NPASS Compound

Natural Product: NPC93953

Natural Product ID	NPC93953
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	BVHIKUCXNBQDEM-JSNMRZPZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5273570
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003422] 7,9'-epoxylignans

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 51 53 0 0 0 0 0 0 0 0999 V2000 -5.6728 0.0948 -2.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8765 0.9148 -1.1477 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9641 0.8439 -0.0951 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8833 -0.0077 -0.1552 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9883 -0.0647 0.8988 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2307 0.7535 1.9801 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3137 1.6062 2.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2035 1.6659 0.9964 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3149 2.5070 0.9989 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8026 -0.9927 0.8475 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6658 -0.2355 0.2131 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4108 0.9731 1.1145 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8148 1.3950 0.5361 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5988 0.2139 0.5486 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6166 0.3902 -0.4885 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4086 0.8723 -1.7394 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4524 0.9909 -2.6301 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7482 0.6317 -2.3054 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9712 0.1405 -1.0365 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9280 0.0258 -0.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2635 -0.2442 -0.6378 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4754 -0.7431 0.6587 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8082 0.7463 -3.1933 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6659 -0.9197 0.3789 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6890 -1.9566 1.4417 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9432 -2.5184 1.5124 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9243 0.1397 -1.0798 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6688 -0.9844 -1.9657 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4716 0.2385 -3.0212 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6581 0.2734 -2.7217 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6962 -0.6534 -1.0136 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5199 0.7087 2.8199 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4548 2.2260 2.9126 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6985 2.8526 0.1093 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5986 -1.2584 1.9044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0855 -1.9042 0.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2063 1.6924 0.9350 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2235 0.6887 2.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0573 0.1509 1.5590 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4364 1.1615 -2.0376 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2629 1.3780 -3.6229 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1578 -0.3718 0.8436 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5532 -1.0191 0.7486 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1821 -0.0250 1.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8338 -1.6597 0.7706 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5610 0.0749 -3.0999 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8647 -1.4463 -0.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0155 -2.7696 1.1357 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3902 -1.6351 2.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1488 -2.9639 2.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2833 -0.6222 -1.5686 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 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 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 18 23 1 0 14 24 1 0 24 25 1 0 25 26 1 0 11 27 1 6 8 3 1 0 24 11 1 0 20 15 1 0 1 28 1 0 1 29 1 0 1 30 1 0 4 31 1 0 6 32 1 0 7 33 1 0 9 34 1 0 10 35 1 0 10 36 1 0 12 37 1 0 12 38 1 0 14 39 1 1 16 40 1 0 17 41 1 0 20 42 1 0 22 43 1 0 22 44 1 0 22 45 1 0 23 46 1 0 24 47 1 6 25 48 1 0 25 49 1 0 26 50 1 0 27 51 1 0 M END

Standard InCHIKey	BVHIKUCXNBQDEM-JSNMRZPZSA-N
Standard InCHI	InChI=1S/C20H24O7/c1-25-17-7-12(3-5-15(17)22)9-20(24)11-27-19(14(20)10-21)13-4-6-16(23)18(8-13)26-2/h3-8,14,19,21-24H,9-11H2,1-2H3/t14-,19-,20-/m1/s1
SMILES	COc1cc(ccc1O)C[C@]1(CO[C@H](c2ccc(c(c2)OC)O)[C@H]1CO)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	376.15	Volume:	374.52 ? Van der Waals volume.
Dense:	1.004	LogP:	0.566 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.025 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.923 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	17.0
TPSA:	108.61 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.608	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.656	Fsp³:	0.4
MCE-18:	65.714 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.101	Fluc inhibitor:	0.45 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.119 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.13	Promiscuous compounds:	0.254

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.429	MDCK Permeability:	-4.929
Pgp-inhibitor:	0.008	Pgp-substrate:	0.851
PAMPA:	0.323 ? 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):	0.063
20% Bioavailability (F20%):	0.62	30% Bioavailability (F30%):	0.557
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.675
Plasma Protein Binding (PPB):	66.535%	Volume Distribution (VD):	0.078
Fu:	34.674% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.489
BSEP inhibitor:	0.209

ADMET: Metabolism

CYP1A2-inhibitor:	0.792	CYP1A2-substrate:	0.007
CYP2C19-inhibitor:	0.984	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.991	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.737	CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.702	CYP3A4-substrate:	0.055
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.25
HLM stability:	0.02 ? 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):

8.021

Half-life (T1/2):

1.887

ADMET: Toxicity

hERG Blockers:	0.063	hERG Blockers (10um):	0.328
Human Hepatotoxicity (H-HT):	0.745	Drug-induced Liver Injury (DILI):	0.302
AMES Toxicity:	0.72	Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.293	Skin Sensitization:	0.886
Carcinogencity:	0.401	Eye Corrosion:	0.003
Eye Irritation:	0.941	Respiratory Toxicity:	0.108
Drug-induced Neurotoxicity:	0.25	Ototoxicity:	0.454
Hematotoxicity:	0.171	Drug-induced Nephrotoxicity:	0.466
Genotoxicity:	0.676	RPMI-8226 Immunitoxicity:	0.103
A549 Cytotoxicity:	0.135	Hek293 Cytotoxicity:	0.282
BCF:	0.653 ? 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:	3.048 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.944 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.43 ? 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
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2007.07.001]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[12762787]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762809]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	root	n.a.	n.a.	PMID[15921428]
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795843]
NPO12498	Carpesium cernuum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27668963]
NPO12498	Carpesium cernuum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33810440]
NPO8129	Inocybe geophylla	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12736	Galleria mellonella	Species	Pyralidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10010	Evernia vulpina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12828	Dysidea tupha	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1695	Monascus pilosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7874	Helichrysum lepidissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5534	Alternaria kikuchiana	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11339	Litsea salicifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8609	Hopea utilis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12498	Carpesium cernuum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10298	Symbiodinium microadriaticum	Species	Symbiodiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO35	Zanthoxylum dinklagei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4759	Helleborus multifidus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO218	Acer carpinifolium	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11506	Stipa vaseyi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26095	Hypericum revolutum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5534	Alternaria kikuchiana	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1695	Monascus pilosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9871.1	Ficus benghalensis var. krishnae	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12118	Cleistopholis staudtii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11339	Litsea salicifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12602	Leuzea centauroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO940	Vernonia anisochaetoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12828	Dysidea tupha	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6861	Galium dasypodum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10970	Osmorhiza aristata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8129	Inocybe geophylla	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7874	Helichrysum lepidissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4322	Scabiosa succisa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12498	Carpesium cernuum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6514	Desmotrichum fimbriatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12736	Galleria mellonella	Species	Pyralidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10825	Nerine sarniensis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8609	Hopea utilis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9577	Triclisia dictyophylla	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6012	Dumoria heckelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10010	Evernia vulpina	Species	Parmeliaceae	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

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 NPC93953 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	20334
0.1-0.2	25143
0.2-0.3	3714
0.3-0.4	490
0.4-0.5	132
0.5-0.6	36
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC277804
0.7167	Intermediate Similarity	NPC471988
0.661	Remote Similarity	NPC481088
0.6438	Remote Similarity	NPC129417
0.6438	Remote Similarity	NPC470235
0.6167	Remote Similarity	NPC187998
0.6167	Remote Similarity	NPC257582
0.6167	Remote Similarity	NPC241522
0.5741	Remote Similarity	NPC242807
0.5741	Remote Similarity	NPC153739
0.5714	Remote Similarity	NPC282833
0.5593	Remote Similarity	NPC478955
0.5593	Remote Similarity	NPC478700
0.5574	Remote Similarity	NPC181049
0.5556	Remote Similarity	NPC23646
0.5556	Remote Similarity	NPC485397
0.5556	Remote Similarity	NPC610652
0.5538	Remote Similarity	NPC42300
0.5469	Remote Similarity	NPC486558
0.5455	Remote Similarity	NPC115207
0.5455	Remote Similarity	NPC158079
0.5455	Remote Similarity	NPC228346
0.5455	Remote Similarity	NPC40432
0.5455	Remote Similarity	NPC161557
0.5357	Remote Similarity	NPC4940
0.5345	Remote Similarity	NPC5428
0.5224	Remote Similarity	NPC64201
0.5185	Remote Similarity	NPC85488
0.5172	Remote Similarity	NPC147379
0.5172	Remote Similarity	NPC469480
0.5156	Remote Similarity	NPC272
0.5156	Remote Similarity	NPC77040
0.5156	Remote Similarity	NPC485398
0.5152	Remote Similarity	NPC67247
0.5091	Remote Similarity	NPC282703
0.5091	Remote Similarity	NPC184733
0.5091	Remote Similarity	NPC128208
0.5091	Remote Similarity	NPC129570
0.5091	Remote Similarity	NPC63238
0.5091	Remote Similarity	NPC602603
0.5085	Remote Similarity	NPC126409
0.5085	Remote Similarity	NPC99572
0.5079	Remote Similarity	NPC253481
0.5079	Remote Similarity	NPC253722

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC93953 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4056
0.1-0.2	4944
0.2-0.3	146
0.3-0.4	3
0.4-0.5	1
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