NPASS Compound

Natural Product: NPC209037

Natural Product ID	NPC209037
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PTEYJUIKYIKULL-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	38762
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

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 53 52 0 0 0 0 0 0 0 0999 V2000 6.3222 -0.3473 1.6667 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2759 -0.2297 0.1675 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0076 1.1783 -0.2324 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8193 1.8808 0.2177 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4371 1.4592 -0.1080 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0051 0.1596 0.4364 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5382 -0.1788 0.1088 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2828 -0.2525 -1.3487 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0839 -0.5449 -1.7977 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7709 -1.7979 -1.5067 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0507 -2.2419 -0.1328 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8558 -1.2959 0.7207 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2200 -1.0148 0.1085 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9312 -0.0749 1.0890 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2850 0.2750 0.5935 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3826 0.7943 -0.5481 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4457 0.0645 1.3083 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7457 0.3834 0.8669 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8957 1.8796 0.6219 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3076 -0.2337 2.0768 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7638 -1.3163 2.0105 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9129 0.5034 2.0931 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3403 -0.5054 -0.2195 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6653 -0.9764 -0.3114 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9384 1.7799 0.0520 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0753 1.2446 -1.3772 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9329 3.0100 -0.0473 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9233 1.9828 1.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2819 1.5187 -1.2372 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7397 2.2428 0.3379 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9919 0.2689 1.5653 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6282 -0.6942 0.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9485 0.6489 0.5258 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3425 -1.1532 0.5783 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0494 -0.9147 -1.8609 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5376 0.7734 -1.7668 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0483 -0.4614 -2.9484 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7173 0.3720 -1.5184 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7242 -1.9232 -2.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1264 -2.6343 -1.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7229 -3.1949 -0.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2116 -2.6404 0.4337 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0585 -1.8121 1.6936 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3549 -0.3523 0.9176 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8076 -1.9282 -0.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1198 -0.5238 -0.8852 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2977 0.8225 1.2029 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9465 -0.5923 2.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0565 -0.2089 -0.0247 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4509 0.1175 1.6797 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3515 2.3583 1.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9705 2.1469 0.6389 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4355 2.1791 -0.3207 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 1 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 2 0 15 17 1 0 17 18 1 0 18 19 1 0 1 20 1 0 1 21 1 0 1 22 1 0 2 23 1 0 2 24 1 0 3 25 1 0 3 26 1 0 4 27 1 0 4 28 1 0 5 29 1 0 5 30 1 0 6 31 1 0 6 32 1 0 7 33 1 0 7 34 1 0 8 35 1 0 8 36 1 0 9 37 1 0 9 38 1 0 10 39 1 0 10 40 1 0 11 41 1 0 11 42 1 0 12 43 1 0 12 44 1 0 13 45 1 0 13 46 1 0 14 47 1 0 14 48 1 0 18 49 1 0 18 50 1 0 19 51 1 0 19 52 1 0 19 53 1 0 M END

Standard InCHIKey	PTEYJUIKYIKULL-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C17H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19-4-2/h3-16H2,1-2H3
SMILES	CCCCCCCCCCCCCCC(=O)OCC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	270.26	Volume:	317.532 ? Van der Waals volume.
Dense:	0.851	LogP:	6.889 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.189 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.718 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	1.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.301	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.729	Fsp³:	0.941
MCE-18:	0.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.065	Fluc inhibitor:	0.017 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.997	Promiscuous compounds:	0.185

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.048	MDCK Permeability:	-4.752
Pgp-inhibitor:	0.02	Pgp-substrate:	0.029
PAMPA:	0.001 ? 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):	0.238
20% Bioavailability (F20%):	0.916	30% Bioavailability (F30%):	0.957
50% Bioavailability (F50%):	0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.996
Plasma Protein Binding (PPB):	97.985%	Volume Distribution (VD):	0.641
Fu:	2.01% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.114
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.559
BSEP inhibitor:	0.994

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.077	CYP2C19-substrate:	0.965
CYP2C9-inhibitor:	0.245	CYP2C9-substrate:	0.182
CYP2D6-inhibitor:	0.034	CYP2D6-substrate:	0.739
CYP3A4-inhibitor:	0.007	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.943	CYP2C8-inhibitor:	1.0
HLM stability:	0.816 ? 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):

5.53

Half-life (T1/2):

0.433

ADMET: Toxicity

hERG Blockers:	0.322	hERG Blockers (10um):	0.779
Human Hepatotoxicity (H-HT):	0.282	Drug-induced Liver Injury (DILI):	0.152
AMES Toxicity:	0.057	Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.117	Skin Sensitization:	0.953
Carcinogencity:	0.408	Eye Corrosion:	0.988
Eye Irritation:	0.998	Respiratory Toxicity:	0.797
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.124
Hematotoxicity:	0.141	Drug-induced Nephrotoxicity:	0.144
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.034
A549 Cytotoxicity:	0.123	Hek293 Cytotoxicity:	0.055
BCF:	1.214 ? 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:	4.742 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.922 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.114 ? 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
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(00)97029-8]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Ouled Ziad, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Metlili, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Maarif, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Djemaa Ouled Chikh, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Bougtob, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Boghar, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Tidda, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Mougheul, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Oued Nougued, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Ouled Ziad, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Tidda, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Boghar, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Bougtob, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Djemaa Ouled Chikh, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Maarif, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Metlili, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Mougheul, Algeria		DOI[10.2139/ssrn.4105036]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Oued Nougued, Algeria		DOI[10.2139/ssrn.4105036]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18603435]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[20469887]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25340465]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[25340465]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25577087]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30827604]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Leaves	Beni Mellal, Morocco	Between 2016-Sep and 2016-Oct	PMID[35056798]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Beni Mellal, Morocco	Between 2016-Sep and 2016-Oct	PMID[35056798]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Roots	Beni Mellal, Morocco	Between 2016-Sep and 2016-Oct	PMID[35056798]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	Beni Mellal, Morocco	Between 2016-Sep and 2016-Oct	PMID[35056798]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37331322]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37656744]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38719900]
NPO44662	Helix aspersa	Species	Helicidae	Eukaryota	n.a.	n.a.	n.a.	PMID[39157072]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2345	Coriandrum sativum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31073	Ligusticum chuanxiong	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21707	Trichosanthes kirilowii	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2345	Coriandrum sativum	Species	Apiaceae	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
NPO2345	Coriandrum sativum	Raw	Fruit	0.25	0	0.5	mg/100g	Database [DUKE]
NPO42044	Anredera scandens	n.a.	Seeds	4	n.a.	n.a.	mg/g of DW	PMID[35056798]
NPO44662	Helix aspersa	Chloroform extract	n.a.	01.73	n.a.	n.a.	%	PMID[39157072]

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 NPC209037 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	26429
0.1-0.2	21300
0.2-0.3	1788
0.3-0.4	204
0.4-0.5	75
0.5-0.6	23
0.6-0.7	24
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC250028
1.0	High Similarity	NPC236579
1.0	High Similarity	NPC80234
1.0	High Similarity	NPC203531
1.0	High Similarity	NPC256163
1.0	High Similarity	NPC40597
0.9	High Similarity	NPC53541
0.7692	Intermediate Similarity	NPC128061
0.72	Intermediate Similarity	NPC603612
0.7143	Intermediate Similarity	NPC143211
0.6923	Remote Similarity	NPC149299
0.6923	Remote Similarity	NPC310746
0.6897	Remote Similarity	NPC28779
0.6667	Remote Similarity	NPC26253
0.6538	Remote Similarity	NPC80396
0.6538	Remote Similarity	NPC154642
0.6538	Remote Similarity	NPC600941
0.6522	Remote Similarity	NPC201622
0.6522	Remote Similarity	NPC305660
0.6522	Remote Similarity	NPC12156
0.6522	Remote Similarity	NPC161097
0.6522	Remote Similarity	NPC28598
0.6522	Remote Similarity	NPC22903
0.6522	Remote Similarity	NPC54980
0.6429	Remote Similarity	NPC488257
0.6429	Remote Similarity	NPC469937
0.6429	Remote Similarity	NPC94699
0.6429	Remote Similarity	NPC320588
0.6429	Remote Similarity	NPC53463
0.6207	Remote Similarity	NPC55678
0.6	Remote Similarity	NPC81263
0.6	Remote Similarity	NPC47363
0.6	Remote Similarity	NPC287231
0.6	Remote Similarity	NPC317128
0.5926	Remote Similarity	NPC80641
0.5882	Remote Similarity	NPC143857
0.5882	Remote Similarity	NPC229252
0.5806	Remote Similarity	NPC10316
0.5806	Remote Similarity	NPC200845
0.5806	Remote Similarity	NPC223677
0.5769	Remote Similarity	NPC223249
0.5769	Remote Similarity	NPC476550
0.5714	Remote Similarity	NPC32280
0.5667	Remote Similarity	NPC163345
0.5556	Remote Similarity	NPC154396
0.5556	Remote Similarity	NPC286695
0.5556	Remote Similarity	NPC603863
0.5455	Remote Similarity	NPC277597
0.5333	Remote Similarity	NPC308301
0.5294	Remote Similarity	NPC188686
0.5294	Remote Similarity	NPC104537
0.5217	Remote Similarity	NPC99700
0.5217	Remote Similarity	NPC219536
0.5217	Remote Similarity	NPC31551
0.52	Remote Similarity	NPC326758
0.5185	Remote Similarity	NPC12904
0.5172	Remote Similarity	NPC309606

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC209037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6644
0.1-0.2	2293
0.2-0.3	183
0.3-0.4	17
0.4-0.5	8
0.5-0.6	2
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
0.6207	Remote Similarity	NPD6125	Phase 4
0.6	Remote Similarity	NPD2699	Pre-clinical
0.5455	Remote Similarity	NPD3730	Pre-clinical
0.5161	Remote Similarity	NPD5343	Phase 4

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