NPASS Compound

Natural Product: NPC112819

Natural Product ID	NPC112819
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Vitisin C
IUPAC Name	5-[(2S,3S)-4-[(E)-2-[(3S)-3-[(3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-4-yl]-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-5-yl]ethenyl]-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuran-3-yl]benzene-1,3-diol
Synonyms	Vitisin C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1082603
PubChem CID	46890015
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 110120 0 0 0 0 0 0 0 0999 V2000 2.5409 -0.6704 -1.2251 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7776 -1.6853 -0.4717 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0012 -2.2673 0.0210 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9576 -3.6742 0.1938 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0224 -4.3894 0.6644 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1922 -3.7333 0.9875 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2917 -2.3736 0.8430 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1748 -1.6530 0.3597 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6121 -0.2710 0.5481 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9623 0.9053 0.1532 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9111 1.3963 0.9485 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2459 2.5461 0.6720 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5815 3.3018 -0.4295 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6027 2.8697 -1.2431 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2731 1.6942 -0.9492 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9576 3.6309 -2.3728 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2049 2.9770 1.5097 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0873 -0.3881 0.1866 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8769 0.7382 0.6500 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5783 1.5315 -0.2326 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3375 2.6120 0.1959 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4200 2.9383 1.5409 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7201 2.1464 2.4240 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9697 1.0755 1.9850 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1877 4.0275 1.9526 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3670 -1.4880 1.0935 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9489 -5.7729 0.8245 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2448 -0.1545 -1.6607 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1845 0.9249 -2.5314 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0022 1.4575 -2.9852 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1987 0.9343 -2.5883 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1729 -0.1559 -1.7086 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0272 -0.6725 -1.2676 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5963 -0.4373 -1.4747 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9911 -1.5875 -0.7149 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3640 -2.8137 -0.7379 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7931 -3.8432 0.0377 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8763 -3.6715 0.8665 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5428 -2.4727 0.9312 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0999 -1.4318 0.1430 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9993 -0.2873 0.4449 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5323 0.6069 1.5024 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1634 1.9167 1.1666 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7009 2.8248 2.0834 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5851 2.4502 3.4098 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9312 1.1836 3.7935 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3938 0.3000 2.8319 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8243 0.7737 5.1351 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 4.1164 1.7038 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2796 -1.0570 0.8390 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1596 -0.1326 1.5510 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8531 -0.5602 2.6614 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6892 0.3098 3.3224 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8564 1.6258 2.8957 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1586 2.0410 1.7844 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3117 1.1550 1.1161 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7146 2.4569 3.6059 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6630 -2.0349 1.6752 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1012 -5.0511 -0.0438 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2511 -0.0586 -2.7427 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9286 -0.7517 -3.9936 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7723 0.0493 -5.1504 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5041 -0.4953 -6.3624 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3652 -1.8615 -6.5544 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5186 -2.6306 -5.4279 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7921 -2.1010 -4.1835 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0909 -2.4236 -7.7952 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5417 1.2553 -2.8751 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3926 -0.1645 -1.6531 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8503 -2.2059 -0.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0507 -4.2302 -0.0511 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0357 -4.3047 1.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6758 -0.2168 1.7362 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6104 0.8321 1.8321 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0188 4.2096 -0.6036 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0532 1.4056 -1.6131 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6349 4.5872 -2.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6313 2.3438 2.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2223 -0.6347 -0.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5527 1.3264 -1.3091 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8945 3.2449 -0.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7648 2.3761 3.4801 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4175 0.4473 2.6820 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1088 3.8924 2.3935 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4054 -6.3836 0.1669 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1096 1.3761 -2.8741 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0110 2.3130 -3.6752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0706 -1.4992 -0.5793 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8673 0.5001 -0.7875 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5233 -2.8989 -1.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1979 -4.5204 1.4818 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2639 0.2492 -0.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2512 2.2320 0.1148 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2133 3.1764 4.1474 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6623 -0.7019 3.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4647 1.2578 5.7840 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9576 4.8093 1.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7025 -1.5036 -0.0787 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7117 -1.5857 2.9764 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2492 -0.0070 4.2093 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2853 3.0601 1.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8065 1.5413 0.2428 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3165 3.0634 3.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6059 -5.4731 0.7238 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3051 0.2482 -2.6763 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8806 1.1389 -5.0030 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3875 0.1390 -7.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4175 -3.7039 -5.5307 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9156 -2.7742 -3.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1019 -2.6821 -7.9351 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 12 17 1 0 9 18 1 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 22 25 1 0 18 26 1 0 5 27 1 0 1 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 46 48 1 0 44 49 1 0 41 50 1 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 54 55 1 0 55 56 2 0 54 57 1 0 50 58 1 0 37 59 1 0 34 60 1 0 60 61 1 0 61 62 2 0 62 63 1 0 63 64 2 0 64 65 1 0 65 66 2 0 64 67 1 0 60 68 1 0 8 3 1 0 15 10 1 0 24 19 1 0 33 28 1 0 40 35 1 0 47 42 1 0 56 51 1 0 66 61 1 0 26 7 1 0 68 31 1 0 58 39 1 0 1 69 1 0 2 70 1 0 4 71 1 0 6 72 1 0 9 73 1 1 11 74 1 0 13 75 1 0 15 76 1 0 16 77 1 0 17 78 1 0 18 79 1 6 20 80 1 0 21 81 1 0 23 82 1 0 24 83 1 0 25 84 1 0 27 85 1 0 29 86 1 0 30 87 1 0 33 88 1 0 34 89 1 1 36 90 1 0 38 91 1 0 41 92 1 6 43 93 1 0 45 94 1 0 47 95 1 0 48 96 1 0 49 97 1 0 50 98 1 0 52 99 1 0 53100 1 0 55101 1 0 56102 1 0 57103 1 0 59104 1 0 60105 1 0 62106 1 0 63107 1 0 65108 1 0 66109 1 0 67110 1 0 M END

Standard InCHIKey	WZKKRZSJTLGPHH-GXHOOJFBSA-N
Standard InCHI	InChI=1S/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/b3-1+/t50-,51-,52+,54+,55?,56?/m0/s1
SMILES	C(=Cc1cc(cc2c1[C@H](c1cc(cc(c1)O)O)[C@@H](c1ccc(cc1)O)O2)O)/c1ccc2c(c1)[C@H](c1cc(cc3c1[C@H](c1cc(cc(c1)O)O)C(c1ccc(cc1)O)O3)O)C(c1ccc(cc1)O)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	906.27	Volume:	922.582 ? Van der Waals volume.
Dense:	0.982	LogP:	6.949 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.135 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.891 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	61.0
TPSA:	209.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	9.0	Rings:	11.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.065	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.071	Fsp³:	0.107
MCE-18:	198.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	0.925 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.188 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.649 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.669	Promiscuous compounds:	0.043

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.089	MDCK Permeability:	-4.716
Pgp-inhibitor:	0.0	Pgp-substrate:	0.071
PAMPA:	0.006 ? 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%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.337
Plasma Protein Binding (PPB):	92.636%	Volume Distribution (VD):	-0.056
Fu:	11.973% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.275
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.683
CYP2C9-inhibitor:	0.89	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.108	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.102 ? 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):

4.946

Half-life (T1/2):

4.348

ADMET: Toxicity

hERG Blockers:	0.969	hERG Blockers (10um):	0.96
Human Hepatotoxicity (H-HT):	0.995	Drug-induced Liver Injury (DILI):	0.007
AMES Toxicity:	0.379	Rat Oral Acute Toxicity:	0.658
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	0.975
Carcinogencity:	0.016	Eye Corrosion:	0.0
Eye Irritation:	0.395	Respiratory Toxicity:	0.546
Drug-induced Neurotoxicity:	0.887	Ototoxicity:	0.94
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.282
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.997	Hek293 Cytotoxicity:	1.0
BCF:	1.285 ? 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:	5.5 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.279 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.143 ? 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]
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]
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]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros AgrÃƒÂ³nomos de Albacete	2007	PMID[19256538]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
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]
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]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37120447]
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]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	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]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	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]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17024	Vitis vinifera	Species	Vitaceae	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
Inhibition	1

Activity Type	# Activity
Others	1

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
NPT2	Others	Unspecified	n.a.	Inhibition	=	32.0	%	PMID[20452207]

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 NPC112819 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	31145
0.1-0.2	16853
0.2-0.3	1736
0.3-0.4	68
0.4-0.5	31
0.5-0.6	7
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133209
1.0	High Similarity	NPC6702
0.8095	Intermediate Similarity	NPC149633
0.7742	Intermediate Similarity	NPC76424
0.7742	Intermediate Similarity	NPC15109
0.7742	Intermediate Similarity	NPC291103
0.7742	Intermediate Similarity	NPC11727
0.7385	Intermediate Similarity	NPC478982
0.7302	Intermediate Similarity	NPC125579
0.7015	Intermediate Similarity	NPC173203
0.7015	Intermediate Similarity	NPC163508
0.6716	Remote Similarity	NPC304894
0.6716	Remote Similarity	NPC15659
0.6582	Remote Similarity	NPC111134
0.6571	Remote Similarity	NPC480680
0.6494	Remote Similarity	NPC157333
0.6212	Remote Similarity	NPC175765
0.6111	Remote Similarity	NPC480677
0.5753	Remote Similarity	NPC478879
0.5753	Remote Similarity	NPC478881
0.5738	Remote Similarity	NPC176804
0.5738	Remote Similarity	NPC71686
0.5556	Remote Similarity	NPC480681
0.5352	Remote Similarity	NPC141717
0.5281	Remote Similarity	NPC59692

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC112819 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6522
0.1-0.2	2597
0.2-0.3	27
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