NPASS Compound

Natural Product: NPC150908

Natural Product ID	NPC150908
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Isoginkgetin
IUPAC Name	8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one
Synonyms	Isoginkgetin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1208903
PubChem CID	5318569
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 64 69 0 0 0 0 0 0 0 0999 V2000 3.7063 5.2937 -1.5815 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6486 4.4678 -0.9732 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3945 3.1388 -0.6184 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3493 2.3544 -0.0195 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0848 1.0229 0.3325 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8648 0.4589 0.0909 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9063 1.2600 -0.5149 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1624 2.5696 -0.8625 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5141 -0.9121 0.4257 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4262 -1.7443 1.0260 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0948 -3.0536 1.3469 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9109 -3.8357 1.8965 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8211 -3.4778 1.0393 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9365 -2.6083 0.4364 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3035 -1.3860 0.1571 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6622 -3.0790 0.1442 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3267 -4.3778 0.4602 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1896 -5.2553 1.0582 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4586 -4.7850 1.3486 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4071 -5.5914 1.9531 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9557 -4.8255 0.1574 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2549 -2.1528 -0.4892 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0799 -1.3429 0.2547 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9639 -0.4506 -0.3341 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0118 -0.3784 -1.7115 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2052 -1.1697 -2.4701 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3257 -2.0579 -1.8621 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4721 -2.8396 -2.6696 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3857 -2.7286 -4.0673 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8468 0.4166 0.4334 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8519 0.3972 1.8110 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7235 1.2547 2.4904 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 1.2589 3.7392 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5595 2.1010 1.7934 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4851 2.0513 0.4167 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6583 1.2368 -0.1671 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3136 2.8911 -0.3300 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1714 3.7350 0.3368 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2331 3.7719 1.7242 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4180 2.9456 2.4648 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4550 2.9580 3.8446 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9910 4.5656 -0.3927 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9683 6.3669 -1.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6716 5.1371 -2.6759 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6743 5.1790 -1.1887 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3282 2.7555 0.1915 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8693 0.4281 0.8080 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9390 0.8139 -0.7068 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3850 3.1661 -1.3361 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4217 -1.4320 1.2728 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9552 -6.2758 1.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7838 -6.4256 1.5219 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5466 -5.2769 0.8318 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0158 -1.4258 1.3230 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6942 0.3107 -2.1807 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2641 -1.0921 -3.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5262 -1.6725 -4.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2380 -3.2894 -4.5177 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5932 -3.0537 -4.4586 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2269 -0.2368 2.3978 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2743 2.8710 -1.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9330 4.4621 2.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0412 2.3428 4.3791 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9432 4.2497 -0.5507 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 6 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 11 13 1 0 13 14 2 0 14 15 1 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 17 21 1 0 16 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 24 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 35 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 38 42 1 0 8 3 1 0 15 9 1 0 27 22 1 0 36 30 1 0 19 13 1 0 40 34 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 5 47 1 0 7 48 1 0 8 49 1 0 10 50 1 0 18 51 1 0 20 52 1 0 21 53 1 0 23 54 1 0 25 55 1 0 26 56 1 0 29 57 1 0 29 58 1 0 29 59 1 0 31 60 1 0 37 61 1 0 39 62 1 0 41 63 1 0 42 64 1 0 M END

Standard InCHIKey	HUOOMAOYXQFIDQ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C32H22O10/c1-39-18-6-3-15(4-7-18)26-14-24(38)31-22(36)12-21(35)29(32(31)42-26)19-9-16(5-8-25(19)40-2)27-13-23(37)30-20(34)10-17(33)11-28(30)41-27/h3-14,33-36H,1-2H3
SMILES	COc1ccc(cc1)c1cc(=O)c2c(o1)c(c(cc2O)O)c1cc(ccc1OC)c1cc(=O)c2c(o1)cc(cc2O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	566.12	Volume:	556.408 ? Van der Waals volume.
Dense:	1.017	LogP:	4.536 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.003 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.927 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	36.0
TPSA:	159.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.203	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.966	Fsp³:	0.062
MCE-18:	36.0 ? 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:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.996	Fluc inhibitor:	0.478 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.967 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.998 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.378	Promiscuous compounds:	0.931

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.044	MDCK Permeability:	-4.804
Pgp-inhibitor:	0.066	Pgp-substrate:	0.806
PAMPA:	0.133 ? 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):	0.007
20% Bioavailability (F20%):	0.409	30% Bioavailability (F30%):	0.93
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.919
Plasma Protein Binding (PPB):	97.66%	Volume Distribution (VD):	-0.182
Fu:	1.357% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.658
OATP1B3 inhibitor:	0.978	BCRP inhibitor:	0.985
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.941	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.96	CYP2C9-substrate:	0.999
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.973 ? 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):

1.221

Half-life (T1/2):

1.76

ADMET: Toxicity

hERG Blockers:	0.1	hERG Blockers (10um):	0.47
Human Hepatotoxicity (H-HT):	0.464	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.833	Rat Oral Acute Toxicity:	0.581
Maximum Recommended Daily Dose:	0.984	Skin Sensitization:	0.226
Carcinogencity:	0.901	Eye Corrosion:	0.001
Eye Irritation:	0.989	Respiratory Toxicity:	0.936
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.048
Hematotoxicity:	0.054	Drug-induced Nephrotoxicity:	0.023
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.152
A549 Cytotoxicity:	0.637	Hek293 Cytotoxicity:	0.951
BCF:	1.282 ? 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:	4.545 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.304 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.964 ? 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
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32872604]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36352904]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39679248]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39680258]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7378	Rubritalea squalenifaciens	Species	Rubritaleaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27231	Herba selaginellae doederleinii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	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]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7378	Rubritalea squalenifaciens	Species	Rubritaleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4
Potency	16
Inhibition	6
Activity	48
EC50	1

Activity Type	# Activity
Individual protein	15
Cell line	37
Unchecked	13
Organism	2
Protein-protein interaction	3
Others	3
Non-molecular	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT2930	Individual protein	Hemoglobin beta chain	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT2930	Individual protein	Hemoglobin beta chain	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	3981.1	nM	PubChem BioAssay data set
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	19952.6	nM	PubChem BioAssay data set
NPT72	Individual protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	63.51	%	PMID[23571415]
NPT740	Individual protein	Beta-secretase 1	Homo sapiens	IC50	=	3010.0	nM	PMID[20598535]
NPT444	Individual protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	50118.7	nM	PubChem BioAssay data set
NPT73	Individual protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	36.16	%	PMID[23571415]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	316227.8	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	223872.1	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	398107.2	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	12589.3	nM	PubChem BioAssay data set
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Inhibition	n.a.	n.a.	%	PMID[36700552]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell line	L6	Rattus norvegicus	IC50	=	11000.0	nM	PMID[22989363]
NPT1045	Cell line	U2OS	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[35235336]
NPT2170	Cell line	RKO	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	58.4	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	9.54	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	3.82	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	2.58	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	3.37	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	0.92	%	PMID[36700552]
NPT114	Cell line	LoVo	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	44.5	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	40.6	%	PMID[36700552]
NPT139	Cell line	HT-29	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	46.6	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	36.7	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	52.6	%	PMID[36700552]
NPT323	Cell line	SW-620	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	47.3	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	0.79	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	70.0	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	26.5	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	1.38	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	49.1	%	PMID[36700552]
NPT28438	Unchecked	Unchecked	n.a.	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT28438	Unchecked	Unchecked	n.a.	Inhibition	n.a.	n.a.	%	PMID[36700552]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	=	22810.0	nM	PMID[36965227]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	1900.0	nM	PMID[22989363]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	83.1	%	PMID[26004578]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	EC50	=	5180.0	nM	PMID[26004578]
NPT2	Others	Unspecified	n.a.	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11220.2	nM	PubChem BioAssay data set

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 NPC150908 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	30796
0.1-0.2	16362
0.2-0.3	1788
0.3-0.4	707
0.4-0.5	144
0.5-0.6	43
0.6-0.7	8
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
0.8923	High Similarity	NPC71061
0.8235	Intermediate Similarity	NPC14606
0.8088	Intermediate Similarity	NPC303485
0.7971	Intermediate Similarity	NPC186227
0.7639	Intermediate Similarity	NPC265624
0.7541	Intermediate Similarity	NPC231772
0.7123	Intermediate Similarity	NPC215203
0.7083	Intermediate Similarity	NPC72425
0.7027	Intermediate Similarity	NPC601565
0.6667	Remote Similarity	NPC121649
0.6429	Remote Similarity	NPC138299
0.6351	Remote Similarity	NPC248739
0.6184	Remote Similarity	NPC290830
0.6176	Remote Similarity	NPC52005
0.6176	Remote Similarity	NPC12200
0.6154	Remote Similarity	NPC18699
0.6104	Remote Similarity	NPC194593
0.597	Remote Similarity	NPC483773
0.5949	Remote Similarity	NPC205026
0.5897	Remote Similarity	NPC159707
0.5735	Remote Similarity	NPC241838
0.5735	Remote Similarity	NPC62536
0.5735	Remote Similarity	NPC120464
0.5735	Remote Similarity	NPC601901
0.5733	Remote Similarity	NPC183
0.5733	Remote Similarity	NPC254351
0.5732	Remote Similarity	NPC55443
0.5658	Remote Similarity	NPC610480
0.5641	Remote Similarity	NPC600972
0.5634	Remote Similarity	NPC183950
0.5588	Remote Similarity	NPC52611
0.5588	Remote Similarity	NPC156222
0.5588	Remote Similarity	NPC29353
0.5584	Remote Similarity	NPC259757
0.557	Remote Similarity	NPC158027
0.5556	Remote Similarity	NPC67322
0.5538	Remote Similarity	NPC50898
0.5538	Remote Similarity	NPC78540
0.5507	Remote Similarity	NPC184136
0.5507	Remote Similarity	NPC59951
0.5493	Remote Similarity	NPC606638
0.5479	Remote Similarity	NPC605634
0.5467	Remote Similarity	NPC288840
0.5455	Remote Similarity	NPC222713
0.5432	Remote Similarity	NPC143851
0.5429	Remote Similarity	NPC603662
0.5417	Remote Similarity	NPC610914
0.5362	Remote Similarity	NPC600177
0.5333	Remote Similarity	NPC111112
0.5309	Remote Similarity	NPC272064
0.5286	Remote Similarity	NPC266597
0.5211	Remote Similarity	NPC600900
0.5147	Remote Similarity	NPC279121
0.5128	Remote Similarity	NPC196179
0.507	Remote Similarity	NPC57030
0.507	Remote Similarity	NPC145379
0.5065	Remote Similarity	NPC112954
0.5063	Remote Similarity	NPC280975
0.5062	Remote Similarity	NPC601984
0.5062	Remote Similarity	NPC603508

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC150908 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5898
0.1-0.2	3189
0.2-0.3	53
0.3-0.4	7
0.4-0.5	2
0.5-0.6	1
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
0.5147	Remote Similarity	NPD1511	Phase 2

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