NPASS Compound

Natural Product: NPC276377

Natural Product ID	NPC276377
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kaempferol 3-O-Alpha-L-Arabinopyranosyl-7-O-Alpha-L-Rhamnopyranoside
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1929026
PubChem CID	57401109
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 68 72 0 0 0 0 0 0 0 0999 V2000 7.1673 -1.2680 2.7754 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7629 -0.7969 1.3917 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6603 -1.9958 0.4754 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4870 -1.4924 -0.9489 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8478 -0.1041 -0.9286 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8691 -0.0674 0.2593 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6311 -0.0171 1.4311 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1465 1.1190 0.1786 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7763 1.2355 0.0278 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2481 2.5339 -0.0321 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9158 2.7928 -0.1794 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0461 1.7047 -0.2741 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5332 0.4229 -0.2190 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9053 0.1817 -0.0670 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2777 -0.5783 -0.3080 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6058 -0.4898 -0.4543 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3405 -1.7465 -0.5378 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7185 -2.9320 -0.1331 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3155 -4.1469 -0.2342 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5914 -4.1913 -0.7615 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2276 -3.0535 -1.1670 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5899 -1.8119 -1.0531 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2584 -5.4125 -0.8899 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1230 0.7653 -0.5078 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3048 1.8877 -0.4207 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7219 3.0537 -0.4685 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4774 0.9932 -0.6389 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3190 1.1853 0.4927 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7924 2.6446 0.5863 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2508 2.5729 1.0114 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0124 2.0192 -0.1744 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3068 0.7432 -0.5858 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4188 0.3876 0.4233 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8597 2.9329 -1.2208 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7342 3.7859 1.4421 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0414 3.3711 1.5094 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3754 4.0580 -0.2398 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1530 0.1432 -2.0899 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6546 -2.3539 -1.6278 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8418 -2.6995 0.5403 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0283 -1.9565 2.6416 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2974 -1.8215 3.2203 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4478 -0.3781 3.3697 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6040 -0.1518 1.0298 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7827 -2.6147 0.7339 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4766 -1.4466 -1.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6581 0.6235 -0.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2267 -0.9448 0.2167 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9253 3.3731 0.0410 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2647 -0.8372 -0.0265 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7149 -2.8303 0.2747 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8221 -5.0555 0.0817 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2198 -3.1063 -1.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1296 -0.9752 -1.4156 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8335 -6.2814 -0.6452 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6963 1.0374 1.3872 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7368 3.0523 -0.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2917 1.7805 1.7977 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0799 1.8416 0.0661 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6933 0.8963 -1.5019 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0537 -0.0610 -0.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7351 3.8574 -0.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0855 3.7524 2.3821 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5958 3.4424 2.3211 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1356 4.5060 -1.0985 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5835 -0.3665 -2.8179 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0067 -2.5332 -2.5428 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5170 -2.1789 0.0297 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 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 16 24 2 0 24 25 1 0 25 26 2 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 30 35 1 0 29 36 1 0 11 37 1 0 5 38 1 0 4 39 1 0 3 40 1 0 7 2 1 0 14 9 1 0 22 17 1 0 33 28 1 0 25 12 1 0 1 41 1 0 1 42 1 0 1 43 1 0 2 44 1 6 3 45 1 1 4 46 1 6 5 47 1 1 6 48 1 1 10 49 1 0 14 50 1 0 18 51 1 0 19 52 1 0 21 53 1 0 22 54 1 0 23 55 1 0 28 56 1 1 29 57 1 6 30 58 1 1 31 59 1 1 32 60 1 0 32 61 1 0 34 62 1 0 35 63 1 0 36 64 1 0 37 65 1 0 38 66 1 0 39 67 1 0 40 68 1 0 M END

Standard InCHIKey	DQBVFTJNUYZVQL-CLFUFSEMSA-N
Standard InCHI	InChI=1S/C26H28O14/c1-9-17(30)20(33)22(35)26(37-9)38-12-6-13(28)16-15(7-12)39-23(10-2-4-11(27)5-3-10)24(19(16)32)40-25-21(34)18(31)14(29)8-36-25/h2-7,9,14,17-18,20-22,25-31,33-35H,8H2,1H3/t9-,14-,17-,18-,20+,21+,22+,25-,26-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc(c2c(c1)oc(c1ccc(cc1)O)c(c2=O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	564.15	Volume:	517.441 ? Van der Waals volume.
Dense:	1.09	LogP:	1.419 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.676 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.548 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	30.0
TPSA:	228.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.184	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.602	Fsp³:	0.423
MCE-18:	116.838 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.635	Fluc inhibitor:	0.28 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.902 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.796 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.077	Promiscuous compounds:	0.514

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.391	MDCK Permeability:	-5.073
Pgp-inhibitor:	0.0	Pgp-substrate:	0.908
PAMPA:	1.0 ? 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):	0.532
20% Bioavailability (F20%):	0.212	30% Bioavailability (F30%):	0.992
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.053
Plasma Protein Binding (PPB):	84.54%	Volume Distribution (VD):	-0.017
Fu:	15.248% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.665
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.986
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.228 ? 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):

1.945

Half-life (T1/2):

4.613

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.172
Human Hepatotoxicity (H-HT):	0.741	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.93	Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.034	Skin Sensitization:	0.999
Carcinogencity:	0.056	Eye Corrosion:	0.0
Eye Irritation:	0.454	Respiratory Toxicity:	0.036
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.872
Hematotoxicity:	0.151	Drug-induced Nephrotoxicity:	0.662
Genotoxicity:	0.944	RPMI-8226 Immunitoxicity:	0.205
A549 Cytotoxicity:	0.889	Hek293 Cytotoxicity:	0.682
BCF:	0.474 ? 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:	3.066 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.536 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.663 ? 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
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[16180811]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	branch	n.a.	PMID[22014228]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	branch	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014228]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014228]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39355945]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO528	Dorycnium hirsutum	Species	Fabaceae	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	3

Activity Type	# Activity
Individual protein	2
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	IC50	=	250000.0	nM	PMID[22014228]
NPT1044	Individual protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	330000.0	nM	PMID[22014228]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	IC50	=	240000.0	nM	PMID[22014228]

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 NPC276377 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	18609
0.1-0.2	27740
0.2-0.3	2615
0.3-0.4	408
0.4-0.5	259
0.5-0.6	136
0.6-0.7	45
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9014	High Similarity	NPC249281
0.8514	High Similarity	NPC46420
0.8375	Intermediate Similarity	NPC150164
0.8312	Intermediate Similarity	NPC116458
0.8312	Intermediate Similarity	NPC246943
0.8049	Intermediate Similarity	NPC186816
0.7976	Intermediate Similarity	NPC72016
0.7662	Intermediate Similarity	NPC297987
0.7564	Intermediate Similarity	NPC271692
0.7407	Intermediate Similarity	NPC605784
0.7179	Intermediate Similarity	NPC111929
0.7179	Intermediate Similarity	NPC320283
0.7179	Intermediate Similarity	NPC41121
0.716	Intermediate Similarity	NPC611303
0.7159	Intermediate Similarity	NPC32641
0.7159	Intermediate Similarity	NPC256188
0.7159	Intermediate Similarity	NPC35119
0.7	Intermediate Similarity	NPC158674
0.6962	Remote Similarity	NPC331652
0.6875	Remote Similarity	NPC108831
0.6875	Remote Similarity	NPC182634
0.6795	Remote Similarity	NPC54802
0.6795	Remote Similarity	NPC197304
0.679	Remote Similarity	NPC136042
0.6744	Remote Similarity	NPC251417
0.6742	Remote Similarity	NPC64425
0.6667	Remote Similarity	NPC289667
0.6667	Remote Similarity	NPC25523
0.6596	Remote Similarity	NPC14187
0.6522	Remote Similarity	NPC142142
0.6477	Remote Similarity	NPC471079
0.6463	Remote Similarity	NPC127546
0.6463	Remote Similarity	NPC57625
0.6463	Remote Similarity	NPC19709
0.6463	Remote Similarity	NPC173637
0.6463	Remote Similarity	NPC317489
0.6463	Remote Similarity	NPC238376
0.6463	Remote Similarity	NPC223424
0.6463	Remote Similarity	NPC600591
0.6413	Remote Similarity	NPC606657
0.6404	Remote Similarity	NPC173582
0.6404	Remote Similarity	NPC265885
0.6404	Remote Similarity	NPC181465
0.6404	Remote Similarity	NPC215710
0.6404	Remote Similarity	NPC473438
0.6404	Remote Similarity	NPC253788
0.6374	Remote Similarity	NPC240306
0.6354	Remote Similarity	NPC121703
0.631	Remote Similarity	NPC84362
0.631	Remote Similarity	NPC27640
0.6235	Remote Similarity	NPC59534
0.6222	Remote Similarity	NPC44931
0.6098	Remote Similarity	NPC276222
0.6098	Remote Similarity	NPC274618
0.6098	Remote Similarity	NPC118284
0.6098	Remote Similarity	NPC608147
0.6071	Remote Similarity	NPC77672
0.6071	Remote Similarity	NPC133671
0.6071	Remote Similarity	NPC135391
0.6071	Remote Similarity	NPC78263
0.6071	Remote Similarity	NPC250069
0.6023	Remote Similarity	NPC223747
0.6	Remote Similarity	NPC480441
0.5978	Remote Similarity	NPC65563
0.5978	Remote Similarity	NPC470949
0.5955	Remote Similarity	NPC66087
0.5952	Remote Similarity	NPC473043
0.5952	Remote Similarity	NPC135599
0.5952	Remote Similarity	NPC73855
0.5952	Remote Similarity	NPC113968
0.5952	Remote Similarity	NPC328940
0.5952	Remote Similarity	NPC277174
0.5952	Remote Similarity	NPC606877
0.593	Remote Similarity	NPC305811
0.593	Remote Similarity	NPC24043
0.5914	Remote Similarity	NPC473571
0.5914	Remote Similarity	NPC110941
0.5889	Remote Similarity	NPC265115
0.5882	Remote Similarity	NPC39360
0.5882	Remote Similarity	NPC29763
0.5882	Remote Similarity	NPC210003
0.5882	Remote Similarity	NPC348541
0.5876	Remote Similarity	NPC221342
0.5876	Remote Similarity	NPC476470
0.587	Remote Similarity	NPC67326
0.587	Remote Similarity	NPC67105
0.5862	Remote Similarity	NPC27942
0.5842	Remote Similarity	NPC164704
0.5814	Remote Similarity	NPC265530
0.5814	Remote Similarity	NPC323593
0.5814	Remote Similarity	NPC203500
0.5806	Remote Similarity	NPC203259
0.5806	Remote Similarity	NPC33054
0.5806	Remote Similarity	NPC210073
0.5806	Remote Similarity	NPC176740
0.5806	Remote Similarity	NPC471725
0.5806	Remote Similarity	NPC134532
0.5806	Remote Similarity	NPC602582
0.5795	Remote Similarity	NPC219904
0.5747	Remote Similarity	NPC349108
0.5714	Remote Similarity	NPC288084
0.5701	Remote Similarity	NPC209550
0.5698	Remote Similarity	NPC476405
0.567	Remote Similarity	NPC486577
0.5625	Remote Similarity	NPC470443
0.5625	Remote Similarity	NPC483414
0.5625	Remote Similarity	NPC483415
0.5618	Remote Similarity	NPC159579
0.5607	Remote Similarity	NPC470720
0.5604	Remote Similarity	NPC476215
0.5604	Remote Similarity	NPC190003
0.56	Remote Similarity	NPC146679
0.5591	Remote Similarity	NPC480466
0.5577	Remote Similarity	NPC470716
0.5568	Remote Similarity	NPC488080
0.5568	Remote Similarity	NPC169977
0.5567	Remote Similarity	NPC483416
0.5556	Remote Similarity	NPC138990
0.5543	Remote Similarity	NPC116864
0.5543	Remote Similarity	NPC244776
0.5534	Remote Similarity	NPC470715
0.5521	Remote Similarity	NPC488074
0.5521	Remote Similarity	NPC64051
0.5514	Remote Similarity	NPC470717
0.5505	Remote Similarity	NPC175429
0.5481	Remote Similarity	NPC277532
0.5474	Remote Similarity	NPC304741
0.5464	Remote Similarity	NPC12013
0.5464	Remote Similarity	NPC11432
0.5464	Remote Similarity	NPC477613
0.5455	Remote Similarity	NPC145038
0.5455	Remote Similarity	NPC476472
0.5455	Remote Similarity	NPC8573
0.5455	Remote Similarity	NPC56077
0.5455	Remote Similarity	NPC294815
0.5455	Remote Similarity	NPC281131
0.5455	Remote Similarity	NPC470447
0.5455	Remote Similarity	NPC64305
0.5455	Remote Similarity	NPC253662
0.5455	Remote Similarity	NPC473073
0.5455	Remote Similarity	NPC179950
0.5455	Remote Similarity	NPC16194
0.5455	Remote Similarity	NPC277205
0.5455	Remote Similarity	NPC37919
0.5455	Remote Similarity	NPC88789
0.5455	Remote Similarity	NPC189142
0.5455	Remote Similarity	NPC77660
0.5455	Remote Similarity	NPC491374
0.5444	Remote Similarity	NPC175107
0.5444	Remote Similarity	NPC129217
0.5435	Remote Similarity	NPC355481
0.5426	Remote Similarity	NPC139320
0.5417	Remote Similarity	NPC129264
0.54	Remote Similarity	NPC101636
0.54	Remote Similarity	NPC298171
0.5392	Remote Similarity	NPC203145
0.5368	Remote Similarity	NPC470405
0.5368	Remote Similarity	NPC39834
0.5368	Remote Similarity	NPC163242
0.5368	Remote Similarity	NPC272068
0.5368	Remote Similarity	NPC227508
0.5361	Remote Similarity	NPC470125
0.5361	Remote Similarity	NPC126784
0.5361	Remote Similarity	NPC241423
0.534	Remote Similarity	NPC189564
0.5333	Remote Similarity	NPC216496
0.5333	Remote Similarity	NPC472459
0.5312	Remote Similarity	NPC22062
0.5312	Remote Similarity	NPC65003
0.5312	Remote Similarity	NPC473634
0.5312	Remote Similarity	NPC303913
0.5312	Remote Similarity	NPC138811
0.5312	Remote Similarity	NPC605592
0.53	Remote Similarity	NPC85751
0.53	Remote Similarity	NPC76831
0.53	Remote Similarity	NPC19240
0.5275	Remote Similarity	NPC488071
0.5253	Remote Similarity	NPC270448
0.5253	Remote Similarity	NPC209296
0.5253	Remote Similarity	NPC473327
0.5248	Remote Similarity	NPC292929
0.5227	Remote Similarity	NPC160515
0.5204	Remote Similarity	NPC153755
0.52	Remote Similarity	NPC270675
0.52	Remote Similarity	NPC195685
0.5196	Remote Similarity	NPC602448
0.5169	Remote Similarity	NPC261866
0.5165	Remote Similarity	NPC599850
0.5158	Remote Similarity	NPC480463
0.5158	Remote Similarity	NPC278419
0.5158	Remote Similarity	NPC179198
0.5155	Remote Similarity	NPC156869
0.5152	Remote Similarity	NPC65711
0.5149	Remote Similarity	NPC80068
0.5146	Remote Similarity	NPC470455
0.5146	Remote Similarity	NPC214621
0.5146	Remote Similarity	NPC34267
0.5114	Remote Similarity	NPC67037
0.5114	Remote Similarity	NPC255615

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC276377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4905
0.1-0.2	4176
0.2-0.3	58
0.3-0.4	4
0.4-0.5	2
0.5-0.6	3
0.6-0.7	2
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
0.663	Remote Similarity	NPD7251	Phase 2
0.602	Remote Similarity	NPD7808	Phase 3
0.5806	Remote Similarity	NPD6797	Phase 2
0.5253	Remote Similarity	NPD7054	Phase 4
0.505	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