NPASS Compound

Natural Product: NPC71061

Natural Product ID	NPC71061
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Bilobetin
IUPAC Name	8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-methoxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Synonyms	Bilobetin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL378188
PubChem CID	5315459
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 61 66 0 0 0 0 0 0 0 0999 V2000 1.9868 -2.4537 4.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6977 -2.4491 2.6820 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5806 -1.7947 2.1832 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2510 -1.1433 3.0532 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3708 -0.4837 2.5806 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -0.4496 1.2425 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8210 -1.1275 0.3940 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2930 -1.7869 0.8398 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2098 -2.4952 -0.0449 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0467 -3.8268 -0.3644 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9562 -4.4571 -1.2182 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0197 -3.7639 -1.7487 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1667 -2.4271 -1.4160 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2214 -1.7049 -1.9306 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0540 -2.2304 -2.6954 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3076 -0.3610 -1.5523 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4024 0.2359 -0.7125 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4686 1.6354 -0.3017 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4587 2.4862 -0.7283 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4933 3.8257 -0.3146 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5333 4.3315 0.5344 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5335 3.4885 0.9704 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5126 2.1746 0.5554 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5443 5.6579 0.9605 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4153 -0.5289 -0.2598 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2741 -1.7933 -0.5730 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9537 -4.3186 -2.5952 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0317 -4.5068 0.1810 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8689 0.2352 0.7128 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7410 0.9062 1.5323 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8607 1.5628 1.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6710 2.1827 1.7731 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0526 1.5046 -0.3339 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1364 2.1241 -0.9337 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3523 2.0829 -2.2946 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4455 1.3946 -3.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3619 0.7755 -2.4744 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1399 0.8122 -1.1179 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0857 0.2038 -0.5787 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6131 1.3202 -4.4530 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0558 2.8194 -0.1602 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9684 -2.8724 4.2851 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2296 -3.0212 4.6121 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9947 -1.3917 4.4388 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0063 -1.1602 4.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9851 0.0075 3.2996 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0568 -1.1157 -0.6663 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8349 -5.4985 -1.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1225 0.2073 -1.9466 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2428 2.1320 -1.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2809 4.4942 -0.6567 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7778 3.8986 1.6427 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7351 1.5059 0.8902 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5194 6.3688 0.2399 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6168 -4.9912 -2.2390 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9498 -4.5520 -0.2790 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5980 0.9534 2.5839 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1937 2.5611 -2.7801 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6840 0.2507 -3.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4801 2.0976 -5.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9416 2.4683 0.1313 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 21 24 1 0 17 25 1 0 25 26 1 0 12 27 1 0 10 28 1 0 6 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 36 40 1 0 34 41 1 0 8 3 1 0 26 9 1 0 39 29 1 0 26 13 2 0 38 33 1 0 23 18 1 0 1 42 1 0 1 43 1 0 1 44 1 0 4 45 1 0 5 46 1 0 7 47 1 0 11 48 1 0 16 49 1 0 19 50 1 0 20 51 1 0 22 52 1 0 23 53 1 0 24 54 1 0 27 55 1 0 28 56 1 0 30 57 1 0 35 58 1 0 37 59 1 0 40 60 1 0 41 61 1 0 M END

Standard InCHIKey	IWEIJEPIYMAGTH-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C31H20O10/c1-39-24-7-4-15(26-12-22(37)29-19(34)9-17(33)10-27(29)40-26)8-18(24)28-20(35)11-21(36)30-23(38)13-25(41-31(28)30)14-2-5-16(32)6-3-14/h2-13,32-36H,1H3
SMILES	COc1ccc(cc1c1c(cc(c2c(=O)cc(c3ccc(cc3)O)oc12)O)O)c1cc(=O)c2c(cc(cc2o1)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	552.11	Volume:	539.112 ? Van der Waals volume.
Dense:	1.024	LogP:	4.63 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.714 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.5 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	36.0
TPSA:	170.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.19	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.01	Fsp³:	0.032
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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.996	Fluc inhibitor:	0.41 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.978 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.996 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.431	Promiscuous compounds:	0.926

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.043	MDCK Permeability:	-4.793
Pgp-inhibitor:	0.003	Pgp-substrate:	0.696
PAMPA:	0.583 ? 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):	0.0
20% Bioavailability (F20%):	0.437	30% Bioavailability (F30%):	0.92
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.934
Plasma Protein Binding (PPB):	96.727%	Volume Distribution (VD):	-0.363
Fu:	2.515% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.724
OATP1B3 inhibitor:	0.957	BCRP inhibitor:	0.962
BSEP inhibitor:	0.968

ADMET: Metabolism

CYP1A2-inhibitor:	0.483	CYP1A2-substrate:	0.008
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.446	CYP2C9-substrate:	0.996
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.913 ? 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):

1.546

Half-life (T1/2):

1.984

ADMET: Toxicity

hERG Blockers:	0.075	hERG Blockers (10um):	0.492
Human Hepatotoxicity (H-HT):	0.47	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.775	Rat Oral Acute Toxicity:	0.63
Maximum Recommended Daily Dose:	0.988	Skin Sensitization:	0.427
Carcinogencity:	0.869	Eye Corrosion:	0.001
Eye Irritation:	0.995	Respiratory Toxicity:	0.896
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.044
Hematotoxicity:	0.023	Drug-induced Nephrotoxicity:	0.009
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.108
A549 Cytotoxicity:	0.701	Hek293 Cytotoxicity:	0.978
BCF:	1.24 ? 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:	4.537 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.931 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.698 ? 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]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16574412]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994703]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20335035]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25559759]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[27140807]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29144743]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31244143]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	n.a.	n.a.	PMID[33127538]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	fresh sarcotestas	Kwanak Campus of Seoul National University, Seoul, Korea	1996-Sep	PMID[9677265]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	leaves	St. Louis	1996-SEP	PMID[9834151]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834158]
NPO7378	Rubritalea squalenifaciens	Species	Rubritaleaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28466	Torreya nucifera	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	Wood	n.a.	n.a.	Database[FooDB]
NPO29719	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1923	Podocarpus elongatu	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1923	Podocarpus elongatu	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	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]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28466	Torreya nucifera	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14158	Selaginella tamariscina	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28400	Selaginella pulvinata	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7378	Rubritalea squalenifaciens	Species	Rubritaleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2284	Cephalotaxus koreana	Species	Taxaceae	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

Activity Type	# Activity
IC50	12
Inhibition	5
Activity	48

Activity Type	# Activity
Individual protein	7
Cell line	41
Unchecked	13
Others	2
Organism	1
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT280	Individual protein	Matrix metalloproteinase 9	Homo sapiens	IC50	=	10330.0	nM	PMID[29921475]
NPT740	Individual protein	Beta-secretase 1	Homo sapiens	IC50	=	2020.0	nM	PMID[20598535]
NPT567	Individual protein	Matrix metalloproteinase 3	Homo sapiens	IC50	>	100000.0	nM	PMID[29921475]
NPT3595	Individual protein	Cathepsin K	Homo sapiens	IC50	=	0.84	ug.mL-1	PMID[17027271]
NPT568	Individual protein	Matrix metalloproteinase-2	Homo sapiens	IC50	>	100000.0	nM	PMID[29921475]
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
NPT1309	Cell line	Osteoblasts	n.a.	Activity	=	100.9	%	PMID[16574412]
NPT1309	Cell line	Osteoblasts	n.a.	Activity	=	131.9	%	PMID[16574412]
NPT1309	Cell line	Osteoblasts	n.a.	Activity	=	130.6	%	PMID[16574412]
NPT3140	Cell line	MGC-803	Homo sapiens	IC50	>	50000.0	nM	PMID[29921475]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[29921475]
NPT81	Cell line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[29921475]
NPT550	Cell line	T-24	Homo sapiens	IC50	>	50000.0	nM	PMID[29921475]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	n.a.	n.a.	n.a.	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	=	67.9	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	6.94	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	1.81	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	52.6	%	PMID[36700552]
NPT2170	Cell line	RKO	Homo sapiens	Activity	n.a.	n.a.	n.a.	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	59.9	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	7.24	%	PMID[36700552]
NPT114	Cell line	LoVo	Homo sapiens	Activity	n.a.	n.a.	n.a.	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	=	51.2	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	64.4	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	4.88	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	28.0	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	0.49	%	PMID[36700552]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	26500.0	nM	PMID[34875389]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	32.7	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	3.58	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	33.4	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	39.9	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	41.0	%	PMID[36700552]
NPT393	Cell line	HCT-116	Homo sapiens	Activity	=	0.46	%	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]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	2700.0	nM	PMID[22989363]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	44.7	%	PMID[26004578]
NPT2	Others	Unspecified	n.a.	Inhibition	=	84.0	%	PMID[9834158]
NPT2	Others	Unspecified	n.a.	IC50	=	360.0	nM	PMID[9834158]

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 NPC71061 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	30255
0.1-0.2	16785
0.2-0.3	1812
0.3-0.4	778
0.4-0.5	163
0.5-0.6	32
0.6-0.7	20
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	NPC150908
0.8286	Intermediate Similarity	NPC265624
0.8	Intermediate Similarity	NPC215203
0.7714	Intermediate Similarity	NPC72425
0.7714	Intermediate Similarity	NPC303485
0.7361	Intermediate Similarity	NPC14606
0.7313	Intermediate Similarity	NPC138299
0.7123	Intermediate Similarity	NPC186227
0.6986	Remote Similarity	NPC290830
0.6711	Remote Similarity	NPC601565
0.6667	Remote Similarity	NPC194593
0.6615	Remote Similarity	NPC231772
0.6528	Remote Similarity	NPC254351
0.6452	Remote Similarity	NPC50898
0.6447	Remote Similarity	NPC159707
0.64	Remote Similarity	NPC600972
0.6364	Remote Similarity	NPC121649
0.6351	Remote Similarity	NPC259757
0.6349	Remote Similarity	NPC222713
0.6282	Remote Similarity	NPC205026
0.625	Remote Similarity	NPC288840
0.6143	Remote Similarity	NPC67322
0.6087	Remote Similarity	NPC52005
0.6087	Remote Similarity	NPC12200
0.6049	Remote Similarity	NPC55443
0.6026	Remote Similarity	NPC272064
0.6	Remote Similarity	NPC183950
0.6	Remote Similarity	NPC610480
0.589	Remote Similarity	NPC111112
0.5658	Remote Similarity	NPC34089
0.5658	Remote Similarity	NPC183
0.5658	Remote Similarity	NPC196179
0.5652	Remote Similarity	NPC62536
0.5652	Remote Similarity	NPC120464
0.5652	Remote Similarity	NPC483773
0.5652	Remote Similarity	NPC601901
0.5641	Remote Similarity	NPC248739
0.56	Remote Similarity	NPC291746
0.557	Remote Similarity	NPC603508
0.5556	Remote Similarity	NPC610914
0.5522	Remote Similarity	NPC279121
0.5507	Remote Similarity	NPC241498
0.5488	Remote Similarity	NPC18699
0.5455	Remote Similarity	NPC78540
0.5429	Remote Similarity	NPC234133
0.5417	Remote Similarity	NPC606638
0.5405	Remote Similarity	NPC605634
0.5395	Remote Similarity	NPC112954
0.5316	Remote Similarity	NPC606549
0.5309	Remote Similarity	NPC158027
0.5294	Remote Similarity	NPC274121
0.5286	Remote Similarity	NPC301323
0.5286	Remote Similarity	NPC103342
0.5185	Remote Similarity	NPC601984
0.5172	Remote Similarity	NPC604941
0.5139	Remote Similarity	NPC600900
0.507	Remote Similarity	NPC47815
0.506	Remote Similarity	NPC63454
0.506	Remote Similarity	NPC183851
0.5057	Remote Similarity	NPC607079

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC71061 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5989
0.1-0.2	3105
0.2-0.3	48
0.3-0.4	5
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
0.5522	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