NPASS Compound

Natural Product: NPC252617

Natural Product ID	NPC252617
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LMQGCNAOWXUOEU-RKJZCXAYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	13918509
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 5.5329 2.0617 0.6928 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3375 0.5809 0.4210 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0933 -0.1590 1.5151 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8787 0.2181 0.4913 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3793 -0.2999 1.5918 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9776 -0.6934 1.7864 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0999 -0.1002 0.7128 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6741 -0.1929 -0.6484 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7661 -1.5365 -1.2622 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7542 0.6231 -1.5719 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6656 0.1218 -1.5518 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2243 0.2013 -0.1440 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3222 1.6917 0.1403 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6216 -0.3414 -0.1025 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5098 0.5539 -0.9773 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9469 0.0373 -1.0170 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0936 -1.1557 -1.9089 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4894 -0.2030 0.3582 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4692 0.2993 1.3401 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1805 -0.5405 1.2631 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7246 -1.9688 1.4719 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3229 -0.1357 2.3923 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8762 0.0243 2.1943 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3385 -0.4951 0.8532 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4496 -1.9644 0.8871 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7716 1.1947 -1.6021 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6396 2.3070 -0.7665 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0226 0.4613 -0.6856 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8113 0.0477 -1.9233 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0829 0.9104 -1.9513 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9756 0.2569 -0.8844 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9177 -1.1352 -1.0592 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7920 2.2546 1.7554 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6383 2.6364 0.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3796 2.4692 0.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1675 -0.1317 1.2485 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7961 -1.2158 1.5947 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9775 0.3884 2.4905 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0654 -0.4477 2.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8703 -1.7759 1.9350 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6966 -0.2731 2.8068 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1381 1.0090 0.9631 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4041 -2.2623 -0.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2461 -1.3851 -2.2788 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7736 -1.9625 -1.5884 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1347 0.6217 -2.6110 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7514 1.6791 -1.2363 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8415 -0.8231 -2.0539 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2198 0.8979 -2.1651 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6503 2.1992 -0.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3815 2.1798 0.3828 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0410 1.9555 0.9068 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6474 -1.3287 -0.6320 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1711 0.4387 -2.0357 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5685 1.5776 -0.6217 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2269 -2.1129 -1.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0301 -1.0201 -2.5124 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2702 -1.2061 -2.6485 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4307 0.3654 0.5693 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7400 -1.2558 0.4471 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8784 0.1015 2.3747 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3248 1.3583 1.2579 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0513 -2.5314 2.1876 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6904 -1.9750 2.0264 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8048 -2.4760 0.5088 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4745 -0.8947 3.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6988 0.8083 2.8966 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5380 1.0750 2.3066 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2802 -0.5512 2.9645 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5077 -2.5328 0.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6969 -2.3605 1.9205 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1729 -2.4323 0.2094 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8458 0.9232 -1.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3982 1.4226 -2.5992 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9064 3.1250 -1.2518 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9280 1.5789 -0.7628 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1797 -0.9968 -1.8729 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2273 0.2774 -2.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8596 1.9491 -1.6995 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5831 0.7667 -2.9166 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9887 0.6439 -0.9135 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2174 -1.4212 -1.9373 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 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 6 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 1 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 6 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 16 26 1 0 26 27 1 0 8 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 2 1 0 28 4 1 0 24 7 1 0 24 12 1 0 20 14 1 0 1 33 1 0 1 34 1 0 1 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 5 39 1 0 6 40 1 0 6 41 1 0 7 42 1 1 9 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 13 50 1 0 13 51 1 0 13 52 1 0 14 53 1 6 15 54 1 0 15 55 1 0 17 56 1 0 17 57 1 0 17 58 1 0 18 59 1 0 18 60 1 0 19 61 1 0 19 62 1 0 21 63 1 0 21 64 1 0 21 65 1 0 22 66 1 0 22 67 1 0 23 68 1 0 23 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 27 75 1 0 28 76 1 6 29 77 1 0 29 78 1 0 30 79 1 0 30 80 1 0 31 81 1 1 32 82 1 0 M END

Standard InCHIKey	LMQGCNAOWXUOEU-RKJZCXAYSA-N
Standard InCHI	InChI=1S/C30H50O2/c1-25(2)20-8-10-22-28(5,21(20)9-11-24(25)32)15-17-30(7)23-18-26(3,19-31)12-13-27(23,4)14-16-29(22,30)6/h8,21-24,31-32H,9-19H2,1-7H3/t21-,22+,23-,24+,26-,27-,28+,29-,30+/m1/s1
SMILES	CC1(C)C2=CC[C@H]3[C@@](C)(CC[C@@]4(C)[C@@H]5C[C@@](C)(CC[C@]5(C)CC[C@]34C)CO)[C@@H]2CC[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.38	Volume:	499.598 ? Van der Waals volume.
Dense:	0.885	LogP:	4.5 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.158 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.248 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	26.0
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:	0.424	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.938	Fsp³:	0.933
MCE-18:	102.207 ? 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:	0.773	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.576	Promiscuous compounds:	0.141

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.792	MDCK Permeability:	-4.686
Pgp-inhibitor:	0.926	Pgp-substrate:	0.044
PAMPA:	0.946 ? 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):	0.001
20% Bioavailability (F20%):	0.993	30% Bioavailability (F30%):	0.745
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973	MRP1:	0.918
Plasma Protein Binding (PPB):	89.922%	Volume Distribution (VD):	-0.029
Fu:	10.045% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.95	BCRP inhibitor:	0.912
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.064
CYP2C19-inhibitor:	0.891	CYP2C19-substrate:	0.121
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.022	CYP2D6-substrate:	0.433
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.964
HLM stability:	0.892 ? 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):

11.114

Half-life (T1/2):

0.371

ADMET: Toxicity

hERG Blockers:	0.134	hERG Blockers (10um):	0.274
Human Hepatotoxicity (H-HT):	0.695	Drug-induced Liver Injury (DILI):	0.225
AMES Toxicity:	0.423	Rat Oral Acute Toxicity:	0.579
Maximum Recommended Daily Dose:	0.607	Skin Sensitization:	0.985
Carcinogencity:	0.915	Eye Corrosion:	0.002
Eye Irritation:	0.313	Respiratory Toxicity:	0.884
Drug-induced Neurotoxicity:	0.306	Ototoxicity:	0.549
Hematotoxicity:	0.526	Drug-induced Nephrotoxicity:	0.771
Genotoxicity:	0.836	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.706	Hek293 Cytotoxicity:	0.62
BCF:	2.439 ? 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:	4.272 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.441 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.03 ? 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 NPC252617 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	27688
0.1-0.2	18981
0.2-0.3	2844
0.3-0.4	320
0.4-0.5	22
0.5-0.6	1
0.6-0.7	2
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC106364
0.6731	Remote Similarity	NPC602278
0.6034	Remote Similarity	NPC300324
0.5455	Remote Similarity	NPC146554

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC252617 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8105
0.1-0.2	1024
0.2-0.3	19
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