NPASS Compound

Natural Product: NPC204188

Natural Product ID	NPC204188
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cerevisterol
IUPAC Name	(3S,5R,6R,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-1,2,3,4,6,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-3,5,6-triol
Synonyms	Cerevisterol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL491546
PubChem CID	10181133
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

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 80 0 0 0 0 0 0 0 0999 V2000 7.6374 1.5501 0.7651 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3217 0.7579 0.6981 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5168 -0.4133 1.6360 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1030 0.3354 -0.7168 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2088 -0.5461 -1.2410 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7681 -0.2240 -1.0002 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9028 -0.5264 -0.0663 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5304 -1.1020 -0.3562 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5175 -2.4403 0.3519 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5602 -0.1266 0.2066 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7925 1.2059 -0.5087 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3887 1.7491 -0.8128 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4310 1.0228 0.1712 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8792 0.9474 -0.1218 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4501 1.5806 -1.1287 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9054 1.5114 -1.4304 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6884 1.1094 -0.1812 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1176 0.9144 -0.5917 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9293 0.1797 0.4378 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1860 0.0034 1.7406 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8538 -0.6371 1.5801 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0657 -0.1236 0.3945 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0980 -1.2179 -0.6408 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6576 0.0952 0.8162 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9703 -1.2405 1.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4926 -1.1446 1.2161 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1202 -0.4092 0.0423 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3048 -1.0286 -1.2389 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3591 -1.0689 0.0113 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6378 2.1974 0.6788 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2038 0.7298 -2.5268 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5046 0.8847 0.8125 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6876 2.3240 -0.0009 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5931 2.0753 1.7598 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5322 1.4524 1.0010 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5979 -0.5315 1.9431 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2582 -1.3890 1.1905 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9227 -0.2379 2.5336 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1735 1.2832 -1.3336 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8785 -0.8841 -2.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1410 0.0449 -1.4183 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3815 -1.4480 -0.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4400 -0.4123 -2.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1070 -0.3827 0.9880 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5072 -1.2293 -1.4433 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7558 -3.1240 -0.0375 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5102 -2.9179 0.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5063 -2.2928 1.4374 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7805 -0.0296 1.2924 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2540 1.9173 0.1979 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3112 1.0910 -1.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3494 2.8415 -0.5999 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1271 1.6183 -1.8643 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2386 1.3867 1.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8367 2.1795 -1.7681 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2104 2.5638 -1.7018 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2337 0.4433 -1.5930 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5491 1.9509 -0.7221 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8509 0.7623 0.6808 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8184 -0.6527 2.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1645 0.9907 2.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2763 -0.4586 2.5304 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0019 -1.7379 1.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2462 -2.2304 -0.1615 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9600 -1.1255 -1.3317 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1955 -1.2437 -1.2807 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5859 0.6363 1.8106 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3747 -1.5854 2.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2963 -2.0300 0.3673 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0859 -2.1410 1.3626 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2652 -0.5366 2.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5403 -1.2379 -1.8870 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0159 -0.4134 -1.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8210 -1.9888 -1.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3367 -1.1083 -0.1393 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1223 2.0462 1.4915 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5114 1.2357 -3.3097 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 4 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 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 6 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 6 19 29 1 0 17 30 1 1 16 31 1 0 27 10 1 0 27 13 1 0 24 14 1 0 22 17 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 0 3 36 1 0 3 37 1 0 3 38 1 0 4 39 1 6 5 40 1 0 5 41 1 0 5 42 1 0 6 43 1 0 7 44 1 0 8 45 1 6 9 46 1 0 9 47 1 0 9 48 1 0 10 49 1 1 11 50 1 0 11 51 1 0 12 52 1 0 12 53 1 0 13 54 1 1 15 55 1 0 16 56 1 6 18 57 1 0 18 58 1 0 19 59 1 1 20 60 1 0 20 61 1 0 21 62 1 0 21 63 1 0 23 64 1 0 23 65 1 0 23 66 1 0 24 67 1 1 25 68 1 0 25 69 1 0 26 70 1 0 26 71 1 0 28 72 1 0 28 73 1 0 28 74 1 0 29 75 1 0 30 76 1 0 31 77 1 0 M END

Standard InCHIKey	ARXHRTZAVQOQEU-BRVLHLJYSA-N
Standard InCHI	InChI=1S/C28H46O3/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-15-25(30)28(31)16-20(29)11-14-27(28,6)24(21)12-13-26(22,23)5/h7-8,15,17-20,22-25,29-31H,9-14,16H2,1-6H3/b8-7+/t18-,19+,20-,22+,23-,24-,25+,26+,27+,28-/m0/s1
SMILES	CC(C)[C@@H](C)/C=C/[C@@H](C)[C@H]1CC[C@H]2C3=C[C@H]([C@]4(C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	430.34	Volume:	479.716 ? Van der Waals volume.
Dense:	0.897	LogP:	4.09 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.753 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.668 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	21.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	4.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.516	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.926	Fsp³:	0.857
MCE-18:	77.308 ? 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:	0.865	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.422	Promiscuous compounds:	0.262

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.466	MDCK Permeability:	-5.055
Pgp-inhibitor:	0.0	Pgp-substrate:	0.043
PAMPA:	0.966 ? 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%):	0.942	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.006
Plasma Protein Binding (PPB):	98.449%	Volume Distribution (VD):	0.07
Fu:	1.209% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.419
BSEP inhibitor:	0.991

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.022
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.376
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.656 ? 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):

9.317

Half-life (T1/2):

1.933

ADMET: Toxicity

hERG Blockers:	0.07	hERG Blockers (10um):	0.314
Human Hepatotoxicity (H-HT):	0.609	Drug-induced Liver Injury (DILI):	0.11
AMES Toxicity:	0.064	Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.787	Skin Sensitization:	0.799
Carcinogencity:	0.702	Eye Corrosion:	0.005
Eye Irritation:	0.841	Respiratory Toxicity:	0.884
Drug-induced Neurotoxicity:	0.015	Ototoxicity:	0.879
Hematotoxicity:	0.26	Drug-induced Nephrotoxicity:	0.766
Genotoxicity:	0.025	RPMI-8226 Immunitoxicity:	0.135
A549 Cytotoxicity:	0.157	Hek293 Cytotoxicity:	0.334
BCF:	2.6 ? 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:	4.552 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.661 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.305 ? 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
NPO64873	Astragalus membranaceus + Fusarium sp. symbiont	Species	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1007/s10600-015-1532-0]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(02)00378-3]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(99)01878-X]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170686]
NPO33440	Xylaria sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921427]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16156520]
NPO32920	homaxinella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[16441084]
NPO33440	Xylaria sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17892262]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17978529]
NPO33440	Xylaria sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18500842]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21043476]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21226484]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21226484]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21275386]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428374]
NPO33440	Xylaria sp.	Species	Xylariaceae	Eukaryota	Isolated from the lichen Leptogium saturninum (Dicks.) Nyl.	Zixi Mountain, Yunnan, China	2006-NOV	PMID[21428374]
NPO30237	Xylaria	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510613]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21563811]
NPO20231	Sarcodon scabrosus	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22401866]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22671987]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23373216]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35872238]
NPO32920	homaxinella sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[9834174]
NPO20231	Sarcodon scabrosus	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO33440	Xylaria sp.	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11051	Nicotiana cavicola	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4483	Ganonema farinosum	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20231	Sarcodon scabrosus	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19426	Diospyros ferrea	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO155	Artemisia lanata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO370	Rhizophora apiculata	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1779	Sargassum kjellmanianum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO370	Rhizophora apiculata	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6631	Elaeagnus glabra	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO155	Artemisia lanata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5288	Stomatanthes corumbensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4483	Ganonema farinosum	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9378	Halocynthia aurantium	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20231	Sarcodon scabrosus	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11051	Nicotiana cavicola	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3499	Macaranga conifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2271	Cassia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28869	Neonectria obtusispora	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8684	Nymphaea ampla	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19426	Diospyros ferrea	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25682	Acorus calamus	Species	Acoraceae	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
ED50	5

Activity Type	# Activity
Cell line	5

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
NPT81	Cell line	A549	Homo sapiens	ED50	=	3.9	ug ml-1	PMID[16441084]
NPT146	Cell line	SK-OV-3	Homo sapiens	ED50	=	6.0	ug ml-1	PMID[16441084]
NPT147	Cell line	SK-MEL-2	Homo sapiens	ED50	=	2.8	ug ml-1	PMID[16441084]
NPT574	Cell line	XF498	Homo sapiens	ED50	=	3.3	ug ml-1	PMID[16441084]
NPT148	Cell line	HCT-15	Homo sapiens	ED50	=	3.0	ug ml-1	PMID[16441084]

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 NPC204188 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	23733
0.1-0.2	23979
0.2-0.3	1961
0.3-0.4	138
0.4-0.5	22
0.5-0.6	17
0.6-0.7	0
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC80561
1.0	High Similarity	NPC329596
0.9	High Similarity	NPC291484
0.8627	High Similarity	NPC488362
0.8269	Intermediate Similarity	NPC11216
0.8269	Intermediate Similarity	NPC3345
0.7593	Intermediate Similarity	NPC470361
0.5833	Remote Similarity	NPC310013
0.5833	Remote Similarity	NPC41554
0.5789	Remote Similarity	NPC307965
0.5789	Remote Similarity	NPC18603
0.5789	Remote Similarity	NPC491013
0.5714	Remote Similarity	NPC127718
0.5692	Remote Similarity	NPC227583
0.5692	Remote Similarity	NPC12103
0.5672	Remote Similarity	NPC472218
0.5517	Remote Similarity	NPC134330
0.5362	Remote Similarity	NPC5475
0.5323	Remote Similarity	NPC97404
0.5231	Remote Similarity	NPC65402
0.5217	Remote Similarity	NPC98457
0.5085	Remote Similarity	NPC299068
0.5082	Remote Similarity	NPC129165
0.5067	Remote Similarity	NPC472217

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC204188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7684
0.1-0.2	1334
0.2-0.3	120
0.3-0.4	7
0.4-0.5	5
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