NPASS Compound

Natural Product: NPC48367

Natural Product ID	NPC48367
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WJXSYUJKJSOJOG-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	3083633
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

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 34 36 0 0 0 0 0 0 0 0999 V2000 5.2395 0.9489 -1.6893 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9318 -0.1257 -0.8639 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6623 -0.4491 -0.4162 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5691 0.3088 -0.7766 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3016 -0.0474 -0.3057 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0896 -1.1347 0.5127 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1967 -1.8857 0.8657 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4591 -1.5393 0.4028 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9854 -2.9807 1.6895 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2414 -1.4842 0.9895 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4069 -2.4793 1.7337 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3511 -0.6416 0.5711 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1641 0.4525 -0.2480 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2469 1.2438 -0.6340 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5106 0.9500 -0.2087 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6840 -0.1407 0.6056 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6310 -0.9428 1.0045 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8020 -2.0452 1.8268 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6345 1.8207 -0.6450 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8538 2.8715 0.2372 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1812 0.7751 -0.7079 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3510 1.7755 -1.4565 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4356 1.1635 -2.4214 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4243 1.8373 -1.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1867 0.7302 -2.2207 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6582 1.1823 -1.4203 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3193 -2.1411 0.6902 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6521 -3.8279 1.2498 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0087 2.0857 -1.2802 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6694 -0.4044 0.9622 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3253 -2.8427 1.5058 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4091 2.2160 -1.6600 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5978 1.2454 -0.6827 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1064 3.5050 0.1290 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 7 9 1 0 6 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 15 19 1 0 19 20 1 0 13 21 1 0 21 22 2 0 8 3 1 0 17 12 1 0 21 5 1 0 1 23 1 0 1 24 1 0 1 25 1 0 4 26 1 0 8 27 1 0 9 28 1 0 14 29 1 0 16 30 1 0 18 31 1 0 19 32 1 0 19 33 1 0 20 34 1 0 M END

Standard InCHIKey	WJXSYUJKJSOJOG-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C16H12O6/c1-22-8-4-10-14(12(19)5-8)16(21)13-9(15(10)20)2-7(6-17)3-11(13)18/h2-5,17-19H,6H2,1H3
SMILES	COc1cc2c(c(c1)O)C(=O)c1c(cc(cc1O)CO)C2=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	300.06	Volume:	291.273 ? Van der Waals volume.
Dense:	1.03	LogP:	3.41 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.111 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.479 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	18.0
TPSA:	104.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.66	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.418	Fsp³:	0.125
MCE-18:	38.0 ? 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:	0	PAINS Alert:	1
Colloidal aggregators:	0.212	Fluc inhibitor:	0.445 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.152 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.405 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.347	Promiscuous compounds:	0.686

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.151	MDCK Permeability:	-4.755
Pgp-inhibitor:	0.083	Pgp-substrate:	0.032
PAMPA:	0.873 ? 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):	0.347
20% Bioavailability (F20%):	0.096	30% Bioavailability (F30%):	0.947
50% Bioavailability (F50%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.586
Plasma Protein Binding (PPB):	94.76%	Volume Distribution (VD):	0.795
Fu:	7.434% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.959
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.46
BSEP inhibitor:	0.131

ADMET: Metabolism

CYP1A2-inhibitor:	0.302	CYP1A2-substrate:	0.704
CYP2C19-inhibitor:	0.987	CYP2C19-substrate:	0.153
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.025	CYP3A4-substrate:	0.332
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.966 ? 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):

5.196

Half-life (T1/2):

1.22

ADMET: Toxicity

hERG Blockers:	0.049	hERG Blockers (10um):	0.363
Human Hepatotoxicity (H-HT):	0.787	Drug-induced Liver Injury (DILI):	0.973
AMES Toxicity:	0.94	Rat Oral Acute Toxicity:	0.395
Maximum Recommended Daily Dose:	0.504	Skin Sensitization:	0.763
Carcinogencity:	0.872	Eye Corrosion:	0.0
Eye Irritation:	0.946	Respiratory Toxicity:	0.873
Drug-induced Neurotoxicity:	0.403	Ototoxicity:	0.632
Hematotoxicity:	0.833	Drug-induced Nephrotoxicity:	0.831
Genotoxicity:	0.993	RPMI-8226 Immunitoxicity:	0.413
A549 Cytotoxicity:	0.894	Hek293 Cytotoxicity:	0.52
BCF:	1.321 ? 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:	3.629 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.873 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.032 ? 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
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	DOI[10.1016/0045-6535(91)90110-Y]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.abb.2017.09.009]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003Ã¢â‚¬â€œ2005	DOI[10.1016/j.jfca.2006.05.007]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0885-5765(05)80069-4]
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/jo00051a050]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11454355]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17703773]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21800857]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21800857]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	Aerial Parts	n.a.	n.a.	PMID[28581290]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38830452]
NPO26866	Copaifera reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39147955]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6821187]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO638	Aralia fargesii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26680	Amsinckia intermedia	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9075.1	Peucedanum govanianum var. bicolo	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13716	Aconitum tasiromontanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14217	Adansonia grandidieri	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14412	Aphyllocladus denticulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2631	Aster sedifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4345	Caulocystis cephalornithos	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16590	Cytophaga hutchinsoni	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14104	Dendriopoterium menendezii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9448	Dictyopteris australis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8386	Enceliopsis argophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11749	Eria mollis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10688	Flacourtia jangomas	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13403	Gadus morhua callarias	Species	Gadidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO624	Isaria fumosorosea	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22526	Justicia secunda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3214	Lavandula vera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9752	Miliusa velutina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13523	Neobalanocarpus heimii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12252	Psychotria stachyoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO986	Rattus rattus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2198	Rivularia firma	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1501	Senecio subdentatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13421	Sphaerella laricina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26886	Carex brevicollis	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7455	Phlomis rigida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26929	Stachybotrys microspora	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO638	Aralia fargesii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9075.1	Peucedanum govanianum var. bicolo	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27120	Seseli yunnanense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9075.1	Peucedanum govanianum var. bicolo	Varieties	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO638	Aralia fargesii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27120	Seseli yunnanense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO638	Aralia fargesii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27120	Seseli yunnanense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16590	Cytophaga hutchinsoni	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2631	Aster sedifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12252	Psychotria stachyoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO624	Isaria fumosorosea	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14412	Aphyllocladus denticulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8386	Enceliopsis argophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9448	Dictyopteris australis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4345	Caulocystis cephalornithos	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2198	Rivularia firma	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13523	Neobalanocarpus heimii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3214	Lavandula vera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14217	Adansonia grandidieri	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10688	Flacourtia jangomas	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13716	Aconitum tasiromontanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1501	Senecio subdentatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22526	Justicia secunda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12817	Leopoldia comosa	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26886	Carex brevicollis	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14104	Dendriopoterium menendezii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13403	Gadus morhua callarias	Species	Gadidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13421	Sphaerella laricina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9752	Miliusa velutina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11749	Eria mollis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26680	Amsinckia intermedia	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO986	Rattus rattus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7455	Phlomis rigida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26171	Solanum linnaeanum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26929	Stachybotrys microspora	Species	Stachybotryaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26703	Coryphantha ottonis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26866	Copaifera reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25954	Smilax corbularia	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26983	Oncoba welwitschii	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO163	Daucus carota	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26111	Lobelia camporum	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25875	Parkia biglandulosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24573	Teloschistes flavicans	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO638	Aralia fargesii	Species	Araliaceae	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 NPC48367 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	24139
0.1-0.2	20917
0.2-0.3	4393
0.3-0.4	361
0.4-0.5	28
0.5-0.6	14
0.6-0.7	5
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	Natural Product ID
0.7209	Intermediate Similarity	NPC312929
0.6591	Remote Similarity	NPC56433
0.6304	Remote Similarity	NPC107109
0.6304	Remote Similarity	NPC294646
0.6222	Remote Similarity	NPC19896
0.6	Remote Similarity	NPC190457
0.5957	Remote Similarity	NPC126767
0.5909	Remote Similarity	NPC136588
0.587	Remote Similarity	NPC70622
0.56	Remote Similarity	NPC472052
0.551	Remote Similarity	NPC118027
0.5417	Remote Similarity	NPC52407
0.54	Remote Similarity	NPC263660
0.5319	Remote Similarity	NPC199253
0.5273	Remote Similarity	NPC470569
0.5208	Remote Similarity	NPC134191
0.52	Remote Similarity	NPC489035
0.52	Remote Similarity	NPC603651
0.5185	Remote Similarity	NPC154683
0.5094	Remote Similarity	NPC147735

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC48367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4548
0.1-0.2	4421
0.2-0.3	174
0.3-0.4	6
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