NPASS Compound

Natural Product: NPC525407

Natural Product ID	NPC525407
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Docosyl acetate
IUPAC Name	docosyl acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic 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 74 73 0 0 0 0 0 0 0 0999 V2000 5.5626 -0.3697 -3.3769 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3014 0.7054 -2.5971 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6479 0.1927 -2.2000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6041 -1.0436 -1.3310 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8333 -0.6706 -0.0589 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7367 -1.8330 0.8711 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0194 -1.5351 2.1465 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5879 -1.1072 1.8231 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8202 -0.8221 3.0641 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4707 -0.3379 2.8868 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3605 -1.0423 2.2470 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3731 -1.4441 0.8465 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -2.1056 0.3593 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1471 -1.4352 0.2125 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8604 -0.7623 1.3064 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2612 -0.2724 0.8543 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2037 0.6979 -0.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6490 1.0979 -0.6148 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3466 1.7361 0.5284 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7589 2.1022 0.1711 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7978 3.0715 -0.9770 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2755 3.3866 -1.2285 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9336 2.1833 -1.5388 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6801 1.3586 -2.5958 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4172 0.0932 -2.8614 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7737 1.6637 -3.4093 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1222 0.0381 -4.2967 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2273 -1.1953 -3.6402 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7589 -0.7383 -2.7034 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7068 1.1526 -1.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4961 1.5580 -3.3126 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1824 1.0220 -1.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1997 -0.0401 -3.1465 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6493 -1.2967 -1.0676 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1482 -1.8863 -1.8590 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8643 -0.2714 -0.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4243 0.1257 0.4243 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7647 -2.2550 1.0982 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2307 -2.7079 0.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5675 -0.7402 2.6761 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0105 -2.4187 2.8114 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6460 -0.2461 1.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1968 -1.9696 1.2500 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9341 -1.6471 3.8249 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4136 0.0161 3.5755 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5406 0.7276 2.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0579 -0.0255 3.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1443 -2.0024 2.8766 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4462 -0.4500 2.4727 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1944 -2.1403 0.5495 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5257 -0.5520 0.1703 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3579 -2.5748 -0.6775 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0619 -3.0655 0.9630 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1443 -0.7630 -0.7370 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8850 -2.2445 -0.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0402 -1.4268 2.1478 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2985 0.1748 1.5843 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8251 -1.1932 0.6288 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6336 0.2668 1.7590 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7102 1.6563 -0.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7341 0.3460 -1.1976 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5933 1.8355 -1.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1419 0.1977 -0.9879 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4178 1.0917 1.4307 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7589 2.6219 0.8597 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2710 2.5400 1.0731 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3022 1.1603 -0.0689 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2355 3.9879 -0.7304 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3515 2.5861 -1.8620 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2949 4.0995 -2.0995 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6894 3.8491 -0.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3717 0.0853 -2.3009 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8477 -0.7965 -2.5045 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5443 -0.0002 -3.9462 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 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 2 0 1 27 1 0 1 28 1 0 1 29 1 0 2 30 1 0 2 31 1 0 3 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 5 36 1 0 5 37 1 0 6 38 1 0 6 39 1 0 7 40 1 0 7 41 1 0 8 42 1 0 8 43 1 0 9 44 1 0 9 45 1 0 10 46 1 0 10 47 1 0 11 48 1 0 11 49 1 0 12 50 1 0 12 51 1 0 13 52 1 0 13 53 1 0 14 54 1 0 14 55 1 0 15 56 1 0 15 57 1 0 16 58 1 0 16 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 20 66 1 0 20 67 1 0 21 68 1 0 21 69 1 0 22 70 1 0 22 71 1 0 25 72 1 0 25 73 1 0 25 74 1 0 M END

Standard InCHIKey	AWYRDXDPCQRJHE-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C24H48O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-26-24(2)25/h3-23H2,1-2H3
SMILES	CCCCCCCCCCCCCCCCCCCCCCOC(C)=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	368.37	Volume:	438.604 ? Van der Waals volume.
Dense:	0.84	LogP:	8.828 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.621 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.44 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	22.0	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:	0.15	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.796	Fsp³:	0.958
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:	0.538	Fluc inhibitor:	0.293 ? 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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.995	Promiscuous compounds:	0.288

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.079	MDCK Permeability:	-4.884
Pgp-inhibitor:	0.0	Pgp-substrate:	0.044
PAMPA:	0.0 ? 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):	0.676
20% Bioavailability (F20%):	0.91	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027	MRP1:	0.998
Plasma Protein Binding (PPB):	101.328%	Volume Distribution (VD):	1.8
Fu:	0.402% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.308
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.947
BSEP inhibitor:	0.469

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.008	CYP2C19-substrate:	0.012
CYP2C9-inhibitor:	0.101	CYP2C9-substrate:	0.95
CYP2D6-inhibitor:	0.024	CYP2D6-substrate:	0.308
CYP3A4-inhibitor:	0.013	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.759	CYP2C8-inhibitor:	1.0
HLM stability:	0.901 ? 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):

4.54

Half-life (T1/2):

1.734

ADMET: Toxicity

hERG Blockers:	0.691	hERG Blockers (10um):	0.921
Human Hepatotoxicity (H-HT):	0.342	Drug-induced Liver Injury (DILI):	0.151
AMES Toxicity:	0.03	Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.17	Skin Sensitization:	0.993
Carcinogencity:	0.452	Eye Corrosion:	0.98
Eye Irritation:	0.997	Respiratory Toxicity:	0.93
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.075
Hematotoxicity:	0.082	Drug-induced Nephrotoxicity:	0.085
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.727	Hek293 Cytotoxicity:	0.16
BCF:	0.739 ? 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:	5.33 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.658 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.987 ? 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
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[25154406]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30183289]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30551419]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35999251]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432786]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36675004]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37653914]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37759401]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37893598]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38592874]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38719900]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39065713]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39683666]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21460	Anethum graveolens	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
NPO18952	Sambucus nigra	Oil	Flowers	0.2	n.a.	n.a.	%	PMID[37759401]
NPO18952	Sambucus nigra	Oil	Flowers	0.1	n.a.	n.a.	%	PMID[37759401]
NPO21460	Anethum graveolens	Oil	n.a.	0.24Â±0.04	n.a.	n.a.	%	PMID[38719900]

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 NPC525407 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	28342
0.1-0.2	19551
0.2-0.3	1641
0.3-0.4	238
0.4-0.5	53
0.5-0.6	10
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86545
1.0	High Similarity	NPC286498
1.0	High Similarity	NPC223374
1.0	High Similarity	NPC196442
1.0	High Similarity	NPC301398
1.0	High Similarity	NPC608162
1.0	High Similarity	NPC609004
0.95	High Similarity	NPC40965
0.8095	Intermediate Similarity	NPC248233
0.72	Intermediate Similarity	NPC80641
0.7143	Intermediate Similarity	NPC3693
0.7143	Intermediate Similarity	NPC476549
0.7083	Intermediate Similarity	NPC322892
0.6923	Remote Similarity	NPC149299
0.6923	Remote Similarity	NPC223675
0.6923	Remote Similarity	NPC68577
0.68	Remote Similarity	NPC154396
0.68	Remote Similarity	NPC155872
0.6538	Remote Similarity	NPC80396
0.6429	Remote Similarity	NPC207815
0.6296	Remote Similarity	NPC14608
0.6	Remote Similarity	NPC147054
0.5926	Remote Similarity	NPC154642
0.5926	Remote Similarity	NPC603612
0.5769	Remote Similarity	NPC223249
0.5769	Remote Similarity	NPC12904
0.56	Remote Similarity	NPC159398
0.5556	Remote Similarity	NPC286695
0.5417	Remote Similarity	NPC140229
0.5217	Remote Similarity	NPC99700
0.52	Remote Similarity	NPC166804
0.5185	Remote Similarity	NPC476550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC525407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6648
0.1-0.2	2309
0.2-0.3	158
0.3-0.4	27
0.4-0.5	5
0.5-0.6	2
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
0.5455	Remote Similarity	NPD631	Phase 4
0.5294	Remote Similarity	NPD630	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