NPASS Compound

Structure

CID91369 OpenBabel06191715432D 23 24 0 0 1 0 0 0 0 0999 V2000 -3.4641 5.0000 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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 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 -2.5981 3.5000 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 3.0000 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 5.0000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 1 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 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 15 2 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 9 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 13 1 0 0 0 0 10 14 1 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 1 1 6 0 0 0 15 16 1 0 0 0 0 16 19 1 6 0 0 0 17 19 1 6 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.25
Volume:	358.461
LogP:	3.836
LogD:	3.627
LogS:	-3.855
# Rotatable Bonds:	6
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	4.154
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.223
MDCK Permeability:	1.2103554581699427e-05
Pgp-inhibitor:	0.036
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.351
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.401
Plasma Protein Binding (PPB):	66.71683502197266%
Volume Distribution (VD):	0.491
Pgp-substrate:	19.541488647460938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.217
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.753
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.471
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.113
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.101

ADMET: Excretion

Clearance (CL):	3.643
Half-life (T1/2):	0.373

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.624
Skin Sensitization:	0.739
Carcinogencity:	0.189
Eye Corrosion:	0.768
Eye Irritation:	0.717
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC91369

Natural Product ID:	NPC91369
*Common Name:**	Imbricatolic Acid
IUPAC Name:	(1S,4aR,5S,8aR)-5-[(3S)-5-hydroxy-3-methylpentyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
Synonyms:	Imbricatolic Acid
Standard InCHIKey:	NSRKLZRKJJQJLD-BEUFEYIVSA-N
Standard InCHI:	InChI=1S/C20H34O3/c1-14(10-13-21)6-8-16-15(2)7-9-17-19(16,3)11-5-12-20(17,4)18(22)23/h14,16-17,21H,2,5-13H2,1,3-4H3,(H,22,23)/t14-,16-,17+,19+,20-/m0/s1
SMILES:	OCC[C@H](CC[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCC[C@]2(C)C(=O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048004
PubChem CID:	70688370
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
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	Spanish		DOI[10.1021/jf00010a019]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		DOI[10.1021/jf00016a013]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	Germany		DOI[10.1021/jf00016a013]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	Italy		DOI[10.1021/jf00016a013]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	Turkey		DOI[10.1111/j.1745-4557.2003.tb00250.x]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		DOI[10.17660/ActaHortic.2003.610.16]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[10794642]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[10820090]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11032480]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[11754554]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[15315387]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[16076125]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[16920856]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[19358604]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19481938]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[21190690]
NPO6674	Burkholderia ambifaria	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22988812]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[23394984]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	Germany		PMID[23394984]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	New Zealand		PMID[23394984]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[2413754]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24216090]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28294615]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30673219]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31291099]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	Fruits	n.a.		PMID[9542132]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6671	Ulva conglobata	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7925	Asparagus officinalis	Species	Asparagaceae	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]
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]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12796	Periploca sepium	Species	Apocynaceae	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]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9704	Sonneratia caseolaris	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9319	Pterocaulon virgatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8934	Gypsophila perfoliata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23384	Rhodiola semenovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21720	Talaromyces variabilis	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17386	Securidaca longepedunculata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3740	Trisetum flavescens	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO865	Dendrobium loddigesii	Species	Orchidaceae	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]
NPO19898	Stevia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3385	Cassine transvaalensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6671	Ulva conglobata	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10638	Plectranthus myrianthus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9532	Vernonia cistifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5827	Dalea tuberculata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3873	Crotalaria candicans	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12091	Martensia denticulata	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2384	Ircinia ramosa	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9512	Phlomis fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO936	Pinalia spicata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO526	Salvia sessei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13135	Campylotropis hirtella	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6289	Ceropegia dichotoma	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10738	Cotoneaster horizontalis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2300	Actinidia deliciosa	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6731	Ononis spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12998	Salvia rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5456	Juniperus drupacea	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11555	Pterocaulon purpurascens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11843	Stephania zippeliana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12205	Eucalyptus apodophylla	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12192	Coronilla scorpioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11097	Lepidium apetalum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12565	Hypericum polyanthemum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11576	Glycosmis macrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7345	Ptilonia magellanica	Species	Bonnemaisoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7773	Crinum moorei	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11257	Momordica dioica	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11190	Veronica polita	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6938	Astragalus dissectus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8484	Codonopsis lanceolata	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6674	Burkholderia ambifaria	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5013	Loranthus spicatus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10399	Manfreda virginica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9928	Cephalaria cilicica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12891	Minasia alpestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10922	Pentaclethra macrophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7048	Eucalyptus rariflora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1257	Distephanus angulifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1185	Stereocaulon strictum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7925	Asparagus officinalis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10605	Tristania conferta	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7705	Navanax inermis	Species	Aglajidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9040	Elsinoe annonae	Species	Elsinoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO468	Dryopteris oligophlebia	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5392	Pachycereus pecten-aboriginum	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9307	Ficus indica	Species	Ficidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16164	Podocarpus urbani	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11815	Mikania hirsutissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8186	Ocotea minarum	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6256	Eucalyptus umbra	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22691	Mentha cardiaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1815	Breonia chinensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12796	Periploca sepium	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5043	Eria japonica	Species	Orchidaceae	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
IC50	1
Others	6

Activity Type	# Activity
Cell Line	1
Individual Protein	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	Activity	=	34.41	%	PMID[519994]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	8800.0	nM	PMID[519995]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	5.9	%	PMID[519995]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	19.2	%	PMID[519995]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	59.2	%	PMID[519995]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	67.2	%	PMID[519995]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	=	71.1	%	PMID[519995]

☑ 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 NPC91369 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	160
0.1-0.2	1462
0.2-0.3	7677
0.3-0.4	15407
0.4-0.5	6854
0.5-0.6	6340
0.6-0.7	3659
0.7-0.8	1027
0.8-0.85	83
0.85-0.9	19
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9552	High Similarity	NPC72343
0.9394	High Similarity	NPC290445
0.9394	High Similarity	NPC36616
0.9286	High Similarity	NPC476601
0.9028	High Similarity	NPC239098
0.8889	High Similarity	NPC474433
0.8857	High Similarity	NPC36310
0.8767	High Similarity	NPC269543
0.8767	High Similarity	NPC247783
0.8732	High Similarity	NPC46610
0.8732	High Similarity	NPC18819
0.8611	High Similarity	NPC476844
0.8592	High Similarity	NPC161187
0.8592	High Similarity	NPC330659
0.8592	High Similarity	NPC244708
0.8571	High Similarity	NPC235586
0.8514	High Similarity	NPC59436
0.8514	High Similarity	NPC476810
0.8493	Intermediate Similarity	NPC89294
0.8493	Intermediate Similarity	NPC246445
0.8493	Intermediate Similarity	NPC20466
0.8472	Intermediate Similarity	NPC183503
0.8472	Intermediate Similarity	NPC3753
0.8472	Intermediate Similarity	NPC283908
0.8472	Intermediate Similarity	NPC237591
0.8472	Intermediate Similarity	NPC255168
0.8472	Intermediate Similarity	NPC161923
0.8472	Intermediate Similarity	NPC103958
0.8451	Intermediate Similarity	NPC160817
0.8442	Intermediate Similarity	NPC245866
0.8421	Intermediate Similarity	NPC14203
0.8421	Intermediate Similarity	NPC229584
0.84	Intermediate Similarity	NPC327674
0.8378	Intermediate Similarity	NPC107039
0.8378	Intermediate Similarity	NPC66105
0.8378	Intermediate Similarity	NPC471899
0.8378	Intermediate Similarity	NPC471897
0.8378	Intermediate Similarity	NPC68828
0.8378	Intermediate Similarity	NPC238227
0.8378	Intermediate Similarity	NPC469867
0.8356	Intermediate Similarity	NPC192540
0.8356	Intermediate Similarity	NPC279666
0.8333	Intermediate Similarity	NPC279241
0.8333	Intermediate Similarity	NPC263974
0.8333	Intermediate Similarity	NPC476038
0.8333	Intermediate Similarity	NPC472813
0.8333	Intermediate Similarity	NPC194937
0.8312	Intermediate Similarity	NPC170985
0.8312	Intermediate Similarity	NPC476292
0.8312	Intermediate Similarity	NPC474605
0.8289	Intermediate Similarity	NPC104545
0.8267	Intermediate Similarity	NPC476986
0.8267	Intermediate Similarity	NPC280654
0.8267	Intermediate Similarity	NPC470905
0.8267	Intermediate Similarity	NPC321514
0.8267	Intermediate Similarity	NPC260385
0.8267	Intermediate Similarity	NPC321690
0.8267	Intermediate Similarity	NPC110094
0.8261	Intermediate Similarity	NPC103734
0.8243	Intermediate Similarity	NPC69143
0.8228	Intermediate Similarity	NPC294438
0.8228	Intermediate Similarity	NPC201655
0.8228	Intermediate Similarity	NPC264317
0.8228	Intermediate Similarity	NPC283733
0.8219	Intermediate Similarity	NPC251970
0.8219	Intermediate Similarity	NPC476046
0.8219	Intermediate Similarity	NPC241854
0.8219	Intermediate Similarity	NPC166797
0.8205	Intermediate Similarity	NPC471037
0.8205	Intermediate Similarity	NPC215893
0.8205	Intermediate Similarity	NPC312480
0.8182	Intermediate Similarity	NPC473420
0.8182	Intermediate Similarity	NPC40228
0.8182	Intermediate Similarity	NPC327002
0.8182	Intermediate Similarity	NPC209318
0.8182	Intermediate Similarity	NPC90055
0.8182	Intermediate Similarity	NPC223330
0.8158	Intermediate Similarity	NPC16394
0.8158	Intermediate Similarity	NPC263951
0.8158	Intermediate Similarity	NPC231431
0.8158	Intermediate Similarity	NPC158846
0.8158	Intermediate Similarity	NPC192744
0.8158	Intermediate Similarity	NPC201459
0.8158	Intermediate Similarity	NPC199595
0.8133	Intermediate Similarity	NPC106078
0.8133	Intermediate Similarity	NPC165711
0.8133	Intermediate Similarity	NPC212661
0.8133	Intermediate Similarity	NPC61952
0.8133	Intermediate Similarity	NPC471035
0.8133	Intermediate Similarity	NPC149249
0.8125	Intermediate Similarity	NPC12774
0.8125	Intermediate Similarity	NPC325594
0.8125	Intermediate Similarity	NPC80590
0.8125	Intermediate Similarity	NPC2783
0.8125	Intermediate Similarity	NPC324063
0.8125	Intermediate Similarity	NPC70661
0.8125	Intermediate Similarity	NPC475007
0.8125	Intermediate Similarity	NPC187545
0.8125	Intermediate Similarity	NPC322159
0.8125	Intermediate Similarity	NPC155011
0.8125	Intermediate Similarity	NPC73038
0.8108	Intermediate Similarity	NPC39362
0.8101	Intermediate Similarity	NPC165064
0.8082	Intermediate Similarity	NPC177826
0.8077	Intermediate Similarity	NPC123880
0.8077	Intermediate Similarity	NPC471159
0.8052	Intermediate Similarity	NPC2482
0.8052	Intermediate Similarity	NPC477057
0.8052	Intermediate Similarity	NPC37038
0.8052	Intermediate Similarity	NPC164999
0.8026	Intermediate Similarity	NPC198240
0.8026	Intermediate Similarity	NPC179028
0.8025	Intermediate Similarity	NPC264005
0.8025	Intermediate Similarity	NPC142415
0.8025	Intermediate Similarity	NPC130577
0.8025	Intermediate Similarity	NPC134197
0.8025	Intermediate Similarity	NPC96496
0.8025	Intermediate Similarity	NPC158141
0.8025	Intermediate Similarity	NPC68160
0.8025	Intermediate Similarity	NPC51700
0.8025	Intermediate Similarity	NPC242468
0.8025	Intermediate Similarity	NPC269360
0.8025	Intermediate Similarity	NPC477926
0.8025	Intermediate Similarity	NPC171203
0.8025	Intermediate Similarity	NPC474684
0.8025	Intermediate Similarity	NPC307426
0.8025	Intermediate Similarity	NPC88716
0.8025	Intermediate Similarity	NPC18064
0.8025	Intermediate Similarity	NPC173089
0.8025	Intermediate Similarity	NPC33768
0.8025	Intermediate Similarity	NPC71507
0.8025	Intermediate Similarity	NPC293564
0.8025	Intermediate Similarity	NPC98442
0.8025	Intermediate Similarity	NPC142361
0.8025	Intermediate Similarity	NPC102683
0.8	Intermediate Similarity	NPC106416
0.8	Intermediate Similarity	NPC104806
0.8	Intermediate Similarity	NPC309399
0.8	Intermediate Similarity	NPC86316
0.7975	Intermediate Similarity	NPC200752
0.7975	Intermediate Similarity	NPC243347
0.7973	Intermediate Similarity	NPC301065
0.7949	Intermediate Similarity	NPC103754
0.7949	Intermediate Similarity	NPC3915
0.7949	Intermediate Similarity	NPC263272
0.7949	Intermediate Similarity	NPC142244
0.7949	Intermediate Similarity	NPC147066
0.7949	Intermediate Similarity	NPC274050
0.7949	Intermediate Similarity	NPC267691
0.7949	Intermediate Similarity	NPC162632
0.7949	Intermediate Similarity	NPC278459
0.7949	Intermediate Similarity	NPC474484
0.7949	Intermediate Similarity	NPC232625
0.7949	Intermediate Similarity	NPC471898
0.7949	Intermediate Similarity	NPC221647
0.7927	Intermediate Similarity	NPC182797
0.7927	Intermediate Similarity	NPC16377
0.7927	Intermediate Similarity	NPC52169
0.7927	Intermediate Similarity	NPC474511
0.7927	Intermediate Similarity	NPC104560
0.7927	Intermediate Similarity	NPC181225
0.7927	Intermediate Similarity	NPC17733
0.7927	Intermediate Similarity	NPC211162
0.7927	Intermediate Similarity	NPC255176
0.7927	Intermediate Similarity	NPC40552
0.7927	Intermediate Similarity	NPC474512
0.7927	Intermediate Similarity	NPC474719
0.7927	Intermediate Similarity	NPC146937
0.7927	Intermediate Similarity	NPC473242
0.7927	Intermediate Similarity	NPC183374
0.7927	Intermediate Similarity	NPC246708
0.7927	Intermediate Similarity	NPC290690
0.7927	Intermediate Similarity	NPC1753
0.7927	Intermediate Similarity	NPC471900
0.7927	Intermediate Similarity	NPC470629
0.7922	Intermediate Similarity	NPC192999
0.7922	Intermediate Similarity	NPC471475
0.7922	Intermediate Similarity	NPC477371
0.7922	Intermediate Similarity	NPC476812
0.7922	Intermediate Similarity	NPC476438
0.7917	Intermediate Similarity	NPC476734
0.7917	Intermediate Similarity	NPC252032
0.7917	Intermediate Similarity	NPC319671
0.7917	Intermediate Similarity	NPC469941
0.7901	Intermediate Similarity	NPC28252
0.7901	Intermediate Similarity	NPC82979
0.7901	Intermediate Similarity	NPC72638
0.7901	Intermediate Similarity	NPC185638
0.7901	Intermediate Similarity	NPC55309
0.7901	Intermediate Similarity	NPC472505
0.7895	Intermediate Similarity	NPC476811
0.7895	Intermediate Similarity	NPC472746
0.7875	Intermediate Similarity	NPC130966
0.7875	Intermediate Similarity	NPC97505
0.7875	Intermediate Similarity	NPC171789
0.7867	Intermediate Similarity	NPC476795
0.7867	Intermediate Similarity	NPC201027
0.7848	Intermediate Similarity	NPC310989
0.7848	Intermediate Similarity	NPC476984
0.7848	Intermediate Similarity	NPC48362

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 NPC91369 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	2080
0.2-0.3	3982
0.3-0.4	1944
0.4-0.5	544
0.5-0.6	246
0.6-0.7	181
0.7-0.8	24
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8228	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD4788	Approved
0.7654	Intermediate Similarity	NPD4786	Approved
0.7647	Intermediate Similarity	NPD7515	Phase 2
0.7625	Intermediate Similarity	NPD3667	Approved
0.75	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD8034	Phase 2
0.7442	Intermediate Similarity	NPD8035	Phase 2
0.7439	Intermediate Similarity	NPD3665	Phase 1
0.7439	Intermediate Similarity	NPD3666	Approved
0.7439	Intermediate Similarity	NPD3133	Approved
0.7407	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6399	Phase 3
0.7308	Intermediate Similarity	NPD6117	Approved
0.7273	Intermediate Similarity	NPD7748	Approved
0.7262	Intermediate Similarity	NPD6409	Approved
0.7262	Intermediate Similarity	NPD3618	Phase 1
0.7262	Intermediate Similarity	NPD5330	Approved
0.7262	Intermediate Similarity	NPD6684	Approved
0.7262	Intermediate Similarity	NPD7334	Approved
0.7262	Intermediate Similarity	NPD7521	Approved
0.7262	Intermediate Similarity	NPD7146	Approved
0.726	Intermediate Similarity	NPD4224	Phase 2
0.7222	Intermediate Similarity	NPD6083	Phase 2
0.7222	Intermediate Similarity	NPD6084	Phase 2
0.7215	Intermediate Similarity	NPD6116	Phase 1
0.7209	Intermediate Similarity	NPD5328	Approved
0.716	Intermediate Similarity	NPD4695	Discontinued
0.7125	Intermediate Similarity	NPD6114	Approved
0.7125	Intermediate Similarity	NPD6118	Approved
0.7125	Intermediate Similarity	NPD6115	Approved
0.7125	Intermediate Similarity	NPD6697	Approved
0.7105	Intermediate Similarity	NPD4245	Approved
0.7105	Intermediate Similarity	NPD4789	Approved
0.7105	Intermediate Similarity	NPD4244	Approved
0.7093	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6672	Approved
0.7093	Intermediate Similarity	NPD5737	Approved
0.7093	Intermediate Similarity	NPD6903	Approved
0.7059	Intermediate Similarity	NPD5279	Phase 3
0.7045	Intermediate Similarity	NPD6411	Approved
0.7045	Intermediate Similarity	NPD6079	Approved
0.7033	Intermediate Similarity	NPD7902	Approved
0.7013	Intermediate Similarity	NPD6081	Approved
0.7013	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4753	Phase 2
0.7011	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4223	Phase 3
0.6988	Remote Similarity	NPD4221	Approved
0.6974	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3698	Phase 2
0.6962	Remote Similarity	NPD3702	Approved
0.6941	Remote Similarity	NPD5329	Approved
0.6914	Remote Similarity	NPD3617	Approved
0.6914	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6098	Approved
0.6835	Remote Similarity	NPD6926	Approved
0.6835	Remote Similarity	NPD6924	Approved
0.6824	Remote Similarity	NPD4197	Approved
0.6824	Remote Similarity	NPD3668	Phase 3
0.6818	Remote Similarity	NPD6101	Approved
0.6818	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5695	Phase 3
0.6795	Remote Similarity	NPD5777	Approved
0.6778	Remote Similarity	NPD4202	Approved
0.6774	Remote Similarity	NPD5696	Approved
0.6774	Remote Similarity	NPD7638	Approved
0.675	Remote Similarity	NPD7339	Approved
0.675	Remote Similarity	NPD6942	Approved
0.675	Remote Similarity	NPD8039	Approved
0.6703	Remote Similarity	NPD7900	Approved
0.6703	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7639	Approved
0.6702	Remote Similarity	NPD7640	Approved
0.6701	Remote Similarity	NPD6675	Approved
0.6701	Remote Similarity	NPD7128	Approved
0.6701	Remote Similarity	NPD6402	Approved
0.6701	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD3198	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD6933	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD5281	Approved
0.663	Remote Similarity	NPD4629	Approved
0.663	Remote Similarity	NPD5210	Approved
0.6629	Remote Similarity	NPD6673	Approved
0.6629	Remote Similarity	NPD6904	Approved
0.6629	Remote Similarity	NPD6080	Approved
0.6627	Remote Similarity	NPD7645	Phase 2
0.6623	Remote Similarity	NPD5360	Phase 3
0.6623	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5779	Approved
0.6593	Remote Similarity	NPD5778	Approved
0.6591	Remote Similarity	NPD3573	Approved
0.6566	Remote Similarity	NPD6881	Approved
0.6566	Remote Similarity	NPD7320	Approved
0.6566	Remote Similarity	NPD6899	Approved
0.6566	Remote Similarity	NPD6686	Approved
0.6559	Remote Similarity	NPD4697	Phase 3
0.6559	Remote Similarity	NPD7614	Phase 1
0.6559	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD5221	Approved
0.6559	Remote Similarity	NPD5222	Approved
0.6548	Remote Similarity	NPD5368	Approved
0.6548	Remote Similarity	NPD7525	Registered
0.6543	Remote Similarity	NPD3703	Phase 2
0.6538	Remote Similarity	NPD6922	Approved
0.6538	Remote Similarity	NPD6923	Approved
0.6517	Remote Similarity	NPD5208	Approved
0.6512	Remote Similarity	NPD5362	Discontinued
0.65	Remote Similarity	NPD6373	Approved
0.65	Remote Similarity	NPD6372	Approved
0.6489	Remote Similarity	NPD5173	Approved
0.6489	Remote Similarity	NPD4755	Approved
0.6484	Remote Similarity	NPD7637	Suspended
0.6477	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5690	Phase 2
0.6477	Remote Similarity	NPD5280	Approved
0.6477	Remote Similarity	NPD4694	Approved
0.6471	Remote Similarity	NPD4139	Approved
0.6471	Remote Similarity	NPD5369	Approved
0.6471	Remote Similarity	NPD4692	Approved
0.6465	Remote Similarity	NPD5701	Approved
0.6465	Remote Similarity	NPD5697	Approved
0.6462	Remote Similarity	NPD634	Phase 3
0.6456	Remote Similarity	NPD7143	Approved
0.6456	Remote Similarity	NPD7144	Approved
0.6452	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD7341	Phase 2
0.6436	Remote Similarity	NPD6883	Approved
0.6436	Remote Similarity	NPD7102	Approved
0.6436	Remote Similarity	NPD7290	Approved
0.6429	Remote Similarity	NPD3196	Approved
0.6429	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6929	Approved
0.6429	Remote Similarity	NPD4266	Approved
0.6429	Remote Similarity	NPD3194	Approved
0.6429	Remote Similarity	NPD3195	Phase 2
0.6421	Remote Similarity	NPD4225	Approved
0.64	Remote Similarity	NPD6011	Approved
0.6395	Remote Similarity	NPD4269	Approved
0.6395	Remote Similarity	NPD4270	Approved
0.6395	Remote Similarity	NPD6435	Approved
0.6377	Remote Similarity	NPD3186	Phase 1
0.6375	Remote Similarity	NPD7151	Approved
0.6375	Remote Similarity	NPD4243	Approved
0.6375	Remote Similarity	NPD7150	Approved
0.6375	Remote Similarity	NPD7152	Approved
0.6373	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6869	Approved
0.6373	Remote Similarity	NPD6617	Approved
0.6373	Remote Similarity	NPD6649	Approved
0.6373	Remote Similarity	NPD6847	Approved
0.6373	Remote Similarity	NPD6650	Approved
0.6373	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD7331	Phase 2
0.6354	Remote Similarity	NPD5285	Approved
0.6354	Remote Similarity	NPD6404	Discontinued
0.6354	Remote Similarity	NPD5286	Approved
0.6354	Remote Similarity	NPD4700	Approved
0.6354	Remote Similarity	NPD4696	Approved
0.6353	Remote Similarity	NPD6931	Approved
0.6353	Remote Similarity	NPD7509	Discontinued
0.6353	Remote Similarity	NPD6930	Phase 2
0.6337	Remote Similarity	NPD6014	Approved
0.6337	Remote Similarity	NPD6012	Approved
0.6337	Remote Similarity	NPD6013	Approved
0.6329	Remote Similarity	NPD3725	Approved
0.6329	Remote Similarity	NPD4137	Phase 3
0.6329	Remote Similarity	NPD3726	Approved
0.6322	Remote Similarity	NPD7154	Phase 3
0.6316	Remote Similarity	NPD7909	Approved
0.6316	Remote Similarity	NPD3197	Phase 1
0.6311	Remote Similarity	NPD6882	Approved
0.6311	Remote Similarity	NPD8297	Approved
0.631	Remote Similarity	NPD3671	Phase 1
0.6304	Remote Similarity	NPD5693	Phase 1
0.6304	Remote Similarity	NPD6050	Approved
0.63	Remote Similarity	NPD6412	Phase 2
0.6289	Remote Similarity	NPD5223	Approved
0.6286	Remote Similarity	NPD3172	Approved
0.6279	Remote Similarity	NPD857	Phase 3
0.6269	Remote Similarity	NPD622	Approved
0.625	Remote Similarity	NPD4691	Approved
0.625	Remote Similarity	NPD8133	Approved
0.625	Remote Similarity	NPD4747	Approved
0.6238	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4195	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