NPASS Compound

Natural Product: NPC79490

Natural Product ID	NPC79490
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AZRLXPLRYMPSOI-KDRMIRIHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44178932
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 82 86 0 0 0 0 0 0 0 0999 V2000 4.2438 1.2806 -2.9458 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9869 1.9694 -1.6476 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1697 2.9082 -1.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9194 1.0411 -0.4542 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2431 0.3150 -0.3236 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9137 -1.1865 -0.3338 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5197 -1.1362 0.2614 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6671 -0.7148 1.6800 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7359 -2.3935 0.0659 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3356 -2.1576 0.5618 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6602 -0.9529 -0.0475 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2882 -1.2498 -1.4818 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5567 0.2332 -0.0831 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1503 1.4196 0.2875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2348 1.7289 0.7807 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1536 0.6162 0.3076 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5909 0.8579 0.5891 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8833 1.4862 1.9191 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0963 1.8477 -0.4723 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2150 1.3001 -1.2864 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3546 0.7380 -0.4824 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8048 -0.3581 0.3841 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2814 -1.6804 -0.2544 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4115 -0.3584 1.7730 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3280 -0.4234 0.3548 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8153 -1.5013 1.2676 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4350 -1.8581 0.7380 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5430 -0.6449 0.8024 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0929 -0.5467 2.2488 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0495 1.7115 0.2353 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9277 -0.0413 -0.5969 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2998 -3.3793 0.8739 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3779 0.6833 -3.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1764 0.6995 -3.0015 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3631 2.0886 -3.7265 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1138 2.6083 -1.7605 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2611 3.0485 -0.2737 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9933 3.9028 -1.8384 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1220 2.4454 -1.7117 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7793 1.6290 0.4485 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9421 0.4855 -1.1413 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7166 0.5037 0.6616 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6281 -1.7357 0.3132 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8450 -1.5849 -1.3482 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1521 -1.4645 2.3373 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7329 -0.6885 2.0227 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2060 0.2742 1.8242 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7773 -2.6795 -0.9991 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7254 -3.0481 0.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3731 -2.1693 1.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7874 -1.1615 -1.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9124 -0.6609 -2.1985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5478 -2.3084 -1.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8610 2.2375 0.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5415 2.6846 0.3223 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1546 1.8351 1.8579 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0370 0.6322 -0.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8353 2.0725 1.8157 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1161 2.2766 2.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0345 0.8085 2.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2845 2.1350 -1.1824 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4378 2.8018 -0.0217 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9097 0.5231 -2.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6263 2.1365 -1.8878 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1019 0.3601 -1.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4166 -2.4499 0.5461 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5923 -2.0055 -1.0481 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2775 -1.5372 -0.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3571 -0.9794 1.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7453 0.6522 2.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7469 -0.8502 2.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0408 -0.7520 -0.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4830 -2.3941 1.2576 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6724 -1.1380 2.2897 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5485 -2.3114 -0.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9789 -2.6285 1.4018 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7332 0.1529 2.8285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1508 -1.5175 2.7852 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9341 -0.1650 2.3714 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4323 2.3289 -0.4218 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8390 -0.3846 -1.6553 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3344 -4.2623 0.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 1 21 30 1 0 13 31 1 0 9 32 1 0 31 4 1 0 31 7 1 0 28 11 1 0 28 16 1 0 25 17 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 0 3 37 1 0 3 38 1 0 3 39 1 0 4 40 1 1 5 41 1 0 5 42 1 0 6 43 1 0 6 44 1 0 8 45 1 0 8 46 1 0 8 47 1 0 9 48 1 6 10 49 1 0 10 50 1 0 12 51 1 0 12 52 1 0 12 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 6 18 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 20 63 1 0 20 64 1 0 21 65 1 6 23 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 24 70 1 0 24 71 1 0 25 72 1 6 26 73 1 0 26 74 1 0 27 75 1 0 27 76 1 0 29 77 1 0 29 78 1 0 29 79 1 0 30 80 1 0 31 81 1 6 32 82 1 0 M END

Standard InCHIKey	AZRLXPLRYMPSOI-KDRMIRIHSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-18(2)19-11-14-28(6)24(32)17-30(8)20(25(19)28)9-10-22-27(5)15-13-23(31)26(3,4)21(27)12-16-29(22,30)7/h9,18-19,21-25,31-32H,10-17H2,1-8H3/t19-,21-,22+,23-,24-,25+,27-,28+,29+,30+/m0/s1
SMILES	CC(C)[C@@H]1CC[C@]2(C)[C@H](C[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	5.752 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.621 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.321 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	25.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.429	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.802	Fsp³:	0.933
MCE-18:	100.897 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.656	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.04 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.394	Promiscuous compounds:	0.065

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.313	MDCK Permeability:	-4.966
Pgp-inhibitor:	0.655	Pgp-substrate:	0.177
PAMPA:	0.939 ? 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%):	0.73	30% Bioavailability (F30%):	0.342
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.959	MRP1:	0.906
Plasma Protein Binding (PPB):	97.769%	Volume Distribution (VD):	-0.202
Fu:	2.381% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.975	BCRP inhibitor:	0.655
BSEP inhibitor:	0.968

ADMET: Metabolism

CYP1A2-inhibitor:	0.054	CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.745
CYP2C9-inhibitor:	0.019	CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.817	CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.161	CYP3A4-substrate:	0.631
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.848
HLM stability:	0.989 ? 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):

12.762

Half-life (T1/2):

0.534

ADMET: Toxicity

hERG Blockers:	0.058	hERG Blockers (10um):	0.244
Human Hepatotoxicity (H-HT):	0.487	Drug-induced Liver Injury (DILI):	0.279
AMES Toxicity:	0.397	Rat Oral Acute Toxicity:	0.402
Maximum Recommended Daily Dose:	0.653	Skin Sensitization:	0.827
Carcinogencity:	0.921	Eye Corrosion:	0.04
Eye Irritation:	0.556	Respiratory Toxicity:	0.821
Drug-induced Neurotoxicity:	0.077	Ototoxicity:	0.504
Hematotoxicity:	0.36	Drug-induced Nephrotoxicity:	0.695
Genotoxicity:	0.37	RPMI-8226 Immunitoxicity:	0.08
A549 Cytotoxicity:	0.486	Hek293 Cytotoxicity:	0.522
BCF:	2.181 ? 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:	3.968 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.099 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.675 ? 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
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11112781]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	Tanzania	n.a.	PMID[11430019]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[12027753]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12502337]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[153409]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[16557460]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	root	n.a.	PMID[17960072]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17960072]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21673922]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23265519]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23317005]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23488669]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26221771]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27524650]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29115831]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31287310]
NPO783	Pholiota squarrosa	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2642	Maytenus apurimacensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6076	Pentzia calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15601	Pyrus x bretschneideri	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20434	Tolypocladium ophioglossoides	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO783	Pholiota squarrosa	Species	Strophariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8106	Kadsura heteroclita	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15769	Solidago chinensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5923	Bidens cernua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3835	Reticulitermes flavipes	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2642	Maytenus apurimacensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6076	Pentzia calva	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO62	Tetracera asiatica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1019	Citrus hybr	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3588	Crucianella maritima	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1358	Iris pallida	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8278	Perenniporia ochroleuca	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20523	Bacillus subtilis	Species	Bacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO24527	Plazia daphnoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25151	Euphorbia cheiradenia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15601	Pyrus x bretschneideri	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20434	Tolypocladium ophioglossoides	Species	Ophiocordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8408	Symphonia globulifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2309	Achillea micrantha	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6313	Phormidium sp	Species	Oscillatoriaceae	Bacteria	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 NPC79490 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	27588
0.1-0.2	18828
0.2-0.3	2748
0.3-0.4	548
0.4-0.5	100
0.5-0.6	31
0.6-0.7	7
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
0.7963	Intermediate Similarity	NPC132478
0.6724	Remote Similarity	NPC34177
0.6207	Remote Similarity	NPC27765
0.6207	Remote Similarity	NPC122418
0.6207	Remote Similarity	NPC491014
0.6167	Remote Similarity	NPC311078
0.6066	Remote Similarity	NPC253807
0.6066	Remote Similarity	NPC158662
0.5968	Remote Similarity	NPC159168
0.5806	Remote Similarity	NPC40394
0.5758	Remote Similarity	NPC488519
0.5714	Remote Similarity	NPC95594
0.5672	Remote Similarity	NPC18872
0.5672	Remote Similarity	NPC290614
0.5667	Remote Similarity	NPC290598
0.5667	Remote Similarity	NPC120098
0.5667	Remote Similarity	NPC30590
0.5625	Remote Similarity	NPC480950
0.5538	Remote Similarity	NPC40552
0.5455	Remote Similarity	NPC477579
0.5397	Remote Similarity	NPC101475
0.5373	Remote Similarity	NPC610937
0.5362	Remote Similarity	NPC164349
0.5312	Remote Similarity	NPC235341
0.5312	Remote Similarity	NPC291379
0.5303	Remote Similarity	NPC246708
0.5238	Remote Similarity	NPC474989
0.5224	Remote Similarity	NPC477872
0.5143	Remote Similarity	NPC228784
0.5143	Remote Similarity	NPC324341
0.5143	Remote Similarity	NPC601810
0.5072	Remote Similarity	NPC7260
0.5072	Remote Similarity	NPC210037
0.5072	Remote Similarity	NPC120968
0.5072	Remote Similarity	NPC227467
0.5072	Remote Similarity	NPC273621
0.5072	Remote Similarity	NPC195019
0.5072	Remote Similarity	NPC112866
0.5072	Remote Similarity	NPC606443

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC79490 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8177
0.1-0.2	937
0.2-0.3	32
0.3-0.4	3
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