NPASS Compound

Natural Product: NPC490151

Natural Product ID	NPC490151
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6''-Acetylhyperin 7-rhamnoside
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
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 78 82 0 0 0 0 0 0 0 0999 V2000 -8.8579 0.0712 -2.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6433 -0.4294 -1.3137 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8130 0.6659 -1.1304 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9793 0.5195 -0.0209 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1059 1.6070 -0.0254 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7236 1.5775 -0.0336 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0051 2.7857 -0.0373 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6357 2.8470 -0.0453 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9696 4.0548 -0.0486 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8996 1.6771 -0.0501 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5734 0.4806 -0.0468 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8694 -0.5994 -0.0520 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4634 -0.6630 -0.0586 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0664 -1.9799 -0.0684 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3415 -2.2390 -0.4236 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8173 -3.5446 -0.3358 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1487 -3.8223 -0.7042 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0365 -4.5738 0.0968 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5084 -5.8939 0.1886 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7331 -4.3318 0.4624 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2842 -3.0356 0.3685 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1677 0.5026 -0.0558 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5676 0.5886 -0.0450 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3587 0.6173 1.1148 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3777 -0.3411 1.1300 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5666 0.1253 0.5371 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4167 -1.0041 0.0881 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6178 -0.8016 -0.5100 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0538 -0.3585 -1.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5134 -0.2242 -2.0548 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2542 -0.0306 -2.5888 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4115 1.2298 -0.4114 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6489 0.9455 -1.5441 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8344 2.4599 0.3025 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8970 3.2487 0.7121 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0013 1.9554 1.4270 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1953 2.9145 1.9374 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4756 1.7109 -0.0547 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0764 2.8238 -0.0619 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9679 0.4305 -0.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7979 0.6518 1.2733 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0412 0.1865 2.3194 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1252 -0.0447 1.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1584 0.8735 0.9061 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1373 -1.0170 -0.0249 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4799 -1.4191 -0.1959 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2507 -0.7021 -2.7720 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5695 0.9335 -2.7541 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6378 0.4668 -1.4128 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1710 -1.2374 -1.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4523 -0.4479 -0.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5963 3.6924 -0.0334 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5685 4.4726 -0.8821 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0251 -1.4767 -0.8156 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6686 -4.3657 -0.0008 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8532 -6.1601 1.1224 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0867 -5.1387 0.8119 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7647 -2.8678 0.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7005 0.4056 1.9798 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1271 0.5631 1.4401 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7823 -1.6390 -0.6356 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5653 -1.6815 0.9833 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6209 -0.6087 -3.0913 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8353 0.8360 -2.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1520 -0.8255 -1.4070 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4080 1.5614 -0.7529 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8551 1.5489 -2.2931 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2333 3.0020 -0.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5353 3.3002 -0.0512 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7515 1.7223 2.2667 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2942 3.8172 1.5346 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4773 -0.5208 -0.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0071 1.7356 1.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4669 0.9278 2.6761 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3283 -0.6056 2.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8131 1.7163 0.5510 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5543 -1.9047 0.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8871 -1.7161 0.6472 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 2 0 7 8 1 0 8 9 1 0 8 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 16 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 13 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 2 0 26 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 22 38 1 0 38 39 2 0 11 40 2 0 4 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 45 2 1 0 40 6 1 0 38 10 1 0 21 14 1 0 36 24 1 0 1 47 1 0 1 48 1 0 1 49 1 0 2 50 1 0 4 51 1 0 7 52 1 0 9 53 1 0 15 54 1 0 17 55 1 0 19 56 1 0 20 57 1 0 21 58 1 0 24 59 1 0 26 60 1 0 27 61 1 0 27 62 1 0 30 63 1 0 30 64 1 0 30 65 1 0 32 66 1 0 33 67 1 0 34 68 1 0 35 69 1 0 36 70 1 0 37 71 1 0 40 72 1 0 41 73 1 0 42 74 1 0 43 75 1 0 44 76 1 0 45 77 1 0 46 78 1 0 M END

Standard InCHIKey	QBFLREGYLMFMCL-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C29H32O17/c1-9-19(34)22(37)24(39)28(42-9)43-12-6-15(33)18-16(7-12)44-26(11-3-4-13(31)14(32)5-11)27(21(18)36)46-29-25(40)23(38)20(35)17(45-29)8-41-10(2)30/h3-7,9,17,19-20,22-25,28-29,31-35,37-40H,8H2,1-2H3
SMILES	CC1OC(OC2=CC(O)=C3C(OC(C4=CC(O)=C(O)C=C4)=C(OC4OC(COC(C)=O)C(O)C(O)C4O)C3=O)=C2)C(O)C(O)C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.16	Volume:	593.063 ? Van der Waals volume.
Dense:	1.1	LogP:	-0.401 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.502 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.647 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	31.0
TPSA:	275.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.834	Fsp³:	0.448
MCE-18:	125.143 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.242	Fluc inhibitor:	0.078 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.964 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.972 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.084	Promiscuous compounds:	0.349

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.204	MDCK Permeability:	-5.069
Pgp-inhibitor:	0.0	Pgp-substrate:	0.763
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):	0.996
20% Bioavailability (F20%):	0.976	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.678
Plasma Protein Binding (PPB):	77.25%	Volume Distribution (VD):	-0.239
Fu:	24.498% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.04
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.192
BSEP inhibitor:	0.015

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.982
HLM stability:	0.037 ? 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):

2.216

Half-life (T1/2):

4.249

ADMET: Toxicity

hERG Blockers:	0.03	hERG Blockers (10um):	0.464
Human Hepatotoxicity (H-HT):	0.368	Drug-induced Liver Injury (DILI):	0.932
AMES Toxicity:	0.819	Rat Oral Acute Toxicity:	0.238
Maximum Recommended Daily Dose:	0.33	Skin Sensitization:	0.376
Carcinogencity:	0.166	Eye Corrosion:	0.0
Eye Irritation:	0.008	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.984
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.018
Genotoxicity:	0.781	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.245	Hek293 Cytotoxicity:	0.655
BCF:	0.476 ? 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:	3.15 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.071 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.042 ? 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.	n.a.	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.	branch	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39355945]
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		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	Sprout Seedling	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	Oil	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	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]
NPO23510	Vicia faba	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
NPO23510	Vicia faba	Raw	n.a.	6.300000072	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

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 NPC490151 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	16932
0.1-0.2	29411
0.2-0.3	2599
0.3-0.4	429
0.4-0.5	248
0.5-0.6	113
0.6-0.7	74
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8205	Intermediate Similarity	NPC271692
0.7805	Intermediate Similarity	NPC605784
0.7791	Intermediate Similarity	NPC186816
0.7619	Intermediate Similarity	NPC116864
0.7619	Intermediate Similarity	NPC244776
0.75	Intermediate Similarity	NPC249281
0.7317	Intermediate Similarity	NPC46420
0.7294	Intermediate Similarity	NPC276377
0.7195	Intermediate Similarity	NPC158674
0.7195	Intermediate Similarity	NPC136042
0.7143	Intermediate Similarity	NPC72016
0.7143	Intermediate Similarity	NPC611303
0.7065	Intermediate Similarity	NPC486577
0.6977	Remote Similarity	NPC116458
0.6977	Remote Similarity	NPC246943
0.6966	Remote Similarity	NPC67105
0.6889	Remote Similarity	NPC203259
0.6889	Remote Similarity	NPC33054
0.6889	Remote Similarity	NPC210073
0.6889	Remote Similarity	NPC176740
0.6889	Remote Similarity	NPC471725
0.6889	Remote Similarity	NPC134532
0.6889	Remote Similarity	NPC150164
0.6889	Remote Similarity	NPC602582
0.6867	Remote Similarity	NPC238376
0.6848	Remote Similarity	NPC470443
0.6837	Remote Similarity	NPC480441
0.6742	Remote Similarity	NPC251417
0.6706	Remote Similarity	NPC84362
0.6706	Remote Similarity	NPC27640
0.6701	Remote Similarity	NPC121703
0.6667	Remote Similarity	NPC127546
0.6667	Remote Similarity	NPC57625
0.6667	Remote Similarity	NPC19709
0.6667	Remote Similarity	NPC173637
0.6667	Remote Similarity	NPC317489
0.6667	Remote Similarity	NPC223424
0.6667	Remote Similarity	NPC600591
0.6632	Remote Similarity	NPC473073
0.6598	Remote Similarity	NPC14187
0.6596	Remote Similarity	NPC229409
0.6596	Remote Similarity	NPC606657
0.6559	Remote Similarity	NPC126784
0.6559	Remote Similarity	NPC241423
0.6458	Remote Similarity	NPC471669
0.6444	Remote Similarity	NPC265115
0.6437	Remote Similarity	NPC59534
0.6395	Remote Similarity	NPC297987
0.6392	Remote Similarity	NPC470445
0.6383	Remote Similarity	NPC153755
0.6322	Remote Similarity	NPC305811
0.6316	Remote Similarity	NPC483414
0.6316	Remote Similarity	NPC483415
0.6279	Remote Similarity	NPC289667
0.625	Remote Similarity	NPC483416
0.6237	Remote Similarity	NPC173582
0.6237	Remote Similarity	NPC44931
0.6237	Remote Similarity	NPC265885
0.6237	Remote Similarity	NPC181465
0.6237	Remote Similarity	NPC67326
0.6237	Remote Similarity	NPC215710
0.6237	Remote Similarity	NPC473438
0.6237	Remote Similarity	NPC227508
0.6237	Remote Similarity	NPC253788
0.6196	Remote Similarity	NPC254540
0.6176	Remote Similarity	NPC25523
0.617	Remote Similarity	NPC156869
0.6162	Remote Similarity	NPC223426
0.6154	Remote Similarity	NPC190003
0.6129	Remote Similarity	NPC609888
0.6117	Remote Similarity	NPC277532
0.61	Remote Similarity	NPC81042
0.6092	Remote Similarity	NPC108831
0.6092	Remote Similarity	NPC182634
0.6082	Remote Similarity	NPC32641
0.6082	Remote Similarity	NPC256188
0.6082	Remote Similarity	NPC35119
0.6064	Remote Similarity	NPC39834
0.6042	Remote Similarity	NPC64425
0.6042	Remote Similarity	NPC64051
0.602	Remote Similarity	NPC142142
0.6	Remote Similarity	NPC22062
0.6	Remote Similarity	NPC470446
0.6	Remote Similarity	NPC65563
0.6	Remote Similarity	NPC473634
0.6	Remote Similarity	NPC470949
0.6	Remote Similarity	NPC138811
0.5979	Remote Similarity	NPC65711
0.5977	Remote Similarity	NPC111929
0.5977	Remote Similarity	NPC320283
0.5977	Remote Similarity	NPC473043
0.5977	Remote Similarity	NPC331652
0.5977	Remote Similarity	NPC41121
0.5957	Remote Similarity	NPC480466
0.5918	Remote Similarity	NPC37668
0.5918	Remote Similarity	NPC209296
0.5918	Remote Similarity	NPC473327
0.5876	Remote Similarity	NPC488073
0.5876	Remote Similarity	NPC488074
0.5843	Remote Similarity	NPC277205
0.5843	Remote Similarity	NPC37919
0.5825	Remote Similarity	NPC470451
0.5824	Remote Similarity	NPC175107
0.58	Remote Similarity	NPC476472
0.58	Remote Similarity	NPC294815
0.58	Remote Similarity	NPC16194
0.58	Remote Similarity	NPC89127
0.5795	Remote Similarity	NPC135599
0.5795	Remote Similarity	NPC73855
0.5795	Remote Similarity	NPC113968
0.5795	Remote Similarity	NPC328940
0.5795	Remote Similarity	NPC277174
0.5795	Remote Similarity	NPC606877
0.5773	Remote Similarity	NPC473571
0.5773	Remote Similarity	NPC110941
0.5769	Remote Similarity	NPC292019
0.5769	Remote Similarity	NPC202908
0.5743	Remote Similarity	NPC101636
0.5743	Remote Similarity	NPC298171
0.5727	Remote Similarity	NPC209550
0.5714	Remote Similarity	NPC46202
0.57	Remote Similarity	NPC270675
0.57	Remote Similarity	NPC195685
0.567	Remote Similarity	NPC233994
0.5667	Remote Similarity	NPC145038
0.5667	Remote Similarity	NPC56077
0.5667	Remote Similarity	NPC281131
0.5667	Remote Similarity	NPC253662
0.5667	Remote Similarity	NPC179950
0.5667	Remote Similarity	NPC88789
0.5667	Remote Similarity	NPC189142
0.5667	Remote Similarity	NPC77660
0.5667	Remote Similarity	NPC491374
0.5652	Remote Similarity	NPC219904
0.5652	Remote Similarity	NPC488071
0.5644	Remote Similarity	NPC80068
0.5644	Remote Similarity	NPC470447
0.5644	Remote Similarity	NPC85751
0.5644	Remote Similarity	NPC19240
0.5638	Remote Similarity	NPC355481
0.5636	Remote Similarity	NPC488078
0.5631	Remote Similarity	NPC214621
0.5631	Remote Similarity	NPC34267
0.5625	Remote Similarity	NPC471079
0.5604	Remote Similarity	NPC349108
0.56	Remote Similarity	NPC122467
0.5579	Remote Similarity	NPC172807
0.5579	Remote Similarity	NPC477848
0.5567	Remote Similarity	NPC275454
0.5556	Remote Similarity	NPC240306
0.5534	Remote Similarity	NPC472994
0.5532	Remote Similarity	NPC223747
0.551	Remote Similarity	NPC605592
0.55	Remote Similarity	NPC211532
0.55	Remote Similarity	NPC488364
0.5455	Remote Similarity	NPC129264
0.5446	Remote Similarity	NPC270448
0.5443	Remote Similarity	NPC188871
0.5429	Remote Similarity	NPC11468
0.5417	Remote Similarity	NPC211594
0.5405	Remote Similarity	NPC488740
0.54	Remote Similarity	NPC154741
0.5393	Remote Similarity	NPC276222
0.5393	Remote Similarity	NPC274618
0.5393	Remote Similarity	NPC118284
0.5393	Remote Similarity	NPC608147
0.5392	Remote Similarity	NPC488089
0.5392	Remote Similarity	NPC64755
0.5385	Remote Similarity	NPC470450
0.5376	Remote Similarity	NPC42773
0.5376	Remote Similarity	NPC45522
0.5376	Remote Similarity	NPC599850
0.5357	Remote Similarity	NPC480444
0.5354	Remote Similarity	NPC303913
0.534	Remote Similarity	NPC483413
0.534	Remote Similarity	NPC483412
0.5333	Remote Similarity	NPC470455
0.5333	Remote Similarity	NPC67037
0.5333	Remote Similarity	NPC255615
0.5327	Remote Similarity	NPC480796
0.5327	Remote Similarity	NPC472993
0.5326	Remote Similarity	NPC265530
0.5321	Remote Similarity	NPC139571
0.5294	Remote Similarity	NPC473623
0.5288	Remote Similarity	NPC36138
0.5288	Remote Similarity	NPC470449
0.5278	Remote Similarity	NPC217520
0.5268	Remote Similarity	NPC488736
0.5268	Remote Similarity	NPC488733
0.5258	Remote Similarity	NPC95866
0.5248	Remote Similarity	NPC470125
0.5238	Remote Similarity	NPC135358
0.5234	Remote Similarity	NPC189564
0.5213	Remote Similarity	NPC27942
0.521	Remote Similarity	NPC223860
0.5204	Remote Similarity	NPC480463
0.52	Remote Similarity	NPC293626
0.5185	Remote Similarity	NPC477895
0.5179	Remote Similarity	NPC298666
0.5175	Remote Similarity	NPC488737

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC490151 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4696
0.1-0.2	4392
0.2-0.3	51
0.3-0.4	5
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	1
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
0.7753	Intermediate Similarity	NPD7251	Phase 2
0.6889	Remote Similarity	NPD6797	Phase 2
0.6531	Remote Similarity	NPD7808	Phase 3
0.5918	Remote Similarity	NPD7054	Phase 4

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