NPASS Compound

Natural Product: NPC316844

Natural Product ID	NPC316844
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Prostaglandin H2
IUPAC Name	(Z)-7-[(1S,4R,5R,6R)-5-[(E,3S)-3-hydroxyoct-1-enyl]-2,3-dioxabicyclo[2.2.1]heptan-6-yl]hept-5-enoic acid
Synonyms	Prostaglandin H2
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2074582
PubChem CID	445049
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

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 57 58 0 0 0 0 0 0 0 0999 V2000 -6.8039 1.6623 -1.6940 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8218 1.8775 -0.5623 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1905 0.5434 -0.2195 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1946 0.6448 0.8972 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0430 1.5674 0.6433 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2292 1.1532 -0.5554 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7168 -0.2392 -0.2738 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5481 -0.4534 0.3092 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0396 -1.7531 0.6262 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7646 -2.9391 0.2582 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2026 -4.0437 0.9346 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9910 -4.2274 0.4901 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2372 -3.3734 -0.5779 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3890 -1.9777 -0.0712 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5349 -1.8074 0.9024 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7693 -2.0416 0.1434 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7155 -1.1450 0.0128 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7018 0.2164 0.5912 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7950 1.1900 -0.5891 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7849 2.6254 -0.1849 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9276 2.9839 0.6593 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8754 2.2371 0.9887 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0139 4.2947 1.1789 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1977 -3.2603 -1.1377 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8964 1.1887 -1.7498 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8127 2.5063 -2.4106 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6217 0.6802 -2.1997 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8291 1.6205 -1.2302 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 2.6256 -0.9032 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3403 2.2279 0.3701 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7754 0.0528 -1.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0275 -0.0963 0.1794 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7073 0.9108 1.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7759 -0.3991 1.0184 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3713 1.4900 1.5478 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3619 2.6330 0.5826 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2996 1.7957 -0.5869 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3052 -1.1024 -0.5481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0238 0.4357 0.5744 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2569 -1.8159 1.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8213 -2.8872 0.3012 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9468 -3.7142 -1.3023 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4617 -1.2388 -0.8638 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4790 -0.7918 1.2705 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4248 -2.4994 1.7691 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9077 -3.0493 -0.3531 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6119 -1.4504 -0.5955 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6160 0.3929 1.2142 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7964 0.4917 1.1424 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9916 0.9955 -1.3274 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7599 1.0101 -1.1479 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8974 3.2290 -1.1309 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8129 2.8731 0.3025 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4826 4.4093 2.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5539 -4.2160 -1.5158 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2608 -2.4120 -1.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6908 0.3694 -2.2650 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 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 13 24 1 0 6 25 1 0 14 9 1 0 24 10 1 0 1 26 1 0 1 27 1 0 1 28 1 0 2 29 1 0 2 30 1 0 3 31 1 0 3 32 1 0 4 33 1 0 4 34 1 0 5 35 1 0 5 36 1 0 6 37 1 6 7 38 1 0 8 39 1 0 9 40 1 1 10 41 1 6 13 42 1 6 14 43 1 6 15 44 1 0 15 45 1 0 16 46 1 0 17 47 1 0 18 48 1 0 18 49 1 0 19 50 1 0 19 51 1 0 20 52 1 0 20 53 1 0 23 54 1 0 24 55 1 0 24 56 1 0 25 57 1 0 M END

Standard InCHIKey	YIBNHAJFJUQSRA-YNNPMVKQSA-N
Standard InCHI	InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
SMILES	CCCCC[C@@H](/C=C/[C@H]1[C@@H]2OO[C@H]([C@@H]1C/C=CCCCC(=O)O)C2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	352.22	Volume:	373.405 ? Van der Waals volume.
Dense:	0.943	LogP:	3.489 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.189 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.709 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	11.0
TPSA:	75.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	2.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.315	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.022	Fsp³:	0.75
MCE-18:	27.429 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.212	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.002 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.587	Promiscuous compounds:	0.724

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.337	MDCK Permeability:	-5.091
Pgp-inhibitor:	0.0	Pgp-substrate:	0.006
PAMPA:	0.733 ? 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):	0.261
20% Bioavailability (F20%):	0.848	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.209
Plasma Protein Binding (PPB):	96.627%	Volume Distribution (VD):	-0.443
Fu:	3.44% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.731
OATP1B3 inhibitor:	0.94	BCRP inhibitor:	0.014
BSEP inhibitor:	0.533

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.024	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.006
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
HLM stability:	0.013 ? 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):

8.868

Half-life (T1/2):

0.98

ADMET: Toxicity

hERG Blockers:	0.072	hERG Blockers (10um):	0.314
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.241
AMES Toxicity:	0.601	Rat Oral Acute Toxicity:	0.415
Maximum Recommended Daily Dose:	0.283	Skin Sensitization:	1.0
Carcinogencity:	0.175	Eye Corrosion:	0.86
Eye Irritation:	0.95	Respiratory Toxicity:	0.373
Drug-induced Neurotoxicity:	0.066	Ototoxicity:	0.652
Hematotoxicity:	0.23	Drug-induced Nephrotoxicity:	0.309
Genotoxicity:	0.013	RPMI-8226 Immunitoxicity:	0.074
A549 Cytotoxicity:	0.096	Hek293 Cytotoxicity:	0.102
BCF:	0.767 ? 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:	3.546 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.968 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.09 ? 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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
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]
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]
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]
NPO20338	Mus musculus	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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
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.	bile	n.a.	PMID[20708442]
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.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
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]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
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
Ki	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1024	Individual protein	Solute carrier organic anion transporter family member 2A1	Rattus norvegicus	Ki	=	38.2	nM	PMID[8863817]

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 NPC316844 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	21772
0.1-0.2	26472
0.2-0.3	1440
0.3-0.4	124
0.4-0.5	29
0.5-0.6	13
0.6-0.7	4
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
0.6271	Remote Similarity	NPC260814
0.6271	Remote Similarity	NPC323249
0.6271	Remote Similarity	NPC27949
0.6271	Remote Similarity	NPC39547
0.5893	Remote Similarity	NPC327112
0.5806	Remote Similarity	NPC319163
0.5806	Remote Similarity	NPC67076
0.5781	Remote Similarity	NPC321728
0.5714	Remote Similarity	NPC115418
0.5714	Remote Similarity	NPC201225
0.5714	Remote Similarity	NPC600545
0.5606	Remote Similarity	NPC127526
0.5455	Remote Similarity	NPC326828
0.5263	Remote Similarity	NPC255863
0.5263	Remote Similarity	NPC136164
0.5263	Remote Similarity	NPC245947
0.5217	Remote Similarity	NPC485454

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC316844 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5902
0.1-0.2	3093
0.2-0.3	118
0.3-0.4	21
0.4-0.5	10
0.5-0.6	3
0.6-0.7	1
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
0.6271	Remote Similarity	NPD4271	Phase 4
0.5893	Remote Similarity	NPD4246	Phase 2
0.5714	Remote Similarity	NPD4252	Phase 4
0.5692	Remote Similarity	NPD4268	Approved

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