NPASS Compound

Structure

CID177996 OpenBabel06191715552D 32 34 0 0 1 0 0 0 0 0999 V2000 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 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 7.7942 -3.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.1962 -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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -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 7.7942 -4.5000 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 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 9 2 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 10 2 0 0 0 0 4 10 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 21 1 0 0 0 0 8 11 1 0 0 0 0 8 22 2 0 0 0 0 9 16 1 0 0 0 0 10 21 1 0 0 0 0 11 23 2 0 0 0 0 12 18 1 0 0 0 0 12 24 1 0 0 0 0 13 27 2 0 0 0 0 13 28 1 0 0 0 0 14 15 2 0 0 0 0 14 17 1 0 0 0 0 14 23 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 24 1 0 0 0 0 16 29 2 0 0 0 0 17 26 2 0 0 0 0 17 30 1 0 0 0 0 18 31 2 0 0 0 0 18 32 1 0 0 0 0 19 20 2 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	441.14
Volume:	412.228
LogP:	-2.489
LogD:	-0.734
LogS:	-3.899
# Rotatable Bonds:	10
TPSA:	214.01
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	3
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.233
Synthetic Accessibility Score:	3.231
Fsp3:	0.211
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.74
MDCK Permeability:	4.223591076879529e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.928
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	87.33032989501953%
Volume Distribution (VD):	0.256
Pgp-substrate:	34.39715576171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.026
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.005

ADMET: Excretion

Clearance (CL):	3.085
Half-life (T1/2):	0.885

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.993
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.074
Carcinogencity:	0.529
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.662

Download Data

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

Natural Product: NPC177996

Natural Product ID:	NPC177996
*Common Name:**	2-[[4-[(2-Amino-4-Oxo-1H-Pteridin-6-Yl)Methylamino]Benzoyl]Amino]Pentanedioic Acid
IUPAC Name:	2-[[4-[(2-amino-4-oxo-1H-pteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid
Synonyms:
Standard InCHIKey:	OVBPIULPVIDEAO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19N7O6/c20-19-25-15-14(17(30)26-19)23-11(8-22-15)7-21-10-3-1-9(2-4-10)16(29)24-12(18(31)32)5-6-13(27)28/h1-4,8,12,21H,5-7H2,(H,24,29)(H,27,28)(H,31,32)(H3,20,22,25,26,30)
SMILES:	c1cc(ccc1C(=O)NC(CCC(=O)O)C(=O)O)NCc1cnc2c(c(nc(=N)[nH]2)O)n1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL277040
PubChem CID:	3405
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000109] Pteridines and derivatives [CHEMONTID:0000110] Pterins and derivatives [CHEMONTID:0001228] Pteroic acids and derivatives [CHEMONTID:0000255] Folic acids and derivatives [CHEMONTID:0003039] Folic acids

*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
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94679-X]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	branch	n.a.	PMID[17202693]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[28134521]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30199256]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9433811]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	Leaves	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921.1	Angelica acutiloba var. sugiyamae	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921.1	Angelica acutiloba var. sugiyamae	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921.1	Angelica acutiloba var. sugiyamae	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9138	Syzygium cumini	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14582	Spinacia oleracea	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22104	Trifolium pratense	Species	Fabaceae	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
GI50	50
Potency	14

Activity Type	# Activity
Cell Line	50
Individual Protein	11
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	50118.7	nM	PMID[473155]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	50118.7	nM	PMID[473156]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	35481.3	nM	PMID[473154]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	31622.8	nM	PMID[473156]
NPT501	Individual Protein	Alpha-galactosidase A	Homo sapiens	Potency	=	44668.4	nM	PMID[473156]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[473156]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[473157]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	899.5	nM	PMID[473158]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	10000.0	nM	PMID[473158]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[473158]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	11885.6	nM	PMID[473155]
NPT1098	Individual Protein	Eyes absent homolog 2	Homo sapiens	Potency	n.a.	16946.9	nM	PMID[473157]
NPT2	Others	Unspecified		Potency	=	3162.3	nM	PMID[473154]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[473157]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	22387.2	nM	PMID[473157]
NPT2	Others	Unspecified		Potency	n.a.	316.2	nM	PMID[473157]
NPT2	Others	Unspecified		Potency	n.a.	13461.4	nM	PMID[473157]

☑ 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 NPC177996 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	673
0.1-0.2	8409
0.2-0.3	14185
0.3-0.4	13450
0.4-0.5	2838
0.5-0.6	2494
0.6-0.7	610
0.7-0.8	28
0.8-0.85	0
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC147983
0.7979	Intermediate Similarity	NPC248862
0.7979	Intermediate Similarity	NPC328611
0.7897	Intermediate Similarity	NPC14849
0.7857	Intermediate Similarity	NPC131450
0.7857	Intermediate Similarity	NPC182057
0.7857	Intermediate Similarity	NPC147298
0.7227	Intermediate Similarity	NPC471193
0.7227	Intermediate Similarity	NPC471194
0.7182	Intermediate Similarity	NPC72956
0.7149	Intermediate Similarity	NPC153980
0.7149	Intermediate Similarity	NPC6865
0.713	Intermediate Similarity	NPC471192
0.7104	Intermediate Similarity	NPC54981
0.709	Intermediate Similarity	NPC74619
0.7064	Intermediate Similarity	NPC473376
0.7056	Intermediate Similarity	NPC116622
0.7046	Intermediate Similarity	NPC295452
0.7046	Intermediate Similarity	NPC171393
0.7019	Intermediate Similarity	NPC285923
0.697	Remote Similarity	NPC476491
0.6968	Remote Similarity	NPC71238
0.6957	Remote Similarity	NPC40530
0.6957	Remote Similarity	NPC314281
0.6938	Remote Similarity	NPC228835
0.6923	Remote Similarity	NPC89987
0.6913	Remote Similarity	NPC229893
0.6913	Remote Similarity	NPC64216
0.691	Remote Similarity	NPC69843
0.6897	Remote Similarity	NPC323244
0.6895	Remote Similarity	NPC57398
0.6892	Remote Similarity	NPC116555
0.6872	Remote Similarity	NPC238945
0.6851	Remote Similarity	NPC328924
0.6849	Remote Similarity	NPC471944
0.6847	Remote Similarity	NPC41717
0.684	Remote Similarity	NPC17059
0.6827	Remote Similarity	NPC11126
0.6822	Remote Similarity	NPC210123
0.6816	Remote Similarity	NPC476524
0.6814	Remote Similarity	NPC282247
0.6814	Remote Similarity	NPC54744
0.6806	Remote Similarity	NPC202812
0.6787	Remote Similarity	NPC317701
0.6786	Remote Similarity	NPC472070
0.6777	Remote Similarity	NPC477003
0.6777	Remote Similarity	NPC207851
0.6771	Remote Similarity	NPC243850
0.6769	Remote Similarity	NPC281049
0.6767	Remote Similarity	NPC476817
0.6725	Remote Similarity	NPC267811
0.6714	Remote Similarity	NPC62749
0.6712	Remote Similarity	NPC474916
0.6711	Remote Similarity	NPC477979
0.671	Remote Similarity	NPC272174
0.6696	Remote Similarity	NPC470786
0.6696	Remote Similarity	NPC471155
0.6683	Remote Similarity	NPC154478
0.668	Remote Similarity	NPC477420
0.668	Remote Similarity	NPC477418
0.6667	Remote Similarity	NPC99939
0.6667	Remote Similarity	NPC84317
0.6667	Remote Similarity	NPC311282
0.6667	Remote Similarity	NPC273532
0.6667	Remote Similarity	NPC308931
0.6667	Remote Similarity	NPC270241
0.6652	Remote Similarity	NPC471191
0.6652	Remote Similarity	NPC225400
0.6636	Remote Similarity	NPC94752
0.6623	Remote Similarity	NPC118940
0.6623	Remote Similarity	NPC469717
0.6622	Remote Similarity	NPC472538
0.6621	Remote Similarity	NPC102592
0.6621	Remote Similarity	NPC470787
0.6621	Remote Similarity	NPC79356
0.6621	Remote Similarity	NPC472540
0.6621	Remote Similarity	NPC472539
0.662	Remote Similarity	NPC83111
0.662	Remote Similarity	NPC469489
0.662	Remote Similarity	NPC21429
0.6609	Remote Similarity	NPC474896
0.6606	Remote Similarity	NPC293917
0.6606	Remote Similarity	NPC103361
0.6605	Remote Similarity	NPC278434
0.6593	Remote Similarity	NPC476525
0.6593	Remote Similarity	NPC266249
0.6592	Remote Similarity	NPC472069
0.6592	Remote Similarity	NPC472062
0.6592	Remote Similarity	NPC472063
0.6591	Remote Similarity	NPC141454
0.6591	Remote Similarity	NPC472541
0.6591	Remote Similarity	NPC473814
0.6591	Remote Similarity	NPC472542
0.6591	Remote Similarity	NPC74153
0.6591	Remote Similarity	NPC78767
0.6588	Remote Similarity	NPC256268
0.6588	Remote Similarity	NPC283219
0.6587	Remote Similarity	NPC302647
0.6586	Remote Similarity	NPC314882
0.6581	Remote Similarity	NPC478141
0.6581	Remote Similarity	NPC327095
0.6581	Remote Similarity	NPC31097
0.6581	Remote Similarity	NPC312942
0.6579	Remote Similarity	NPC82370
0.6579	Remote Similarity	NPC320968
0.6578	Remote Similarity	NPC472064
0.6575	Remote Similarity	NPC93390
0.6573	Remote Similarity	NPC243058
0.6567	Remote Similarity	NPC251391
0.656	Remote Similarity	NPC216550
0.6558	Remote Similarity	NPC476527
0.6557	Remote Similarity	NPC73994
0.6557	Remote Similarity	NPC16659
0.6553	Remote Similarity	NPC40455
0.6549	Remote Similarity	NPC244741
0.6544	Remote Similarity	NPC324091
0.6542	Remote Similarity	NPC203635
0.654	Remote Similarity	NPC219848
0.654	Remote Similarity	NPC186351
0.6537	Remote Similarity	NPC470731
0.6537	Remote Similarity	NPC470732
0.6535	Remote Similarity	NPC123839
0.6535	Remote Similarity	NPC120070
0.6532	Remote Similarity	NPC313421
0.6532	Remote Similarity	NPC284338
0.653	Remote Similarity	NPC473821
0.6525	Remote Similarity	NPC19170
0.6524	Remote Similarity	NPC315804
0.6524	Remote Similarity	NPC313804
0.6524	Remote Similarity	NPC469938
0.6514	Remote Similarity	NPC476460
0.6512	Remote Similarity	NPC133003
0.6509	Remote Similarity	NPC248041
0.6509	Remote Similarity	NPC265710
0.6509	Remote Similarity	NPC126709
0.6508	Remote Similarity	NPC63109
0.65	Remote Similarity	NPC135950
0.6495	Remote Similarity	NPC270834
0.6491	Remote Similarity	NPC478158
0.6489	Remote Similarity	NPC165599
0.6482	Remote Similarity	NPC302159
0.6482	Remote Similarity	NPC478006
0.6481	Remote Similarity	NPC90415
0.648	Remote Similarity	NPC471536
0.6479	Remote Similarity	NPC61011
0.6479	Remote Similarity	NPC24864
0.6479	Remote Similarity	NPC91179
0.6476	Remote Similarity	NPC477976
0.6473	Remote Similarity	NPC98864
0.6471	Remote Similarity	NPC213914
0.6466	Remote Similarity	NPC322064
0.6465	Remote Similarity	NPC46895
0.6463	Remote Similarity	NPC316224
0.6462	Remote Similarity	NPC217372
0.6462	Remote Similarity	NPC15573
0.6462	Remote Similarity	NPC240088
0.6462	Remote Similarity	NPC473380
0.6462	Remote Similarity	NPC183662
0.6459	Remote Similarity	NPC315467
0.6458	Remote Similarity	NPC475969
0.6458	Remote Similarity	NPC474877
0.6458	Remote Similarity	NPC475859
0.6455	Remote Similarity	NPC326422
0.6446	Remote Similarity	NPC182222
0.6445	Remote Similarity	NPC203468
0.6445	Remote Similarity	NPC149155
0.6445	Remote Similarity	NPC110500
0.6445	Remote Similarity	NPC469529
0.6444	Remote Similarity	NPC182507
0.6444	Remote Similarity	NPC297862
0.6444	Remote Similarity	NPC156003
0.6441	Remote Similarity	NPC220851
0.6441	Remote Similarity	NPC106824
0.6441	Remote Similarity	NPC167710
0.6438	Remote Similarity	NPC472285
0.6438	Remote Similarity	NPC471197
0.6438	Remote Similarity	NPC473763
0.6438	Remote Similarity	NPC117244
0.6438	Remote Similarity	NPC27041
0.6438	Remote Similarity	NPC312645
0.6434	Remote Similarity	NPC478010
0.6434	Remote Similarity	NPC478009
0.6432	Remote Similarity	NPC478039
0.6432	Remote Similarity	NPC472065
0.6432	Remote Similarity	NPC219336
0.6425	Remote Similarity	NPC294693
0.6425	Remote Similarity	NPC113056
0.6425	Remote Similarity	NPC138293
0.6422	Remote Similarity	NPC478157
0.6422	Remote Similarity	NPC213629
0.6422	Remote Similarity	NPC321708
0.6418	Remote Similarity	NPC282531
0.6418	Remote Similarity	NPC123906
0.6417	Remote Similarity	NPC477176
0.6417	Remote Similarity	NPC470730
0.6417	Remote Similarity	NPC470729
0.6417	Remote Similarity	NPC477175
0.6416	Remote Similarity	NPC143325
0.6415	Remote Similarity	NPC267885
0.6413	Remote Similarity	NPC171317

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 NPC177996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	265
0.1-0.2	738
0.2-0.3	1173
0.3-0.4	2255
0.4-0.5	2093
0.5-0.6	1854
0.6-0.7	702
0.7-0.8	43
0.8-0.85	9
0.85-0.9	14
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3353	Approved
0.9479	High Similarity	NPD3411	Phase 2
0.9479	High Similarity	NPD3410	Approved
0.9381	High Similarity	NPD3968	Approved
0.9227	High Similarity	NPD3967	Approved
0.8706	High Similarity	NPD5510	Approved
0.8612	High Similarity	NPD6752	Phase 1
0.8612	High Similarity	NPD6753	Phase 1
0.8134	Intermediate Similarity	NPD3917	Approved
0.8134	Intermediate Similarity	NPD3916	Clinical (unspecified phase)
0.8134	Intermediate Similarity	NPD3918	Approved
0.8088	Intermediate Similarity	NPD3890	Phase 2
0.8088	Intermediate Similarity	NPD3891	Phase 2
0.8086	Intermediate Similarity	NPD3915	Approved
0.8037	Intermediate Similarity	NPD6210	Phase 3
0.7979	Intermediate Similarity	NPD3522	Approved
0.7897	Intermediate Similarity	NPD4092	Approved
0.7868	Intermediate Similarity	NPD3990	Phase 3
0.7857	Intermediate Similarity	NPD3998	Approved
0.7857	Intermediate Similarity	NPD3999	Approved
0.7857	Intermediate Similarity	NPD3997	Approved
0.7846	Intermediate Similarity	NPD4091	Approved
0.7817	Intermediate Similarity	NPD3989	Phase 3
0.7806	Intermediate Similarity	NPD3991	Approved
0.7806	Intermediate Similarity	NPD3993	Approved
0.7806	Intermediate Similarity	NPD3995	Approved
0.7806	Intermediate Similarity	NPD3996	Approved
0.7806	Intermediate Similarity	NPD3992	Approved
0.7806	Intermediate Similarity	NPD3994	Approved
0.7703	Intermediate Similarity	NPD7887	Approved
0.7703	Intermediate Similarity	NPD7888	Approved
0.7623	Intermediate Similarity	NPD1571	Phase 2
0.7557	Intermediate Similarity	NPD5001	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD1572	Phase 2
0.7512	Intermediate Similarity	NPD4559	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7232	Discontinued
0.7431	Intermediate Similarity	NPD7557	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5856	Discontinued
0.7427	Intermediate Similarity	NPD5686	Approved
0.7427	Intermediate Similarity	NPD5685	Approved
0.7404	Intermediate Similarity	NPD1173	Approved
0.7366	Intermediate Similarity	NPD5046	Discontinued
0.7342	Intermediate Similarity	NPD5199	Approved
0.7342	Intermediate Similarity	NPD5198	Approved
0.733	Intermediate Similarity	NPD3805	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1506	Discontinued
0.7311	Intermediate Similarity	NPD5854	Approved
0.7308	Intermediate Similarity	NPD8310	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD5446	Phase 2
0.7281	Intermediate Similarity	NPD6486	Approved
0.7281	Intermediate Similarity	NPD6487	Approved
0.7268	Intermediate Similarity	NPD1096	Discontinued
0.7255	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD6481	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6724	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6328	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2814	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6022	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5855	Phase 3
0.7204	Intermediate Similarity	NPD5853	Phase 3
0.7202	Intermediate Similarity	NPD4882	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6665	Discontinued
0.7177	Intermediate Similarity	NPD3439	Approved
0.7163	Intermediate Similarity	NPD7817	Phase 1
0.715	Intermediate Similarity	NPD7245	Approved
0.715	Intermediate Similarity	NPD7246	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD5887	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6470	Phase 3
0.7137	Intermediate Similarity	NPD4070	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD6173	Approved
0.713	Intermediate Similarity	NPD3775	Approved
0.713	Intermediate Similarity	NPD3773	Approved
0.713	Intermediate Similarity	NPD3774	Approved
0.7119	Intermediate Similarity	NPD7860	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6887	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD3406	Suspended
0.7104	Intermediate Similarity	NPD4863	Approved
0.7103	Intermediate Similarity	NPD1982	Phase 1
0.71	Intermediate Similarity	NPD5611	Phase 2
0.7098	Intermediate Similarity	NPD2813	Phase 3
0.7098	Intermediate Similarity	NPD2812	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4883	Approved
0.7083	Intermediate Similarity	NPD5017	Discontinued
0.708	Intermediate Similarity	NPD5827	Discontinued
0.7078	Intermediate Similarity	NPD3371	Approved
0.7067	Intermediate Similarity	NPD1623	Approved
0.7067	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD1292	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD7207	Approved
0.7064	Intermediate Similarity	NPD944	Approved
0.7064	Intermediate Similarity	NPD7209	Approved
0.7064	Intermediate Similarity	NPD7208	Approved
0.7059	Intermediate Similarity	NPD5072	Discontinued
0.7051	Intermediate Similarity	NPD6269	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3497	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6268	Phase 1
0.7045	Intermediate Similarity	NPD2442	Approved
0.7045	Intermediate Similarity	NPD2443	Approved
0.7032	Intermediate Similarity	NPD5489	Phase 1
0.7032	Intermediate Similarity	NPD5491	Phase 3
0.7031	Intermediate Similarity	NPD7269	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD5935	Discontinued
0.7023	Intermediate Similarity	NPD4364	Phase 1
0.7019	Intermediate Similarity	NPD721	Approved
0.6987	Remote Similarity	NPD3222	Phase 2
0.6987	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5042	Phase 1
0.697	Remote Similarity	NPD4517	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7415	Suspended
0.6952	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4376	Phase 3
0.6948	Remote Similarity	NPD5973	Phase 2
0.6948	Remote Similarity	NPD5974	Approved
0.6947	Remote Similarity	NPD1591	Approved
0.6947	Remote Similarity	NPD6218	Discontinued
0.6947	Remote Similarity	NPD8271	Discontinued
0.6937	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1600	Suspended
0.693	Remote Similarity	NPD6226	Phase 3
0.6927	Remote Similarity	NPD5333	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3839	Phase 2
0.6923	Remote Similarity	NPD3840	Phase 2
0.6919	Remote Similarity	NPD3246	Discontinued
0.6919	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4988	Discontinued
0.6916	Remote Similarity	NPD460	Discontinued
0.6916	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6829	Phase 2
0.6912	Remote Similarity	NPD2405	Phase 3
0.6909	Remote Similarity	NPD4299	Phase 1
0.6909	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4558	Phase 2
0.6901	Remote Similarity	NPD1658	Discontinued
0.6898	Remote Similarity	NPD4438	Approved
0.6897	Remote Similarity	NPD6164	Phase 2
0.6897	Remote Similarity	NPD6165	Phase 2
0.6895	Remote Similarity	NPD7724	Phase 2
0.6892	Remote Similarity	NPD6521	Phase 3
0.6892	Remote Similarity	NPD6520	Phase 3
0.6891	Remote Similarity	NPD2893	Phase 3
0.6887	Remote Similarity	NPD1657	Approved
0.6884	Remote Similarity	NPD8641	Approved
0.6872	Remote Similarity	NPD7850	Discontinued
0.6872	Remote Similarity	NPD7851	Phase 1
0.6872	Remote Similarity	NPD706	Phase 1
0.6869	Remote Similarity	NPD3430	Approved
0.6869	Remote Similarity	NPD3431	Approved
0.6866	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD2408	Discontinued
0.686	Remote Similarity	NPD3041	Approved
0.6858	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD8242	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD7970	Approved
0.6856	Remote Similarity	NPD6579	Phase 2
0.6855	Remote Similarity	NPD5116	Phase 1
0.6855	Remote Similarity	NPD7923	Phase 2
0.6853	Remote Similarity	NPD8289	Discontinued
0.6849	Remote Similarity	NPD7727	Phase 2
0.6847	Remote Similarity	NPD6135	Phase 1
0.684	Remote Similarity	NPD6849	Phase 2
0.684	Remote Similarity	NPD6850	Phase 2
0.6833	Remote Similarity	NPD5901	Discontinued
0.6833	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.683	Remote Similarity	NPD8261	Discontinued
0.683	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7543	Phase 2
0.6824	Remote Similarity	NPD8292	Phase 2
0.6818	Remote Similarity	NPD7079	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD4612	Discontinued
0.6814	Remote Similarity	NPD7616	Discontinued
0.6808	Remote Similarity	NPD7175	Phase 1
0.6808	Remote Similarity	NPD5016	Approved
0.6806	Remote Similarity	NPD7406	Phase 2
0.6804	Remote Similarity	NPD2912	Approved
0.6804	Remote Similarity	NPD2911	Approved
0.6802	Remote Similarity	NPD2317	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2008	Discontinued
0.6798	Remote Similarity	NPD5643	Phase 2
0.6794	Remote Similarity	NPD5508	Phase 1
0.6794	Remote Similarity	NPD1618	Phase 2
0.6792	Remote Similarity	NPD7026	Phase 2
0.6782	Remote Similarity	NPD4564	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4565	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD2480	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4024	Phase 3
0.6777	Remote Similarity	NPD2091	Phase 2
0.6777	Remote Similarity	NPD2096	Phase 2
0.6776	Remote Similarity	NPD3321	Discontinued
0.6774	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7656	Approved
0.677	Remote Similarity	NPD7657	Approved
0.677	Remote Similarity	NPD2411	Approved
0.6768	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2928	Phase 2

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