NPASS Compound

Natural Product: NPC323785

Natural Product ID	NPC323785
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	JSFATNQSLKRBCI-USWFWKISSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	9966861
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000046] Hydroxyeicosatetraenoic acids

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 54 0 0 0 0 0 0 0 0999 V2000 -7.6446 -0.2280 0.0393 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1210 -1.5738 -0.3587 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6887 -1.4335 -0.8669 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7899 -0.8662 0.1887 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3674 -0.7114 -0.2594 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2726 0.2264 -1.4642 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7718 1.5688 -1.1943 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1337 2.5072 -0.5692 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8016 2.3333 -0.0438 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2253 3.3533 0.5838 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1303 3.2105 1.1313 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6218 1.8353 0.8529 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7184 1.6950 0.1203 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2250 0.3318 -0.1687 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6021 0.2479 0.3957 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6700 -0.0029 -0.3264 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9978 -0.0673 0.3203 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5558 -1.4521 0.0769 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9153 -1.6422 0.6921 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3781 -3.0082 0.4073 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6672 -3.7890 -0.2486 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6060 -3.4244 0.8701 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9832 0.2934 -1.9777 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1236 0.6104 -0.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7251 -0.1614 -0.2672 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6159 -0.1729 1.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7567 -2.0254 -1.1335 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1176 -2.2877 0.5087 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 -0.7238 -1.7418 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3252 -2.3998 -1.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2268 0.0714 0.5633 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7972 -1.5899 1.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7881 -0.2515 0.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9097 -1.6815 -0.4660 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8652 -0.2748 -2.2926 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7882 1.8119 -1.5548 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5785 3.5015 -0.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2888 1.3910 -0.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7543 4.2819 0.6890 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8062 3.9780 0.7073 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0805 3.3578 2.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0861 0.9616 1.2516 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2486 2.5537 -0.2693 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2575 0.1270 -1.2613 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5891 -0.3950 0.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7085 0.4049 1.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5933 -0.1625 -1.3829 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9168 0.0809 1.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6937 0.7242 -0.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8326 -2.1698 0.4918 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5709 -1.6123 -1.0199 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8265 -1.5035 1.8095 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6406 -0.8755 0.3706 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8906 -4.3998 0.9053 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6054 -0.5729 -2.2215 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 3 8 9 1 0 9 10 2 3 10 11 1 0 11 12 1 0 12 13 2 3 13 14 1 0 14 15 1 0 15 16 2 3 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 6 23 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 9 38 1 0 10 39 1 0 11 40 1 0 11 41 1 0 12 42 1 0 13 43 1 0 14 44 1 0 14 45 1 0 15 46 1 0 16 47 1 0 17 48 1 0 17 49 1 0 18 50 1 0 18 51 1 0 19 52 1 0 19 53 1 0 22 54 1 0 23 55 1 0 M END

Standard InCHIKey	JSFATNQSLKRBCI-USWFWKISSA-N
Standard InCHI	InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+
SMILES	CCCCCC(C=CC=CCC=CCC=CCCCC(=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	320.24	Volume:	367.665 ? Van der Waals volume.
Dense:	0.871	LogP:	5.143 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.993 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.854 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	5.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.263	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.329	Fsp³:	0.55
MCE-18:	2.0 ? 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:	0.092	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.138 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.956	Promiscuous compounds:	0.242

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.138	MDCK Permeability:	-4.889
Pgp-inhibitor:	0.0	Pgp-substrate:	0.015
PAMPA:	0.855 ? 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):	0.204
20% Bioavailability (F20%):	0.217	30% Bioavailability (F30%):	0.944
50% Bioavailability (F50%):	0.423

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.281	MRP1:	0.858
Plasma Protein Binding (PPB):	93.619%	Volume Distribution (VD):	-0.613
Fu:	5.432% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.021
OATP1B3 inhibitor:	0.227	BCRP inhibitor:	0.026
BSEP inhibitor:	0.1

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.304	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.459	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.364
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	0.977
HLM stability:	0.011 ? 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):

7.036

Half-life (T1/2):

0.466

ADMET: Toxicity

hERG Blockers:	0.082	hERG Blockers (10um):	0.193
Human Hepatotoxicity (H-HT):	0.299	Drug-induced Liver Injury (DILI):	0.002
AMES Toxicity:	0.581	Rat Oral Acute Toxicity:	0.105
Maximum Recommended Daily Dose:	0.641	Skin Sensitization:	0.999
Carcinogencity:	0.229	Eye Corrosion:	0.02
Eye Irritation:	0.809	Respiratory Toxicity:	0.955
Drug-induced Neurotoxicity:	0.025	Ototoxicity:	0.902
Hematotoxicity:	0.029	Drug-induced Nephrotoxicity:	0.187
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.026
A549 Cytotoxicity:	0.01	Hek293 Cytotoxicity:	0.062
BCF:	0.835 ? 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:	3.572 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.877 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.917 ? 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

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 NPC323785 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	28979
0.1-0.2	19237
0.2-0.3	1358
0.3-0.4	155
0.4-0.5	53
0.5-0.6	53
0.6-0.7	11
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC327112
0.8372	Intermediate Similarity	NPC323045
0.8372	Intermediate Similarity	NPC317881
0.8	Intermediate Similarity	NPC605544
0.8	Intermediate Similarity	NPC607260
0.7273	Intermediate Similarity	NPC255863
0.7273	Intermediate Similarity	NPC136164
0.7273	Intermediate Similarity	NPC245947
0.6739	Remote Similarity	NPC321838
0.6458	Remote Similarity	NPC49863
0.6383	Remote Similarity	NPC325627
0.6341	Remote Similarity	NPC91495
0.619	Remote Similarity	NPC59051
0.6122	Remote Similarity	NPC328311
0.6038	Remote Similarity	NPC260814
0.6038	Remote Similarity	NPC323249
0.6038	Remote Similarity	NPC27949
0.6038	Remote Similarity	NPC39547
0.6	Remote Similarity	NPC322002
0.5952	Remote Similarity	NPC321062
0.5918	Remote Similarity	NPC325977
0.5893	Remote Similarity	NPC316844
0.5833	Remote Similarity	NPC99619
0.5814	Remote Similarity	NPC154245
0.5814	Remote Similarity	NPC85813
0.5814	Remote Similarity	NPC223697
0.5814	Remote Similarity	NPC6095
0.5769	Remote Similarity	NPC329249
0.5714	Remote Similarity	NPC323477
0.5686	Remote Similarity	NPC322461
0.5652	Remote Similarity	NPC323436
0.5625	Remote Similarity	NPC324475
0.561	Remote Similarity	NPC117572
0.56	Remote Similarity	NPC320642
0.56	Remote Similarity	NPC470320
0.5581	Remote Similarity	NPC5413
0.5536	Remote Similarity	NPC319163
0.5536	Remote Similarity	NPC67076
0.551	Remote Similarity	NPC243532
0.5439	Remote Similarity	NPC115418
0.5439	Remote Similarity	NPC236208
0.5439	Remote Similarity	NPC201225
0.5439	Remote Similarity	NPC600545
0.5319	Remote Similarity	NPC606120
0.5294	Remote Similarity	NPC329550
0.5283	Remote Similarity	NPC328653
0.5254	Remote Similarity	NPC321728
0.5246	Remote Similarity	NPC319021
0.5227	Remote Similarity	NPC324004
0.5227	Remote Similarity	NPC328497
0.5227	Remote Similarity	NPC70387
0.52	Remote Similarity	NPC323597
0.52	Remote Similarity	NPC211752
0.52	Remote Similarity	NPC323498
0.5192	Remote Similarity	NPC26500
0.5167	Remote Similarity	NPC326828
0.5116	Remote Similarity	NPC424
0.5116	Remote Similarity	NPC36061
0.5116	Remote Similarity	NPC69510
0.5116	Remote Similarity	NPC77272
0.5116	Remote Similarity	NPC290563
0.5116	Remote Similarity	NPC139029
0.5116	Remote Similarity	NPC281972
0.5116	Remote Similarity	NPC261831
0.5116	Remote Similarity	NPC87564
0.5111	Remote Similarity	NPC52955
0.5111	Remote Similarity	NPC88966
0.5111	Remote Similarity	NPC25417
0.5111	Remote Similarity	NPC1813
0.5111	Remote Similarity	NPC472808
0.5098	Remote Similarity	NPC320305
0.5082	Remote Similarity	NPC127526

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC323785 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6530
0.1-0.2	2410
0.2-0.3	162
0.3-0.4	22
0.4-0.5	13
0.5-0.6	9
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	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD4246	Phase 2
0.6458	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6038	Remote Similarity	NPD4271	Phase 4
0.5814	Remote Similarity	NPD4266	Phase 2
0.561	Remote Similarity	NPD4222	Phase 3
0.5581	Remote Similarity	NPD3173	Phase 4
0.5439	Remote Similarity	NPD4252	Phase 4
0.5424	Remote Similarity	NPD4268	Approved
0.54	Remote Similarity	NPD39	Phase 4
0.5116	Remote Similarity	NPD3195	Phase 2
0.5116	Remote Similarity	NPD3196	Approved
0.5111	Remote Similarity	NPD3172	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