NPASS Compound

Structure

CID226108 OpenBabel06191716022D 42 48 0 0 1 0 0 0 0 0999 V2000 4.9732 0.9580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7720 1.2741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8019 1.4367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3829 2.0105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8024 -0.4773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4966 2.3321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4861 3.3501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8281 3.3499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3161 -1.9137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8290 -1.4357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9734 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8289 1.4349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6570 3.8286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4870 -1.4353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6308 0.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0505 2.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6581 -1.9142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6310 0.0014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1074 3.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4862 2.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1450 -1.4349 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8282 2.3926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8288 -0.4785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6573 1.9141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6577 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6575 0.9571 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1448 -0.4777 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4868 -0.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8286 0.4785 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0002 0.9568 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6568 4.7856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4595 1.4372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6614 3.6441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6584 -2.8712 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4599 -0.4768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7751 3.9657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3151 1.9145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9739 -1.9132 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8287 -0.4785 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3157 0.0007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0004 1.9138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 11 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 11 2 0 0 0 0 5 18 1 0 0 0 0 6 12 2 0 0 0 0 6 19 1 0 0 0 0 7 13 2 0 0 0 0 7 20 1 0 0 0 0 8 13 1 0 0 0 0 8 22 2 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 17 2 0 0 0 0 10 23 1 0 0 0 0 13 31 1 0 0 0 0 14 17 1 0 0 0 0 14 28 2 0 0 0 0 15 18 2 0 0 0 0 15 32 1 0 0 0 0 16 19 2 0 0 0 0 16 33 1 0 0 0 0 17 34 1 0 0 0 0 18 35 1 0 0 0 0 19 36 1 0 0 0 0 20 24 2 0 0 0 0 20 37 1 0 0 0 0 21 27 1 0 0 0 0 21 38 1 1 0 0 0 22 24 1 0 0 0 0 22 41 1 0 0 0 0 23 25 2 0 0 0 0 23 42 1 0 0 0 0 25 26 1 0 0 0 0 25 28 1 0 0 0 0 26 24 1 6 0 0 0 26 29 1 0 0 0 0 27 11 1 6 0 0 0 27 40 1 0 0 0 0 28 40 1 0 0 0 0 29 30 1 1 0 0 0 29 39 1 0 0 0 0 30 12 1 1 0 0 0 30 41 1 0 0 0 0 30 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.13
Volume:	541.386
LogP:	2.778
LogD:	1.742
LogS:	-3.913
# Rotatable Bonds:	2
TPSA:	209.76
# H-Bond Aceptor:	12
# H-Bond Donor:	9
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.158
Synthetic Accessibility Score:	5.361
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.742
MDCK Permeability:	5.432660145743284e-06
Pgp-inhibitor:	0.055
Pgp-substrate:	0.06
Human Intestinal Absorption (HIA):	0.416
20% Bioavailability (F20%):	0.883
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	89.05946350097656%
Volume Distribution (VD):	0.413
Pgp-substrate:	9.138472557067871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.119
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.583
CYP2C9-substrate:	0.787
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.145
CYP3A4-substrate:	0.452

ADMET: Excretion

Clearance (CL):	11.308
Half-life (T1/2):	0.585

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.44
Rat Oral Acute Toxicity:	0.627
Maximum Recommended Daily Dose:	0.74
Skin Sensitization:	0.956
Carcinogencity:	0.5
Eye Corrosion:	0.003
Eye Irritation:	0.904
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC226108

Natural Product ID:	NPC226108
*Common Name:**	Proanthocyanidin A1
IUPAC Name:	n.a.
Synonyms:	Proanthocyanidin A1
Standard InCHIKey:	NSEWTSAADLNHNH-TXZJYACMSA-N
Standard InCHI:	InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26+,27+,29+,30-/m0/s1
SMILES:	c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc3c([C@H]4c5c(cc(cc5O[C@](c5ccc(c(c5)O)O)([C@@H]4O)O3)O)O)c2O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450916
PubChem CID:	9872976
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	2007; 2008	DOI[10.1007/s11746-010-1589-7]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)00169-2]
NPO4654	Critonia quadrangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)81431-4]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	cotyledon	n.a.	PMID[11283027]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473412]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575960]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11975485]
NPO32562	ecdysanthera utilis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11975489]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[12670184]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15128023]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730255]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[15730255]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724861]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315967]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	leaf	n.a.	n.a.	PMID[20035557]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	atlantic-forest-soil	n.a.	PMID[20450206]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302965]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	seed	n.a.	PMID[21348467]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21446699]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22537213]
NPO16874	Campsiandra guayanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23268742]
NPO5183	Feretia apodanthera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23268742]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO40346	Serjania marginata	Species	Sapindaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[25517504]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26566007]
NPO16601	Styrax perkinsiae	Species	Styracaceae	Eukaryota	n.a.	bark	n.a.	PMID[26762060]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27684202]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Peanut Skins	n.a.	n.a.	PMID[28231711]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31763840]
NPO12697	Baccharis megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3437280]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288445]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9748368]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oil	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.		Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Oils	n.a.		Database[Phenol-Explorer]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	Seeds	n.a.		Database[Phenol-Explorer]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16289	Marrubium supinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15760	Aconitum pseudohuiliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13872	Amanita cokeri	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16856	Solanum elaeagnifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO130	Galeopsis bifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21913	Verbesina rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26436	Citrus glauca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11233	Pseudocyphellaria impressa	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14413	Bombus muscorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9107	Metalasia bolusii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO576	Oxyanthus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15969	Alcyonium molle	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16522	Ceratozamia fuscoviridis	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13396	Aplophyllum popovii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12438	Fomes cajanderi	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16766	Haplophyllum dauricum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16435	Cacalia bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15531	Quercus dentata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25426	Arachis hypogaea	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7515	Codium decorticatum	Species	Codiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14723	Streptomyces xantholiticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14572	Senecio latifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9823	Centrosema pascuorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29175	Strychnos tabascana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2372	Cryptotermes cynocephalus	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5468	Dacrydium fonki	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16601	Styrax perkinsiae	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16874	Campsiandra guayanensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16289	Marrubium supinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14892	Flemingia congesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13563	Alstonia deplanchei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24501	Asteriscus graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16071	Erigeron crispus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4654	Critonia quadrangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10802	Rhinoceros sondaicus	Species	Rhinocerotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4448	Relhania pumila	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8136	Pterospermum heyneanum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14046	Stevia mercedensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12697	Baccharis megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26287	Spodoptera eridania	Species	0ctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5183	Feretia apodanthera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8954	Torilis scabra	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11915	Lecanora planaica	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18873.8	Salmonella enterica subsp. enterica serovar typhimurium	Subspecies	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15760	Aconitum pseudohuiliense	Species	Ranunculaceae	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	10
Kd	2
MIC	8
Others	9

Activity Type	# Activity
Cell Line	6
Individual Protein	2
NON-MOLECULAR	1
Organism	16
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	30600.0	nM	PMID[511906]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	25000.0	nM	PMID[511906]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	5100.0	nM	PMID[511906]
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	144.3	ug.mL-1	PMID[511907]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	70000.0	nM	PMID[511908]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	70000.0	nM	PMID[511908]
NPT4535	Individual Protein	Vascular endothelial growth factor A	Homo sapiens	Kd	=	476.0	nM	PMID[511908]
NPT4536	Individual Protein	Placenta growth factor	Homo sapiens	Kd	=	394.0	nM	PMID[511908]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[511907]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	>	100.0	ug ml-1	PMID[511907]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[511907]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MBC	>	100.0	ug ml-1	PMID[511907]
NPT1398	Organism	Salmonella paratyphi	Salmonella enterica subsp. enterica serovar Paratyphi A	MIC	>	100.0	ug.mL-1	PMID[511907]
NPT1398	Organism	Salmonella paratyphi	Salmonella enterica subsp. enterica serovar Paratyphi A	MBC	>	100.0	ug ml-1	PMID[511907]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	100.0	ug.mL-1	PMID[511907]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MBC	>	100.0	ug ml-1	PMID[511907]
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MIC	>	100.0	ug.mL-1	PMID[511907]
NPT1176	Organism	Mycobacterium fortuitum	Mycobacterium fortuitum	MBC	>	100.0	ug ml-1	PMID[511907]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[511907]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	>	100.0	ug ml-1	PMID[511907]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	100.0	ug.mL-1	PMID[511907]
NPT20	Organism	Candida albicans	Candida albicans	MBC	>	100.0	ug ml-1	PMID[511907]
NPT766	Organism	Proteus vulgaris	Proteus vulgaris	MIC	=	50.0	ug.mL-1	PMID[511907]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	10.0	n.a.	PMID[511907]
NPT1114	Organism	Human immunodeficiency virus	Human immunodeficiency virus	IC50	=	14.0	ug.mL-1	PMID[511907]
NPT610	Others	Molecular identity unknown		IC50	=	105000.0	nM	PMID[511907]
NPT610	Others	Molecular identity unknown		IC50	=	57100.0	nM	PMID[511907]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	14700.0	nM	PMID[511907]
NPT35	Others	n.a.		IC50	=	8.55	ug.mL-1	PMID[511909]

☑ 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 NPC226108 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	530
0.1-0.2	1835
0.2-0.3	4802
0.3-0.4	11068
0.4-0.5	6923
0.5-0.6	4384
0.6-0.7	6426
0.7-0.8	5320
0.8-0.85	948
0.85-0.9	377
0.9-0.95	40
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC322899
1.0	High Similarity	NPC134911
1.0	High Similarity	NPC469944
1.0	High Similarity	NPC44192
1.0	High Similarity	NPC272552
1.0	High Similarity	NPC46283
0.9795	High Similarity	NPC20050
0.9795	High Similarity	NPC306267
0.9664	High Similarity	NPC147743
0.9664	High Similarity	NPC4809
0.9664	High Similarity	NPC73517
0.9653	High Similarity	NPC18185
0.9653	High Similarity	NPC262911
0.9653	High Similarity	NPC294558
0.9653	High Similarity	NPC58190
0.9653	High Similarity	NPC236202
0.9653	High Similarity	NPC82917
0.9653	High Similarity	NPC108811
0.9653	High Similarity	NPC202742
0.9653	High Similarity	NPC263940
0.9653	High Similarity	NPC170103
0.9653	High Similarity	NPC204770
0.9653	High Similarity	NPC70409
0.96	High Similarity	NPC106601
0.96	High Similarity	NPC212614
0.96	High Similarity	NPC185231
0.96	High Similarity	NPC205613
0.96	High Similarity	NPC159526
0.96	High Similarity	NPC151474
0.96	High Similarity	NPC86630
0.96	High Similarity	NPC471404
0.9583	High Similarity	NPC96576
0.9583	High Similarity	NPC102280
0.9583	High Similarity	NPC248053
0.9583	High Similarity	NPC155564
0.9521	High Similarity	NPC211561
0.9459	High Similarity	NPC279406
0.9459	High Similarity	NPC226809
0.9452	High Similarity	NPC227516
0.9452	High Similarity	NPC20757
0.9412	High Similarity	NPC12326
0.9396	High Similarity	NPC224161
0.9333	High Similarity	NPC46335
0.9324	High Similarity	NPC477612
0.931	High Similarity	NPC28440
0.931	High Similarity	NPC171932
0.9262	High Similarity	NPC259707
0.9262	High Similarity	NPC471403
0.9252	High Similarity	NPC473480
0.9252	High Similarity	NPC15538
0.9236	High Similarity	NPC277331
0.9236	High Similarity	NPC178054
0.9236	High Similarity	NPC100482
0.92	High Similarity	NPC59692
0.9189	High Similarity	NPC280945
0.9178	High Similarity	NPC138227
0.9178	High Similarity	NPC469313
0.9178	High Similarity	NPC168579
0.9178	High Similarity	NPC76176
0.9156	High Similarity	NPC1253
0.9156	High Similarity	NPC100936
0.911	High Similarity	NPC37793
0.9054	High Similarity	NPC125755
0.9048	High Similarity	NPC475492
0.9034	High Similarity	NPC262189
0.9007	High Similarity	NPC473621
0.8986	High Similarity	NPC161700
0.8986	High Similarity	NPC277867
0.8947	High Similarity	NPC21902
0.8947	High Similarity	NPC233467
0.894	High Similarity	NPC472709
0.894	High Similarity	NPC472710
0.8933	High Similarity	NPC281549
0.8926	High Similarity	NPC190714
0.8926	High Similarity	NPC99515
0.8926	High Similarity	NPC260397
0.8919	High Similarity	NPC473108
0.8919	High Similarity	NPC15659
0.8919	High Similarity	NPC304894
0.8904	High Similarity	NPC22317
0.8897	High Similarity	NPC474390
0.8889	High Similarity	NPC78809
0.8874	High Similarity	NPC318373
0.8874	High Similarity	NPC321657
0.8868	High Similarity	NPC9309
0.8859	High Similarity	NPC475096
0.8851	High Similarity	NPC473044
0.8851	High Similarity	NPC163508
0.8851	High Similarity	NPC173203
0.8846	High Similarity	NPC98083
0.8846	High Similarity	NPC7543
0.8846	High Similarity	NPC94220
0.8846	High Similarity	NPC166456
0.8846	High Similarity	NPC24339
0.8844	High Similarity	NPC469661
0.8836	High Similarity	NPC260741
0.8836	High Similarity	NPC70682
0.8831	High Similarity	NPC157333
0.8831	High Similarity	NPC8712
0.8828	High Similarity	NPC470802
0.8816	High Similarity	NPC225815
0.8816	High Similarity	NPC9933
0.8816	High Similarity	NPC185955
0.8816	High Similarity	NPC469706
0.8816	High Similarity	NPC218041
0.8816	High Similarity	NPC214326
0.8816	High Similarity	NPC182368
0.8816	High Similarity	NPC145979
0.8816	High Similarity	NPC260781
0.8816	High Similarity	NPC469707
0.8808	High Similarity	NPC270751
0.8808	High Similarity	NPC329836
0.8808	High Similarity	NPC175976
0.8792	High Similarity	NPC25292
0.8792	High Similarity	NPC225445
0.8792	High Similarity	NPC473045
0.8784	High Similarity	NPC59841
0.8784	High Similarity	NPC475084
0.8784	High Similarity	NPC189115
0.8784	High Similarity	NPC2613
0.8784	High Similarity	NPC475891
0.8784	High Similarity	NPC204347
0.8776	High Similarity	NPC61783
0.8776	High Similarity	NPC20520
0.8776	High Similarity	NPC291101
0.8776	High Similarity	NPC266197
0.8767	High Similarity	NPC211549
0.8759	High Similarity	NPC164787
0.8759	High Similarity	NPC473413
0.8758	High Similarity	NPC321972
0.8758	High Similarity	NPC329343
0.8758	High Similarity	NPC324517
0.875	High Similarity	NPC476969
0.8742	High Similarity	NPC31325
0.8742	High Similarity	NPC474397
0.8742	High Similarity	NPC114505
0.8742	High Similarity	NPC224674
0.8742	High Similarity	NPC227902
0.8742	High Similarity	NPC101376
0.8742	High Similarity	NPC275284
0.8742	High Similarity	NPC213074
0.8742	High Similarity	NPC193473
0.8742	High Similarity	NPC15956
0.8742	High Similarity	NPC39657
0.8734	High Similarity	NPC155754
0.8734	High Similarity	NPC109061
0.8734	High Similarity	NPC124747
0.8733	High Similarity	NPC181615
0.8733	High Similarity	NPC23807
0.8725	High Similarity	NPC81638
0.8725	High Similarity	NPC252169
0.8725	High Similarity	NPC472451
0.8725	High Similarity	NPC116922
0.8718	High Similarity	NPC165483
0.8716	High Similarity	NPC87725
0.8716	High Similarity	NPC35216
0.8716	High Similarity	NPC471389
0.8716	High Similarity	NPC263261
0.871	High Similarity	NPC159922
0.8707	High Similarity	NPC22517
0.8707	High Similarity	NPC32630
0.8701	High Similarity	NPC476391
0.8701	High Similarity	NPC325860
0.8699	High Similarity	NPC306441
0.8699	High Similarity	NPC162659
0.8699	High Similarity	NPC242028
0.8699	High Similarity	NPC265433
0.8699	High Similarity	NPC302701
0.8699	High Similarity	NPC203230
0.8699	High Similarity	NPC270456
0.8699	High Similarity	NPC248727
0.8699	High Similarity	NPC16435
0.8699	High Similarity	NPC269091
0.8693	High Similarity	NPC238140
0.869	High Similarity	NPC66840
0.869	High Similarity	NPC256307
0.8684	High Similarity	NPC473876
0.8681	High Similarity	NPC261619
0.8681	High Similarity	NPC126029
0.8681	High Similarity	NPC61477
0.8681	High Similarity	NPC219876
0.8681	High Similarity	NPC15658
0.8681	High Similarity	NPC185604
0.8681	High Similarity	NPC78770
0.8675	High Similarity	NPC274454
0.8675	High Similarity	NPC95652
0.8675	High Similarity	NPC317053
0.8675	High Similarity	NPC268515
0.8675	High Similarity	NPC215678
0.8675	High Similarity	NPC150714
0.8675	High Similarity	NPC40222
0.8675	High Similarity	NPC324492
0.8667	High Similarity	NPC45257
0.8667	High Similarity	NPC280092
0.8667	High Similarity	NPC151704
0.8667	High Similarity	NPC93323
0.8667	High Similarity	NPC12641
0.8667	High Similarity	NPC177597
0.8662	High Similarity	NPC470827
0.8662	High Similarity	NPC125495

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 NPC226108 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	437
0.1-0.2	915
0.2-0.3	2034
0.3-0.4	2701
0.4-0.5	1560
0.5-0.6	883
0.6-0.7	518
0.7-0.8	95
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8681	High Similarity	NPD1613	Approved
0.8681	High Similarity	NPD1612	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8403	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD4908	Phase 1
0.8219	Intermediate Similarity	NPD3027	Phase 3
0.8144	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD7228	Approved
0.8125	Intermediate Similarity	NPD8455	Phase 2
0.8105	Intermediate Similarity	NPD6674	Discontinued
0.8038	Intermediate Similarity	NPD1653	Approved
0.8025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7054	Approved
0.7929	Intermediate Similarity	NPD7472	Approved
0.7927	Intermediate Similarity	NPD6234	Discontinued
0.7917	Intermediate Similarity	NPD1610	Phase 2
0.7882	Intermediate Similarity	NPD6797	Phase 2
0.784	Intermediate Similarity	NPD37	Approved
0.7836	Intermediate Similarity	NPD7251	Discontinued
0.7831	Intermediate Similarity	NPD7199	Phase 2
0.7805	Intermediate Similarity	NPD4965	Approved
0.7805	Intermediate Similarity	NPD4966	Approved
0.7805	Intermediate Similarity	NPD4967	Phase 2
0.7791	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD7266	Discontinued
0.7718	Intermediate Similarity	NPD2861	Phase 2
0.7706	Intermediate Similarity	NPD3818	Discontinued
0.7688	Intermediate Similarity	NPD7808	Phase 3
0.7671	Intermediate Similarity	NPD1091	Approved
0.7661	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD5844	Phase 1
0.7651	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD8312	Approved
0.7644	Intermediate Similarity	NPD8313	Approved
0.7633	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7240	Approved
0.7622	Intermediate Similarity	NPD1934	Approved
0.7619	Intermediate Similarity	NPD6959	Discontinued
0.7616	Intermediate Similarity	NPD4625	Phase 3
0.7586	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3787	Discontinued
0.7566	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD4380	Phase 2
0.7468	Intermediate Similarity	NPD4060	Phase 1
0.745	Intermediate Similarity	NPD4749	Approved
0.7436	Intermediate Similarity	NPD7097	Phase 1
0.7425	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5124	Phase 1
0.7401	Intermediate Similarity	NPD8053	Approved
0.7401	Intermediate Similarity	NPD8054	Approved
0.7391	Intermediate Similarity	NPD5058	Phase 3
0.7365	Intermediate Similarity	NPD1465	Phase 2
0.7353	Intermediate Similarity	NPD5494	Approved
0.7346	Intermediate Similarity	NPD7213	Phase 3
0.7346	Intermediate Similarity	NPD7212	Phase 2
0.7333	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7680	Approved
0.7301	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7447	Phase 1
0.7299	Intermediate Similarity	NPD3751	Discontinued
0.7297	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD7549	Discontinued
0.7283	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD6232	Discontinued
0.7263	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2801	Approved
0.7255	Intermediate Similarity	NPD3018	Phase 2
0.7244	Intermediate Similarity	NPD3620	Phase 2
0.7244	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7473	Discontinued
0.7239	Intermediate Similarity	NPD1511	Approved
0.7235	Intermediate Similarity	NPD7075	Discontinued
0.7235	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4536	Approved
0.7215	Intermediate Similarity	NPD4538	Approved
0.7171	Intermediate Similarity	NPD8651	Approved
0.717	Intermediate Similarity	NPD5588	Approved
0.717	Intermediate Similarity	NPD5960	Phase 3
0.7152	Intermediate Similarity	NPD1512	Approved
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7118	Intermediate Similarity	NPD3817	Phase 2
0.7105	Intermediate Similarity	NPD2983	Phase 2
0.7105	Intermediate Similarity	NPD2982	Phase 2
0.7099	Intermediate Similarity	NPD1652	Phase 2
0.7086	Intermediate Similarity	NPD3705	Approved
0.7081	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3882	Suspended
0.7065	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD8156	Discontinued
0.7059	Intermediate Similarity	NPD7819	Suspended
0.7059	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5283	Phase 1
0.7041	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2981	Phase 2
0.7033	Intermediate Similarity	NPD4663	Approved
0.703	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5402	Approved
0.7012	Intermediate Similarity	NPD6190	Approved
0.7011	Intermediate Similarity	NPD8127	Discontinued
0.7006	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.7006	Intermediate Similarity	NPD8099	Discontinued
0.7006	Intermediate Similarity	NPD8252	Approved
0.7006	Intermediate Similarity	NPD8251	Approved
0.7006	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6801	Discontinued
0.6993	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5735	Approved
0.6975	Remote Similarity	NPD5762	Approved
0.6975	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5763	Approved
0.6975	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7229	Phase 3
0.6961	Remote Similarity	NPD4578	Approved
0.6961	Remote Similarity	NPD4577	Approved
0.6959	Remote Similarity	NPD7157	Approved
0.6959	Remote Similarity	NPD8151	Discontinued
0.6957	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5126	Approved
0.6954	Remote Similarity	NPD5846	Approved
0.6954	Remote Similarity	NPD5125	Phase 3
0.6954	Remote Similarity	NPD6516	Phase 2
0.6951	Remote Similarity	NPD3892	Phase 2
0.6951	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3750	Approved
0.6951	Remote Similarity	NPD7466	Approved
0.6944	Remote Similarity	NPD7685	Pre-registration
0.6933	Remote Similarity	NPD1549	Phase 2
0.6928	Remote Similarity	NPD7041	Phase 2
0.6928	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD228	Approved
0.6914	Remote Similarity	NPD6100	Approved
0.6914	Remote Similarity	NPD6099	Approved
0.6905	Remote Similarity	NPD5403	Approved
0.6902	Remote Similarity	NPD7906	Approved
0.6897	Remote Similarity	NPD3021	Approved
0.6897	Remote Similarity	NPD3022	Approved
0.6893	Remote Similarity	NPD2489	Approved
0.6893	Remote Similarity	NPD27	Approved
0.689	Remote Similarity	NPD5177	Phase 3
0.6888	Remote Similarity	NPD7783	Phase 2
0.6888	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD1357	Approved
0.6886	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3051	Approved
0.6875	Remote Similarity	NPD6355	Discontinued
0.6871	Remote Similarity	NPD7843	Approved
0.6868	Remote Similarity	NPD7311	Approved
0.6868	Remote Similarity	NPD7310	Approved
0.6868	Remote Similarity	NPD7312	Approved
0.6868	Remote Similarity	NPD7313	Approved
0.6863	Remote Similarity	NPD422	Phase 1
0.6859	Remote Similarity	NPD6584	Phase 3
0.6855	Remote Similarity	NPD6233	Phase 2
0.6852	Remote Similarity	NPD4108	Discontinued
0.6848	Remote Similarity	NPD6331	Phase 2
0.6846	Remote Similarity	NPD6671	Approved
0.6836	Remote Similarity	NPD2970	Approved
0.6836	Remote Similarity	NPD2969	Approved
0.6835	Remote Similarity	NPD7095	Approved
0.6831	Remote Similarity	NPD7309	Approved
0.6829	Remote Similarity	NPD2424	Discontinued
0.6829	Remote Similarity	NPD7037	Approved
0.6828	Remote Similarity	NPD2684	Approved
0.6824	Remote Similarity	NPD7458	Discontinued
0.6821	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4140	Approved
0.6813	Remote Similarity	NPD1558	Phase 1
0.6811	Remote Similarity	NPD6841	Approved
0.6811	Remote Similarity	NPD6843	Phase 3
0.6811	Remote Similarity	NPD6842	Approved
0.6807	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2677	Approved
0.6806	Remote Similarity	NPD6779	Approved
0.6806	Remote Similarity	NPD6776	Approved
0.6806	Remote Similarity	NPD6782	Approved
0.6806	Remote Similarity	NPD6781	Approved
0.6806	Remote Similarity	NPD6780	Approved
0.6806	Remote Similarity	NPD6778	Approved
0.6806	Remote Similarity	NPD6777	Approved
0.679	Remote Similarity	NPD7119	Phase 2
0.6788	Remote Similarity	NPD7421	Clinical (unspecified phase)

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