NPASS Compound

Natural Product: NPC59692

Natural Product ID	NPC59692
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Resveratrol (E)-Dehydrodimer 11-O-Beta-D-Glucopyranoside
IUPAC Name	(2S,3R,4S,5S,6R)-2-[3-[(2S,3S)-5-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL503412
PubChem CID	10746383
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

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 77 82 0 0 0 0 0 0 0 0999 V2000 -2.1243 -4.4468 1.6301 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3058 -4.4334 0.9038 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8152 -2.9950 0.7359 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8358 -2.3119 0.0694 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1187 -0.9713 -0.1541 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5949 -0.6276 -1.3888 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6047 0.2553 -1.7192 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2920 0.3936 -3.0745 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3183 1.2528 -3.4830 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0147 1.4108 -4.8288 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3668 1.9965 -2.5340 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0885 1.8881 -1.1981 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8962 1.0154 -0.8158 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7998 2.6726 -0.2059 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1063 4.0900 -0.5999 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3122 4.4019 0.1185 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9786 3.1902 0.3289 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1315 2.1326 0.1485 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5999 0.8169 0.3121 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8901 0.5515 0.6501 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4319 -0.8140 0.8350 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7378 -1.9052 0.6896 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2922 -3.2240 0.8766 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5903 -3.4327 1.2294 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1147 -4.7224 1.4049 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4412 -4.9237 1.7652 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2795 -5.8099 1.2114 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9648 -5.6168 0.8545 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4763 -4.3215 0.6884 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1607 -6.7269 0.6698 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7286 1.6391 0.8272 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3173 2.9439 0.6784 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0969 5.0464 -0.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7270 5.6908 -0.9994 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6925 6.6016 -0.5584 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8220 6.8585 0.7888 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0083 6.2236 1.6807 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0619 5.3288 1.2301 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8044 7.7794 1.1872 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5866 -0.6584 -0.0104 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4712 -1.7345 -0.5831 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0808 -3.1122 -0.0971 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0867 -3.7137 0.6440 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5311 -1.7291 -1.9561 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8892 -0.5048 1.3374 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3088 -4.4356 2.6032 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0862 -4.8672 -0.0956 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0767 -5.0399 1.3813 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0279 -2.6374 1.7581 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6049 -0.4064 0.6422 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8341 -0.1948 -3.8255 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7234 1.8224 -5.4199 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1416 2.6707 -2.9232 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1657 0.8836 0.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2398 2.7514 0.7664 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3270 4.2369 -1.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8968 0.0367 0.1592 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4730 -0.9091 1.1084 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6835 -1.7760 0.4111 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3009 -2.6442 1.3977 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2109 -4.6530 1.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7162 -6.8028 1.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4346 -4.2472 0.4076 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4851 -7.3840 -0.0565 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7764 1.4233 1.1021 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9851 3.7853 0.8203 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6474 5.5081 -2.0651 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3247 7.0918 -1.2804 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0909 6.4082 2.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6091 4.8012 1.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0181 8.5898 0.6250 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7856 0.2842 -0.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4987 -1.5385 -0.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8246 -3.7535 -0.9591 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9215 -3.6957 0.1209 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9798 -0.9205 -2.2542 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6143 0.1680 1.4061 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 1 0 7 8 2 0 8 9 1 0 9 10 1 0 9 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 25 27 2 0 27 28 1 0 28 29 2 0 28 30 1 0 20 31 1 0 31 32 2 0 15 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 36 39 1 0 5 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 40 45 1 0 42 3 1 0 13 7 1 0 18 14 1 0 29 23 1 0 38 33 1 0 32 17 1 0 1 46 1 0 2 47 1 0 2 48 1 0 3 49 1 1 5 50 1 1 8 51 1 0 10 52 1 0 11 53 1 0 13 54 1 0 14 55 1 1 15 56 1 6 19 57 1 0 21 58 1 0 22 59 1 0 24 60 1 0 26 61 1 0 27 62 1 0 29 63 1 0 30 64 1 0 31 65 1 0 32 66 1 0 34 67 1 0 35 68 1 0 37 69 1 0 38 70 1 0 39 71 1 0 40 72 1 6 41 73 1 1 42 74 1 6 43 75 1 0 44 76 1 0 45 77 1 0 M END

Standard InCHIKey	ZJIBDVBTKQSZQZ-REZQOROLSA-N
Standard InCHI	InChI=1S/C34H32O11/c35-16-28-30(40)31(41)32(42)34(45-28)43-25-13-20(12-24(39)15-25)29-26-11-17(1-2-18-9-22(37)14-23(38)10-18)3-8-27(26)44-33(29)19-4-6-21(36)7-5-19/h1-15,28-42H,16H2/b2-1+/t28-,29+,30-,31+,32-,33-,34-/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2cc(O)cc(c2)[C@@H]2[C@H](Oc3c2cc(/C=C/c2cc(O)cc(c2)O)cc3)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	616.19	Volume:	607.7 ? Van der Waals volume.
Dense:	1.014	LogP:	2.866 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.449 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.08 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	35.0
TPSA:	189.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.142	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.528	Fsp³:	0.235
MCE-18:	120.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.942	Fluc inhibitor:	0.992 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.213 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.959 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.578	Promiscuous compounds:	0.191

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.369	MDCK Permeability:	-5.045
Pgp-inhibitor:	0.0	Pgp-substrate:	0.017
PAMPA:	0.684 ? 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%):	0.974	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.012
Plasma Protein Binding (PPB):	86.543%	Volume Distribution (VD):	0.055
Fu:	15.171% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.056
BSEP inhibitor:	0.031

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.959
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.582 ? 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):

2.972

Half-life (T1/2):

4.004

ADMET: Toxicity

hERG Blockers:	0.364	hERG Blockers (10um):	0.503
Human Hepatotoxicity (H-HT):	0.981	Drug-induced Liver Injury (DILI):	0.519
AMES Toxicity:	0.862	Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.871	Skin Sensitization:	0.981
Carcinogencity:	0.029	Eye Corrosion:	0.0
Eye Irritation:	0.26	Respiratory Toxicity:	0.037
Drug-induced Neurotoxicity:	0.081	Ototoxicity:	0.944
Hematotoxicity:	0.013	Drug-induced Nephrotoxicity:	0.786
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.215
A549 Cytotoxicity:	0.953	Hek293 Cytotoxicity:	0.988
BCF:	1.313 ? 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:	4.155 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.679 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.099 ? 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
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80Ã‚Â°N and longitude 4Ã‚Â°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-015-0761-z]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s12010-013-0354-4]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.bse.2004.02.008]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1055/S-2006-958077]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1080/01496395.2011.635623]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1186/s40064-015-0831-z]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1501/Tarimbil_0000001065]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11324918]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497936]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	stem bark	Veikabu bridge along the Hiritano highway 40 km from Port Moresby, Papua New Guinea	1998-FEB	PMID[16038553]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros AgrÃƒÂ³nomos de Albacete	2007	PMID[19256538]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19863101]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121250]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[20973551]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	Hainan soft coral	n.a.	PMID[23357636]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25611131]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO7562	Premna odorata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32521614]
NPO16857	Hypericum laricifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36365414]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446586]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38416335]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[464561]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7513747]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561895]
NPO17544	Acacia adunca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17169	Adiantum lunulatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16611	Alstonia spathulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17865	Amathia pinnata	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15552	Anacystis montana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10989	Annona cornifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15803	Artemisia assoana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17702	Astragalus sempervirens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14859	Bishovia boliviensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4325	Blastochloris viridis	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3964	Calostephane divaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6881	Caragana aurantiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8506	Cotyledon secunda	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17472	Drechslera avenae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16089	Dumortiera hirsuta	Species	Dumortieraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12703	Eucalyptus melliodora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13407	Goniothalamus malayanus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15467	Hedysarum connatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15227	Helipterum roseum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16857	Hypericum laricifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10417	Ipomoea digitata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17242	Laurencia spectabilis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16369	Lepisorus ussuriensis	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14395	Lysimachia mauritiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17786	Marrubium anisodon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16493	Nasutitermes ephratae	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18022	Naucleopsis ternstroemiiflora	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17400	Peltostigma guatemalense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16731	Phoebe pittieri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7562	Premna odorata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2507	Rumex maritimus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21724	Sabina sargentii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11538	Salvia syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17633	Viguiera incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17942	Wikstroemia retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Root Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16857	Hypericum laricifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2507	Rumex maritimus	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10417	Ipomoea digitata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12703	Eucalyptus melliodora	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17094	Sinularia depressa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21724	Sabina sargentii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13167	Scutellaria amoena	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15552	Anacystis montana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9516	Gnetum latifolium	Species	Gnetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16857	Hypericum laricifolium	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3964	Calostephane divaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16611	Alstonia spathulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13642	Pastinaca sativa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16089	Dumortiera hirsuta	Species	Dumortieraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16493	Nasutitermes ephratae	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17400	Peltostigma guatemalense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14685	Swertia franchetiana	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17633	Viguiera incana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16369	Lepisorus ussuriensis	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17169	Adiantum lunulatum	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13847	Streptomyces avermectinius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17942	Wikstroemia retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO947	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15227	Helipterum roseum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15803	Artemisia assoana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14395	Lysimachia mauritiana	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15063	Leathesia nana	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4181	Pseudoalteromonas luteoviolacea	Species	Pseudoalteromonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7562	Premna odorata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15659	Zanthoxylum tetraspermum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11917	Asterospicularia laurae	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13407	Goniothalamus malayanus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6160	Vaccinium oxycoccos	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18022	Naucleopsis ternstroemiiflora	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14859	Bishovia boliviensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17242	Laurencia spectabilis	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16731	Phoebe pittieri	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6881	Caragana aurantiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17544	Acacia adunca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11641	Solanum laxum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11538	Salvia syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4325	Blastochloris viridis	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17865	Amathia pinnata	Species	Vesiculariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8506	Cotyledon secunda	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10989	Annona cornifolia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17786	Marrubium anisodon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17702	Astragalus sempervirens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15467	Hedysarum connatum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17472	Drechslera avenae	Species	Pleosporaceae	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	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual protein	Cyclooxygenase-1	Homo sapiens	IC50	=	5200.0	nM	PMID[11170689]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	IC50	=	7500.0	nM	PMID[11170689]

In vitro activity

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

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 NPC59692 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	24312
0.1-0.2	22013
0.2-0.3	2856
0.3-0.4	568
0.4-0.5	78
0.5-0.6	22
0.6-0.7	9
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	Natural Product ID
0.6966	Remote Similarity	NPC478880
0.6966	Remote Similarity	NPC478878
0.6932	Remote Similarity	NPC23431
0.6629	Remote Similarity	NPC233467
0.6556	Remote Similarity	NPC157396
0.6404	Remote Similarity	NPC152346
0.6404	Remote Similarity	NPC197703
0.6234	Remote Similarity	NPC125579
0.6098	Remote Similarity	NPC480677
0.5875	Remote Similarity	NPC85799
0.5875	Remote Similarity	NPC303422
0.5789	Remote Similarity	NPC478877
0.5714	Remote Similarity	NPC480680
0.5696	Remote Similarity	NPC26080
0.5696	Remote Similarity	NPC165686
0.5542	Remote Similarity	NPC242028
0.5542	Remote Similarity	NPC294166
0.5542	Remote Similarity	NPC203230
0.5542	Remote Similarity	NPC115022
0.5349	Remote Similarity	NPC98777
0.5301	Remote Similarity	NPC59324
0.5301	Remote Similarity	NPC218003
0.5294	Remote Similarity	NPC8497
0.5294	Remote Similarity	NPC604095
0.5281	Remote Similarity	NPC112819
0.5281	Remote Similarity	NPC133209
0.5281	Remote Similarity	NPC6702
0.5238	Remote Similarity	NPC480681
0.5192	Remote Similarity	NPC48880
0.5176	Remote Similarity	NPC65530
0.5172	Remote Similarity	NPC212770

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC59692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5908
0.1-0.2	3175
0.2-0.3	63
0.3-0.4	4
0.4-0.5	0
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