NPASS Compound

Natural Product: NPC330426

Natural Product ID	NPC330426
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-O-(9Z,12Z-Octadecadienoyl)Glycerol
IUPAC Name	2,3-dihydroxypropyl (9Z,12Z)-octadeca-9,12-dienoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL458250
PubChem CID	5283469
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids 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 63 62 0 0 0 0 0 0 0 0999 V2000 -7.3918 2.5201 -1.4023 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0837 1.2566 -1.8257 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1396 0.0884 -1.6713 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7472 0.0123 -0.2051 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7810 -1.1760 -0.0086 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5800 -1.0072 -0.8126 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3809 -0.9341 -0.3129 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1131 -1.0148 1.1334 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4515 0.1832 1.6597 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2859 0.1667 2.2476 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4876 -1.0268 2.4636 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8563 -0.8928 1.7120 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6315 0.2595 2.2123 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9602 0.5396 1.6084 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0752 -0.3936 1.7385 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0128 -1.7701 1.2301 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6993 -1.9445 -0.2155 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6313 -1.3354 -1.1584 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6837 -2.0073 -1.4376 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5112 -0.1196 -1.7855 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4530 0.3850 -2.6795 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8331 0.5681 -2.1245 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9251 1.5903 -1.0236 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4294 2.7972 -1.5161 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6239 1.0783 -3.1813 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4383 2.6240 -0.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9698 3.3947 -1.8113 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3349 2.5842 -1.7042 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4253 1.3657 -2.8787 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9903 1.1283 -1.1917 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2431 0.3280 -2.2787 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6444 -0.8123 -2.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6484 -0.1650 0.4150 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2380 0.9621 0.0413 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7017 -1.4522 1.0254 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3819 -2.0337 -0.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6871 -0.9367 -1.9240 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4783 -0.8058 -0.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9938 -1.2390 1.7688 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4526 -1.8945 1.2617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9713 1.1705 1.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8853 1.1387 2.6260 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9458 -1.9917 2.2375 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1626 -1.0163 3.5616 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3463 -1.8692 1.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5028 -0.6818 0.6437 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9591 1.1640 2.1292 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7302 0.1604 3.3491 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3001 1.5185 2.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7791 0.8596 0.5331 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0752 0.1023 1.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2579 -0.5022 2.8733 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0876 -2.1780 1.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4153 -2.4316 1.8526 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6755 -3.0583 -0.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6702 -1.6081 -0.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5429 -0.2087 -3.6120 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1083 1.4099 -3.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3212 -0.3978 -1.8509 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0196 1.7332 -0.7919 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4680 1.3000 -0.0781 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8696 3.5253 -0.9931 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5800 0.9900 -3.0019 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 2 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 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 22 25 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 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 10 42 1 0 11 43 1 0 11 44 1 0 12 45 1 0 12 46 1 0 13 47 1 0 13 48 1 0 14 49 1 0 14 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 21 57 1 0 21 58 1 0 22 59 1 0 23 60 1 0 23 61 1 0 24 62 1 0 25 63 1 0 M END

Standard InCHIKey	WECGLUPZRHILCT-HZJYTTRNSA-N
Standard InCHI	InChI=1S/C21H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,20,22-23H,2-5,8,11-19H2,1H3/b7-6-,10-9-
SMILES	CCCCC/C=CC/C=CCCCCCCCC(=O)OCC(CO)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	354.28	Volume:	399.024 ? Van der Waals volume.
Dense:	0.888	LogP:	4.959 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.619 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.967 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	18.0	Rigid Bonds:	3.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.226	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.973	Fsp³:	0.762
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:	0.12	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.903	Promiscuous compounds:	0.084

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.073	MDCK Permeability:	-4.856
Pgp-inhibitor:	0.003	Pgp-substrate:	0.005
PAMPA:	0.014 ? 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):	0.006
20% Bioavailability (F20%):	0.613	30% Bioavailability (F30%):	0.604
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	1.0
Plasma Protein Binding (PPB):	97.482%	Volume Distribution (VD):	-0.311
Fu:	2.328% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	0.331	BCRP inhibitor:	0.079
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.976
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.02
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.981	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.57 ? 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):

5.535

Half-life (T1/2):

0.449

ADMET: Toxicity

hERG Blockers:	0.185	hERG Blockers (10um):	0.556
Human Hepatotoxicity (H-HT):	0.086	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.424	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	1.0
Carcinogencity:	0.037	Eye Corrosion:	0.9
Eye Irritation:	0.946	Respiratory Toxicity:	0.073
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.555
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.51
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.029
A549 Cytotoxicity:	0.383	Hek293 Cytotoxicity:	0.091
BCF:	1.513 ? 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:	4.822 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.106 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.518 ? 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
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Tidda, 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	n.a.	Ouled Ziad, 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.	Mougheul, 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	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]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Seeds	Ouled Ziad, Algeria		DOI[10.2139/ssrn.4105036]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087586]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11858758]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19860383]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25747495]
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]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	Leaves	Beni Mellal, Morocco	Between 2016-Sep and 2016-Oct	PMID[35056798]
NPO30971	Cheiranthus cheiri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[39575377]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30971	Cheiranthus cheiri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO42044	Anredera scandens	Genus	Basellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30971	Cheiranthus cheiri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30067.1	Polyalthia longifolia var. pendula	Varieties	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO30971	Cheiranthus cheiri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18781	Hyoscyamus niger	Species	Solanaceae	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
NPO30971	Cheiranthus cheiri	n-hexane extract	n.a.	0.57	n.a.	n.a.	%	PMID[39575377]
NPO42044	Anredera scandens	n.a.	Leaves	30	n.a.	n.a.	mg/g of DW	PMID[35056798]
NPO42044	Anredera scandens	n.a.	Roots	3	n.a.	n.a.	mg/g of DW	PMID[35056798]
NPO42044	Anredera scandens	n.a.	Seeds	35	n.a.	n.a.	mg/g of DW	PMID[35056798]

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
IC50	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
NPT858	Cell line	LNCaP	Homo sapiens	IC50	>	100000.0	nM	DrugMatrix in vitro pharmacology data

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 NPC330426 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	15572
0.1-0.2	30390
0.2-0.3	3268
0.3-0.4	486
0.4-0.5	84
0.5-0.6	21
0.6-0.7	14
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC127091
1.0	High Similarity	NPC22101
0.9167	High Similarity	NPC321919
0.9143	High Similarity	NPC104537
0.8919	High Similarity	NPC271921
0.8158	Intermediate Similarity	NPC475443
0.8158	Intermediate Similarity	NPC473829
0.7692	Intermediate Similarity	NPC476654
0.7692	Intermediate Similarity	NPC476655
0.7692	Intermediate Similarity	NPC476656
0.7429	Intermediate Similarity	NPC488257
0.7429	Intermediate Similarity	NPC469937
0.7429	Intermediate Similarity	NPC94699
0.7429	Intermediate Similarity	NPC320588
0.7429	Intermediate Similarity	NPC53463
0.7368	Intermediate Similarity	NPC277597
0.7297	Intermediate Similarity	NPC28779
0.7073	Intermediate Similarity	NPC209327
0.7045	Intermediate Similarity	NPC473559
0.7045	Intermediate Similarity	NPC324981
0.6905	Remote Similarity	NPC273508
0.6596	Remote Similarity	NPC474321
0.6591	Remote Similarity	NPC473772
0.6512	Remote Similarity	NPC54925
0.6486	Remote Similarity	NPC128061
0.641	Remote Similarity	NPC10316
0.641	Remote Similarity	NPC200845
0.6364	Remote Similarity	NPC48218
0.6364	Remote Similarity	NPC141481
0.6364	Remote Similarity	NPC464342
0.6316	Remote Similarity	NPC39633
0.6226	Remote Similarity	NPC489083
0.6	Remote Similarity	NPC223677
0.6	Remote Similarity	NPC609455
0.5814	Remote Similarity	NPC81896
0.5789	Remote Similarity	NPC21693
0.5714	Remote Similarity	NPC148192
0.5581	Remote Similarity	NPC485026
0.5526	Remote Similarity	NPC309606
0.55	Remote Similarity	NPC139545
0.5385	Remote Similarity	NPC26253
0.5333	Remote Similarity	NPC39290
0.5319	Remote Similarity	NPC42526
0.5263	Remote Similarity	NPC488689
0.5254	Remote Similarity	NPC236649
0.5185	Remote Similarity	NPC178758
0.5185	Remote Similarity	NPC192326
0.5185	Remote Similarity	NPC322769
0.5156	Remote Similarity	NPC470313
0.5156	Remote Similarity	NPC473500
0.5156	Remote Similarity	NPC611497
0.5122	Remote Similarity	NPC71761
0.5111	Remote Similarity	NPC476660
0.5088	Remote Similarity	NPC317263
0.5082	Remote Similarity	NPC110813

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC330426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6030
0.1-0.2	2920
0.2-0.3	161
0.3-0.4	31
0.4-0.5	4
0.5-0.6	3
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
0.5778	Remote Similarity	NPD3728	Approved
0.55	Remote Similarity	NPD5343	Phase 4
0.5238	Remote Similarity	NPD6096	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