NPASS Compound

Natural Product: NPC71002

Natural Product ID	NPC71002
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-(Heptadeca-8,11-Dienyl)Benzene-1,3-Diol
IUPAC Name	5-[(8Z,11Z)-heptadeca-8,11-dienyl]benzene-1,3-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL253004
PubChem CID	14235913
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 61 61 0 0 0 0 0 0 0 0999 V2000 -9.2597 1.7517 0.2283 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0908 2.1861 1.0879 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3382 0.9671 1.5272 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8097 0.1836 0.3242 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0468 -1.0543 0.8163 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5671 -1.7601 -0.3914 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3007 -1.9751 -0.6480 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1705 -1.5560 0.2055 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2679 -0.6686 -0.5402 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0057 -0.9007 -0.7962 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3529 -2.1292 -0.3385 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7796 -1.7294 0.5721 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8081 -0.8691 -0.0820 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4890 -1.4742 -1.2515 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5048 -0.5189 -1.8358 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5735 -0.1316 -0.8662 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5274 0.8198 -1.5634 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5765 1.1832 -0.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4744 2.2552 0.2802 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5027 2.5055 1.1651 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6346 1.7267 1.2389 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7390 0.6526 0.3899 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7274 0.3909 -0.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8570 -0.1633 0.4231 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4047 3.5876 2.0249 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6873 0.7937 0.5937 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8772 1.5861 -0.7857 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0524 2.5001 0.2113 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4136 2.7917 0.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4573 2.7047 1.9765 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9862 0.2691 2.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4666 1.2711 2.1154 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6870 -0.0927 -0.2796 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1587 0.8334 -0.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3421 -0.7640 1.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8687 -1.6808 1.3145 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3189 -2.1295 -1.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0390 -2.5118 -1.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7390 -2.3692 0.7743 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6037 -0.8693 1.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7078 0.2799 -0.9139 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4632 -0.1282 -1.3705 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0178 -2.7611 -1.1927 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0414 -2.7709 0.2017 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3456 -1.1725 1.4265 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2278 -2.6548 0.9853 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5880 -0.6593 0.6960 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3863 0.1189 -0.3578 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0671 -2.3924 -0.9435 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8333 -1.7937 -2.0646 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9612 0.3912 -2.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9999 -0.9390 -2.7345 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1080 -1.0146 -0.5146 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1046 0.4703 -0.0473 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0087 1.6859 -1.9829 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0336 0.2874 -2.4035 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5859 2.8760 0.2303 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4083 1.9722 1.9534 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7983 -0.4599 -1.1738 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8010 -1.0840 0.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2459 4.1367 2.1611 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 20 25 1 0 23 18 1 0 1 26 1 0 1 27 1 0 1 28 1 0 2 29 1 0 2 30 1 0 3 31 1 0 3 32 1 0 4 33 1 0 4 34 1 0 5 35 1 0 5 36 1 0 6 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 10 42 1 0 11 43 1 0 11 44 1 0 12 45 1 0 12 46 1 0 13 47 1 0 13 48 1 0 14 49 1 0 14 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 19 57 1 0 21 58 1 0 23 59 1 0 24 60 1 0 25 61 1 0 M END

Standard InCHIKey	LQLSZSURMCEKFF-HZJYTTRNSA-N
Standard InCHI	InChI=1S/C23H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21-18-22(24)20-23(25)19-21/h6-7,9-10,18-20,24-25H,2-5,8,11-17H2,1H3/b7-6-,10-9-
SMILES	CCCCC/C=CC/C=CCCCCCCCc1cc(cc(c1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	344.27	Volume:	402.206 ? Van der Waals volume.
Dense:	0.856	LogP:	8.888 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.066 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.982 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	8.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.28	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.521	Fsp³:	0.565
MCE-18:	6.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.722	Fluc inhibitor:	0.355 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.095 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.915	Promiscuous compounds:	0.102

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.224	MDCK Permeability:	-4.765
Pgp-inhibitor:	0.507	Pgp-substrate:	0.001
PAMPA:	0.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.721	30% Bioavailability (F30%):	0.808
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036	MRP1:	0.999
Plasma Protein Binding (PPB):	98.923%	Volume Distribution (VD):	0.732
Fu:	0.585% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.057
OATP1B3 inhibitor:	0.616	BCRP inhibitor:	0.584
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.755	CYP2C19-substrate:	0.997
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.862
CYP2D6-inhibitor:	0.977	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.994	CYP2C8-inhibitor:	1.0
HLM stability:	0.825 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

4.77

Half-life (T1/2):

0.74

ADMET: Toxicity

hERG Blockers:	0.744	hERG Blockers (10um):	0.887
Human Hepatotoxicity (H-HT):	0.175	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.179	Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.165	Skin Sensitization:	1.0
Carcinogencity:	0.015	Eye Corrosion:	0.998
Eye Irritation:	0.999	Respiratory Toxicity:	0.814
Drug-induced Neurotoxicity:	0.009	Ototoxicity:	0.096
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.152
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.053
A549 Cytotoxicity:	0.956	Hek293 Cytotoxicity:	0.833
BCF:	1.445 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	5.073 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.045 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.711 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO6797	Hyoscyamus reticulatus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/elsc.201800087]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309313]
NPO25294	Merulius incarnatus	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643059]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724859]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125236]
NPO5292	Stylogyne turbacensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17629327]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17716892]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	leaves	Kibale National Park, Uganda	2000-2001	PMID[19299148]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	South China Sea	n.a.	PMID[25211032]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31117521]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31873014]
NPO456	Swertia dilatata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4472648]
NPO456	Swertia dilatata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29068	Papilio phorcas	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6110	Iryanthera elliptica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6797	Hyoscyamus reticulatus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25294	Merulius incarnatus	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5519	Aplidium uouo	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO869	Elaeagnus multiflora	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7829	Embelia robusta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4552	Gnephosis arachnoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1595	Grindelia paludosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4052	Lophura armata	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7669	Micromphale perforans	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5741	Nymphaea elegans	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7306	Onchidella binneyi	Species	Onchidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15010	Packera aurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO799	Psoralea bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7094	Salvia candicans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8193	Streptomyces morookaense	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5292	Stylogyne turbacensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO456	Swertia dilatata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7829	Embelia robusta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7829	Embelia robusta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23840	Taxus x media	Species	Taxaceae	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]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29242	Salvia dorrii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29225	Oncoba echinata	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28949	Croton cumingii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29363	Aconitum nevadense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26192	Cordylanthus kingii	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28864	Nauclea officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27269	Annona impressivenia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29415	Hovenia acerba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27743	Aaptos aaptos	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29203	Gymnocarpium robertianum	Species	Cystopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29450	Streptomyces parvisporogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3340	Fridericia chica	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29127	Cystophora scalaris	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28898	Grewia mollis	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29400	Conocephalum japonicum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29446	Stevia polycephala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28918	Ophiolepis superba	Species	Ophiolepididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29047	Disynaphia halimifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28971	Bersama yangambiensis	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4055	Aspergillus unguis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13818	Narcissus concolor	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28784	Alseodaphne corneri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4244	Doodia picta	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29142	Kaunia saltensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28805	Thymus piperella	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28937	Heterotheca grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28845	Eragrostis viscosa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28824	Forsteronia refracta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29004	Ruta pinnata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29510	Aulacocephalus temmincki	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29154	Heliotropium floridum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29292	Teucrium depressum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29189	Castanopsis sclerophylla	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25981	Crinipellis scabella	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3744	Polycephalomyces nipponicus	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9157	Rubrivivax gelatinosus	Species	n.a.	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29488	Sophora angustifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29344	Parabenzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO29068	Papilio phorcas	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5741	Nymphaea elegans	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25294	Merulius incarnatus	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4052	Lophura armata	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1595	Grindelia paludosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7669	Micromphale perforans	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15010	Packera aurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7829	Embelia robusta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO456	Swertia dilatata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5292	Stylogyne turbacensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8193	Streptomyces morookaense	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO869	Elaeagnus multiflora	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7094	Salvia candicans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO799	Psoralea bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6797	Hyoscyamus reticulatus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7306	Onchidella binneyi	Species	Onchidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5519	Aplidium uouo	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4552	Gnephosis arachnoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6110	Iryanthera elliptica	Species	Myristicaceae	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	Organism Name	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	11

Activity Type	# Activity
Cell line	8
Organism	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	8700.0	nM	PMID[17629327]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	8700.0	nM	PMID[17629327]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	148000.0	nM	PMID[17629327]
NPT81	Cell line	A549	Homo sapiens	IC50	=	1420.0	nM	PMID[17125236]
NPT179	Cell line	A2780	Homo sapiens	IC50	=	1570.0	nM	PMID[17125236]
NPT181	Cell line	Bel-7402	Homo sapiens	IC50	=	1910.0	nM	PMID[17125236]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	=	1790.0	nM	PMID[17125236]
NPT180	Cell line	HCT-8	Homo sapiens	IC50	=	1540.0	nM	PMID[17125236]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	30000.0	nM	PMID[17629327]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	600.0	nM	PMID[17629327]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	6.5	ug.mL-1	PMID[16643059]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC71002 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	27534
0.1-0.2	20445
0.2-0.3	1570
0.3-0.4	178
0.4-0.5	50
0.5-0.6	28
0.6-0.7	18
0.7-0.8	0
0.8-0.85	8
0.85-0.9	6
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC249828
0.9459	High Similarity	NPC302219
0.9167	High Similarity	NPC146798
0.9167	High Similarity	NPC222522
0.9167	High Similarity	NPC106396
0.9167	High Similarity	NPC94351
0.9167	High Similarity	NPC168303
0.8947	High Similarity	NPC242342
0.8947	High Similarity	NPC85479
0.8889	High Similarity	NPC53051
0.8889	High Similarity	NPC24404
0.8889	High Similarity	NPC313030
0.8684	High Similarity	NPC166761
0.8462	Intermediate Similarity	NPC10588
0.8333	Intermediate Similarity	NPC470700
0.8333	Intermediate Similarity	NPC54844
0.8333	Intermediate Similarity	NPC39097
0.8333	Intermediate Similarity	NPC302681
0.8333	Intermediate Similarity	NPC118286
0.8333	Intermediate Similarity	NPC109691
0.825	Intermediate Similarity	NPC72947
0.7895	Intermediate Similarity	NPC39664
0.75	Intermediate Similarity	NPC294186
0.75	Intermediate Similarity	NPC147310
0.75	Intermediate Similarity	NPC137415
0.75	Intermediate Similarity	NPC166313
0.75	Intermediate Similarity	NPC192032
0.75	Intermediate Similarity	NPC24407
0.75	Intermediate Similarity	NPC11280
0.7174	Intermediate Similarity	NPC305603
0.7045	Intermediate Similarity	NPC210497
0.6977	Remote Similarity	NPC158253
0.6744	Remote Similarity	NPC94139
0.6744	Remote Similarity	NPC284011
0.6744	Remote Similarity	NPC147284
0.6667	Remote Similarity	NPC246056
0.6667	Remote Similarity	NPC232523
0.6512	Remote Similarity	NPC488413
0.6512	Remote Similarity	NPC483454
0.6512	Remote Similarity	NPC162314
0.6512	Remote Similarity	NPC488412
0.6458	Remote Similarity	NPC61033
0.6304	Remote Similarity	NPC192
0.6279	Remote Similarity	NPC486908
0.6275	Remote Similarity	NPC123559
0.6275	Remote Similarity	NPC140521
0.6222	Remote Similarity	NPC204901
0.6122	Remote Similarity	NPC127894
0.6122	Remote Similarity	NPC470759
0.5957	Remote Similarity	NPC48730
0.5714	Remote Similarity	NPC241891
0.5714	Remote Similarity	NPC134829
0.5714	Remote Similarity	NPC470760
0.5682	Remote Similarity	NPC55561
0.5652	Remote Similarity	NPC129373
0.5652	Remote Similarity	NPC488416
0.5556	Remote Similarity	NPC196479
0.5556	Remote Similarity	NPC487734
0.551	Remote Similarity	NPC483450
0.549	Remote Similarity	NPC249836
0.5455	Remote Similarity	NPC177420
0.5349	Remote Similarity	NPC3358
0.5349	Remote Similarity	NPC306884
0.5349	Remote Similarity	NPC603092
0.5306	Remote Similarity	NPC219070
0.5306	Remote Similarity	NPC483449
0.5294	Remote Similarity	NPC248396
0.5294	Remote Similarity	NPC486909
0.5283	Remote Similarity	NPC17840
0.5283	Remote Similarity	NPC247477
0.5238	Remote Similarity	NPC59506
0.5227	Remote Similarity	NPC487946
0.5227	Remote Similarity	NPC487945
0.52	Remote Similarity	NPC471498
0.5116	Remote Similarity	NPC488411
0.5116	Remote Similarity	NPC488410
0.5116	Remote Similarity	NPC488409

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC71002 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6460
0.1-0.2	2572
0.2-0.3	106
0.3-0.4	11
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
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
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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