NPASS Compound

Structure

CID238140 OpenBabel06191716042D 32 37 0 0 1 0 0 0 0 0999 V2000 -3.4628 -0.0228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2978 -0.5046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6282 -1.4691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6395 -3.3969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6391 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7519 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2984 -3.3975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9587 -2.4320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6280 -0.5050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2981 -1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8040 -2.9150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1337 -2.9153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4633 -1.9509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8038 -1.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4743 -2.9146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4741 -1.9499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8758 -0.5060 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8756 -1.5174 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0005 -2.0229 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8763 -1.5170 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1335 -1.9506 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8761 -0.5055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6277 -0.5064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7514 -2.0234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 -3.0344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7524 -2.0225 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4635 -2.9156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3918 -3.2125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3915 -1.6517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7519 0.0005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9688 -1.4684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 9 2 0 0 0 0 3 13 1 0 0 0 0 4 11 2 0 0 0 0 4 15 1 0 0 0 0 5 14 2 0 0 0 0 5 16 1 0 0 0 0 6 23 1 0 0 0 0 7 27 1 0 0 0 0 8 28 1 0 0 0 0 8 29 1 0 0 0 0 9 30 1 0 0 0 0 10 13 2 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 7 1 1 0 0 0 12 21 1 0 0 0 0 13 27 1 0 0 0 0 14 31 1 0 0 0 0 15 16 2 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 6 1 6 0 0 0 17 18 1 0 0 0 0 17 32 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 22 1 0 0 0 0 20 26 1 1 0 0 0 21 10 1 1 0 0 0 21 31 1 0 0 0 0 22 30 1 6 0 0 0 22 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.12
Volume:	409.813
LogP:	0.871
LogD:	1.258
LogS:	-4.405
# Rotatable Bonds:	3
TPSA:	136.3
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	4.269
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:	-6.14
MDCK Permeability:	3.447219205554575e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.433
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	95.1161880493164%
Volume Distribution (VD):	0.626
Pgp-substrate:	3.594585418701172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.124
CYP1A2-substrate:	0.385
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.678
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.479
CYP2D6-inhibitor:	0.814
CYP2D6-substrate:	0.292
CYP3A4-inhibitor:	0.805
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	4.407
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.735
Drug-inuced Liver Injury (DILI):	0.634
AMES Toxicity:	0.92
Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.271
Skin Sensitization:	0.401
Carcinogencity:	0.884
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC238140

Natural Product ID:	NPC238140
*Common Name:**	Trifolirhizin
IUPAC Name:	n.a.
Synonyms:	Trifolirhizin; Trifolrhizin
Standard InCHIKey:	VGSYCWGXBYZLLE-QEEQPWONSA-N
Standard InCHI:	InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/m0/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc3c(c2)OC[C@@H]2[C@H]3Oc3c2cc2c(c3)OCO2)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454878
PubChem CID:	442827
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11054840]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	twigs	n.a.	n.a.	PMID[1453182]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15165152]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15911254]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18348535]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19407970]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19586051]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	stems	n.a.	n.a.	PMID[20095629]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24345512]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24459770]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[24959987]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25506718]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	root bark	Mongolian	n.a.	PMID[26073007]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	Rhizomes	Nanning, Guangxi Province, China	2012-Dec	PMID[26132528]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27494664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	Roots; Rhizomes	n.a.	n.a.	PMID[30698432]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30917277]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[31747283]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28072	Theonella conica	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21243	Siphonaria capensis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21108	Eria anomala	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8372	Picrasma quassioides	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21631	Faramea salicifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5903	Conus mus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21038	Lemaireocereus longispinus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20084	Atraphaxis spinosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28202	Helichrysum tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20421	Aplophyllum alberti-regelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22937	Vernonia fagifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19995	Baccharis neglecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19912	Vellozia nanuzae	Species	Velloziaceae	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
EC50	1
IC50	2
Ki	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[509392]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	>	300.0	ug.mL-1	PMID[509390]
NPT2	Others	Unspecified		IC50	=	237000.0	nM	PMID[509391]
NPT2	Others	Unspecified		Ki	=	190000.0	nM	PMID[509391]

☑ 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 NPC238140 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	474
0.1-0.2	1595
0.2-0.3	4131
0.3-0.4	10304
0.4-0.5	8268
0.5-0.6	4799
0.6-0.7	7433
0.7-0.8	4510
0.8-0.85	826
0.85-0.9	286
0.9-0.95	70
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9384	High Similarity	NPC35877
0.9384	High Similarity	NPC95392
0.9384	High Similarity	NPC55715
0.9375	High Similarity	NPC11422
0.9375	High Similarity	NPC178014
0.9375	High Similarity	NPC474749
0.9375	High Similarity	NPC42716
0.9315	High Similarity	NPC166584
0.9315	High Similarity	NPC301961
0.9315	High Similarity	NPC270751
0.931	High Similarity	NPC226540
0.931	High Similarity	NPC162193
0.9301	High Similarity	NPC80326
0.9252	High Similarity	NPC240521
0.9252	High Similarity	NPC51328
0.9252	High Similarity	NPC55158
0.9252	High Similarity	NPC286235
0.9231	High Similarity	NPC300798
0.9231	High Similarity	NPC108674
0.9231	High Similarity	NPC58137
0.92	High Similarity	NPC159922
0.9184	High Similarity	NPC71726
0.9184	High Similarity	NPC130449
0.9184	High Similarity	NPC248132
0.9184	High Similarity	NPC175976
0.9178	High Similarity	NPC205796
0.9178	High Similarity	NPC125755
0.9178	High Similarity	NPC276753
0.9172	High Similarity	NPC138227
0.9172	High Similarity	NPC469313
0.9172	High Similarity	NPC168579
0.9172	High Similarity	NPC76176
0.9167	High Similarity	NPC174522
0.9167	High Similarity	NPC246947
0.9161	High Similarity	NPC226547
0.9116	High Similarity	NPC227902
0.9116	High Similarity	NPC39657
0.911	High Similarity	NPC307466
0.911	High Similarity	NPC277867
0.911	High Similarity	NPC161700
0.9103	High Similarity	NPC37793
0.9103	High Similarity	NPC252169
0.9103	High Similarity	NPC474808
0.9091	High Similarity	NPC156376
0.9067	High Similarity	NPC302610
0.906	High Similarity	NPC472710
0.906	High Similarity	NPC472709
0.9048	High Similarity	NPC190714
0.9048	High Similarity	NPC99515
0.9041	High Similarity	NPC217635
0.9041	High Similarity	NPC79429
0.9041	High Similarity	NPC471063
0.9041	High Similarity	NPC471667
0.9034	High Similarity	NPC472562
0.9034	High Similarity	NPC472353
0.9021	High Similarity	NPC185908
0.9021	High Similarity	NPC283949
0.9007	High Similarity	NPC78809
0.8986	High Similarity	NPC15538
0.8986	High Similarity	NPC473480
0.898	High Similarity	NPC43508
0.898	High Similarity	NPC180953
0.898	High Similarity	NPC476301
0.898	High Similarity	NPC22150
0.898	High Similarity	NPC205316
0.898	High Similarity	NPC475096
0.898	High Similarity	NPC279298
0.898	High Similarity	NPC38041
0.8966	High Similarity	NPC471908
0.8966	High Similarity	NPC469661
0.8958	High Similarity	NPC292487
0.8933	High Similarity	NPC98624
0.8933	High Similarity	NPC475224
0.8926	High Similarity	NPC280945
0.8919	High Similarity	NPC112861
0.8912	High Similarity	NPC472713
0.8912	High Similarity	NPC473045
0.8912	High Similarity	NPC187774
0.8912	High Similarity	NPC25292
0.8912	High Similarity	NPC118385
0.8912	High Similarity	NPC473046
0.8912	High Similarity	NPC472712
0.8904	High Similarity	NPC189115
0.8904	High Similarity	NPC107161
0.8904	High Similarity	NPC475084
0.8904	High Similarity	NPC311057
0.8903	High Similarity	NPC100936
0.8903	High Similarity	NPC1253
0.8897	High Similarity	NPC56091
0.8897	High Similarity	NPC46591
0.8897	High Similarity	NPC27495
0.8881	High Similarity	NPC150534
0.8859	High Similarity	NPC31325
0.8859	High Similarity	NPC114505
0.8859	High Similarity	NPC213074
0.8859	High Similarity	NPC101376
0.8859	High Similarity	NPC15956
0.8859	High Similarity	NPC193473
0.8859	High Similarity	NPC224674
0.8859	High Similarity	NPC275284
0.8851	High Similarity	NPC469586
0.8851	High Similarity	NPC18979
0.8844	High Similarity	NPC81638
0.8844	High Similarity	NPC470950
0.8844	High Similarity	NPC185307
0.8844	High Similarity	NPC477898
0.8844	High Similarity	NPC473044
0.8836	High Similarity	NPC471389
0.8836	High Similarity	NPC311530
0.8836	High Similarity	NPC247291
0.8828	High Similarity	NPC9068
0.8828	High Similarity	NPC471388
0.8819	High Similarity	NPC172818
0.8819	High Similarity	NPC25695
0.8819	High Similarity	NPC104167
0.8816	High Similarity	NPC21902
0.8811	High Similarity	NPC474478
0.8811	High Similarity	NPC476411
0.8792	High Similarity	NPC324492
0.8792	High Similarity	NPC317053
0.8784	High Similarity	NPC93323
0.8784	High Similarity	NPC84181
0.8784	High Similarity	NPC45257
0.8784	High Similarity	NPC283995
0.8784	High Similarity	NPC470235
0.8784	High Similarity	NPC12641
0.8784	High Similarity	NPC280092
0.8784	High Similarity	NPC129417
0.8776	High Similarity	NPC287124
0.8776	High Similarity	NPC5262
0.8776	High Similarity	NPC469559
0.8776	High Similarity	NPC302506
0.8776	High Similarity	NPC472714
0.8776	High Similarity	NPC476356
0.8767	High Similarity	NPC254759
0.8767	High Similarity	NPC160283
0.8767	High Similarity	NPC177868
0.8767	High Similarity	NPC284464
0.8767	High Similarity	NPC309124
0.8767	High Similarity	NPC184797
0.8767	High Similarity	NPC106944
0.8766	High Similarity	NPC164152
0.8759	High Similarity	NPC65530
0.8759	High Similarity	NPC87777
0.8759	High Similarity	NPC262328
0.8759	High Similarity	NPC59324
0.875	High Similarity	NPC473621
0.875	High Similarity	NPC236522
0.875	High Similarity	NPC470236
0.8741	High Similarity	NPC196937
0.8741	High Similarity	NPC136750
0.8741	High Similarity	NPC69513
0.8741	High Similarity	NPC215833
0.8741	High Similarity	NPC266848
0.8741	High Similarity	NPC263064
0.8733	High Similarity	NPC327412
0.8733	High Similarity	NPC16269
0.8733	High Similarity	NPC320970
0.8733	High Similarity	NPC328567
0.8733	High Similarity	NPC320671
0.8733	High Similarity	NPC21776
0.8732	High Similarity	NPC9912
0.8725	High Similarity	NPC475868
0.8718	High Similarity	NPC173726
0.8718	High Similarity	NPC241600
0.8716	High Similarity	NPC477616
0.8716	High Similarity	NPC255566
0.8716	High Similarity	NPC46092
0.8716	High Similarity	NPC185071
0.8716	High Similarity	NPC298317
0.8716	High Similarity	NPC102044
0.8716	High Similarity	NPC85264
0.8716	High Similarity	NPC472451
0.8716	High Similarity	NPC47633
0.8716	High Similarity	NPC12728
0.871	High Similarity	NPC189730
0.8707	High Similarity	NPC178054
0.8707	High Similarity	NPC312199
0.8707	High Similarity	NPC210192
0.8707	High Similarity	NPC472711
0.8699	High Similarity	NPC127218
0.8699	High Similarity	NPC473739
0.8699	High Similarity	NPC98777
0.8699	High Similarity	NPC245207
0.8699	High Similarity	NPC236306
0.8699	High Similarity	NPC232164
0.8699	High Similarity	NPC25966
0.8699	High Similarity	NPC292882
0.8699	High Similarity	NPC30951
0.8699	High Similarity	NPC212770
0.8699	High Similarity	NPC319647
0.8699	High Similarity	NPC6369
0.8693	High Similarity	NPC233467
0.8693	High Similarity	NPC215060
0.8693	High Similarity	NPC474442
0.8693	High Similarity	NPC272552
0.8693	High Similarity	NPC59692
0.8693	High Similarity	NPC226108
0.8693	High Similarity	NPC46283
0.8693	High Similarity	NPC322899

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 NPC238140 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	841
0.2-0.3	1923
0.3-0.4	2818
0.4-0.5	1660
0.5-0.6	916
0.6-0.7	509
0.7-0.8	94
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8414	Intermediate Similarity	NPD1613	Approved
0.8414	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1653	Approved
0.8344	Intermediate Similarity	NPD7228	Approved
0.8261	Intermediate Similarity	NPD7199	Phase 2
0.8239	Intermediate Similarity	NPD4966	Approved
0.8239	Intermediate Similarity	NPD4965	Approved
0.8239	Intermediate Similarity	NPD4967	Phase 2
0.8212	Intermediate Similarity	NPD6674	Discontinued
0.8144	Intermediate Similarity	NPD7240	Approved
0.8138	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6234	Discontinued
0.8082	Intermediate Similarity	NPD3027	Phase 3
0.8069	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD37	Approved
0.8049	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.7964	Intermediate Similarity	NPD7054	Approved
0.7945	Intermediate Similarity	NPD2861	Phase 2
0.7917	Intermediate Similarity	NPD7472	Approved
0.7902	Intermediate Similarity	NPD1091	Approved
0.7891	Intermediate Similarity	NPD4908	Phase 1
0.7882	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1610	Phase 2
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.7765	Intermediate Similarity	NPD6797	Phase 2
0.7758	Intermediate Similarity	NPD5494	Approved
0.7744	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7266	Discontinued
0.7719	Intermediate Similarity	NPD7251	Discontinued
0.7669	Intermediate Similarity	NPD8455	Phase 2
0.7655	Intermediate Similarity	NPD3705	Approved
0.7576	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6166	Phase 2
0.7574	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5844	Phase 1
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD1934	Approved
0.7484	Intermediate Similarity	NPD5058	Phase 3
0.7473	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3018	Phase 2
0.7456	Intermediate Similarity	NPD3787	Discontinued
0.7442	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7680	Approved
0.7405	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3383	Approved
0.7394	Intermediate Similarity	NPD3384	Approved
0.7394	Intermediate Similarity	NPD3382	Approved
0.7379	Intermediate Similarity	NPD1548	Phase 1
0.7349	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2801	Approved
0.7345	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1357	Approved
0.7329	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD4749	Approved
0.7315	Intermediate Similarity	NPD2983	Phase 2
0.7315	Intermediate Similarity	NPD2982	Phase 2
0.7305	Intermediate Similarity	NPD3817	Phase 2
0.7301	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7549	Discontinued
0.7273	Intermediate Similarity	NPD5283	Phase 1
0.7261	Intermediate Similarity	NPD5588	Approved
0.7257	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD4625	Phase 3
0.7248	Intermediate Similarity	NPD2981	Phase 2
0.7246	Intermediate Similarity	NPD1465	Phase 2
0.7202	Intermediate Similarity	NPD5402	Approved
0.7202	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1652	Phase 2
0.7184	Intermediate Similarity	NPD3751	Discontinued
0.7179	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5124	Phase 1
0.7178	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4380	Phase 2
0.7167	Intermediate Similarity	NPD6841	Approved
0.7167	Intermediate Similarity	NPD6843	Phase 3
0.7167	Intermediate Similarity	NPD6842	Approved
0.716	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7134	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7685	Pre-registration
0.7115	Intermediate Similarity	NPD4060	Phase 1
0.7108	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4536	Approved
0.7089	Intermediate Similarity	NPD7097	Phase 1
0.7089	Intermediate Similarity	NPD4538	Approved
0.7089	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6355	Discontinued
0.707	Intermediate Similarity	NPD5735	Approved
0.7063	Intermediate Similarity	NPD5762	Approved
0.7063	Intermediate Similarity	NPD5763	Approved
0.7063	Intermediate Similarity	NPD1375	Discontinued
0.7055	Intermediate Similarity	NPD7157	Approved
0.7052	Intermediate Similarity	NPD3051	Approved
0.7047	Intermediate Similarity	NPD5125	Phase 3
0.7047	Intermediate Similarity	NPD5126	Approved
0.7044	Intermediate Similarity	NPD5960	Phase 3
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8651	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7037	Intermediate Similarity	NPD7466	Approved
0.7017	Intermediate Similarity	NPD4663	Approved
0.7012	Intermediate Similarity	NPD1511	Approved
0.7011	Intermediate Similarity	NPD2970	Approved
0.7011	Intermediate Similarity	NPD2969	Approved
0.7006	Intermediate Similarity	NPD3620	Phase 2
0.7006	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3454	Phase 3
0.6994	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8127	Discontinued
0.6975	Remote Similarity	NPD5177	Phase 3
0.6966	Remote Similarity	NPD7843	Approved
0.6957	Remote Similarity	NPD3540	Phase 1
0.6951	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6233	Phase 2
0.6941	Remote Similarity	NPD2977	Approved
0.6941	Remote Similarity	NPD7819	Suspended
0.6941	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2978	Approved
0.6939	Remote Similarity	NPD6671	Approved
0.6937	Remote Similarity	NPD4108	Discontinued
0.6933	Remote Similarity	NPD6331	Phase 2
0.6933	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4110	Phase 3
0.6928	Remote Similarity	NPD1512	Approved
0.6923	Remote Similarity	NPD2684	Approved
0.6919	Remote Similarity	NPD7075	Discontinued
0.6909	Remote Similarity	NPD7213	Phase 3
0.6909	Remote Similarity	NPD7212	Phase 2
0.6905	Remote Similarity	NPD4005	Discontinued
0.6901	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3539	Phase 1
0.689	Remote Similarity	NPD2677	Approved
0.6886	Remote Similarity	NPD5403	Approved
0.6885	Remote Similarity	NPD7906	Approved
0.6879	Remote Similarity	NPD6798	Discontinued
0.6875	Remote Similarity	NPD2489	Approved
0.6875	Remote Similarity	NPD27	Approved
0.6871	Remote Similarity	NPD4237	Approved
0.6871	Remote Similarity	NPD4236	Phase 3
0.6867	Remote Similarity	NPD5401	Approved
0.6867	Remote Similarity	NPD7447	Phase 1
0.6865	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7028	Phase 2
0.6864	Remote Similarity	NPD4675	Approved
0.6864	Remote Similarity	NPD4678	Approved
0.6857	Remote Similarity	NPD6232	Discontinued
0.6857	Remote Similarity	NPD7229	Phase 3
0.6853	Remote Similarity	NPD290	Approved
0.6852	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD4578	Approved
0.6851	Remote Similarity	NPD4577	Approved
0.6836	Remote Similarity	NPD7473	Discontinued
0.6829	Remote Similarity	NPD3750	Approved
0.6824	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5846	Approved
0.6821	Remote Similarity	NPD6516	Phase 2
0.6815	Remote Similarity	NPD7095	Approved
0.6813	Remote Similarity	NPD8053	Approved
0.6813	Remote Similarity	NPD8054	Approved
0.681	Remote Similarity	NPD1549	Phase 2
0.681	Remote Similarity	NPD2424	Discontinued
0.6802	Remote Similarity	NPD2563	Approved
0.6802	Remote Similarity	NPD2560	Approved
0.68	Remote Similarity	NPD6959	Discontinued
0.6792	Remote Similarity	NPD4140	Approved
0.679	Remote Similarity	NPD6099	Approved
0.679	Remote Similarity	NPD2161	Phase 2
0.679	Remote Similarity	NPD6100	Approved
0.6788	Remote Similarity	NPD6190	Approved
0.6784	Remote Similarity	NPD6801	Discontinued
0.6781	Remote Similarity	NPD228	Approved
0.677	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6071	Discontinued
0.676	Remote Similarity	NPD8156	Discontinued
0.6758	Remote Similarity	NPD7312	Approved
0.6758	Remote Similarity	NPD7310	Approved
0.6758	Remote Similarity	NPD7313	Approved
0.6758	Remote Similarity	NPD7311	Approved
0.6757	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6002	Phase 3
0.6748	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6004	Phase 3
0.6748	Remote Similarity	NPD6005	Phase 3
0.6747	Remote Similarity	NPD7124	Phase 2
0.6732	Remote Similarity	NPD422	Phase 1

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