NPASS Compound

Natural Product: NPC141645

Natural Product ID	NPC141645
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OVSQVDMCBVZWGM-QSOFNFLRSA-M
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	25203368
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-glycosides

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 52 55 0 0 0 0 0 0 0 0999 V2000 -0.8598 1.7167 2.2272 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9351 3.0110 2.7507 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0218 3.7990 2.4783 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0373 3.3130 1.6890 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9281 2.0389 1.1926 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8310 1.1996 1.4475 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8493 -0.1031 0.7982 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7406 -0.8507 0.6460 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8921 -2.1021 0.0027 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1216 -2.8097 -0.1443 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1196 -2.4982 -0.4333 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3220 -3.7027 -1.0654 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5899 -4.0537 -1.4890 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6894 -3.2355 -1.3046 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4809 -2.0288 -0.6702 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2121 -1.6857 -0.2502 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0467 -0.5498 0.3413 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9658 -3.5950 -1.7341 O 0 0 0 0 0 1 0 0 0 0 0 0 -1.2378 -4.5435 -1.2639 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5166 -0.5051 1.0458 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4492 0.1205 0.1638 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2860 1.0859 0.8630 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7306 1.1152 0.3755 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8106 0.7063 -1.0759 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1195 -0.5933 -1.2978 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0899 -1.7605 -1.4052 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4044 -2.8862 -1.8614 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1461 -0.9416 -0.4208 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2325 1.6999 -1.8543 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4427 0.2213 1.1616 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8105 2.3920 0.5904 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1236 4.1379 1.4340 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1110 5.0938 2.9941 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0065 1.0996 2.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1313 3.3823 3.3697 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7487 1.6851 0.5705 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7814 -5.0039 -1.9940 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3235 -1.3725 -0.5145 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2008 -5.0635 -2.1279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8653 0.5621 -0.6625 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2629 0.9849 1.9687 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1793 2.1228 0.4827 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8668 0.5894 -1.3931 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6387 -0.5365 -2.3207 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9096 -1.5628 -2.1137 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4862 -2.0458 -0.3890 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9711 -3.4009 -2.4889 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2843 2.5796 -1.4042 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2700 -0.0299 0.6524 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3461 2.9936 1.1904 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5792 3.9961 0.5216 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4751 5.8143 2.3924 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 14 18 1 0 12 19 1 0 8 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 23 30 1 0 22 31 1 0 4 32 1 0 3 33 1 0 6 1 1 0 17 7 1 0 28 21 1 0 16 11 1 0 1 34 1 0 2 35 1 0 5 36 1 0 13 37 1 0 15 38 1 0 19 39 1 0 21 40 1 6 22 41 1 1 23 42 1 6 24 43 1 6 25 44 1 6 26 45 1 0 26 46 1 0 27 47 1 0 29 48 1 0 30 49 1 0 31 50 1 0 32 51 1 0 33 52 1 0 M CHG 1 18 -1 M END

Standard InCHIKey	OVSQVDMCBVZWGM-QSOFNFLRSA-M
Standard InCHI	InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/p-1/t13-,15-,17+,18-,21+/m1/s1
SMILES	c1cc(c(cc1c1c(c(=O)c2c(cc(cc2o1)[O-])O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	464.1	Volume:	421.937 ? Van der Waals volume.
Dense:	1.1	LogP:	0.697 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.087 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.63 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	210.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	8.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.229	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.008	Fsp³:	0.286
MCE-18:	91.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.659	Fluc inhibitor:	0.302 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.932 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.592 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.286	Promiscuous compounds:	0.912

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.255	MDCK Permeability:	-4.959
Pgp-inhibitor:	0.0	Pgp-substrate:	0.094
PAMPA:	0.958 ? 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):	0.194
20% Bioavailability (F20%):	0.409	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.046
Plasma Protein Binding (PPB):	84.361%	Volume Distribution (VD):	-0.086
Fu:	13.667% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.903
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.005	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.723
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.869 ? 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):

3.528

Half-life (T1/2):

3.634

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.198
Human Hepatotoxicity (H-HT):	0.563	Drug-induced Liver Injury (DILI):	0.913
AMES Toxicity:	0.856	Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.209	Skin Sensitization:	0.999
Carcinogencity:	0.239	Eye Corrosion:	0.0
Eye Irritation:	0.88	Respiratory Toxicity:	0.039
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.851
Hematotoxicity:	0.038	Drug-induced Nephrotoxicity:	0.064
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.031
A549 Cytotoxicity:	0.698	Hek293 Cytotoxicity:	0.531
BCF:	0.537 ? 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:	3.16 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.482 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.765 ? 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
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16748484]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	branch	n.a.	PMID[17202693]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20597533]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23656415]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38358042]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO67	Fructus mori	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23516	Potentilla discolor	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO67	Fructus mori	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23516	Potentilla discolor	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO67	Fructus mori	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11457	Chelidonium majus	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23230	Allium cepa	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	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 NPC141645 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	25200
0.1-0.2	21041
0.2-0.3	2423
0.3-0.4	681
0.4-0.5	266
0.5-0.6	110
0.6-0.7	71
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8841	High Similarity	NPC136042
0.8243	Intermediate Similarity	NPC605784
0.8194	Intermediate Similarity	NPC84362
0.7808	Intermediate Similarity	NPC145038
0.7808	Intermediate Similarity	NPC56077
0.7808	Intermediate Similarity	NPC297987
0.7808	Intermediate Similarity	NPC281131
0.7808	Intermediate Similarity	NPC253662
0.7808	Intermediate Similarity	NPC179950
0.7808	Intermediate Similarity	NPC88789
0.7808	Intermediate Similarity	NPC491374
0.7733	Intermediate Similarity	NPC488071
0.7432	Intermediate Similarity	NPC289667
0.7368	Intermediate Similarity	NPC42773
0.7368	Intermediate Similarity	NPC45522
0.7308	Intermediate Similarity	NPC116458
0.7308	Intermediate Similarity	NPC246943
0.7237	Intermediate Similarity	NPC271692
0.7143	Intermediate Similarity	NPC599850
0.6974	Remote Similarity	NPC77672
0.6974	Remote Similarity	NPC133671
0.6974	Remote Similarity	NPC135391
0.6974	Remote Similarity	NPC78263
0.6974	Remote Similarity	NPC250069
0.6951	Remote Similarity	NPC480466
0.6933	Remote Similarity	NPC67037
0.6933	Remote Similarity	NPC255615
0.6883	Remote Similarity	NPC277205
0.6883	Remote Similarity	NPC37919
0.6883	Remote Similarity	NPC189142
0.6883	Remote Similarity	NPC77660
0.6829	Remote Similarity	NPC251417
0.6795	Remote Similarity	NPC24043
0.6753	Remote Similarity	NPC19388
0.6753	Remote Similarity	NPC240431
0.6753	Remote Similarity	NPC55786
0.6667	Remote Similarity	NPC14187
0.6588	Remote Similarity	NPC156869
0.6582	Remote Similarity	NPC27640
0.6548	Remote Similarity	NPC29958
0.6538	Remote Similarity	NPC127546
0.6538	Remote Similarity	NPC249281
0.6538	Remote Similarity	NPC57625
0.6538	Remote Similarity	NPC173637
0.6538	Remote Similarity	NPC317489
0.6538	Remote Similarity	NPC223424
0.6538	Remote Similarity	NPC600591
0.6471	Remote Similarity	NPC471748
0.6456	Remote Similarity	NPC64305
0.6437	Remote Similarity	NPC64425
0.642	Remote Similarity	NPC60735
0.642	Remote Similarity	NPC26230
0.6386	Remote Similarity	NPC203050
0.6386	Remote Similarity	NPC488072
0.6386	Remote Similarity	NPC225434
0.6383	Remote Similarity	NPC480441
0.6375	Remote Similarity	NPC46420
0.6375	Remote Similarity	NPC488080
0.6375	Remote Similarity	NPC169977
0.6341	Remote Similarity	NPC120099
0.6296	Remote Similarity	NPC472459
0.6296	Remote Similarity	NPC59534
0.625	Remote Similarity	NPC8573
0.625	Remote Similarity	NPC488073
0.625	Remote Similarity	NPC158674
0.622	Remote Similarity	NPC175107
0.6173	Remote Similarity	NPC245014
0.6173	Remote Similarity	NPC58716
0.6173	Remote Similarity	NPC305811
0.6173	Remote Similarity	NPC45638
0.6154	Remote Similarity	NPC288084
0.6145	Remote Similarity	NPC101026
0.6145	Remote Similarity	NPC21666
0.6145	Remote Similarity	NPC488077
0.6125	Remote Similarity	NPC39360
0.6125	Remote Similarity	NPC29763
0.6125	Remote Similarity	NPC210003
0.6118	Remote Similarity	NPC254855
0.6118	Remote Similarity	NPC94610
0.6111	Remote Similarity	NPC35119
0.6098	Remote Similarity	NPC325555
0.6098	Remote Similarity	NPC226304
0.6098	Remote Similarity	NPC117260
0.6098	Remote Similarity	NPC201292
0.6049	Remote Similarity	NPC323593
0.6049	Remote Similarity	NPC203500
0.6047	Remote Similarity	NPC480463
0.6044	Remote Similarity	NPC486577
0.6024	Remote Similarity	NPC611303
0.6	Remote Similarity	NPC276377
0.5952	Remote Similarity	NPC609478
0.5949	Remote Similarity	NPC34531
0.5934	Remote Similarity	NPC32641
0.5934	Remote Similarity	NPC256188
0.593	Remote Similarity	NPC116864
0.593	Remote Similarity	NPC244776
0.593	Remote Similarity	NPC265115
0.5854	Remote Similarity	NPC282987
0.5854	Remote Similarity	NPC168822
0.5854	Remote Similarity	NPC609879
0.5843	Remote Similarity	NPC150164
0.5843	Remote Similarity	NPC605592
0.5802	Remote Similarity	NPC111929
0.5802	Remote Similarity	NPC320283
0.5802	Remote Similarity	NPC41121
0.5795	Remote Similarity	NPC139320
0.5783	Remote Similarity	NPC603655
0.5773	Remote Similarity	NPC292019
0.5773	Remote Similarity	NPC202908
0.5765	Remote Similarity	NPC601144
0.575	Remote Similarity	NPC276222
0.575	Remote Similarity	NPC274618
0.575	Remote Similarity	NPC118284
0.575	Remote Similarity	NPC608147
0.5732	Remote Similarity	NPC261866
0.5732	Remote Similarity	NPC19709
0.5732	Remote Similarity	NPC238376
0.573	Remote Similarity	NPC67326
0.5714	Remote Similarity	NPC25523
0.5714	Remote Similarity	NPC164704
0.5698	Remote Similarity	NPC206123
0.5698	Remote Similarity	NPC311830
0.5667	Remote Similarity	NPC203259
0.5667	Remote Similarity	NPC33054
0.5667	Remote Similarity	NPC155877
0.5667	Remote Similarity	NPC176740
0.5667	Remote Similarity	NPC471725
0.5667	Remote Similarity	NPC134532
0.5667	Remote Similarity	NPC602582
0.5663	Remote Similarity	NPC95090
0.5663	Remote Similarity	NPC27408
0.5652	Remote Similarity	NPC470443
0.5652	Remote Similarity	NPC483414
0.5652	Remote Similarity	NPC483415
0.5647	Remote Similarity	NPC168584
0.5647	Remote Similarity	NPC285197
0.5632	Remote Similarity	NPC601586
0.5631	Remote Similarity	NPC488078
0.5618	Remote Similarity	NPC476773
0.561	Remote Similarity	NPC135599
0.561	Remote Similarity	NPC73855
0.561	Remote Similarity	NPC113968
0.561	Remote Similarity	NPC328940
0.561	Remote Similarity	NPC277174
0.561	Remote Similarity	NPC606877
0.5604	Remote Similarity	NPC186816
0.56	Remote Similarity	NPC470716
0.5591	Remote Similarity	NPC483416
0.5581	Remote Similarity	NPC22832
0.5581	Remote Similarity	NPC486578
0.5556	Remote Similarity	NPC470715
0.5543	Remote Similarity	NPC240306
0.5506	Remote Similarity	NPC8856
0.55	Remote Similarity	NPC277532
0.5495	Remote Similarity	NPC607513
0.5481	Remote Similarity	NPC470720
0.5476	Remote Similarity	NPC93337
0.5476	Remote Similarity	NPC146792
0.5474	Remote Similarity	NPC473073
0.5474	Remote Similarity	NPC473071
0.5465	Remote Similarity	NPC307938
0.5455	Remote Similarity	NPC223860
0.5455	Remote Similarity	NPC170052
0.5455	Remote Similarity	NPC135846
0.5435	Remote Similarity	NPC255157
0.5435	Remote Similarity	NPC259896
0.5426	Remote Similarity	NPC37668
0.5426	Remote Similarity	NPC72016
0.5417	Remote Similarity	NPC188871
0.5412	Remote Similarity	NPC84265
0.5412	Remote Similarity	NPC105025
0.5412	Remote Similarity	NPC349108
0.5402	Remote Similarity	NPC148710
0.5402	Remote Similarity	NPC243930
0.5385	Remote Similarity	NPC470719
0.5385	Remote Similarity	NPC470717
0.5376	Remote Similarity	NPC126784
0.5376	Remote Similarity	NPC241423
0.5376	Remote Similarity	NPC488074
0.5341	Remote Similarity	NPC223747
0.5341	Remote Similarity	NPC607707
0.534	Remote Similarity	NPC295625
0.5333	Remote Similarity	NPC473682
0.5287	Remote Similarity	NPC235260
0.5287	Remote Similarity	NPC155763
0.5287	Remote Similarity	NPC219904
0.5281	Remote Similarity	NPC190003
0.5263	Remote Similarity	NPC150767
0.5263	Remote Similarity	NPC606657
0.5253	Remote Similarity	NPC121703
0.525	Remote Similarity	NPC191154
0.5233	Remote Similarity	NPC52550
0.5233	Remote Similarity	NPC610763
0.5222	Remote Similarity	NPC95866
0.5217	Remote Similarity	NPC470405
0.5217	Remote Similarity	NPC275454
0.5208	Remote Similarity	NPC5319
0.5208	Remote Similarity	NPC64755
0.5204	Remote Similarity	NPC223426
0.52	Remote Similarity	NPC189564

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141645 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5990
0.1-0.2	3088
0.2-0.3	59
0.3-0.4	6
0.4-0.5	4
0.5-0.6	2
0.6-0.7	1
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
0.6154	Remote Similarity	NPD7251	Phase 2
0.5667	Remote Similarity	NPD6797	Phase 2
0.5208	Remote Similarity	NPD7804	Clinical (unspecified phase)

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