPD3614	Approved
0.7597	Intermediate Similarity	NPD2584	Suspended
0.7594	Intermediate Similarity	NPD3136	Phase 2
0.7574	Intermediate Similarity	NPD8173	Phase 2
0.7574	Intermediate Similarity	NPD8172	Phase 2
0.7518	Intermediate Similarity	NPD6852	Discontinued
0.75	Intermediate Similarity	NPD4684	Phase 3
0.75	Intermediate Similarity	NPD467	Phase 1
0.75	Intermediate Similarity	NPD4685	Phase 3
0.75	Intermediate Similarity	NPD4686	Approved
0.7481	Intermediate Similarity	NPD6325	Discontinued
0.748	Intermediate Similarity	NPD4479	Discontinued
0.7414	Intermediate Similarity	NPD9566	Approved
0.7388	Intermediate Similarity	NPD5202	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD4806	Approved
0.7385	Intermediate Similarity	NPD4807	Approved
0.7385	Intermediate Similarity	NPD3603	Phase 3
0.7373	Intermediate Similarity	NPD4760	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD2617	Discontinued
0.7324	Intermediate Similarity	NPD3400	Discontinued
0.7324	Intermediate Similarity	NPD2575	Approved
0.7323	Intermediate Similarity	NPD4576	Approved
0.7323	Intermediate Similarity	NPD4574	Approved
0.7313	Intermediate Similarity	NPD3662	Phase 3
0.7313	Intermediate Similarity	NPD3661	Approved
0.7313	Intermediate Similarity	NPD3663	Approved
0.7313	Intermediate Similarity	NPD3664	Approved
0.7308	Intermediate Similarity	NPD4136	Approved
0.7308	Intermediate Similarity	NPD4106	Approved
0.7308	Intermediate Similarity	NPD4135	Approved
0.7299	Intermediate Similarity	NPD8265	Approved
0.7287	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.728	Intermediate Similarity	NPD2607	Approved
0.7279	Intermediate Similarity	NPD4621	Approved
0.7279	Intermediate Similarity	NPD4619	Approved
0.7273	Intermediate Similarity	NPD5048	Discontinued
0.7273	Intermediate Similarity	NPD1040	Phase 2
0.7266	Intermediate Similarity	NPD1758	Phase 1
0.7259	Intermediate Similarity	NPD5201	Approved
0.7259	Intermediate Similarity	NPD4617	Approved
0.7259	Intermediate Similarity	NPD5203	Approved
0.7259	Intermediate Similarity	NPD4620	Approved
0.7252	Intermediate Similarity	NPD5618	Discontinued
0.725	Intermediate Similarity	NPD6647	Phase 2
0.7234	Intermediate Similarity	NPD7978	Discontinued
0.7231	Intermediate Similarity	NPD5305	Approved
0.7231	Intermediate Similarity	NPD5306	Approved
0.7226	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1759	Phase 1
0.7206	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD253	Approved
0.7188	Intermediate Similarity	NPD5292	Approved
0.7188	Intermediate Similarity	NPD5291	Approved
0.7188	Intermediate Similarity	NPD3123	Discovery
0.7185	Intermediate Similarity	NPD5204	Approved
0.7176	Intermediate Similarity	NPD2956	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5121	Approved
0.7174	Intermediate Similarity	NPD5120	Approved
0.7174	Intermediate Similarity	NPD5119	Approved
0.7164	Intermediate Similarity	NPD2628	Approved
0.7164	Intermediate Similarity	NPD2625	Approved
0.7164	Intermediate Similarity	NPD2160	Approved
0.7164	Intermediate Similarity	NPD2159	Approved
0.7164	Intermediate Similarity	NPD2627	Approved
0.7164	Intermediate Similarity	NPD6302	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2626	Approved
0.7154	Intermediate Similarity	NPD6406	Approved
0.7154	Intermediate Similarity	NPD4102	Approved
0.7154	Intermediate Similarity	NPD4105	Approved
0.7122	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4480	Approved
0.7094	Intermediate Similarity	NPD4814	Discontinued
0.7092	Intermediate Similarity	NPD3648	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6864	Phase 2
0.7092	Intermediate Similarity	NPD6865	Phase 2
0.7086	Intermediate Similarity	NPD7972	Discontinued
0.7075	Intermediate Similarity	NPD6390	Discontinued
0.7073	Intermediate Similarity	NPD5706	Approved
0.7073	Intermediate Similarity	NPD5705	Approved
0.7073	Intermediate Similarity	NPD5704	Approved
0.7068	Intermediate Similarity	NPD6624	Discontinued
0.7067	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD3673	Approved
0.7043	Intermediate Similarity	NPD3672	Approved
0.7042	Intermediate Similarity	NPD4172	Approved
0.7042	Intermediate Similarity	NPD4173	Approved
0.704	Intermediate Similarity	NPD4234	Approved
0.704	Intermediate Similarity	NPD4233	Approved
0.7034	Intermediate Similarity	NPD8323	Discontinued
0.7009	Intermediate Similarity	NPD1080	Approved
0.7009	Intermediate Similarity	NPD1066	Discontinued
0.7009	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4125	Approved
0.7	Intermediate Similarity	NPD6065	Approved
0.6993	Remote Similarity	NPD4152	Approved
0.6985	Remote Similarity	NPD3608	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6913	Approved
0.6953	Remote Similarity	NPD1371	Approved
0.6953	Remote Similarity	NPD1373	Approved
0.6953	Remote Similarity	NPD1374	Approved
0.6953	Remote Similarity	NPD1370	Approved
0.695	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6093	Discontinued
0.6944	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6685	Approved
0.6934	Remote Similarity	NPD4175	Approved
0.6934	Remote Similarity	NPD3626	Phase 3
0.6934	Remote Similarity	NPD4177	Approved
0.6934	Remote Similarity	NPD7828	Discontinued
0.6929	Remote Similarity	NPD6311	Approved
0.6929	Remote Similarity	NPD6310	Approved
0.6929	Remote Similarity	NPD6309	Approved
0.6923	Remote Similarity	NPD6690	Approved
0.6923	Remote Similarity	NPD9568	Approved
0.6911	Remote Similarity	NPD5909	Discontinued
0.6905	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1756	Approved
0.6905	Remote Similarity	NPD1752	Approved
0.6901	Remote Similarity	NPD2569	Approved
0.6901	Remote Similarity	NPD2567	Approved
0.6899	Remote Similarity	NPD1711	Phase 2
0.6889	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD855	Approved
0.6885	Remote Similarity	NPD854	Approved
0.6879	Remote Similarity	NPD555	Phase 2
0.687	Remote Similarity	NPD7522	Discontinued
0.686	Remote Similarity	NPD1067	Discontinued
0.686	Remote Similarity	NPD9712	Approved
0.6857	Remote Similarity	NPD7714	Approved
0.6857	Remote Similarity	NPD7715	Approved
0.6855	Remote Similarity	NPD1018	Approved
0.6846	Remote Similarity	NPD256	Approved
0.6846	Remote Similarity	NPD255	Approved
0.6838	Remote Similarity	NPD3098	Discontinued
0.6838	Remote Similarity	NPD2198	Approved
0.6838	Remote Similarity	NPD2199	Approved
0.6838	Remote Similarity	NPD3125	Approved
0.6822	Remote Similarity	NPD1682	Approved
0.6822	Remote Similarity	NPD1680	Approved
0.6822	Remote Similarity	NPD1681	Approved
0.6812	Remote Similarity	NPD4006	Discontinued
0.681	Remote Similarity	NPD5347	Phase 2
0.681	Remote Similarity	NPD5346	Phase 2
0.6809	Remote Similarity	NPD2203	Discontinued
0.6809	Remote Similarity	NPD6623	Phase 3
0.6809	Remote Similarity	NPD8416	Discontinued
0.6809	Remote Similarity	NPD826	Approved
0.6809	Remote Similarity	NPD825	Approved
0.6803	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD5162	Approved
0.6791	Remote Similarity	NPD3881	Discontinued
0.6783	Remote Similarity	NPD6295	Approved
0.6783	Remote Similarity	NPD6294	Approved
0.678	Remote Similarity	NPD1814	Approved
0.678	Remote Similarity	NPD1812	Approved
0.6779	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD9611	Approved
0.6777	Remote Similarity	NPD9711	Approved
0.6777	Remote Similarity	NPD9609	Approved
0.6777	Remote Similarity	NPD9710	Approved
0.6777	Remote Similarity	NPD9612	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