NPASS Compound

Natural Product: NPC294186

Natural Product ID	NPC294186
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-N-Heptadecylresorcinol
IUPAC Name	5-heptadecylbenzene-1,3-diol
Synonyms	5-N-Heptadecylresorcinol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL497530
PubChem CID	181700
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

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 65 65 0 0 0 0 0 0 0 0999 V2000 6.8964 2.1698 2.7073 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8779 1.8193 1.6282 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8530 0.3350 1.3661 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4662 -0.1161 0.9201 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0643 0.5914 -0.3443 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6979 0.1064 -0.7693 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7011 0.4100 0.3011 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3214 -0.0289 -0.1393 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2985 -1.5040 -0.3854 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8981 -1.9294 -0.7643 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4858 -1.2167 -2.0237 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9105 -1.6393 -2.4616 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9120 -1.3110 -1.3835 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3208 -1.7302 -1.8193 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2588 -1.3687 -0.6896 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6845 -1.7495 -1.0340 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6433 -1.4053 0.0646 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6754 0.0338 0.3866 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8161 0.5270 1.3471 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7965 1.8684 1.6958 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9049 2.3222 2.6781 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6609 2.7365 1.0648 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5264 2.2642 0.1034 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5338 0.9247 -0.2329 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4286 3.1023 -0.5719 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2036 3.1005 3.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8856 2.4117 2.2929 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8434 1.3591 3.4610 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9107 2.0723 1.9464 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6981 2.3785 0.6891 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5574 0.0283 0.5903 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1499 -0.1644 2.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4351 -1.2040 0.7400 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7895 0.1619 1.7609 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8021 0.4010 -1.1441 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9500 1.6970 -0.1626 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4131 0.7443 -1.6526 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7372 -0.9634 -1.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6840 1.5099 0.4639 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9045 -0.1169 1.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0937 0.5892 -1.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5501 0.2309 0.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0081 -1.7830 -1.2225 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6222 -1.9923 0.5615 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2499 -1.5850 0.0957 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8040 -3.0281 -0.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4871 -0.1141 -1.8819 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1794 -1.5354 -2.8289 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1138 -1.0867 -3.3995 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8778 -2.7100 -2.7068 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6922 -1.8126 -0.4303 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8766 -0.2197 -1.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3500 -2.8150 -2.0440 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5938 -1.2063 -2.7688 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8944 -1.8479 0.2201 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1627 -0.2602 -0.5402 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6980 -2.8524 -1.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9495 -1.3088 -2.0031 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6448 -1.7710 -0.2409 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3079 -1.9477 0.9771 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1435 -0.1555 1.8364 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2437 2.5702 3.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6853 3.7909 1.3000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1935 0.5062 -0.9800 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0191 3.7165 -0.0512 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 2 0 19 20 1 0 20 21 1 0 20 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 24 18 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 6 38 1 0 7 39 1 0 7 40 1 0 8 41 1 0 8 42 1 0 9 43 1 0 9 44 1 0 10 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 14 53 1 0 14 54 1 0 15 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 17 60 1 0 19 61 1 0 21 62 1 0 22 63 1 0 24 64 1 0 25 65 1 0 M END

Standard InCHIKey	BBGNINPPDHJETF-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C23H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21-18-22(24)20-23(25)19-21/h18-20,24-25H,2-17H2,1H3
SMILES	CCCCCCCCCCCCCCCCCc1cc(O)cc(c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	348.3	Volume:	407.479 ? Van der Waals volume.
Dense:	0.855	LogP:	8.919 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.861 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.765 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	6.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.303	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.001	Fsp³:	0.739
MCE-18:	6.0 ? 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:	0.772	Fluc inhibitor:	0.371 ? 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:	0.012 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.952	Promiscuous compounds:	0.109

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.206	MDCK Permeability:	-4.856
Pgp-inhibitor:	0.002	Pgp-substrate:	0.017
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):	0.107
20% Bioavailability (F20%):	0.979	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034	MRP1:	0.878
Plasma Protein Binding (PPB):	101.385%	Volume Distribution (VD):	1.869
Fu:	0.435% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.82
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.932
BSEP inhibitor:	0.523

ADMET: Metabolism

CYP1A2-inhibitor:	0.124	CYP1A2-substrate:	0.998
CYP2C19-inhibitor:	0.311	CYP2C19-substrate:	0.975
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.998	CYP2D6-substrate:	0.95
CYP3A4-inhibitor:	0.006	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.854	CYP2C8-inhibitor:	1.0
HLM stability:	0.419 ? 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):

3.942

Half-life (T1/2):

1.819

ADMET: Toxicity

hERG Blockers:	0.787	hERG Blockers (10um):	0.937
Human Hepatotoxicity (H-HT):	0.499	Drug-induced Liver Injury (DILI):	0.075
AMES Toxicity:	0.068	Rat Oral Acute Toxicity:	0.193
Maximum Recommended Daily Dose:	0.579	Skin Sensitization:	0.991
Carcinogencity:	0.206	Eye Corrosion:	0.958
Eye Irritation:	0.998	Respiratory Toxicity:	0.955
Drug-induced Neurotoxicity:	0.037	Ototoxicity:	0.134
Hematotoxicity:	0.06	Drug-induced Nephrotoxicity:	0.072
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.049
A549 Cytotoxicity:	0.938	Hek293 Cytotoxicity:	0.762
BCF:	1.027 ? 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:	5.236 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.215 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.097 ? 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
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1111/j.1365-3040.1996.tb00393.x]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10993146]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	Tsukuba, Japan	1998-JUN	PMID[12381108]
NPO25294	Merulius incarnatus	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643059]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18270436]
NPO33268	wheat	n.a.	n.a.	n.a.	wheat germ	n.a.	n.a.	PMID[19284743]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21381697]
NPO33268	wheat	n.a.	n.a.	n.a.	wheat bran	n.a.	n.a.	PMID[21658963]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23793896]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24197199]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24254087]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[24967651]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9134744]
NPO33268	wheat	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO709.1	Triticum durum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25294	Merulius incarnatus	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO709.1	Triticum durum	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO659	Secale cereale	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8589	Triticum aestivum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO659	Secale cereale	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22132	Hordeum vulgare	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25294	Merulius incarnatus	Species	Meruliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8589	Triticum aestivum	Species	Poaceae	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
NPO22132	Hordeum vulgare	Dried Or Powder	n.a.	0.188223074	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO659	Secale cereale	Dried Or Powder	n.a.	15.11282549	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO659	Secale cereale	Dried Or Powder	n.a.	2.138400078	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO659	Secale cereale	n.a.	n.a.	2.13	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO659	Secale cereale	n.a.	n.a.	15.10704	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO709.1	Triticum durum	Dried Or Powder	n.a.	0.245605909	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO8589	Triticum aestivum	Dried Or Powder	n.a.	1.808085061	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO8589	Triticum aestivum	n.a.	n.a.	0.24091	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO8589	Triticum aestivum	n.a.	n.a.	1.80461	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]

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	2

Activity Type	# Activity
Cell line	2

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
NPT393	Cell line	HCT-116	Homo sapiens	IC50	=	18.94	ug.mL-1	PMID[21658963]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	31.15	ug.mL-1	PMID[21658963]

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 NPC294186 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	28932
0.1-0.2	18811
0.2-0.3	1805
0.3-0.4	181
0.4-0.5	51
0.5-0.6	28
0.6-0.7	20
0.7-0.8	0
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC147310
1.0	High Similarity	NPC137415
1.0	High Similarity	NPC166313
1.0	High Similarity	NPC192032
1.0	High Similarity	NPC24407
1.0	High Similarity	NPC11280
0.8889	High Similarity	NPC246056
0.8182	Intermediate Similarity	NPC146798
0.8182	Intermediate Similarity	NPC222522
0.8182	Intermediate Similarity	NPC106396
0.8182	Intermediate Similarity	NPC94351
0.8182	Intermediate Similarity	NPC168303
0.7941	Intermediate Similarity	NPC486908
0.7879	Intermediate Similarity	NPC53051
0.7879	Intermediate Similarity	NPC24404
0.7879	Intermediate Similarity	NPC313030
0.75	Intermediate Similarity	NPC71002
0.75	Intermediate Similarity	NPC249828
0.7273	Intermediate Similarity	NPC470700
0.7273	Intermediate Similarity	NPC54844
0.7273	Intermediate Similarity	NPC39097
0.7273	Intermediate Similarity	NPC302681
0.7273	Intermediate Similarity	NPC241891
0.7273	Intermediate Similarity	NPC118286
0.7273	Intermediate Similarity	NPC134829
0.7273	Intermediate Similarity	NPC109691
0.7027	Intermediate Similarity	NPC302219
0.6857	Remote Similarity	NPC39664
0.6765	Remote Similarity	NPC3358
0.6765	Remote Similarity	NPC306884
0.6765	Remote Similarity	NPC603092
0.6667	Remote Similarity	NPC59506
0.6579	Remote Similarity	NPC242342
0.6579	Remote Similarity	NPC85479
0.6471	Remote Similarity	NPC488411
0.6471	Remote Similarity	NPC488410
0.6471	Remote Similarity	NPC488409
0.6429	Remote Similarity	NPC486909
0.6364	Remote Similarity	NPC123273
0.6364	Remote Similarity	NPC318325
0.6316	Remote Similarity	NPC166761
0.6279	Remote Similarity	NPC305603
0.6176	Remote Similarity	NPC37802
0.6154	Remote Similarity	NPC10588
0.6154	Remote Similarity	NPC284011
0.6	Remote Similarity	NPC114064
0.6	Remote Similarity	NPC72947
0.575	Remote Similarity	NPC94139
0.575	Remote Similarity	NPC147284
0.5745	Remote Similarity	NPC123559
0.5714	Remote Similarity	NPC244513
0.5641	Remote Similarity	NPC232523
0.5556	Remote Similarity	NPC61033
0.5526	Remote Similarity	NPC162113
0.5526	Remote Similarity	NPC62546
0.55	Remote Similarity	NPC488413
0.55	Remote Similarity	NPC473691
0.55	Remote Similarity	NPC483454
0.55	Remote Similarity	NPC477454
0.55	Remote Similarity	NPC162314
0.55	Remote Similarity	NPC488415
0.55	Remote Similarity	NPC488414
0.55	Remote Similarity	NPC488412
0.5405	Remote Similarity	NPC76938
0.5405	Remote Similarity	NPC32714
0.5366	Remote Similarity	NPC115808
0.5366	Remote Similarity	NPC135414
0.5294	Remote Similarity	NPC242240
0.5263	Remote Similarity	NPC487946
0.5263	Remote Similarity	NPC487945
0.5217	Remote Similarity	NPC127894
0.5217	Remote Similarity	NPC470759
0.5152	Remote Similarity	NPC210849
0.5143	Remote Similarity	NPC610566
0.5102	Remote Similarity	NPC140521

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC294186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6105
0.1-0.2	2877
0.2-0.3	154
0.3-0.4	9
0.4-0.5	4
0.5-0.6	1
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
0.5135	Remote Similarity	NPD846	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