NPASS Compound

Natural Product: NPC305603

Natural Product ID	NPC305603
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-(11'(S)-Hydroxy-8'-Heptadecaenyl)Resorcinol
IUPAC Name	5-[(Z,11S)-11-hydroxyheptadec-8-enyl]benzene-1,3-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL253132
PubChem CID	23626633
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

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 64 64 0 0 0 0 0 0 0 0999 V2000 -8.5414 1.0768 0.5091 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8987 -0.0364 -0.2619 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5866 -1.2374 0.5942 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6669 -0.9694 1.7118 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3104 -0.4154 1.2563 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6586 -1.4234 0.3782 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3532 -1.1183 -0.2388 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1571 -0.8386 0.5576 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0925 0.3070 1.4547 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2012 1.2697 1.2406 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2189 1.3299 0.1514 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1861 1.3578 0.7040 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1810 1.4442 -0.4160 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1246 0.2780 -1.3516 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1707 0.4579 -2.4258 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5340 0.5476 -1.8349 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8606 -0.6978 -1.0615 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2599 -0.5410 -0.5114 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4036 0.0327 0.7305 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6913 0.1722 1.2261 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7795 -0.2474 0.5025 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6117 -0.8191 -0.7389 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3317 -0.9614 -1.2394 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7169 -1.2412 -1.4653 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8593 0.7490 2.4784 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1058 -2.2062 -1.1503 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8876 1.4732 1.3128 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7033 1.9182 -0.1959 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5495 0.7938 0.8809 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6092 -0.3414 -1.0580 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0011 0.3491 -0.7827 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2344 -2.0541 -0.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5927 -1.6227 0.9830 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0822 -0.3684 2.5358 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4088 -1.9652 2.1794 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6884 -0.2782 2.1704 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4494 0.5098 0.6787 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5055 -2.4120 0.9481 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3827 -1.7603 -0.4402 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5688 -0.2116 -0.9324 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0661 -1.7500 1.2946 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1991 -0.9979 -0.0176 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7153 0.4557 2.3550 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1870 2.1150 1.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3323 2.3230 -0.3916 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3183 0.5813 -0.6213 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3008 2.2256 1.4184 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3762 0.4502 1.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0517 2.3936 -1.0016 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1792 1.5547 0.0645 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1010 0.2102 -1.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2998 -0.6873 -0.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1339 -0.3977 -3.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9076 1.3775 -3.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6855 1.4519 -1.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2511 0.6692 -2.7037 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8675 -1.5879 -1.7062 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1588 -0.8493 -0.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5751 0.3707 1.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7782 -0.1261 0.9150 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2045 -1.4104 -2.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0912 -0.5769 -2.1357 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1737 0.2655 3.2913 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5739 -1.8738 -1.9145 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 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 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 20 25 1 0 7 26 1 0 23 18 1 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 6 8 41 1 0 8 42 1 0 9 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 19 59 1 0 21 60 1 0 23 61 1 0 24 62 1 0 25 63 1 0 26 64 1 0 M END

Standard InCHIKey	QKJHTDPOTJRZOH-DGDFFNOKSA-N
Standard InCHI	InChI=1S/C23H38O3/c1-2-3-4-12-15-21(24)16-13-10-8-6-5-7-9-11-14-20-17-22(25)19-23(26)18-20/h10,13,17-19,21,24-26H,2-9,11-12,14-16H2,1H3/b13-10-/t21-/m0/s1
SMILES	CCCCCC[C@@H](C/C=CCCCCCCCc1cc(cc(c1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	362.28	Volume:	413.633 ? Van der Waals volume.
Dense:	0.876	LogP:	6.649 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.064 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.825 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	7.0
TPSA:	60.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	3.0	Rings:	1.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.255	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.935	Fsp³:	0.652
MCE-18:	14.0 ? 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:	0.756	Fluc inhibitor:	0.306 ? 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:	0.049 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.769	Promiscuous compounds:	0.174

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.324	MDCK Permeability:	-4.753
Pgp-inhibitor:	0.08	Pgp-substrate:	0.02
PAMPA:	0.004 ? 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):	0.001
20% Bioavailability (F20%):	0.758	30% Bioavailability (F30%):	0.869
50% Bioavailability (F50%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089	MRP1:	0.534
Plasma Protein Binding (PPB):	97.224%	Volume Distribution (VD):	0.284
Fu:	3.223% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.195
OATP1B3 inhibitor:	0.935	BCRP inhibitor:	0.805
BSEP inhibitor:	0.971

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.106	CYP2C19-substrate:	0.982
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.997
CYP2D6-inhibitor:	0.92	CYP2D6-substrate:	0.999
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.507 ? 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):

5.024

Half-life (T1/2):

0.934

ADMET: Toxicity

hERG Blockers:	0.663	hERG Blockers (10um):	0.859
Human Hepatotoxicity (H-HT):	0.416	Drug-induced Liver Injury (DILI):	0.003
AMES Toxicity:	0.111	Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.631	Skin Sensitization:	0.999
Carcinogencity:	0.097	Eye Corrosion:	0.984
Eye Irritation:	0.998	Respiratory Toxicity:	0.886
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.234
Hematotoxicity:	0.025	Drug-induced Nephrotoxicity:	0.258
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.062
A549 Cytotoxicity:	0.972	Hek293 Cytotoxicity:	0.831
BCF:	1.647 ? 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:	5.127 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.987 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.431 ? 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
NPO6797	Hyoscyamus reticulatus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/elsc.201800087]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724859]
NPO5292	Stylogyne turbacensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17629327]
NPO456	Swertia dilatata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[4472648]
NPO456	Swertia dilatata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO1595	Grindelia paludosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6110	Iryanthera elliptica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6797	Hyoscyamus reticulatus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5519	Aplidium uouo	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO869	Elaeagnus multiflora	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7829	Embelia robusta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4552	Gnephosis arachnoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4052	Lophura armata	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7669	Micromphale perforans	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5741	Nymphaea elegans	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7306	Onchidella binneyi	Species	Onchidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15010	Packera aurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO799	Psoralea bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7094	Salvia candicans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8193	Streptomyces morookaense	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5292	Stylogyne turbacensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO456	Swertia dilatata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7829	Embelia robusta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7829	Embelia robusta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4052	Lophura armata	Species	Phasianidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1595	Grindelia paludosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7669	Micromphale perforans	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15010	Packera aurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5741	Nymphaea elegans	Species	Nymphaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7829	Embelia robusta	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14959.1	Codonopsis pilosula subsp. tangshen	Subspecies	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5292	Stylogyne turbacensis	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO456	Swertia dilatata	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7306	Onchidella binneyi	Species	Onchidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6867	Asparagus curillus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8193	Streptomyces morookaense	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO869	Elaeagnus multiflora	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1665	Paris tetraphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7094	Salvia candicans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO799	Psoralea bituminosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6797	Hyoscyamus reticulatus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6110	Iryanthera elliptica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23840	Taxus x media	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4552	Gnephosis arachnoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5519	Aplidium uouo	Species	Polyclinidae	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

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell line	3
Organism	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
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	14000.0	nM	PMID[17629327]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	16000.0	nM	PMID[17629327]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	76000.0	nM	PMID[17629327]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	138000.0	nM	PMID[17629327]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	7000.0	nM	PMID[17629327]

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 NPC305603 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	21708
0.1-0.2	26094
0.2-0.3	1791
0.3-0.4	166
0.4-0.5	50
0.5-0.6	16
0.6-0.7	20
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8298	Intermediate Similarity	NPC61033
0.7674	Intermediate Similarity	NPC146798
0.7674	Intermediate Similarity	NPC222522
0.7674	Intermediate Similarity	NPC106396
0.7674	Intermediate Similarity	NPC94351
0.7674	Intermediate Similarity	NPC168303
0.75	Intermediate Similarity	NPC486908
0.7442	Intermediate Similarity	NPC53051
0.7442	Intermediate Similarity	NPC24404
0.7442	Intermediate Similarity	NPC313030
0.7174	Intermediate Similarity	NPC71002
0.7174	Intermediate Similarity	NPC249828
0.6977	Remote Similarity	NPC470700
0.6977	Remote Similarity	NPC54844
0.6977	Remote Similarity	NPC39097
0.6977	Remote Similarity	NPC302681
0.6977	Remote Similarity	NPC118286
0.6977	Remote Similarity	NPC109691
0.6809	Remote Similarity	NPC302219
0.6667	Remote Similarity	NPC39664
0.6458	Remote Similarity	NPC242342
0.6458	Remote Similarity	NPC85479
0.6279	Remote Similarity	NPC294186
0.6279	Remote Similarity	NPC147310
0.6279	Remote Similarity	NPC137415
0.6279	Remote Similarity	NPC166313
0.6279	Remote Similarity	NPC192032
0.6279	Remote Similarity	NPC24407
0.6279	Remote Similarity	NPC11280
0.625	Remote Similarity	NPC166761
0.6122	Remote Similarity	NPC10588
0.6	Remote Similarity	NPC72947
0.58	Remote Similarity	NPC94139
0.58	Remote Similarity	NPC284011
0.58	Remote Similarity	NPC147284
0.5714	Remote Similarity	NPC232523
0.56	Remote Similarity	NPC488413
0.56	Remote Similarity	NPC483454
0.56	Remote Similarity	NPC162314
0.56	Remote Similarity	NPC488412
0.5581	Remote Similarity	NPC246056
0.5517	Remote Similarity	NPC123559
0.5357	Remote Similarity	NPC127894
0.5357	Remote Similarity	NPC470759
0.5254	Remote Similarity	NPC140521
0.5185	Remote Similarity	NPC210497
0.5094	Remote Similarity	NPC158253
0.5091	Remote Similarity	NPC483450

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC305603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6235
0.1-0.2	2815
0.2-0.3	94
0.3-0.4	6
0.4-0.5	0
0.5-0.6	0
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
		NPD

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