NPASS Compound

Natural Product: NPC211752

Natural Product ID	NPC211752
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(5Z,8Z)-10-[(2R,3S)-((Z)-3-Oct-2-Enyl)-Oxiranyl]-Deca-5,8-Dienoic Acid
IUPAC Name	(5Z,8Z)-10-[(2R,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL132343
PubChem CID	6440793
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0001020] Hepoxilins

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 55 55 0 0 0 0 0 0 0 0999 V2000 8.8495 0.1913 -0.4039 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9297 1.2517 -0.9758 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7656 1.3927 0.0088 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1052 0.0454 0.0836 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9218 0.0511 1.0385 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8859 1.0042 0.6432 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6393 0.6701 0.3475 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1754 -0.7375 0.3917 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0713 -0.9455 1.3719 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2141 -0.3243 1.3420 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9781 0.2724 0.2007 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2833 -0.6947 -0.8666 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4999 -0.9925 -1.2094 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6921 -0.4180 -0.5895 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4810 -1.5728 -0.0133 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7014 -1.8712 -0.3643 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4843 -1.1379 -1.3603 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7470 -0.6031 -0.7060 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5068 0.3351 0.4206 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7794 1.5633 0.0331 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4365 1.8181 -1.1410 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4530 2.4983 1.0324 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0372 -1.7090 1.1550 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7152 0.0447 0.6715 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7151 -0.7905 -0.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8965 0.5818 -0.5395 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4248 2.2237 -1.1089 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4567 0.8750 -1.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0284 2.1355 -0.3739 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1363 1.6617 1.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8012 -0.2726 -0.9387 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8215 -0.7113 0.4705 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6394 -0.9640 1.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3581 0.4613 2.0114 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1137 2.0960 0.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9409 1.4856 0.0592 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9709 -1.4828 0.4584 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7278 -0.9306 -0.6441 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5029 -1.1386 2.4082 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6548 -0.0152 2.3378 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8420 0.8552 0.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3147 1.0686 -0.3042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4629 -1.2007 -1.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6592 -1.7308 -2.0255 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3062 0.1531 -1.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5551 0.2572 0.2528 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0182 -2.2102 0.7467 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2172 -2.7348 0.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8674 -1.9107 -2.0951 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0076 -0.3760 -1.9476 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3037 -0.0641 -1.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3160 -1.4632 -0.3389 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9567 -0.1156 1.2720 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4910 0.6464 0.8437 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3264 3.4786 0.8186 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 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 10 23 1 0 23 9 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 0 5 34 1 0 6 35 1 0 7 36 1 0 8 37 1 0 8 38 1 0 9 39 1 1 10 40 1 1 11 41 1 0 11 42 1 0 12 43 1 0 13 44 1 0 14 45 1 0 14 46 1 0 15 47 1 0 16 48 1 0 17 49 1 0 17 50 1 0 18 51 1 0 18 52 1 0 19 53 1 0 19 54 1 0 22 55 1 0 M END

Standard InCHIKey	DXOYQVHGIODESM-MFYAFOOZSA-N
Standard InCHI	InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6-,12-9-,13-10-/t18-,19+/m0/s1
SMILES	CCCCC/C=CC[C@H]1[C@@H](C/C=CC/C=CCCCC(=O)O)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	320.24	Volume:	361.745 ? Van der Waals volume.
Dense:	0.885	LogP:	5.726 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.553 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.033 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	7.0
TPSA:	49.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.264	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.574	Fsp³:	0.65
MCE-18:	12.727 ? 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:	0.059	Fluc inhibitor:	0.141 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.951	Promiscuous compounds:	0.305

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.164	MDCK Permeability:	-4.938
Pgp-inhibitor:	0.106	Pgp-substrate:	0.0
PAMPA:	0.007 ? 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%):	0.112	30% Bioavailability (F30%):	0.18
50% Bioavailability (F50%):	0.66

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015	MRP1:	1.0
Plasma Protein Binding (PPB):	98.151%	Volume Distribution (VD):	-0.714
Fu:	1.195% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.005
OATP1B3 inhibitor:	0.191	BCRP inhibitor:	0.045
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.738	CYP2C19-substrate:	0.092
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.024	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.995
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.002 ? 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):

6.321

Half-life (T1/2):

0.331

ADMET: Toxicity

hERG Blockers:	0.051	hERG Blockers (10um):	0.173
Human Hepatotoxicity (H-HT):	0.186	Drug-induced Liver Injury (DILI):	0.001
AMES Toxicity:	0.614	Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.035	Skin Sensitization:	1.0
Carcinogencity:	0.019	Eye Corrosion:	0.996
Eye Irritation:	0.996	Respiratory Toxicity:	0.564
Drug-induced Neurotoxicity:	0.019	Ototoxicity:	0.327
Hematotoxicity:	0.066	Drug-induced Nephrotoxicity:	0.598
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.067
A549 Cytotoxicity:	0.686	Hek293 Cytotoxicity:	0.149
BCF:	1.293 ? 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:	4.022 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.267 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.612 ? 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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10388717]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10820136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO31575	Cavia porcellus	Species	Caviidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11060896]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11695850]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1282214]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15102880]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15123652]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[15239850]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15466478]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16538977]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17499416]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18039809]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1814736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1928373]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19572262]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19662622]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20951405]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2188748]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23384552]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23723388]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24085302]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24096206]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24343604]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24503197]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24814225]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070706]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25727742]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26041992]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26485038]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26608498]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26654758]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26676627]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466123]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3025936]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4002232]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[518564]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6273168]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6572072]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6806263]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6825837]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6833497]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7311739]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7645303]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8069858]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8452569]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9179722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9435160]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9606952]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9629662]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9660093]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9694933]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20338	Mus musculus	Species	Muridae	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
Cell line	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
NPT5216	Cell line	HSVEC	Homo sapiens	Inhibition	=	35.0	%	PMID[14592496]

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 NPC211752 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	34843
0.1-0.2	13741
0.2-0.3	994
0.3-0.4	165
0.4-0.5	63
0.5-0.6	35
0.6-0.7	8
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC323597
1.0	High Similarity	NPC323498
0.875	High Similarity	NPC320305
0.875	High Similarity	NPC317583
0.7949	Intermediate Similarity	NPC327388
0.7568	Intermediate Similarity	NPC91495
0.7442	Intermediate Similarity	NPC68343
0.7442	Intermediate Similarity	NPC328089
0.7368	Intermediate Similarity	NPC59051
0.6667	Remote Similarity	NPC321062
0.6667	Remote Similarity	NPC5413
0.65	Remote Similarity	NPC154245
0.65	Remote Similarity	NPC85813
0.65	Remote Similarity	NPC223697
0.65	Remote Similarity	NPC6095
0.6327	Remote Similarity	NPC329249
0.6	Remote Similarity	NPC92558
0.5897	Remote Similarity	NPC117572
0.5854	Remote Similarity	NPC70387
0.575	Remote Similarity	NPC424
0.575	Remote Similarity	NPC36061
0.575	Remote Similarity	NPC69510
0.575	Remote Similarity	NPC77272
0.575	Remote Similarity	NPC290563
0.575	Remote Similarity	NPC139029
0.575	Remote Similarity	NPC281972
0.575	Remote Similarity	NPC92114
0.575	Remote Similarity	NPC261831
0.575	Remote Similarity	NPC87564
0.5714	Remote Similarity	NPC52955
0.5714	Remote Similarity	NPC88966
0.5714	Remote Similarity	NPC25417
0.5714	Remote Similarity	NPC1813
0.561	Remote Similarity	NPC149821
0.561	Remote Similarity	NPC207292
0.56	Remote Similarity	NPC322461
0.551	Remote Similarity	NPC320642
0.55	Remote Similarity	NPC281245
0.549	Remote Similarity	NPC605544
0.549	Remote Similarity	NPC607260
0.54	Remote Similarity	NPC328311
0.5306	Remote Similarity	NPC321838
0.5238	Remote Similarity	NPC95145
0.5238	Remote Similarity	NPC325642
0.5238	Remote Similarity	NPC65174
0.52	Remote Similarity	NPC325977
0.52	Remote Similarity	NPC327112
0.52	Remote Similarity	NPC329550
0.5116	Remote Similarity	NPC48162
0.5116	Remote Similarity	NPC602547
0.5098	Remote Similarity	NPC323045
0.5098	Remote Similarity	NPC317881

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC211752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6744
0.1-0.2	2235
0.2-0.3	126
0.3-0.4	29
0.4-0.5	8
0.5-0.6	6
0.6-0.7	2
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
0.6667	Remote Similarity	NPD3173	Phase 4
0.65	Remote Similarity	NPD4266	Phase 2
0.5957	Remote Similarity	NPD39	Phase 4
0.5897	Remote Similarity	NPD4222	Phase 3
0.575	Remote Similarity	NPD3195	Phase 2
0.575	Remote Similarity	NPD3196	Approved
0.5714	Remote Similarity	NPD3172	Approved
0.52	Remote Similarity	NPD4246	Phase 2

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