NPASS Compound

Natural Product: NPC270213

Natural Product ID	NPC270213
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VKWMVELOQBABEA-NADNLKAXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101503539
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

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 74 77 0 0 0 0 0 0 0 0999 V2000 -2.6671 -0.6682 2.1297 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9247 0.1356 1.0846 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7664 0.0953 -0.1988 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1244 0.6850 0.0219 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9144 0.6492 -1.2315 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3158 1.2516 -1.0449 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2976 2.7372 -1.0318 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9855 0.6684 0.1747 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7743 -0.8029 0.2421 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5015 -1.4287 0.9956 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7611 -1.5402 -0.5292 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3102 -0.7168 -1.7199 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2697 -1.4255 -2.5109 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4462 -0.5501 -2.5092 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0080 0.6684 -2.2559 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7382 -0.5013 0.8020 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3722 0.3509 1.0095 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1635 -0.2281 2.1224 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5373 0.3673 2.2786 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9309 1.1874 1.0953 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3416 0.6529 -0.1858 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0455 -0.6303 -0.6245 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4392 -0.3570 -0.5931 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3910 -1.3012 -0.9338 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9957 -2.4395 -1.2822 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8092 -1.0071 -0.8970 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7320 -1.9677 -1.2418 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0905 -1.6936 -1.2091 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4907 -0.4432 -0.8252 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5924 0.5375 -0.4751 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2417 0.2573 -0.5099 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0205 1.8131 -0.0842 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8501 -0.1080 -0.7731 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0413 -2.6430 -1.5514 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9933 0.5182 -0.1762 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6369 2.5291 1.2477 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4336 -0.7053 2.4850 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4754 0.0388 3.3209 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2869 -1.4653 1.7214 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2334 0.0437 2.7954 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9440 -1.1735 2.8344 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7837 1.1861 1.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8281 -0.9868 -0.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1668 0.6098 -0.9723 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5845 0.1289 0.8652 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0324 1.7295 0.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4074 1.2549 -1.9992 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2759 3.1701 -0.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4623 3.1028 -1.6665 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2339 3.0977 -1.5391 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0856 0.8210 0.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7092 1.1801 1.1141 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2929 -2.4319 -0.9750 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9493 -1.9502 0.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4606 -0.7192 -2.7737 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9211 -2.3848 -2.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7120 -1.7193 -3.5022 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1095 0.6372 -2.1172 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7571 1.3418 -3.1162 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0233 1.3460 1.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1890 -1.3413 2.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6279 1.0098 3.1839 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0430 1.1075 0.9831 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6069 1.4067 -0.9801 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7651 -1.4879 0.0169 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7852 -0.7825 -1.6924 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4023 -2.9645 -1.5476 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5098 0.9855 -0.2469 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3564 2.5452 0.0352 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1864 0.4814 -0.0056 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6948 -2.9266 -0.8082 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5453 2.9981 0.3855 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3245 -1.0705 3.4011 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4041 -0.7650 3.8940 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 1 6 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 1 0 2 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 29 33 1 0 28 34 1 0 21 35 1 0 20 36 1 0 19 37 1 0 18 38 1 0 12 5 1 0 35 17 1 0 15 6 1 0 31 26 1 0 1 39 1 0 1 40 1 0 1 41 1 0 2 42 1 1 3 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 5 47 1 6 7 48 1 0 7 49 1 0 7 50 1 0 8 51 1 0 8 52 1 0 11 53 1 0 11 54 1 0 13 55 1 0 13 56 1 0 13 57 1 0 15 58 1 0 15 59 1 0 17 60 1 1 18 61 1 6 19 62 1 1 20 63 1 6 21 64 1 6 22 65 1 0 22 66 1 0 27 67 1 0 31 68 1 0 32 69 1 0 33 70 1 0 34 71 1 0 36 72 1 0 37 73 1 0 38 74 1 0 M END

Standard InCHIKey	VKWMVELOQBABEA-NADNLKAXSA-N
Standard InCHI	InChI=1S/C26H36O12/c1-12(4-5-18-25(2)8-14(27)9-26(18,3)36-11-25)37-24-22(33)21(32)20(31)17(38-24)10-35-23(34)13-6-15(28)19(30)16(29)7-13/h6-7,12,17-18,20-22,24,28-33H,4-5,8-11H2,1-3H3/t12-,17-,18-,20-,21+,22-,24-,25-,26-/m1/s1
SMILES	C[C@H](CC[C@@H]1[C@]2(C)CC(=O)C[C@@]1(C)OC2)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](COC(=O)c2cc(c(c(c2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	540.22	Volume:	516.327 ? Van der Waals volume.
Dense:	1.046	LogP:	0.903 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.361 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.736 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	23.0
TPSA:	192.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.2	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.724	Fsp³:	0.692
MCE-18:	108.5 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.71	Fluc inhibitor:	0.265 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.059 ? 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:	0.083	Promiscuous compounds:	0.397

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.309	MDCK Permeability:	-5.283
Pgp-inhibitor:	0.009	Pgp-substrate:	0.017
PAMPA:	0.995 ? 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%):	0.705	30% Bioavailability (F30%):	0.693
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.996
Plasma Protein Binding (PPB):	69.929%	Volume Distribution (VD):	-0.485
Fu:	32.224% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.64
BSEP inhibitor:	0.612

ADMET: Metabolism

CYP1A2-inhibitor:	0.007	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.027
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.068
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.961
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.961
HLM stability:	0.409 ? 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):

3.903

Half-life (T1/2):

2.124

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.505
Human Hepatotoxicity (H-HT):	0.164	Drug-induced Liver Injury (DILI):	0.839
AMES Toxicity:	0.937	Rat Oral Acute Toxicity:	0.065
Maximum Recommended Daily Dose:	0.201	Skin Sensitization:	1.0
Carcinogencity:	0.374	Eye Corrosion:	0.0
Eye Irritation:	0.257	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.986
Hematotoxicity:	0.027	Drug-induced Nephrotoxicity:	0.089
Genotoxicity:	0.716	RPMI-8226 Immunitoxicity:	0.023
A549 Cytotoxicity:	0.978	Hek293 Cytotoxicity:	0.319
BCF:	0.522 ? 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:	3.26 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.904 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.122 ? 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
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11087590]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11421757]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975480]
NPO10729	Lechevalieria aerocolonigenes	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15620255]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	Krachong waterfall area, Trang Province, Thailand	2001-APR	PMID[15974621]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15974621]
NPO3453	Elaeocarpus fuscoides	Species	Elaeocarpaceae	Eukaryota	leaves	n.a.	n.a.	PMID[17451272]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18844422]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18844422]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	epidermis of the sclerotia	n.a.	n.a.	PMID[19746919]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27808511]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28972755]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8984162]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO896	Streptomyces kanamyceticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1209	Swartzia madagascariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5344	Calodendrum capense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6330	Croton caudatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3453	Elaeocarpus fuscoides	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15164	Jacobaea adonidifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10729	Lechevalieria aerocolonigenes	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO477	Lepraria xanthina	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8543	Meconopsis horridula	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7087	Oxera splendida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3280	Penicillium crustaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12330	Pseudophryne coriacea	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5508	Stevia purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO305	Vitex pinnata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8543	Meconopsis horridula	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1209	Swartzia madagascariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15164	Jacobaea adonidifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3280	Penicillium crustaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10729	Lechevalieria aerocolonigenes	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19369	Bacillus thuringiensis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO305	Vitex pinnata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8543	Meconopsis horridula	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23577	Wolfiporia cocos	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1209	Swartzia madagascariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5508	Stevia purpurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7087	Oxera splendida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO896	Streptomyces kanamyceticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5344	Calodendrum capense	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6330	Croton caudatus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12330	Pseudophryne coriacea	Species	Myobatrachidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO477	Lepraria xanthina	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11884	Macaranga tanarius	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3453	Elaeocarpus fuscoides	Species	Elaeocarpaceae	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

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

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 NPC270213 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	9968
0.1-0.2	35790
0.2-0.3	3876
0.3-0.4	196
0.4-0.5	25
0.5-0.6	3
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	Natural Product ID
0.5926	Remote Similarity	NPC475058
0.5714	Remote Similarity	NPC476017
0.5616	Remote Similarity	NPC92117

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC270213 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4300
0.1-0.2	4775
0.2-0.3	73
0.3-0.4	2
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