NPASS Compound

Structure

CID219573 OpenBabel06191716012D 21 23 0 0 1 0 0 0 0 0999 V2000 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -1.5000 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 -0.8660 -0.5000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 0.8660 -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 0.0000 1.0000 0.0000 C 0 0 1 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 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 14 2 0 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 20 1 0 0 0 0 17 21 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.21
Volume:	327.051
LogP:	6.062
LogD:	4.643
LogS:	-6.601
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.667
Synthetic Accessibility Score:	3.331
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.85
MDCK Permeability:	1.2745606909447815e-05
Pgp-inhibitor:	0.982
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.948
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.096
Plasma Protein Binding (PPB):	96.76714324951172%
Volume Distribution (VD):	0.67
Pgp-substrate:	4.465691566467285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.269
CYP1A2-substrate:	0.777
CYP2C19-inhibitor:	0.592
CYP2C19-substrate:	0.911
CYP2C9-inhibitor:	0.455
CYP2C9-substrate:	0.512
CYP2D6-inhibitor:	0.53
CYP2D6-substrate:	0.401
CYP3A4-inhibitor:	0.52
CYP3A4-substrate:	0.54

ADMET: Excretion

Clearance (CL):	7.005
Half-life (T1/2):	0.029

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.613
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.422
Maximum Recommended Daily Dose:	0.849
Skin Sensitization:	0.204
Carcinogencity:	0.271
Eye Corrosion:	0.254
Eye Irritation:	0.891
Respiratory Toxicity:	0.952

Download Data

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

Natural Product: NPC219573

Natural Product ID:	NPC219573
*Common Name:**	7-Dehyroabietanone
IUPAC Name:	(4aS,10aS)-1,1,4a-trimethyl-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one
Synonyms:	7-Dehyroabietanone; Dehydroabieta-7-One
Standard InCHIKey:	ISHVJVXYPLFKAL-AZUAARDMSA-N
Standard InCHI:	InChI=1S/C20H28O/c1-13(2)14-7-8-16-15(11-14)17(21)12-18-19(3,4)9-6-10-20(16,18)5/h7-8,11,13,18H,6,9-10,12H2,1-5H3/t18-,20+/m0/s1
SMILES:	CC(C)c1ccc2c(c1)C(=O)C[C@H]1C(C)(C)CCC[C@]21C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL428568
PubChem CID:	11289118
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF00579992]
NPO21179	Streptomyces griseoaurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10048567]
NPO33340	picea glehni	Species	Pinaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[10869208]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	stems, roots, and leaves	Da-Han Mountain, Kaohsiung, Taiwan	2004-OCT	PMID[17417907]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17417907]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17461599]
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193025]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19829679]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506820]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	stem	n.a.	PMID[20961093]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	Stem bark	Lu Mountain, Jiangxi Province, China	2004-AUG	PMID[20961093]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[21087019]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21469692]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21469692]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22314230]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23521110]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24913660]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[26238320]
NPO30984	Fraxinus sieboldiana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26697686]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29775308]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30931559]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO28701	Salvia lanigera	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[8824952]
NPO27927	Alligator sinensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9287418]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834167]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28326	Uncaria longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27988	Salvia pisidica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24010	Buglossoides arvensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28932	Myrrhis odorata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14307	Rhizopus oryzae	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28326	Uncaria longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28807	Laggera pterodonta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22530	Vigna luteola	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23194	Berberis beaniana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28435	Solanum crinitum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20425	Epimedium macranthum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28326	Uncaria longiflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24144	Ophiomastix mixta	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28545	Scymnorhinus lichia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27988	Salvia pisidica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28145	Dendrodoris limbata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27880	Mimusops laurifolia	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28127	Ursinia speciosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27968	Phoma linga	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28669	Cuscuta australis	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23092	Ammodendron karelinii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21704	Papaver suaveolens	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28895	Pinus monticola	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28384	Ascotricha chartarum	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28739	Othonna macrophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13308	Polycitor adriaticus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28578	Uperoleia inundata	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28065	Pentachondra pumila	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28112	Amauris niavius	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28233	Diplotropis ferruginea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21894	Psychotria granadensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17126	Callicarpa pilosissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28280	Cetraria komarovii	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28701	Salvia lanigera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11328	Juniperus chinensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28266	Phlomis ostrowskiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24010	Buglossoides arvensis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28641	Tubocapsicum anomalum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17288	Piliostigma thonningii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22968	Elaeocarpus serratus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28559	Julbernardia globifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14307	Rhizopus oryzae	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28830	Acronychia haplophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7698	Elettaria cardamomum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27927	Alligator sinensis	Species	Alligatoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21179	Streptomyces griseoaurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28688	Aster tataricus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14130	Phagnalon rupestre	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7822.1	Eucalyptus globulus subsp. bicostata	Subspecies	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28337	Pimpinella peregrina	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28855	Salix petiolaris	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28171	Anacyclus pyrethrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28414	Medicosma fareana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22147	Goniothalamus macrophyllus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15469	Myodocarpus gracilis	Species	Myodocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10219	Juniperus communis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28842	Oscillatoria raoi	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6953.1	Aconitum sachalinense subsp. yezoense	Subspecies	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28489	Euphrasia regelii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28932	Myrrhis odorata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28464	Mentha sylvestris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28196	Brachylaena perrieri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28501	Hortonia angustifolia	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28623	Phlox decussata	Species	Polemoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23157	Wigandia kunthii	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28778	Eucalyptus viminalis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28213	Humicola grisea	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21547	Crinum giganteum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	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	6
MIC	1
Others	9

Activity Type	# Activity
Cell Line	7
Organism	5
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	305100.0	nM	PMID[513240]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[513241]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[513243]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[513243]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[513243]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[513243]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[513243]
NPT1515	Organism	SARS coronavirus	SARS coronavirus	EC50	=	4000.0	nM	PMID[513240]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	76.3	n.a.	PMID[513240]
NPT1515	Organism	SARS coronavirus	SARS coronavirus	Inhibition	<	25.0	%	PMID[513240]
NPT2	Others	Unspecified		Inhibition	=	0.0	%	PMID[513241]
NPT2	Others	Unspecified		Inhibition	=	30.2	%	PMID[513241]
NPT2	Others	Unspecified		Inhibition	=	74.7	%	PMID[513241]
NPT2	Others	Unspecified		Inhibition	=	95.0	%	PMID[513241]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	300000.0	nM	PMID[513242]
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	4800.0	nM	PMID[513243]

☑ 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 NPC219573 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	376
0.1-0.2	1593
0.2-0.3	4007
0.3-0.4	13437
0.4-0.5	15721
0.5-0.6	6351
0.6-0.7	959
0.7-0.8	177
0.8-0.85	37
0.85-0.9	23
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC185208
0.967	High Similarity	NPC239185
0.9663	High Similarity	NPC323420
0.957	High Similarity	NPC476993
0.9565	High Similarity	NPC134882
0.9457	High Similarity	NPC265220
0.9362	High Similarity	NPC109514
0.9355	High Similarity	NPC75724
0.9326	High Similarity	NPC298115
0.9239	High Similarity	NPC260233
0.9231	High Similarity	NPC153885
0.9231	High Similarity	NPC59677
0.9149	High Similarity	NPC49994
0.913	High Similarity	NPC289883
0.913	High Similarity	NPC238219
0.9121	High Similarity	NPC133461
0.9022	High Similarity	NPC155232
0.9011	High Similarity	NPC277277
0.9	High Similarity	NPC267262
0.8989	High Similarity	NPC160339
0.8989	High Similarity	NPC307
0.89	High Similarity	NPC470252
0.883	High Similarity	NPC472880
0.8817	High Similarity	NPC188844
0.8817	High Similarity	NPC1682
0.8804	High Similarity	NPC173413
0.8804	High Similarity	NPC19256
0.8776	High Similarity	NPC475939
0.8776	High Similarity	NPC474866
0.8776	High Similarity	NPC471829
0.8776	High Similarity	NPC472691
0.8725	High Similarity	NPC265513
0.871	High Similarity	NPC125226
0.871	High Similarity	NPC284475
0.8696	High Similarity	NPC418308
0.8681	High Similarity	NPC69057
0.8641	High Similarity	NPC280789
0.8587	High Similarity	NPC157778
0.8571	High Similarity	NPC472879
0.8558	High Similarity	NPC93287
0.8515	High Similarity	NPC472699
0.8515	High Similarity	NPC472700
0.8478	Intermediate Similarity	NPC43945
0.8476	Intermediate Similarity	NPC471721
0.8431	Intermediate Similarity	NPC472695
0.8431	Intermediate Similarity	NPC472683
0.8431	Intermediate Similarity	NPC472701
0.8431	Intermediate Similarity	NPC472696
0.8427	Intermediate Similarity	NPC145053
0.84	Intermediate Similarity	NPC247976
0.8396	Intermediate Similarity	NPC215419
0.8387	Intermediate Similarity	NPC153308
0.8381	Intermediate Similarity	NPC470253
0.8316	Intermediate Similarity	NPC103346
0.8315	Intermediate Similarity	NPC285716
0.8315	Intermediate Similarity	NPC17408
0.8315	Intermediate Similarity	NPC190567
0.8302	Intermediate Similarity	NPC326664
0.8222	Intermediate Similarity	NPC12936
0.8222	Intermediate Similarity	NPC273033
0.8208	Intermediate Similarity	NPC143768
0.8172	Intermediate Similarity	NPC164526
0.8155	Intermediate Similarity	NPC100767
0.8111	Intermediate Similarity	NPC71664
0.8105	Intermediate Similarity	NPC113307
0.8105	Intermediate Similarity	NPC325709
0.81	Intermediate Similarity	NPC221825
0.809	Intermediate Similarity	NPC285470
0.809	Intermediate Similarity	NPC103488
0.809	Intermediate Similarity	NPC2785
0.809	Intermediate Similarity	NPC36342
0.8065	Intermediate Similarity	NPC252067
0.8058	Intermediate Similarity	NPC471186
0.8043	Intermediate Similarity	NPC215008
0.8043	Intermediate Similarity	NPC273758
0.8021	Intermediate Similarity	NPC58872
0.802	Intermediate Similarity	NPC133809
0.802	Intermediate Similarity	NPC136810
0.802	Intermediate Similarity	NPC128248
0.8018	Intermediate Similarity	NPC202015
0.8	Intermediate Similarity	NPC300205
0.8	Intermediate Similarity	NPC139901
0.8	Intermediate Similarity	NPC151405
0.7978	Intermediate Similarity	NPC245966
0.7978	Intermediate Similarity	NPC3190
0.7978	Intermediate Similarity	NPC249018
0.7961	Intermediate Similarity	NPC329282
0.7944	Intermediate Similarity	NPC218855
0.7912	Intermediate Similarity	NPC164086
0.79	Intermediate Similarity	NPC226041
0.787	Intermediate Similarity	NPC471481
0.7857	Intermediate Similarity	NPC476645
0.7849	Intermediate Similarity	NPC39600
0.7849	Intermediate Similarity	NPC197581
0.7843	Intermediate Similarity	NPC225079
0.7838	Intermediate Similarity	NPC323440
0.7838	Intermediate Similarity	NPC222968
0.7838	Intermediate Similarity	NPC80605
0.7807	Intermediate Similarity	NPC167323
0.7807	Intermediate Similarity	NPC269923
0.7802	Intermediate Similarity	NPC159661
0.7798	Intermediate Similarity	NPC234637
0.7798	Intermediate Similarity	NPC67377
0.7798	Intermediate Similarity	NPC130591
0.7778	Intermediate Similarity	NPC186128
0.7778	Intermediate Similarity	NPC9796
0.7778	Intermediate Similarity	NPC292834
0.7748	Intermediate Similarity	NPC469843
0.7742	Intermediate Similarity	NPC230068
0.7717	Intermediate Similarity	NPC95868
0.7714	Intermediate Similarity	NPC474910
0.7714	Intermediate Similarity	NPC172483
0.7692	Intermediate Similarity	NPC329556
0.7685	Intermediate Similarity	NPC474057
0.7672	Intermediate Similarity	NPC85511
0.7658	Intermediate Similarity	NPC260886
0.7653	Intermediate Similarity	NPC26224
0.7642	Intermediate Similarity	NPC94751
0.7642	Intermediate Similarity	NPC142326
0.7634	Intermediate Similarity	NPC100039
0.7615	Intermediate Similarity	NPC471189
0.7615	Intermediate Similarity	NPC471188
0.7611	Intermediate Similarity	NPC472698
0.7611	Intermediate Similarity	NPC472697
0.7611	Intermediate Similarity	NPC318173
0.7609	Intermediate Similarity	NPC272260
0.757	Intermediate Similarity	NPC112903
0.757	Intermediate Similarity	NPC203732
0.7568	Intermediate Similarity	NPC93181
0.7568	Intermediate Similarity	NPC474095
0.7565	Intermediate Similarity	NPC472981
0.7549	Intermediate Similarity	NPC240042
0.7547	Intermediate Similarity	NPC134120
0.7528	Intermediate Similarity	NPC285679
0.7528	Intermediate Similarity	NPC54269
0.7527	Intermediate Similarity	NPC477703
0.7527	Intermediate Similarity	NPC157055
0.7524	Intermediate Similarity	NPC274443
0.7523	Intermediate Similarity	NPC137315
0.7523	Intermediate Similarity	NPC475002
0.7523	Intermediate Similarity	NPC95126
0.7522	Intermediate Similarity	NPC61651
0.7522	Intermediate Similarity	NPC268930
0.7521	Intermediate Similarity	NPC328107
0.7478	Intermediate Similarity	NPC77000
0.7478	Intermediate Similarity	NPC472679
0.7478	Intermediate Similarity	NPC238861
0.7478	Intermediate Similarity	NPC232958
0.7478	Intermediate Similarity	NPC472680
0.7477	Intermediate Similarity	NPC37914
0.7477	Intermediate Similarity	NPC83409
0.7477	Intermediate Similarity	NPC196673
0.7477	Intermediate Similarity	NPC185763
0.7475	Intermediate Similarity	NPC303967
0.7475	Intermediate Similarity	NPC67585
0.7475	Intermediate Similarity	NPC110420
0.7455	Intermediate Similarity	NPC66208
0.7447	Intermediate Similarity	NPC73978
0.7429	Intermediate Similarity	NPC222390
0.7429	Intermediate Similarity	NPC244427
0.7417	Intermediate Similarity	NPC115797
0.7417	Intermediate Similarity	NPC478165
0.7417	Intermediate Similarity	NPC478162
0.7417	Intermediate Similarity	NPC51448
0.7416	Intermediate Similarity	NPC74458
0.7414	Intermediate Similarity	NPC476234
0.7411	Intermediate Similarity	NPC228936
0.7411	Intermediate Similarity	NPC186933
0.7411	Intermediate Similarity	NPC217111
0.7407	Intermediate Similarity	NPC470007
0.74	Intermediate Similarity	NPC220596
0.74	Intermediate Similarity	NPC475023
0.74	Intermediate Similarity	NPC475059
0.7391	Intermediate Similarity	NPC179726
0.7339	Intermediate Similarity	NPC192577
0.7328	Intermediate Similarity	NPC476225
0.7327	Intermediate Similarity	NPC475057
0.732	Intermediate Similarity	NPC123476
0.7312	Intermediate Similarity	NPC76455
0.7312	Intermediate Similarity	NPC137847
0.7303	Intermediate Similarity	NPC95289
0.7292	Intermediate Similarity	NPC149263
0.7292	Intermediate Similarity	NPC324624
0.7281	Intermediate Similarity	NPC158157
0.7273	Intermediate Similarity	NPC69424
0.7273	Intermediate Similarity	NPC84672
0.7273	Intermediate Similarity	NPC78364
0.7273	Intermediate Similarity	NPC176130
0.7265	Intermediate Similarity	NPC144547
0.7257	Intermediate Similarity	NPC221275
0.7232	Intermediate Similarity	NPC13784
0.7227	Intermediate Similarity	NPC51079
0.7227	Intermediate Similarity	NPC318067
0.7227	Intermediate Similarity	NPC472681
0.7222	Intermediate Similarity	NPC167336
0.7216	Intermediate Similarity	NPC267704
0.7212	Intermediate Similarity	NPC324602
0.7204	Intermediate Similarity	NPC329318
0.7204	Intermediate Similarity	NPC298023
0.7193	Intermediate Similarity	NPC135730

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 NPC219573 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	971
0.2-0.3	1375
0.3-0.4	3326
0.4-0.5	2197
0.5-0.6	756
0.6-0.7	132
0.7-0.8	32
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.967	High Similarity	NPD3495	Discontinued
0.8817	High Similarity	NPD7631	Approved
0.871	High Similarity	NPD7609	Phase 3
0.8478	Intermediate Similarity	NPD650	Approved
0.8222	Intermediate Similarity	NPD942	Approved
0.8041	Intermediate Similarity	NPD1508	Approved
0.789	Intermediate Similarity	NPD5951	Approved
0.785	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7610	Discontinued
0.78	Intermediate Similarity	NPD1843	Approved
0.7745	Intermediate Similarity	NPD2066	Phase 3
0.7717	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1930	Approved
0.7692	Intermediate Similarity	NPD1929	Approved
0.7692	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD7009	Phase 2
0.7596	Intermediate Similarity	NPD2193	Phase 2
0.7596	Intermediate Similarity	NPD2648	Phase 3
0.7525	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD6049	Phase 2
0.7478	Intermediate Similarity	NPD5836	Discontinued
0.7478	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1932	Approved
0.7429	Intermediate Similarity	NPD2196	Discontinued
0.7414	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7387	Intermediate Similarity	NPD6858	Approved
0.7387	Intermediate Similarity	NPD7094	Approved
0.7353	Intermediate Similarity	NPD4094	Approved
0.7347	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD2329	Discontinued
0.7255	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4657	Approved
0.7212	Intermediate Similarity	NPD4655	Approved
0.7182	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1087	Approved
0.7167	Intermediate Similarity	NPD6330	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD1088	Approved
0.7119	Intermediate Similarity	NPD4879	Approved
0.7103	Intermediate Similarity	NPD2171	Approved
0.7103	Intermediate Similarity	NPD6027	Approved
0.7103	Intermediate Similarity	NPD6024	Approved
0.7064	Intermediate Similarity	NPD2197	Approved
0.7064	Intermediate Similarity	NPD2192	Approved
0.7064	Intermediate Similarity	NPD1677	Discontinued
0.7019	Intermediate Similarity	NPD1693	Approved
0.7016	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7008	Discontinued
0.6991	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2577	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD1090	Approved
0.6961	Remote Similarity	NPD1089	Approved
0.6961	Remote Similarity	NPD1086	Approved
0.6952	Remote Similarity	NPD1989	Approved
0.6939	Remote Similarity	NPD3971	Phase 1
0.6923	Remote Similarity	NPD1563	Approved
0.6905	Remote Similarity	NPD7961	Discontinued
0.6897	Remote Similarity	NPD3317	Approved
0.6887	Remote Similarity	NPD1100	Approved
0.6887	Remote Similarity	NPD1099	Approved
0.6881	Remote Similarity	NPD3357	Discontinued
0.6869	Remote Similarity	NPD4544	Approved
0.6863	Remote Similarity	NPD800	Approved
0.686	Remote Similarity	NPD4878	Approved
0.6857	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5909	Discontinued
0.6814	Remote Similarity	NPD1317	Discontinued
0.6807	Remote Similarity	NPD3025	Approved
0.6807	Remote Similarity	NPD3024	Approved
0.6754	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3019	Approved
0.6746	Remote Similarity	NPD2754	Discontinued
0.6731	Remote Similarity	NPD1239	Approved
0.6729	Remote Similarity	NPD1565	Approved
0.6729	Remote Similarity	NPD1566	Phase 3
0.6729	Remote Similarity	NPD1564	Approved
0.6724	Remote Similarity	NPD7077	Approved
0.6724	Remote Similarity	NPD7076	Approved
0.6721	Remote Similarity	NPD3972	Approved
0.6702	Remote Similarity	NPD4058	Approved
0.6694	Remote Similarity	NPD3026	Approved
0.6694	Remote Similarity	NPD3023	Approved
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD2508	Discontinued
0.6639	Remote Similarity	NPD6287	Discontinued
0.6636	Remote Similarity	NPD813	Approved
0.6635	Remote Similarity	NPD3672	Approved
0.6635	Remote Similarity	NPD3673	Approved
0.6612	Remote Similarity	NPD2932	Approved
0.6612	Remote Similarity	NPD2345	Approved
0.6612	Remote Similarity	NPD4199	Phase 3
0.6604	Remote Similarity	NPD1202	Approved
0.6579	Remote Similarity	NPD2182	Approved
0.6538	Remote Similarity	NPD5346	Phase 2
0.6538	Remote Similarity	NPD5347	Phase 2
0.6532	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD3547	Approved
0.6532	Remote Similarity	NPD3549	Approved
0.6529	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD664	Approved
0.6519	Remote Similarity	NPD7003	Approved
0.6518	Remote Similarity	NPD164	Approved
0.6512	Remote Similarity	NPD7713	Phase 3
0.6504	Remote Similarity	NPD1201	Approved
0.6486	Remote Similarity	NPD4803	Discontinued
0.6457	Remote Similarity	NPD7084	Phase 3
0.6449	Remote Similarity	NPD3980	Approved
0.6449	Remote Similarity	NPD2878	Approved
0.6449	Remote Similarity	NPD3982	Approved
0.6429	Remote Similarity	NPD5653	Discontinued
0.6429	Remote Similarity	NPD227	Approved
0.6429	Remote Similarity	NPD1470	Approved
0.6429	Remote Similarity	NPD225	Approved
0.6423	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5597	Approved
0.6422	Remote Similarity	NPD5598	Approved
0.6408	Remote Similarity	NPD9257	Approved
0.6408	Remote Similarity	NPD9259	Approved
0.6396	Remote Similarity	NPD6354	Discontinued
0.6396	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4691	Approved
0.6364	Remote Similarity	NPD9490	Approved
0.6354	Remote Similarity	NPD4687	Approved
0.6349	Remote Similarity	NPD1876	Approved
0.6346	Remote Similarity	NPD4793	Discontinued
0.633	Remote Similarity	NPD2895	Discontinued
0.633	Remote Similarity	NPD3093	Approved
0.6308	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1238	Approved
0.6306	Remote Similarity	NPD7798	Approved
0.6303	Remote Similarity	NPD6010	Discontinued
0.6283	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6647	Phase 2
0.6279	Remote Similarity	NPD7055	Discontinued
0.6277	Remote Similarity	NPD4137	Phase 3
0.6275	Remote Similarity	NPD9491	Approved
0.6264	Remote Similarity	NPD675	Discontinued
0.626	Remote Similarity	NPD1245	Approved
0.626	Remote Similarity	NPD1651	Approved
0.625	Remote Similarity	NPD2629	Approved
0.625	Remote Similarity	NPD4980	Approved
0.625	Remote Similarity	NPD2319	Discontinued
0.625	Remote Similarity	NPD2798	Approved
0.6239	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD226	Approved
0.6232	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6966	Discovery
0.623	Remote Similarity	NPD6065	Approved
0.623	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5405	Approved
0.6222	Remote Similarity	NPD5404	Approved
0.6222	Remote Similarity	NPD5408	Approved
0.6222	Remote Similarity	NPD5406	Approved
0.6211	Remote Similarity	NPD4747	Approved
0.619	Remote Similarity	NPD3355	Approved
0.619	Remote Similarity	NPD3356	Approved
0.6187	Remote Similarity	NPD7236	Approved
0.6186	Remote Similarity	NPD5733	Approved
0.6183	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD2346	Discontinued
0.6174	Remote Similarity	NPD1766	Approved
0.6174	Remote Similarity	NPD1767	Approved
0.6174	Remote Similarity	NPD1763	Approved
0.6174	Remote Similarity	NPD1765	Approved
0.6174	Remote Similarity	NPD1761	Approved
0.6172	Remote Similarity	NPD3245	Phase 3
0.6172	Remote Similarity	NPD3244	Pre-registration
0.6168	Remote Similarity	NPD9256	Approved
0.6168	Remote Similarity	NPD9258	Approved
0.6161	Remote Similarity	NPD742	Approved
0.6148	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5276	Approved
0.6142	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD5159	Phase 2
0.6142	Remote Similarity	NPD5157	Phase 1
0.6139	Remote Similarity	NPD3903	Approved
0.6139	Remote Similarity	NPD3981	Approved
0.6139	Remote Similarity	NPD3979	Approved
0.6139	Remote Similarity	NPD3904	Approved
0.6136	Remote Similarity	NPD8032	Phase 2
0.6124	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD9716	Approved
0.6117	Remote Similarity	NPD4635	Approved
0.6116	Remote Similarity	NPD3867	Phase 2
0.6116	Remote Similarity	NPD4766	Approved
0.6116	Remote Similarity	NPD1246	Approved
0.6111	Remote Similarity	NPD1281	Approved
0.6106	Remote Similarity	NPD5630	Phase 1
0.6098	Remote Similarity	NPD5990	Approved
0.6098	Remote Similarity	NPD5991	Approved
0.6095	Remote Similarity	NPD3099	Discontinued
0.6094	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD2056	Discontinued
0.6084	Remote Similarity	NPD7239	Suspended
0.6071	Remote Similarity	NPD466	Approved
0.6071	Remote Similarity	NPD5926	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