NPASS Compound

Natural Product: NPC102803

Natural Product ID	NPC102803
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SOSLMHZOJATCCP-MKMJNHTISA-M
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	25202794
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 50 53 0 0 0 0 0 0 0 0999 V2000 3.7502 -1.5968 -1.1954 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1077 -0.6202 -0.2358 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0926 0.1377 0.5818 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6757 1.5538 0.7473 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1716 1.7584 0.8933 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3935 0.7682 0.1142 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2831 0.2796 -0.9053 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2144 1.2533 -0.5205 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8795 0.4082 -0.7032 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8613 -0.3617 -1.8901 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0659 -0.2882 -2.7269 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9303 -1.2005 -2.0697 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0270 -2.0144 -3.2025 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0847 -2.8669 -3.4118 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1022 -2.9419 -2.4853 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0355 -2.1564 -1.3644 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9613 -1.2945 -1.1579 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8899 -0.5471 -0.0996 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8940 0.3081 0.1766 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9870 1.0638 1.4113 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2477 2.1506 1.7693 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3650 2.7990 3.0108 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2653 2.3378 3.9338 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0265 1.2513 3.6124 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8989 0.6261 2.3907 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3862 2.9765 5.1667 O 0 0 0 0 0 1 0 0 0 0 0 0 -5.1947 -3.8178 -2.6946 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9681 -1.8970 -4.1075 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9755 3.0950 0.4603 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1795 2.3826 -0.2789 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2361 -0.4857 1.8415 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6790 -2.0260 -0.7972 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8956 -1.0505 -2.1491 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0325 -2.4255 -1.4158 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4873 -1.2492 0.4735 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1146 0.1539 0.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1397 1.9519 1.6744 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9444 1.7366 1.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1884 -0.1459 0.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1249 -3.4818 -4.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8158 -2.2087 -0.6454 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5655 2.5651 1.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7392 3.6623 3.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7407 0.8808 4.3380 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5065 -0.2335 2.1464 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6428 -4.2863 -1.9133 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5530 -2.7286 -4.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2482 3.6633 1.2190 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8136 3.2884 -0.0808 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0044 -1.1270 1.7789 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 6 8 1 0 8 9 1 0 9 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 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 23 26 1 0 15 27 1 0 13 28 1 0 5 29 1 0 4 30 1 0 3 31 1 0 7 2 1 0 19 9 2 0 25 20 1 0 17 12 1 0 1 32 1 0 1 33 1 0 1 34 1 0 2 35 1 1 3 36 1 6 4 37 1 1 5 38 1 1 6 39 1 1 14 40 1 0 16 41 1 0 21 42 1 0 22 43 1 0 24 44 1 0 25 45 1 0 27 46 1 0 28 47 1 0 29 48 1 0 30 49 1 0 31 50 1 0 M CHG 1 26 -1 M END

Standard InCHIKey	SOSLMHZOJATCCP-MKMJNHTISA-M
Standard InCHI	InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/p-1/t8-,15-,17+,18+,21+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)[O-])O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	432.11	Volume:	404.357 ? Van der Waals volume.
Dense:	1.069	LogP:	1.665 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.846 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.344 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	24.0
TPSA:	170.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.348	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.883	Fsp³:	0.286
MCE-18:	87.63 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.59	Fluc inhibitor:	0.305 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.9 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.735 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.208	Promiscuous compounds:	0.515

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.026	MDCK Permeability:	-4.992
Pgp-inhibitor:	0.0	Pgp-substrate:	0.748
PAMPA:	0.991 ? 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):	0.022
20% Bioavailability (F20%):	0.274	30% Bioavailability (F30%):	0.906
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.427
Plasma Protein Binding (PPB):	87.225%	Volume Distribution (VD):	-0.106
Fu:	11.084% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.952
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.945
BSEP inhibitor:	0.087

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.907
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.409
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.974 ? 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):

2.962

Half-life (T1/2):

2.866

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.232
Human Hepatotoxicity (H-HT):	0.509	Drug-induced Liver Injury (DILI):	0.913
AMES Toxicity:	0.906	Rat Oral Acute Toxicity:	0.172
Maximum Recommended Daily Dose:	0.47	Skin Sensitization:	0.995
Carcinogencity:	0.343	Eye Corrosion:	0.001
Eye Irritation:	0.958	Respiratory Toxicity:	0.298
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.491
Hematotoxicity:	0.149	Drug-induced Nephrotoxicity:	0.155
Genotoxicity:	0.985	RPMI-8226 Immunitoxicity:	0.116
A549 Cytotoxicity:	0.819	Hek293 Cytotoxicity:	0.887
BCF:	0.919 ? 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:	3.56 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.542 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.006 ? 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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/np50070a005]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1080/10575639708043725]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.5897/AJB11.1524]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754604]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270556]
NPO15704	Euphorbia lunulata	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15744103]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	Roots	Simao city, Yunnan Province, China	2007-MAY	PMID[19374435]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	bark	n.a.	n.a.	PMID[20045319]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	leaves	Botanical Garden of Innsbruck, Austria	n.a.	PMID[20100662]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21443171]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21923134]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26341132]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29099182]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32456033]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13782	Dicranopteris pedata	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15704	Euphorbia lunulata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20518	Polygala chinensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20518	Polygala chinensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2724.1	Excoecaria cochinchinensis var. viridis	Varieties	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13782	Dicranopteris pedata	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15704	Euphorbia lunulata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13782	Dicranopteris pedata	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2724.1	Excoecaria cochinchinensis var. viridis	Varieties	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20518	Polygala chinensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15704	Euphorbia lunulata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15704	Euphorbia lunulata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20518	Polygala chinensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15361	Alnus japonica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1436	Houttuynia cordata	Species	Saururaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22819	Rodgersia podophylla	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28450	Phyllanthus emblica	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13782	Dicranopteris pedata	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20518	Polygala chinensis	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25618	Eriobotrya japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12458	Zingiber aromaticum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15704	Euphorbia lunulata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15361	Alnus japonica	Species	Betulaceae	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 NPC102803 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	16075
0.1-0.2	30241
0.2-0.3	2539
0.3-0.4	545
0.4-0.5	181
0.5-0.6	83
0.6-0.7	84
0.7-0.8	0
0.8-0.85	13
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8551	High Similarity	NPC111929
0.8551	High Similarity	NPC320283
0.8551	High Similarity	NPC41121
0.8219	Intermediate Similarity	NPC219904
0.8169	Intermediate Similarity	NPC127546
0.8169	Intermediate Similarity	NPC57625
0.8169	Intermediate Similarity	NPC173637
0.8169	Intermediate Similarity	NPC317489
0.8169	Intermediate Similarity	NPC223424
0.8169	Intermediate Similarity	NPC600591
0.8028	Intermediate Similarity	NPC135599
0.8028	Intermediate Similarity	NPC73855
0.8028	Intermediate Similarity	NPC113968
0.8028	Intermediate Similarity	NPC328940
0.8028	Intermediate Similarity	NPC277174
0.8028	Intermediate Similarity	NPC606877
0.7808	Intermediate Similarity	NPC265530
0.7568	Intermediate Similarity	NPC64305
0.7532	Intermediate Similarity	NPC223747
0.7368	Intermediate Similarity	NPC472459
0.72	Intermediate Similarity	NPC77672
0.72	Intermediate Similarity	NPC133671
0.72	Intermediate Similarity	NPC135391
0.72	Intermediate Similarity	NPC78263
0.72	Intermediate Similarity	NPC250069
0.7073	Intermediate Similarity	NPC173582
0.7073	Intermediate Similarity	NPC265885
0.7073	Intermediate Similarity	NPC181465
0.7073	Intermediate Similarity	NPC215710
0.7073	Intermediate Similarity	NPC473438
0.7073	Intermediate Similarity	NPC253788
0.7051	Intermediate Similarity	NPC60735
0.7051	Intermediate Similarity	NPC26230
0.6962	Remote Similarity	NPC120099
0.6883	Remote Similarity	NPC145038
0.6883	Remote Similarity	NPC56077
0.6883	Remote Similarity	NPC281131
0.6883	Remote Similarity	NPC253662
0.6883	Remote Similarity	NPC179950
0.6883	Remote Similarity	NPC88789
0.6883	Remote Similarity	NPC491374
0.686	Remote Similarity	NPC473327
0.6835	Remote Similarity	NPC175107
0.68	Remote Similarity	NPC288084
0.679	Remote Similarity	NPC476215
0.6786	Remote Similarity	NPC203259
0.6786	Remote Similarity	NPC33054
0.6786	Remote Similarity	NPC176740
0.6786	Remote Similarity	NPC471725
0.6786	Remote Similarity	NPC134532
0.6786	Remote Similarity	NPC602582
0.6753	Remote Similarity	NPC19388
0.6753	Remote Similarity	NPC240431
0.6753	Remote Similarity	NPC249281
0.6753	Remote Similarity	NPC55786
0.6707	Remote Similarity	NPC116864
0.6707	Remote Similarity	NPC244776
0.6667	Remote Similarity	NPC39834
0.6625	Remote Similarity	NPC159579
0.6588	Remote Similarity	NPC605592
0.6582	Remote Similarity	NPC46420
0.6543	Remote Similarity	NPC609478
0.6506	Remote Similarity	NPC95866
0.65	Remote Similarity	NPC216496
0.65	Remote Similarity	NPC325555
0.65	Remote Similarity	NPC226304
0.6494	Remote Similarity	NPC67037
0.6494	Remote Similarity	NPC255615
0.6471	Remote Similarity	NPC163242
0.6471	Remote Similarity	NPC272068
0.6447	Remote Similarity	NPC54802
0.6447	Remote Similarity	NPC197304
0.642	Remote Similarity	NPC129217
0.642	Remote Similarity	NPC611303
0.6386	Remote Similarity	NPC203050
0.6386	Remote Similarity	NPC225434
0.6375	Remote Similarity	NPC305811
0.6364	Remote Similarity	NPC34531
0.6353	Remote Similarity	NPC471079
0.6353	Remote Similarity	NPC139320
0.6353	Remote Similarity	NPC609888
0.6333	Remote Similarity	NPC476472
0.6333	Remote Similarity	NPC294815
0.6333	Remote Similarity	NPC16194
0.6322	Remote Similarity	NPC129264
0.6265	Remote Similarity	NPC116458
0.6265	Remote Similarity	NPC246943
0.625	Remote Similarity	NPC153755
0.622	Remote Similarity	NPC182121
0.6207	Remote Similarity	NPC155877
0.619	Remote Similarity	NPC276377
0.618	Remote Similarity	NPC12013
0.618	Remote Similarity	NPC11432
0.618	Remote Similarity	NPC477613
0.6173	Remote Similarity	NPC52550
0.6173	Remote Similarity	NPC271692
0.6154	Remote Similarity	NPC276222
0.6154	Remote Similarity	NPC274618
0.6154	Remote Similarity	NPC118284
0.6154	Remote Similarity	NPC608147
0.6133	Remote Similarity	NPC268668
0.6111	Remote Similarity	NPC270448
0.6092	Remote Similarity	NPC471748
0.6092	Remote Similarity	NPC67326
0.6071	Remote Similarity	NPC209023
0.6067	Remote Similarity	NPC470125
0.6064	Remote Similarity	NPC203145
0.6049	Remote Similarity	NPC158674
0.6047	Remote Similarity	NPC278419
0.6047	Remote Similarity	NPC251417
0.6047	Remote Similarity	NPC179198
0.6023	Remote Similarity	NPC156869
0.6	Remote Similarity	NPC170052
0.6	Remote Similarity	NPC66087
0.6	Remote Similarity	NPC189564
0.6	Remote Similarity	NPC135846
0.6	Remote Similarity	NPC476771
0.5978	Remote Similarity	NPC85751
0.5978	Remote Similarity	NPC76831
0.5978	Remote Similarity	NPC19240
0.5978	Remote Similarity	NPC89127
0.5977	Remote Similarity	NPC29958
0.5976	Remote Similarity	NPC27640
0.5952	Remote Similarity	NPC85707
0.5952	Remote Similarity	NPC224530
0.5934	Remote Similarity	NPC122467
0.5934	Remote Similarity	NPC37668
0.5934	Remote Similarity	NPC72016
0.5926	Remote Similarity	NPC289667
0.5926	Remote Similarity	NPC476772
0.5914	Remote Similarity	NPC221342
0.5914	Remote Similarity	NPC476470
0.5882	Remote Similarity	NPC605784
0.5851	Remote Similarity	NPC602448
0.5843	Remote Similarity	NPC150164
0.5833	Remote Similarity	NPC48093
0.5806	Remote Similarity	NPC471669
0.5806	Remote Similarity	NPC220173
0.5795	Remote Similarity	NPC187379
0.5789	Remote Similarity	NPC214621
0.5789	Remote Similarity	NPC34267
0.5778	Remote Similarity	NPC186816
0.5773	Remote Similarity	NPC292019
0.5773	Remote Similarity	NPC202908
0.5773	Remote Similarity	NPC477895
0.5765	Remote Similarity	NPC259957
0.5761	Remote Similarity	NPC104883
0.5761	Remote Similarity	NPC488679
0.5747	Remote Similarity	NPC254855
0.5747	Remote Similarity	NPC94610
0.5732	Remote Similarity	NPC143851
0.573	Remote Similarity	NPC470405
0.5714	Remote Similarity	NPC59534
0.5714	Remote Similarity	NPC296018
0.5714	Remote Similarity	NPC21100
0.5686	Remote Similarity	NPC474522
0.5684	Remote Similarity	NPC223426
0.5667	Remote Similarity	NPC65563
0.5667	Remote Similarity	NPC470949
0.5663	Remote Similarity	NPC297987
0.5647	Remote Similarity	NPC235260
0.5647	Remote Similarity	NPC191306
0.5647	Remote Similarity	NPC155763
0.5634	Remote Similarity	NPC59951
0.5625	Remote Similarity	NPC81042
0.5618	Remote Similarity	NPC258044
0.5618	Remote Similarity	NPC217387
0.5612	Remote Similarity	NPC48984
0.5612	Remote Similarity	NPC173837
0.5604	Remote Similarity	NPC35167
0.5604	Remote Similarity	NPC473571
0.5604	Remote Similarity	NPC110941
0.5595	Remote Similarity	NPC488080
0.5595	Remote Similarity	NPC349108
0.5595	Remote Similarity	NPC169977
0.5591	Remote Similarity	NPC32641
0.5591	Remote Similarity	NPC256188
0.5591	Remote Similarity	NPC35119
0.5591	Remote Similarity	NPC606657
0.5588	Remote Similarity	NPC480445
0.5581	Remote Similarity	NPC189913
0.5568	Remote Similarity	NPC265115
0.5567	Remote Similarity	NPC89052
0.5556	Remote Similarity	NPC196127
0.5556	Remote Similarity	NPC470712
0.5543	Remote Similarity	NPC154741
0.5542	Remote Similarity	NPC104677
0.5534	Remote Similarity	NPC156785
0.5529	Remote Similarity	NPC138927
0.5517	Remote Similarity	NPC88023
0.5517	Remote Similarity	NPC309025
0.5495	Remote Similarity	NPC304741
0.5484	Remote Similarity	NPC245452
0.5484	Remote Similarity	NPC483414
0.5476	Remote Similarity	NPC8573
0.5474	Remote Similarity	NPC470447
0.5455	Remote Similarity	NPC355481
0.5429	Remote Similarity	NPC241781
0.5405	Remote Similarity	NPC603596
0.5402	Remote Similarity	NPC484158

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC102803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4637
0.1-0.2	4444
0.2-0.3	54
0.3-0.4	10
0.4-0.5	1
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
0.6786	Remote Similarity	NPD6797	Phase 2
0.5253	Remote Similarity	NPD7808	Phase 3
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