NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	178.06
Volume:	186.148
LogP:	2.325
LogD:	2.554
LogS:	-1.77
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.552
Synthetic Accessibility Score:	1.831
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.512
MDCK Permeability:	2.167187449231278e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.059
30% Bioavailability (F30%):	0.83

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.842
Plasma Protein Binding (PPB):	79.62319946289062%
Volume Distribution (VD):	0.568
Pgp-substrate:	14.830202102661133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.65
CYP2C19-inhibitor:	0.781
CYP2C19-substrate:	0.33
CYP2C9-inhibitor:	0.422
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.822
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	12.352
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.246
Drug-inuced Liver Injury (DILI):	0.057
AMES Toxicity:	0.18
Rat Oral Acute Toxicity:	0.75
Maximum Recommended Daily Dose:	0.181
Skin Sensitization:	0.938
Carcinogencity:	0.474
Eye Corrosion:	0.052
Eye Irritation:	0.477
Respiratory Toxicity:	0.514

Download Data

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

Natural Product: NPC253746

Natural Product ID:	NPC253746
*Common Name:**	Methyl P-Hydroxycinnamate
IUPAC Name:	methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	Methyl 3-(4-Hydroxyphenyl)Acrylate; Methyl P-Hydroxycinnamate; Methyl Trans-P-Coumaric Acid; Methyl-P-Coumarate; P-Hydroxy Cinnamic Acid Methyl Ester
Standard InCHIKey:	NITWSHWHQAQBAW-QPJJXVBHSA-N
Standard InCHI:	InChI=1S/C10H10O3/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-7,11H,1H3/b7-4+
SMILES:	COC(=O)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL146816
PubChem CID:	5319562
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	flowers	n.a.	n.a.	PMID[10075775]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479331]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	Mengha, Yunnan Province, China	1991-Aug	PMID[11277741]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11325233]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[11430002]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678656]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15387664]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	callus	n.a.	PMID[16327202]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17637068]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18302336]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18524603]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22432912]
NPO19141	Aframomum melegueta	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22789014]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	fruits	n.a.	n.a.	PMID[23265871]
NPO32535	dracocephalum ruyschiana	Species	Lamiaceae	Eukaryota	aerial parts	Mongolian	n.a.	PMID[23356964]
NPO8415	Tetragonotheca ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO27632	Idesia polycarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23628332]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	n.a.	n.a.	PMID[25685941]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	leaves and branches	San Antonio, Texas	2004-JUN	PMID[25685941]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26238319]
NPO2330	Alchornea cordifolia	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[26724423]
NPO2330	Alchornea cordifolia	Species	Euphorbiaceae	Eukaryota	n.a.	stem	n.a.	PMID[26724423]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29924604]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[31082231]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	Suriname rainforest	n.a.	PMID[9428162]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461664]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5570	0tholirion hyacinthinum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5570	0tholirion hyacinthinum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18120	Radix rehmanniae	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12315	Lycopodiella inundata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23772	Tetradium glabrifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12487	Juniperus horizontalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10098	Glycosmis pseudoracemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5570	0tholirion hyacinthinum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11967	Delphinium giraldii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3455	Picramnia lindeniana	Species	Picramniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19242	Eucalyptus albens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9906	Zephyranthes flava	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5455	Euploca racemosa	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18602	Melampodium leucanthum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15233	Balanophora japonica	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13278	Strychnos spinosa	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19371	Costasiella ocellifera	Species	Costasiellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1953	Miltochrista calamina	Species	Erebidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17114	Streptomyces melanogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12223	Stellaria media	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24402.1	Coffea liberica var. dewevrei	Varieties	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13737	Tephroseris kirilowii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6728	Rubus niveus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11646	Morella pensylvanica	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14526	Plectranthus caninus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11081	Baccharis grandicapitulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5570	0tholirion hyacinthinum	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16135	Pestalotiopsis oenotherae	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3761	Plectosphaerella cucumerina	Species	Plectosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2330	Alchornea cordifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18598	Languas galanga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3841	Cissus quadrangula	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1109	Corydalis persica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12870	Curcuma aeruginosa	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8525	Pinus torreyana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12914	Sarcophyton flexuosum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5470	Cynoglossum amabile	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18424	Selinum libanotis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3435	Saussurea katochaete	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18765	Juniperus scopulorum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11430	Inula grantioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19769	Boschniakia rossica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12487	Juniperus horizontalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18927	Clinacanthus nutans	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18048	Phlomis crinita	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO143.1	Tephrosia purpurea subsp. apollinea	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15802	Papaver pseudocanescens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16981	Gutierrezia dracunculoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17499	Bursera kerberi	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18302	Chondrostereum purpureum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13458	Acarospora montana	Species	Acarosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18169	Creosphaeria sassafras	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4749	Matricaria caucasica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15127	Senecio congestus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29531	Lupinus cosentinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO92	Barringtonia butonica	Species	Lecythidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3268	Callyspongia flammea	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13848	Amomum daniellii	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17630	Helenium integrifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15145	Rauvolfia salicifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18262	Aspergillus microcysticus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17354	Micromonospora echinospora	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1759	Alexandrium excavatum	Species	Gonyaulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO968	Artemisia pectinata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3965	Corynanthe pachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16801	Cota tinctoria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8415	Tetragonotheca ludoviciana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19709	Pseudocyphellaria australiensis	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4194	Teucrium buxifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25370	Botrychium ternatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1513	Penicillium nalgiovense	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3089	Cistus villosus	Species	Cistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3848	Myrtopsis macrocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18873.2	Salmonella enterica subsp. enterica serovar bovismorbificans	Subspecies	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19170	Lasianthaea podocephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13358	Piper brachystachyum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12315	Lycopodiella inundata	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1783	Euonymus fortunei	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1619	Lactuca triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12278	Borreliella burgdorferi	Species	Borreliaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO470	Prismatomeris connata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10098	Glycosmis pseudoracemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17296	Beesia calthifolia	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23772	Tetradium glabrifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7941	Marshallia obovata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5398	Peucedanum oroselinum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14947	Lathyrus tingitanus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27632	Idesia polycarpa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4821	Hypselodoris infucata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1023	Laportea crenulata	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15329	Rhizoplaca baranowii	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6836	Alpinia blepharocalyx	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18348	Crotalaria stolzii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6906	Atalantia wightii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11164	Renealmia alpinia	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4679	Hedysarum gmelini	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8172	Emericellopsis minima	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7521	Hygrophorus eburneus	Species	Hygrophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16325	Sideritis dasygnaphala	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19141	Aframomum melegueta	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13647	Calcarisporium thermophilum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7193	Persicaria lapathifolia	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18533	Delisea elegans	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7385	Schisandra sphenanthera	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8707.1	Pueraria montana var. lobata	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19436	Annona cherimola	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19083	Alstonia angustiloba	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17230	Psidium acutangulum	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18676	Clerodendrum trichotomum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14233	Ormosia dasycarpa	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19572	Pellacalyx axillaris	Species	Rhizophoraceae	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
GI50	1
IC50	18
Ki	6
MIC	3
Others	29

Activity Type	# Activity
Cell Line	25
Individual Protein	10
NON-MOLECULAR	2
Organism	9
Others	12
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	83.0	uM	PMID[543080]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	123100.0	nM	PMID[543081]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[543082]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[543082]
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	>	100.0	uM	PMID[543083]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	800.0	nM	PMID[543088]
NPT520	Cell Line	3T3-L1	Mus musculus	IC50	=	118800.0	nM	PMID[543089]
NPT113	Cell Line	RAW264.7	Mus musculus	GI50	=	609000.0	nM	PMID[543090]
NPT2245	Cell Line	SiHa	Homo sapiens	IC50	>	150000.0	nM	PMID[543093]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	150000.0	nM	PMID[543093]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	400000.0	nM	PMID[543093]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	311220.0	nM	PMID[543093]
NPT2356	Cell Line	NCI-H661	Homo sapiens	IC50	=	289210.0	nM	PMID[543093]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	322920.0	nM	PMID[543093]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	120010.0	nM	PMID[543093]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	0.44	n.a.	PMID[543093]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	0.68	n.a.	PMID[543093]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	1.06	n.a.	PMID[543093]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	0.39	n.a.	PMID[543093]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	0.6	n.a.	PMID[543093]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	0.93	n.a.	PMID[543093]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	0.45	n.a.	PMID[543093]
NPT83	Cell Line	MCF7	Homo sapiens	CI	=	0.79	n.a.	PMID[543093]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	<	50.0	%	PMID[543094]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	101200.0	nM	PMID[543081]
NPT2	Others	Unspecified		Activity	=	15.7	%	PMID[543082]
NPT2	Others	Unspecified		Activity	=	42.6	%	PMID[543082]
NPT2	Others	Unspecified		Activity	=	77.5	%	PMID[543082]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[543082]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	84.2	uM	PMID[543083]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	0.0	%	PMID[543085]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	0.9	%	PMID[543085]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	7.6	%	PMID[543085]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	GI	=	41.0	%	PMID[543086]
NPT723	Organism	Pythium	Pythium	GI	=	54.0	%	PMID[543086]
NPT723	Organism	Pythium	Pythium	GI	=	0.0	%	PMID[543086]
NPT1	Others	Radical scavenging activity		IC50	>	200.0	ug.mL-1	PMID[543087]
NPT954	Individual Protein	Carbonic anhydrase XIV	Homo sapiens	Ki	=	830.0	nM	PMID[543088]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	810.0	nM	PMID[543088]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	850.0	nM	PMID[543088]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	820.0	nM	PMID[543088]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	780.0	nM	PMID[543088]
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	MIC	>	600000.0	nM	PMID[543090]
NPT2	Others	Unspecified		Selectivity Index	=	2.72	n.a.	PMID[543090]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	337000.0	nM	PMID[543090]
NPT790	Organism	Mycobacterium tuberculosis H37Rv	Mycobacterium tuberculosis H37Rv	MIC	=	224000.0	nM	PMID[543090]
NPT725	Individual Protein	2-heptyl-4(1H)-quinolone synthase PqsD	Pseudomonas aeruginosa	Inhibition	=	22.0	%	PMID[543091]
NPT2	Others	Unspecified		Inhibition	<	10.0	%	PMID[543091]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	IC50	=	30000.0	nM	PMID[543092]
NPT2	Others	Unspecified		IC50	=	1043130.0	nM	PMID[543093]
NPT2	Others	Unspecified		IC50	>	150000.0	nM	PMID[543093]
NPT2	Others	Unspecified		IC50	=	125600.0	nM	PMID[543093]
NPT35	Others	n.a.		Stability	<=	92.0	hr	PMID[543093]
NPT1593	Tissue	Liver	Rattus norvegicus	IC50	=	400.0	nM	PMID[543093]
NPT35	Others	n.a.		IC50	=	345000.0	nM	PMID[543093]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	IC50	=	30000.0	nM	PMID[543095]

☑ 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 NPC253746 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	196
0.1-0.2	1628
0.2-0.3	4810
0.3-0.4	11688
0.4-0.5	7053
0.5-0.6	9519
0.6-0.7	6396
0.7-0.8	1233
0.8-0.85	120
0.85-0.9	35
0.9-0.95	16
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC304638
0.9479	High Similarity	NPC94343
0.9474	High Similarity	NPC171843
0.9462	High Similarity	NPC32977
0.9462	High Similarity	NPC81010
0.9388	High Similarity	NPC127676
0.9286	High Similarity	NPC2518
0.9208	High Similarity	NPC75272
0.9208	High Similarity	NPC471954
0.92	High Similarity	NPC260952
0.9149	High Similarity	NPC181709
0.9109	High Similarity	NPC206341
0.9029	High Similarity	NPC139946
0.9029	High Similarity	NPC226250
0.8958	High Similarity	NPC246679
0.8958	High Similarity	NPC257182
0.8958	High Similarity	NPC286006
0.8932	High Similarity	NPC183700
0.8857	High Similarity	NPC95381
0.8812	High Similarity	NPC288760
0.8812	High Similarity	NPC303141
0.8812	High Similarity	NPC227255
0.88	High Similarity	NPC470202
0.88	High Similarity	NPC179686
0.8776	High Similarity	NPC140619
0.8774	High Similarity	NPC328593
0.8774	High Similarity	NPC33749
0.8774	High Similarity	NPC261453
0.8692	High Similarity	NPC474967
0.8692	High Similarity	NPC233669
0.8654	High Similarity	NPC79543
0.8627	High Similarity	NPC128730
0.8627	High Similarity	NPC243677
0.8611	High Similarity	NPC281277
0.8611	High Similarity	NPC131192
0.8602	High Similarity	NPC248817
0.8598	High Similarity	NPC217472
0.8586	High Similarity	NPC201967
0.8586	High Similarity	NPC175298
0.8585	High Similarity	NPC199462
0.8585	High Similarity	NPC17693
0.8544	High Similarity	NPC294902
0.8544	High Similarity	NPC326447
0.8544	High Similarity	NPC176971
0.8544	High Similarity	NPC1075
0.8544	High Similarity	NPC1786
0.8532	High Similarity	NPC122117
0.8532	High Similarity	NPC65791
0.8529	High Similarity	NPC109637
0.8526	High Similarity	NPC104216
0.8519	High Similarity	NPC296526
0.8511	High Similarity	NPC197783
0.85	High Similarity	NPC130193
0.85	High Similarity	NPC245561
0.8495	Intermediate Similarity	NPC265146
0.8495	Intermediate Similarity	NPC124436
0.8485	Intermediate Similarity	NPC283711
0.8462	Intermediate Similarity	NPC157473
0.8462	Intermediate Similarity	NPC151530
0.8455	Intermediate Similarity	NPC164706
0.8455	Intermediate Similarity	NPC137537
0.8455	Intermediate Similarity	NPC27633
0.8455	Intermediate Similarity	NPC272471
0.8455	Intermediate Similarity	NPC94298
0.8455	Intermediate Similarity	NPC107588
0.8455	Intermediate Similarity	NPC203124
0.8455	Intermediate Similarity	NPC70744
0.8455	Intermediate Similarity	NPC309434
0.8426	Intermediate Similarity	NPC41851
0.8426	Intermediate Similarity	NPC81808
0.8426	Intermediate Similarity	NPC294941
0.8421	Intermediate Similarity	NPC23167
0.8421	Intermediate Similarity	NPC184169
0.8416	Intermediate Similarity	NPC52472
0.8416	Intermediate Similarity	NPC13755
0.8411	Intermediate Similarity	NPC131530
0.8404	Intermediate Similarity	NPC175313
0.8381	Intermediate Similarity	NPC470039
0.8381	Intermediate Similarity	NPC31274
0.8367	Intermediate Similarity	NPC325292
0.8367	Intermediate Similarity	NPC138117
0.8351	Intermediate Similarity	NPC300017
0.835	Intermediate Similarity	NPC79672
0.835	Intermediate Similarity	NPC93831
0.8333	Intermediate Similarity	NPC113460
0.8333	Intermediate Similarity	NPC25493
0.8333	Intermediate Similarity	NPC472585
0.8304	Intermediate Similarity	NPC202474
0.8302	Intermediate Similarity	NPC234639
0.8288	Intermediate Similarity	NPC275519
0.8273	Intermediate Similarity	NPC128825
0.8273	Intermediate Similarity	NPC128249
0.8265	Intermediate Similarity	NPC270547
0.8252	Intermediate Similarity	NPC68269
0.8252	Intermediate Similarity	NPC135784
0.8247	Intermediate Similarity	NPC98772
0.8247	Intermediate Similarity	NPC280347
0.8247	Intermediate Similarity	NPC177420
0.8247	Intermediate Similarity	NPC123273
0.8247	Intermediate Similarity	NPC242240
0.8247	Intermediate Similarity	NPC258219
0.8247	Intermediate Similarity	NPC318325
0.8235	Intermediate Similarity	NPC107101
0.823	Intermediate Similarity	NPC470848
0.823	Intermediate Similarity	NPC204466
0.823	Intermediate Similarity	NPC470849
0.8224	Intermediate Similarity	NPC63345
0.8224	Intermediate Similarity	NPC473809
0.8218	Intermediate Similarity	NPC260000
0.8214	Intermediate Similarity	NPC241634
0.8214	Intermediate Similarity	NPC141791
0.8214	Intermediate Similarity	NPC263386
0.8214	Intermediate Similarity	NPC61779
0.82	Intermediate Similarity	NPC313650
0.819	Intermediate Similarity	NPC19149
0.819	Intermediate Similarity	NPC6984
0.8173	Intermediate Similarity	NPC52087
0.8173	Intermediate Similarity	NPC283546
0.8173	Intermediate Similarity	NPC474603
0.8173	Intermediate Similarity	NPC12987
0.8163	Intermediate Similarity	NPC300478
0.8163	Intermediate Similarity	NPC55561
0.8158	Intermediate Similarity	NPC70752
0.8155	Intermediate Similarity	NPC307425
0.8148	Intermediate Similarity	NPC470355
0.8142	Intermediate Similarity	NPC2058
0.8137	Intermediate Similarity	NPC280869
0.8137	Intermediate Similarity	NPC100870
0.8125	Intermediate Similarity	NPC94637
0.8125	Intermediate Similarity	NPC124916
0.8113	Intermediate Similarity	NPC29883
0.8113	Intermediate Similarity	NPC226699
0.8108	Intermediate Similarity	NPC19290
0.8095	Intermediate Similarity	NPC238115
0.8095	Intermediate Similarity	NPC233396
0.8095	Intermediate Similarity	NPC473855
0.8095	Intermediate Similarity	NPC154899
0.8095	Intermediate Similarity	NPC13495
0.8091	Intermediate Similarity	NPC235250
0.8087	Intermediate Similarity	NPC67300
0.8081	Intermediate Similarity	NPC45040
0.8081	Intermediate Similarity	NPC155908
0.8081	Intermediate Similarity	NPC204210
0.8081	Intermediate Similarity	NPC304541
0.8077	Intermediate Similarity	NPC305205
0.8073	Intermediate Similarity	NPC26615
0.8073	Intermediate Similarity	NPC48525
0.807	Intermediate Similarity	NPC476872
0.8061	Intermediate Similarity	NPC259134
0.8061	Intermediate Similarity	NPC177844
0.8061	Intermediate Similarity	NPC8002
0.8061	Intermediate Similarity	NPC99886
0.8053	Intermediate Similarity	NPC37858
0.8053	Intermediate Similarity	NPC90522
0.8053	Intermediate Similarity	NPC328459
0.8041	Intermediate Similarity	NPC307235
0.8041	Intermediate Similarity	NPC407
0.8036	Intermediate Similarity	NPC39793
0.8036	Intermediate Similarity	NPC240664
0.8021	Intermediate Similarity	NPC150837
0.8021	Intermediate Similarity	NPC286904
0.802	Intermediate Similarity	NPC26244
0.8019	Intermediate Similarity	NPC135464
0.8019	Intermediate Similarity	NPC92623
0.8019	Intermediate Similarity	NPC29989
0.8019	Intermediate Similarity	NPC184658
0.8019	Intermediate Similarity	NPC1065
0.8019	Intermediate Similarity	NPC113457
0.8019	Intermediate Similarity	NPC95178
0.8019	Intermediate Similarity	NPC69332
0.8	Intermediate Similarity	NPC264558
0.8	Intermediate Similarity	NPC11724
0.8	Intermediate Similarity	NPC109241
0.8	Intermediate Similarity	NPC147654
0.8	Intermediate Similarity	NPC148969
0.8	Intermediate Similarity	NPC11824
0.8	Intermediate Similarity	NPC190212
0.7982	Intermediate Similarity	NPC72977
0.7982	Intermediate Similarity	NPC228609
0.7981	Intermediate Similarity	NPC84325
0.7981	Intermediate Similarity	NPC51633
0.798	Intermediate Similarity	NPC71853
0.7965	Intermediate Similarity	NPC311091
0.7965	Intermediate Similarity	NPC471033
0.7963	Intermediate Similarity	NPC95172
0.7963	Intermediate Similarity	NPC326187
0.7961	Intermediate Similarity	NPC128723
0.7959	Intermediate Similarity	NPC173443
0.7959	Intermediate Similarity	NPC27974
0.7949	Intermediate Similarity	NPC184219
0.7949	Intermediate Similarity	NPC146886
0.7949	Intermediate Similarity	NPC20443
0.7949	Intermediate Similarity	NPC265413
0.7949	Intermediate Similarity	NPC10154
0.7949	Intermediate Similarity	NPC474532
0.7949	Intermediate Similarity	NPC60517
0.7949	Intermediate Similarity	NPC246704
0.7941	Intermediate Similarity	NPC473388
0.7938	Intermediate Similarity	NPC155393
0.7931	Intermediate Similarity	NPC291189

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 NPC253746 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	967
0.2-0.3	1390
0.3-0.4	2834
0.4-0.5	2034
0.5-0.6	1152
0.6-0.7	509
0.7-0.8	65
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8544	High Similarity	NPD3134	Approved
0.8495	Intermediate Similarity	NPD111	Approved
0.8462	Intermediate Similarity	NPD1358	Approved
0.8455	Intermediate Similarity	NPD9545	Approved
0.8273	Intermediate Similarity	NPD9493	Approved
0.8113	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.81	Intermediate Similarity	NPD2934	Approved
0.81	Intermediate Similarity	NPD2933	Approved
0.802	Intermediate Similarity	NPD2859	Approved
0.802	Intermediate Similarity	NPD2860	Approved
0.7921	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD422	Phase 1
0.7826	Intermediate Similarity	NPD4626	Approved
0.7788	Intermediate Similarity	NPD3020	Approved
0.7757	Intermediate Similarity	NPD9697	Approved
0.7706	Intermediate Similarity	NPD74	Approved
0.7706	Intermediate Similarity	NPD9266	Approved
0.7658	Intermediate Similarity	NPD228	Approved
0.7642	Intermediate Similarity	NPD846	Approved
0.7642	Intermediate Similarity	NPD940	Approved
0.7615	Intermediate Similarity	NPD9263	Approved
0.7615	Intermediate Similarity	NPD9264	Approved
0.7615	Intermediate Similarity	NPD9267	Approved
0.7563	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1242	Phase 1
0.7544	Intermediate Similarity	NPD256	Approved
0.7544	Intermediate Similarity	NPD255	Approved
0.7523	Intermediate Similarity	NPD968	Approved
0.7522	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD844	Approved
0.75	Intermediate Similarity	NPD1809	Phase 2
0.7479	Intermediate Similarity	NPD9717	Approved
0.7476	Intermediate Similarity	NPD845	Approved
0.7458	Intermediate Similarity	NPD3847	Discontinued
0.7458	Intermediate Similarity	NPD3496	Discontinued
0.7436	Intermediate Similarity	NPD5691	Approved
0.7434	Intermediate Similarity	NPD5535	Approved
0.7429	Intermediate Similarity	NPD288	Approved
0.7426	Intermediate Similarity	NPD9295	Approved
0.7419	Intermediate Similarity	NPD9716	Approved
0.74	Intermediate Similarity	NPD1282	Approved
0.7395	Intermediate Similarity	NPD1535	Discovery
0.7387	Intermediate Similarity	NPD2684	Approved
0.7383	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD9258	Approved
0.7353	Intermediate Similarity	NPD9256	Approved
0.735	Intermediate Similarity	NPD1894	Discontinued
0.7339	Intermediate Similarity	NPD9610	Approved
0.7339	Intermediate Similarity	NPD9608	Approved
0.7333	Intermediate Similarity	NPD1481	Phase 2
0.7328	Intermediate Similarity	NPD9568	Approved
0.7317	Intermediate Similarity	NPD9494	Approved
0.7312	Intermediate Similarity	NPD9087	Approved
0.7297	Intermediate Similarity	NPD290	Approved
0.7295	Intermediate Similarity	NPD1203	Approved
0.7281	Intermediate Similarity	NPD821	Approved
0.728	Intermediate Similarity	NPD3764	Approved
0.7265	Intermediate Similarity	NPD5536	Phase 2
0.7255	Intermediate Similarity	NPD689	Discontinued
0.7248	Intermediate Similarity	NPD9261	Approved
0.7244	Intermediate Similarity	NPD230	Phase 1
0.7227	Intermediate Similarity	NPD1778	Approved
0.7213	Intermediate Similarity	NPD1283	Approved
0.7188	Intermediate Similarity	NPD9088	Approved
0.7168	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3021	Approved
0.7168	Intermediate Similarity	NPD3022	Approved
0.7155	Intermediate Similarity	NPD9281	Approved
0.7154	Intermediate Similarity	NPD1164	Approved
0.7154	Intermediate Similarity	NPD2935	Discontinued
0.7154	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD1357	Approved
0.713	Intermediate Similarity	NPD1238	Approved
0.713	Intermediate Similarity	NPD7843	Approved
0.7099	Intermediate Similarity	NPD7266	Discontinued
0.7083	Intermediate Similarity	NPD9294	Approved
0.7075	Intermediate Similarity	NPD9296	Approved
0.7073	Intermediate Similarity	NPD3225	Approved
0.7073	Intermediate Similarity	NPD196	Phase 1
0.7064	Intermediate Similarity	NPD3028	Approved
0.7059	Intermediate Similarity	NPD1548	Phase 1
0.7043	Intermediate Similarity	NPD969	Suspended
0.704	Intermediate Similarity	NPD5736	Approved
0.7037	Intermediate Similarity	NPD9273	Approved
0.7037	Intermediate Similarity	NPD9495	Approved
0.7034	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD1240	Approved
0.7031	Intermediate Similarity	NPD4060	Phase 1
0.7027	Intermediate Similarity	NPD164	Approved
0.7018	Intermediate Similarity	NPD5451	Approved
0.7016	Intermediate Similarity	NPD987	Approved
0.7009	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1281	Approved
0.6961	Remote Similarity	NPD9259	Approved
0.6961	Remote Similarity	NPD9257	Approved
0.6949	Remote Similarity	NPD6671	Approved
0.6949	Remote Similarity	NPD7157	Approved
0.694	Remote Similarity	NPD8166	Discontinued
0.6937	Remote Similarity	NPD6647	Phase 2
0.6937	Remote Similarity	NPD9500	Approved
0.6929	Remote Similarity	NPD5163	Phase 2
0.6923	Remote Similarity	NPD2228	Approved
0.6923	Remote Similarity	NPD2229	Approved
0.6923	Remote Similarity	NPD2234	Approved
0.6923	Remote Similarity	NPD1607	Approved
0.6917	Remote Similarity	NPD1759	Phase 1
0.6911	Remote Similarity	NPD1608	Approved
0.6911	Remote Similarity	NPD9269	Phase 2
0.6911	Remote Similarity	NPD3972	Approved
0.6905	Remote Similarity	NPD454	Approved
0.6903	Remote Similarity	NPD1444	Approved
0.6903	Remote Similarity	NPD1445	Approved
0.69	Remote Similarity	NPD9089	Approved
0.6897	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD411	Approved
0.6875	Remote Similarity	NPD5909	Discontinued
0.6875	Remote Similarity	NPD6798	Discontinued
0.6875	Remote Similarity	NPD3268	Approved
0.6866	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.686	Remote Similarity	NPD9268	Approved
0.686	Remote Similarity	NPD5585	Approved
0.6855	Remote Similarity	NPD6583	Phase 3
0.6855	Remote Similarity	NPD6582	Phase 2
0.6855	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD447	Suspended
0.6846	Remote Similarity	NPD4340	Discontinued
0.6838	Remote Similarity	NPD9379	Approved
0.6838	Remote Similarity	NPD9377	Approved
0.6833	Remote Similarity	NPD1758	Phase 1
0.6833	Remote Similarity	NPD16	Approved
0.6833	Remote Similarity	NPD856	Approved
0.6833	Remote Similarity	NPD317	Approved
0.6833	Remote Similarity	NPD318	Approved
0.6832	Remote Similarity	NPD3971	Phase 1
0.6832	Remote Similarity	NPD9491	Approved
0.6829	Remote Similarity	NPD1610	Phase 2
0.6825	Remote Similarity	NPD258	Approved
0.6825	Remote Similarity	NPD1019	Discontinued
0.6825	Remote Similarity	NPD257	Approved
0.6822	Remote Similarity	NPD6663	Approved
0.6822	Remote Similarity	NPD259	Phase 1
0.6822	Remote Similarity	NPD4062	Phase 3
0.6822	Remote Similarity	NPD520	Approved
0.6822	Remote Similarity	NPD1202	Approved
0.6822	Remote Similarity	NPD6233	Phase 2
0.6818	Remote Similarity	NPD2799	Discontinued
0.6815	Remote Similarity	NPD4628	Phase 3
0.6815	Remote Similarity	NPD7003	Approved
0.681	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3019	Approved
0.6803	Remote Similarity	NPD2668	Approved
0.6803	Remote Similarity	NPD2932	Approved
0.6803	Remote Similarity	NPD2667	Approved
0.68	Remote Similarity	NPD9093	Approved
0.68	Remote Similarity	NPD1876	Approved
0.6797	Remote Similarity	NPD7095	Approved
0.6797	Remote Similarity	NPD3136	Phase 2
0.6792	Remote Similarity	NPD9365	Approved
0.6791	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2182	Approved
0.6783	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5283	Phase 1
0.6777	Remote Similarity	NPD3091	Approved
0.6769	Remote Similarity	NPD825	Approved
0.6769	Remote Similarity	NPD4140	Approved
0.6769	Remote Similarity	NPD826	Approved
0.6767	Remote Similarity	NPD1551	Phase 2
0.6765	Remote Similarity	NPD6190	Approved
0.6744	Remote Similarity	NPD1048	Approved
0.6726	Remote Similarity	NPD1237	Approved
0.6724	Remote Similarity	NPD4750	Phase 3
0.6724	Remote Similarity	NPD1792	Phase 2
0.6723	Remote Similarity	NPD9618	Approved
0.6723	Remote Similarity	NPD9614	Approved
0.6721	Remote Similarity	NPD1651	Approved
0.672	Remote Similarity	NPD3685	Discontinued
0.6719	Remote Similarity	NPD2614	Approved
0.6719	Remote Similarity	NPD6832	Phase 2
0.6719	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5124	Phase 1
0.6718	Remote Similarity	NPD555	Phase 2
0.6718	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6355	Discontinued
0.6699	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD1138	Approved
0.6693	Remote Similarity	NPD2798	Approved
0.6693	Remote Similarity	NPD5647	Approved
0.6693	Remote Similarity	NPD6584	Phase 3
0.6692	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1510	Phase 2
0.6692	Remote Similarity	NPD5745	Approved
0.6692	Remote Similarity	NPD4308	Phase 3
0.6691	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD9712	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