NPASS Compound

Structure

CID152042 OpenBabel06191715522D 21 23 0 0 0 0 0 0 0 0999 V2000 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 20 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 9 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 12 2 0 0 0 0 9 16 1 0 0 0 0 10 20 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 16 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	3.659
LogD:	2.725
LogS:	-3.685
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.756
Synthetic Accessibility Score:	2.142
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.918
MDCK Permeability:	1.516499924036907e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.709

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	97.53351593017578%
Volume Distribution (VD):	0.579
Pgp-substrate:	3.377686023712158%

ADMET: Metabolism

CYP1A2-inhibitor:	0.974
CYP1A2-substrate:	0.724
CYP2C19-inhibitor:	0.701
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.802
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.739
CYP2D6-substrate:	0.443
CYP3A4-inhibitor:	0.547
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	2.74
Half-life (T1/2):	0.701

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.65
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.215
Skin Sensitization:	0.639
Carcinogencity:	0.108
Eye Corrosion:	0.01
Eye Irritation:	0.909
Respiratory Toxicity:	0.226

Download Data

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

Natural Product: NPC152042

Natural Product ID:	NPC152042
*Common Name:**	Izalpinin
IUPAC Name:	3,5-dihydroxy-7-methoxy-2-phenylchromen-4-one
Synonyms:	Izalpinin
Standard InCHIKey:	PVJNLMXWZXXHSZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-20-10-7-11(17)13-12(8-10)21-16(15(19)14(13)18)9-5-3-2-4-6-9/h2-8,17,19H,1H3
SMILES:	COc1cc(O)c2c(c1)oc(c(c2=O)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464966
PubChem CID:	5318691
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(81)85171-0]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[10579867]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[11141121]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	subterranean part	n.a.	n.a.	PMID[11374949]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11514174]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11536386]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[11975496]
NPO32539	chinese propolis	Species	Rhytismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027739]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	fruit	Hainan Island, China	1998	PMID[12398545]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO22375	Saussurea salicifolia	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[18057725]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[18293903]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341288]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19432411]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO40884	Mexican propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20307087]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22277277]
NPO40192	Macaranga kurzii	Species	Euphorbiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23134335]
NPO25106	Arnica parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23583435]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24035341]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	PMID[24669201]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25757283]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO18650	Carassius auratus	Species	Cyprinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[6880243]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9157192]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[9157192]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2924	Pinus excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18650	Carassius auratus	Species	Cyprinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23288	Justicia betonica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18650	Carassius auratus	Species	Cyprinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2924	Pinus excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18650	Carassius auratus	Species	Cyprinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2673	Alpinia chinensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22924	Bombus terrestris	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22715	Alpinia oxyphylla	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24268	Pteryxia terebinthina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23288	Justicia betonica	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24118	Buxus hildebrandtii	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29503	Alstonia spectabilis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24559	Cotinus coggygria	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23375	Hypericum reptans	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24937	Callicarpa acuminata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23149	Callistemon coccineus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24021	Eucryphia cordifolia	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18650	Carassius auratus	Species	Cyprinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25031	Petunia nyctaginiflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24493	Echinacea simulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25130	Hylotrupes bajulus	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24874	Croton geayi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17445	Streptomyces corchorusii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25068	Zebrina pendula	Species	Enidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24843	Pachygone dasycarpa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25106	Arnica parryi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19716	Uvaria lucida	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1674	Dalbergia nitidula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21242	Neolitsea villosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24754	Tsitsikamma favus	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24688	Streptomyces ramocissimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11542	Laminaria cloustoni	Species	Laminariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6584	Pterodon apparicioi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23837	Rubus laciniatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21483	0nomuraea dietziae	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24191	Drypetes tessmanniana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13455	Hemiselmis virescens	Species	Hemiselmidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28259	Viguiera pinnatilobata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27277	Stenocarpella maydis	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23657	Ophiocordyceps heteropoda	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24589	Grindelia discoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23660	Alpinia zerumbet	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23750	Escontria chiotilla	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24900	Vladimiria muliensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24813	Agardhiella tenera	Species	Solieriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24659	Eremurus chinensis	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7302	Glycosmis parva	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2924	Pinus excelsa	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23478	Uncaria africana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24328	Gratiola officinalis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9865	Cichorium intybus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5704	Pecten caurinus	Species	Pectinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22375	Saussurea salicifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18875	Aconitum contortum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15454	Vitex rotundifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24406	Rhizophora tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23547	Strychnos amazonica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27093	Kniphofia foliosa	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24969	Ageratum mexicanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24456	Salvia lavandulifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21799	Bacillus litoralis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO18045	Holothuria atra	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25226	Kalanchoe spathulata	Species	Crassulaceae	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	5
IC50	1
Others	8

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	27.5	%	PMID[469880]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	8.7	%	PMID[469880]
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	1.6	%	PMID[469880]
NPT453	Cell Line	HT-1080	Homo sapiens	EC50	>	350000.0	nM	PMID[469881]
NPT81	Cell Line	A549	Homo sapiens	EC50	>	350000.0	nM	PMID[469881]
NPT165	Cell Line	HeLa	Homo sapiens	EC50	=	106000.0	nM	PMID[469881]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	>	100.0	uM	PMID[469882]
NPT2	Others	Unspecified		Inhibition	=	13.4	%	PMID[469880]
NPT2	Others	Unspecified		Inhibition	=	6.3	%	PMID[469880]
NPT2	Others	Unspecified		Inhibition	=	14.6	%	PMID[469880]
NPT2	Others	Unspecified		Inhibition	=	41.5	%	PMID[469880]
NPT2	Others	Unspecified		IC50	>	30000.0	nM	PMID[469880]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	350000.0	nM	PMID[469881]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	30300.0	nM	PMID[469881]

☑ 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 NPC152042 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	485
0.1-0.2	2014
0.2-0.3	5293
0.3-0.4	11452
0.4-0.5	5692
0.5-0.6	4237
0.6-0.7	5551
0.7-0.8	4053
0.8-0.85	2162
0.85-0.9	1255
0.9-0.95	418
0.95-1	85

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC241838
1.0	High Similarity	NPC143799
0.9925	High Similarity	NPC230285
0.9925	High Similarity	NPC184536
0.9925	High Similarity	NPC146679
0.9925	High Similarity	NPC59951
0.9925	High Similarity	NPC103342
0.9925	High Similarity	NPC281207
0.9925	High Similarity	NPC269652
0.9925	High Similarity	NPC103904
0.9852	High Similarity	NPC136840
0.9852	High Similarity	NPC90582
0.9852	High Similarity	NPC262094
0.9776	High Similarity	NPC276905
0.9774	High Similarity	NPC187432
0.9774	High Similarity	NPC127447
0.9774	High Similarity	NPC47815
0.9774	High Similarity	NPC473887
0.9774	High Similarity	NPC256042
0.9774	High Similarity	NPC216361
0.9774	High Similarity	NPC281917
0.9774	High Similarity	NPC124784
0.9774	High Similarity	NPC231772
0.9774	High Similarity	NPC29353
0.9774	High Similarity	NPC234133
0.9774	High Similarity	NPC194281
0.9774	High Similarity	NPC116775
0.9708	High Similarity	NPC470216
0.9701	High Similarity	NPC266597
0.9701	High Similarity	NPC299379
0.9701	High Similarity	NPC250266
0.9638	High Similarity	NPC273538
0.9638	High Similarity	NPC216538
0.9635	High Similarity	NPC473042
0.9635	High Similarity	NPC200694
0.9627	High Similarity	NPC13408
0.9624	High Similarity	NPC248872
0.9568	High Similarity	NPC5820
0.9568	High Similarity	NPC124729
0.9568	High Similarity	NPC178343
0.9568	High Similarity	NPC306488
0.9565	High Similarity	NPC9117
0.9565	High Similarity	NPC190637
0.9565	High Similarity	NPC24821
0.9565	High Similarity	NPC158874
0.9565	High Similarity	NPC293053
0.9565	High Similarity	NPC212932
0.9559	High Similarity	NPC18260
0.9559	High Similarity	NPC78913
0.9549	High Similarity	NPC274121
0.9549	High Similarity	NPC50898
0.9549	High Similarity	NPC78540
0.9549	High Similarity	NPC213216
0.9496	High Similarity	NPC326500
0.9489	High Similarity	NPC241100
0.9489	High Similarity	NPC159275
0.9485	High Similarity	NPC99333
0.9485	High Similarity	NPC188947
0.9485	High Similarity	NPC280284
0.9485	High Similarity	NPC201395
0.9481	High Similarity	NPC61546
0.9481	High Similarity	NPC72452
0.9478	High Similarity	NPC172262
0.9474	High Similarity	NPC128216
0.9433	High Similarity	NPC244407
0.9433	High Similarity	NPC296869
0.9429	High Similarity	NPC470458
0.9429	High Similarity	NPC153758
0.942	High Similarity	NPC110969
0.942	High Similarity	NPC282300
0.9416	High Similarity	NPC303633
0.9416	High Similarity	NPC217186
0.9416	High Similarity	NPC274784
0.9416	High Similarity	NPC150648
0.9416	High Similarity	NPC96565
0.9416	High Similarity	NPC329203
0.9416	High Similarity	NPC222342
0.9416	High Similarity	NPC220062
0.9416	High Similarity	NPC53181
0.9416	High Similarity	NPC55018
0.9416	High Similarity	NPC216978
0.9416	High Similarity	NPC310135
0.9416	High Similarity	NPC265871
0.9416	High Similarity	NPC225153
0.9416	High Similarity	NPC301217
0.9416	High Similarity	NPC20709
0.9412	High Similarity	NPC228661
0.9412	High Similarity	NPC290291
0.9412	High Similarity	NPC275055
0.9412	High Similarity	NPC188879
0.9403	High Similarity	NPC57601
0.9398	High Similarity	NPC113006
0.9398	High Similarity	NPC475589
0.9398	High Similarity	NPC278556
0.9398	High Similarity	NPC31872
0.9398	High Similarity	NPC473584
0.9366	High Similarity	NPC470461
0.9366	High Similarity	NPC159103
0.9366	High Similarity	NPC270465
0.9366	High Similarity	NPC87125
0.9362	High Similarity	NPC259632
0.9362	High Similarity	NPC176869
0.9362	High Similarity	NPC44721
0.9362	High Similarity	NPC40086
0.9362	High Similarity	NPC122828
0.9362	High Similarity	NPC476182
0.9362	High Similarity	NPC14001
0.9362	High Similarity	NPC3779
0.9362	High Similarity	NPC166757
0.9362	High Similarity	NPC472918
0.9362	High Similarity	NPC211466
0.9357	High Similarity	NPC71210
0.9353	High Similarity	NPC11561
0.9353	High Similarity	NPC226636
0.9348	High Similarity	NPC188243
0.9348	High Similarity	NPC270883
0.9348	High Similarity	NPC172986
0.9348	High Similarity	NPC284550
0.9348	High Similarity	NPC76445
0.9348	High Similarity	NPC110228
0.9348	High Similarity	NPC261227
0.9348	High Similarity	NPC6407
0.9348	High Similarity	NPC129853
0.9348	High Similarity	NPC150522
0.9343	High Similarity	NPC124269
0.9343	High Similarity	NPC118813
0.9338	High Similarity	NPC121243
0.9338	High Similarity	NPC240147
0.9338	High Similarity	NPC240593
0.9328	High Similarity	NPC257756
0.9328	High Similarity	NPC212631
0.9328	High Similarity	NPC473655
0.9328	High Similarity	NPC10971
0.9328	High Similarity	NPC205468
0.9328	High Similarity	NPC25937
0.9328	High Similarity	NPC129132
0.9328	High Similarity	NPC87231
0.9328	High Similarity	NPC101294
0.9323	High Similarity	NPC5515
0.9323	High Similarity	NPC270369
0.9323	High Similarity	NPC137264
0.9301	High Similarity	NPC188871
0.9301	High Similarity	NPC61258
0.9301	High Similarity	NPC166753
0.9301	High Similarity	NPC50728
0.9301	High Similarity	NPC149127
0.9301	High Similarity	NPC286342
0.9296	High Similarity	NPC470460
0.9291	High Similarity	NPC229190
0.9291	High Similarity	NPC220418
0.9286	High Similarity	NPC113770
0.9281	High Similarity	NPC324386
0.9281	High Similarity	NPC4743
0.9281	High Similarity	NPC147688
0.9281	High Similarity	NPC64908
0.9281	High Similarity	NPC3188
0.9281	High Similarity	NPC213322
0.9281	High Similarity	NPC103362
0.9281	High Similarity	NPC205006
0.9281	High Similarity	NPC156590
0.9281	High Similarity	NPC118840
0.9281	High Similarity	NPC312391
0.9275	High Similarity	NPC140890
0.9275	High Similarity	NPC261234
0.927	High Similarity	NPC294409
0.927	High Similarity	NPC243083
0.927	High Similarity	NPC287246
0.927	High Similarity	NPC7013
0.927	High Similarity	NPC254841
0.927	High Similarity	NPC181124
0.927	High Similarity	NPC116632
0.927	High Similarity	NPC79943
0.927	High Similarity	NPC303644
0.927	High Similarity	NPC209560
0.927	High Similarity	NPC12296
0.927	High Similarity	NPC296490
0.927	High Similarity	NPC32441
0.927	High Similarity	NPC162680
0.927	High Similarity	NPC295261
0.927	High Similarity	NPC13768
0.927	High Similarity	NPC107586
0.9265	High Similarity	NPC9985
0.9265	High Similarity	NPC239495
0.9259	High Similarity	NPC242294
0.9259	High Similarity	NPC144051
0.9259	High Similarity	NPC82225
0.9259	High Similarity	NPC175098
0.9259	High Similarity	NPC56031
0.9259	High Similarity	NPC18877
0.9259	High Similarity	NPC263670
0.9259	High Similarity	NPC192304
0.9259	High Similarity	NPC188646
0.9259	High Similarity	NPC139813
0.9259	High Similarity	NPC294593
0.9259	High Similarity	NPC337373
0.9259	High Similarity	NPC159623
0.9259	High Similarity	NPC28753
0.9259	High Similarity	NPC312318
0.9259	High Similarity	NPC204960
0.9259	High Similarity	NPC223457

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 NPC152042 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	455
0.1-0.2	982
0.2-0.3	1787
0.3-0.4	2715
0.4-0.5	1739
0.5-0.6	1000
0.6-0.7	322
0.7-0.8	96
0.8-0.85	33
0.85-0.9	15
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9638	High Similarity	NPD4378	Clinical (unspecified phase)
0.927	High Similarity	NPD1550	Clinical (unspecified phase)
0.927	High Similarity	NPD1552	Clinical (unspecified phase)
0.9203	High Similarity	NPD1549	Phase 2
0.9155	High Similarity	NPD1512	Approved
0.9124	High Similarity	NPD1510	Phase 2
0.9111	High Similarity	NPD1240	Approved
0.9014	High Similarity	NPD1511	Approved
0.8978	High Similarity	NPD1607	Approved
0.8951	High Similarity	NPD7410	Clinical (unspecified phase)
0.8921	High Similarity	NPD2796	Approved
0.8881	High Similarity	NPD6799	Approved
0.8851	High Similarity	NPD2801	Approved
0.8784	High Similarity	NPD1934	Approved
0.8725	High Similarity	NPD2393	Clinical (unspecified phase)
0.8675	High Similarity	NPD7075	Discontinued
0.8667	High Similarity	NPD3817	Phase 2
0.8658	High Similarity	NPD6801	Discontinued
0.8649	High Similarity	NPD4380	Phase 2
0.8609	High Similarity	NPD3882	Suspended
0.86	High Similarity	NPD7096	Clinical (unspecified phase)
0.8591	High Similarity	NPD7411	Suspended
0.8553	High Similarity	NPD4381	Clinical (unspecified phase)
0.8543	High Similarity	NPD8443	Clinical (unspecified phase)
0.8542	High Similarity	NPD3750	Approved
0.8531	High Similarity	NPD970	Clinical (unspecified phase)
0.8523	High Similarity	NPD6599	Discontinued
0.8462	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD6166	Phase 2
0.8446	Intermediate Similarity	NPD5403	Approved
0.8435	Intermediate Similarity	NPD5401	Approved
0.8418	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1551	Phase 2
0.8355	Intermediate Similarity	NPD7819	Suspended
0.8345	Intermediate Similarity	NPD2800	Approved
0.8313	Intermediate Similarity	NPD6797	Phase 2
0.8261	Intermediate Similarity	NPD7251	Discontinued
0.8219	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD7808	Phase 3
0.8194	Intermediate Similarity	NPD3749	Approved
0.8194	Intermediate Similarity	NPD3748	Approved
0.8188	Intermediate Similarity	NPD1203	Approved
0.8187	Intermediate Similarity	NPD7054	Approved
0.8182	Intermediate Similarity	NPD5402	Approved
0.8163	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD6959	Discontinued
0.8137	Intermediate Similarity	NPD7472	Approved
0.8134	Intermediate Similarity	NPD1548	Phase 1
0.8129	Intermediate Similarity	NPD7768	Phase 2
0.8125	Intermediate Similarity	NPD3818	Discontinued
0.8113	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1243	Approved
0.8082	Intermediate Similarity	NPD2344	Approved
0.8079	Intermediate Similarity	NPD920	Approved
0.8056	Intermediate Similarity	NPD6651	Approved
0.8029	Intermediate Similarity	NPD422	Phase 1
0.8028	Intermediate Similarity	NPD2313	Discontinued
0.8025	Intermediate Similarity	NPD7074	Phase 3
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.7971	Intermediate Similarity	NPD9717	Approved
0.7947	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD3268	Approved
0.7899	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD6832	Phase 2
0.7879	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6232	Discontinued
0.7867	Intermediate Similarity	NPD2309	Approved
0.7862	Intermediate Similarity	NPD5494	Approved
0.7857	Intermediate Similarity	NPD3225	Approved
0.7853	Intermediate Similarity	NPD7286	Phase 2
0.784	Intermediate Similarity	NPD7473	Discontinued
0.7829	Intermediate Similarity	NPD2533	Approved
0.7829	Intermediate Similarity	NPD2532	Approved
0.7829	Intermediate Similarity	NPD2534	Approved
0.7823	Intermediate Similarity	NPD2799	Discontinued
0.7823	Intermediate Similarity	NPD7033	Discontinued
0.7812	Intermediate Similarity	NPD1247	Approved
0.7801	Intermediate Similarity	NPD2797	Approved
0.7799	Intermediate Similarity	NPD919	Approved
0.7793	Intermediate Similarity	NPD943	Approved
0.777	Intermediate Similarity	NPD1610	Phase 2
0.777	Intermediate Similarity	NPD6099	Approved
0.777	Intermediate Similarity	NPD6100	Approved
0.7762	Intermediate Similarity	NPD4908	Phase 1
0.7758	Intermediate Similarity	NPD5953	Discontinued
0.7746	Intermediate Similarity	NPD2798	Approved
0.7742	Intermediate Similarity	NPD3226	Approved
0.7733	Intermediate Similarity	NPD2654	Approved
0.7716	Intermediate Similarity	NPD3926	Phase 2
0.7711	Intermediate Similarity	NPD6559	Discontinued
0.7703	Intermediate Similarity	NPD4308	Phase 3
0.7703	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD4628	Phase 3
0.7676	Intermediate Similarity	NPD3266	Approved
0.7676	Intermediate Similarity	NPD3267	Approved
0.7655	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1933	Approved
0.7619	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD9545	Approved
0.76	Intermediate Similarity	NPD2346	Discontinued
0.7591	Intermediate Similarity	NPD9493	Approved
0.7584	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1465	Phase 2
0.7543	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1296	Phase 2
0.7534	Intermediate Similarity	NPD6798	Discontinued
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.753	Intermediate Similarity	NPD5844	Phase 1
0.7529	Intermediate Similarity	NPD4360	Phase 2
0.7529	Intermediate Similarity	NPD4363	Phase 3
0.7517	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD447	Suspended
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD4288	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7483	Intermediate Similarity	NPD6233	Phase 2
0.747	Intermediate Similarity	NPD3751	Discontinued
0.7465	Intermediate Similarity	NPD1608	Approved
0.7465	Intermediate Similarity	NPD1481	Phase 2
0.7465	Intermediate Similarity	NPD3972	Approved
0.7455	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1613	Approved
0.7432	Intermediate Similarity	NPD4307	Phase 2
0.7432	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD411	Approved
0.7403	Intermediate Similarity	NPD2354	Approved
0.7394	Intermediate Similarity	NPD1535	Discovery
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4361	Phase 2
0.7383	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD1471	Phase 3
0.7349	Intermediate Similarity	NPD2403	Approved
0.7333	Intermediate Similarity	NPD3787	Discontinued
0.7297	Intermediate Similarity	NPD3764	Approved
0.7284	Intermediate Similarity	NPD2296	Approved
0.7279	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1729	Discontinued
0.7273	Intermediate Similarity	NPD1201	Approved
0.7273	Intermediate Similarity	NPD1652	Phase 2
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD6844	Discontinued
0.7261	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2353	Approved
0.7254	Intermediate Similarity	NPD17	Approved
0.7234	Intermediate Similarity	NPD1894	Discontinued
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7229	Intermediate Similarity	NPD5710	Approved
0.7229	Intermediate Similarity	NPD5711	Approved
0.7216	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4287	Approved
0.7197	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6104	Discontinued
0.7192	Intermediate Similarity	NPD1470	Approved
0.7186	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3887	Approved
0.7172	Intermediate Similarity	NPD4749	Approved
0.7152	Intermediate Similarity	NPD4340	Discontinued
0.7143	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7440	Discontinued
0.7133	Intermediate Similarity	NPD4062	Phase 3
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7123	Intermediate Similarity	NPD1876	Approved
0.7114	Intermediate Similarity	NPD3027	Phase 3
0.7107	Intermediate Similarity	NPD5049	Phase 3
0.7099	Intermediate Similarity	NPD5890	Approved
0.7099	Intermediate Similarity	NPD5889	Approved
0.7095	Intermediate Similarity	NPD2861	Phase 2
0.7091	Intermediate Similarity	NPD6971	Discontinued
0.7089	Intermediate Similarity	NPD7212	Phase 2
0.7089	Intermediate Similarity	NPD7213	Phase 3
0.7086	Intermediate Similarity	NPD3142	Approved
0.7086	Intermediate Similarity	NPD3140	Approved
0.7086	Intermediate Similarity	NPD8434	Phase 2
0.7081	Intermediate Similarity	NPD7584	Approved
0.7081	Intermediate Similarity	NPD7458	Discontinued
0.7075	Intermediate Similarity	NPD1164	Approved
0.707	Intermediate Similarity	NPD6190	Approved
0.7066	Intermediate Similarity	NPD7199	Phase 2
0.7059	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4661	Approved
0.7044	Intermediate Similarity	NPD4662	Approved
0.7044	Intermediate Similarity	NPD7447	Phase 1
0.7037	Intermediate Similarity	NPD6585	Discontinued
0.7033	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD74	Approved
0.7007	Intermediate Similarity	NPD9266	Approved
0.7006	Intermediate Similarity	NPD7003	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