NPASS Compound

Natural Product: NPC477895

Natural Product ID	NPC477895
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2R,3S,4S,5R,6S)-6-[2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	118707633
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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 76 80 0 0 0 0 0 0 0 0999 V2000 -4.0743 -5.5506 0.3361 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7157 -4.4968 0.9916 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4084 -3.1658 0.8235 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0942 -2.1938 1.5109 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7876 -0.8688 1.3430 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7700 -0.4144 0.4741 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1148 -1.3879 -0.1883 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4239 -2.7468 -0.0202 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6027 1.0299 0.3684 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4986 1.7185 -0.0228 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5519 3.1362 -0.0435 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5609 3.8298 -0.3953 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6932 3.7916 0.3242 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7478 5.1882 0.3050 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9295 5.7552 0.6899 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0258 5.0078 1.0813 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9630 3.6321 1.0972 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7711 3.0261 0.7100 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6861 1.7320 0.7164 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2129 5.6595 1.4658 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6550 5.9444 -0.0850 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3439 1.1797 -0.3904 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6973 0.7618 -1.5401 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1712 1.8271 -2.2039 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4244 2.0766 -1.4148 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1807 0.7836 -1.3399 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3423 -0.4393 -1.3856 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0125 -0.3604 -1.2606 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7989 -1.4324 -0.2843 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1611 -1.6114 -0.2374 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9306 -2.1025 -1.2385 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4370 -2.4492 -2.3291 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3837 -2.2078 -0.9786 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9177 -1.8443 0.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3378 -1.9261 0.4823 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7280 -1.4899 1.7518 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0624 -1.5512 2.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0320 -2.0234 1.2059 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6076 -2.4435 -0.0332 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2598 -2.3952 -0.3971 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3819 -2.0693 1.5754 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2116 0.7829 -2.2899 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2225 2.6117 -0.1597 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6164 1.3065 -3.4519 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1080 -2.5704 2.3850 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8127 -1.5976 3.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5198 -6.5272 0.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0188 -5.5754 0.6858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0345 -5.4261 -0.7648 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3752 -0.1624 1.9248 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3582 -1.1384 -0.8939 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8522 -3.4777 -0.5883 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0251 6.8315 0.6930 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8322 3.0707 1.4061 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3678 6.5754 1.0514 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8916 6.1770 0.5424 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4613 0.5405 -2.3617 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3163 2.7510 -2.4413 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0718 2.8167 -1.9577 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7277 0.8056 -0.3494 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6648 -0.9897 -2.3344 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3763 -1.0133 0.6474 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2341 -2.3766 -0.5104 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9880 -2.5971 -1.7777 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1991 -1.4618 0.9055 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9791 -1.1095 2.4655 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3927 -1.2149 3.0663 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3297 -2.8251 -0.7605 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9442 -2.7284 -1.3739 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8002 -1.1758 1.8769 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9815 1.3053 -1.9646 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6575 2.0848 0.4285 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1585 1.2504 -4.0752 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1501 -0.8896 3.6659 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5330 -2.0233 3.8151 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4224 -0.9391 2.4085 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 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 16 20 1 0 14 21 1 0 10 22 1 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 27 29 1 0 29 30 1 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 39 40 2 0 38 41 1 0 26 42 1 0 25 43 1 0 24 44 1 0 4 45 1 0 45 46 1 0 8 3 1 0 19 9 1 0 18 13 1 0 28 23 1 0 40 35 1 0 1 47 1 0 1 48 1 0 1 49 1 0 5 50 1 0 7 51 1 0 8 52 1 0 15 53 1 0 17 54 1 0 20 55 1 0 21 56 1 0 23 57 1 6 24 58 1 6 25 59 1 6 26 60 1 1 27 61 1 6 29 62 1 0 29 63 1 0 33 64 1 0 34 65 1 0 36 66 1 0 37 67 1 0 39 68 1 0 40 69 1 0 41 70 1 0 42 71 1 0 43 72 1 0 44 73 1 0 46 74 1 0 46 75 1 0 46 76 1 0 M END

Standard InCHIKey	NIGHTWHFGRAECY-VOLQWMFUSA-N
Standard InCHI	InChI=1S/C32H30O14/c1-41-20-9-6-16(11-21(20)42-2)30-31(27(38)25-19(35)12-18(34)13-22(25)44-30)46-32-29(40)28(39)26(37)23(45-32)14-43-24(36)10-5-15-3-7-17(33)8-4-15/h3-13,23,26,28-29,32-35,37,39-40H,14H2,1-2H3/b10-5+/t23-,26-,28+,29-,32+/m1/s1
SMILES	COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)/C=C/C5=CC=C(C=C5)O)O)O)O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.16	Volume:	608.035 ? Van der Waals volume.
Dense:	1.05	LogP:	2.092 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.066 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.678 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	32.0
TPSA:	214.81 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.114	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.188	Fsp³:	0.25
MCE-18:	107.25 ? 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:	0.73	Fluc inhibitor:	0.96 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.908 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.987 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.037	Promiscuous compounds:	0.499

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.081	MDCK Permeability:	-5.396
Pgp-inhibitor:	0.328	Pgp-substrate:	0.051
PAMPA:	0.55 ? 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):	0.113
20% Bioavailability (F20%):	0.472	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	94.449%	Volume Distribution (VD):	-0.199
Fu:	4.825% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.897
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.881
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.987
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.989 ? 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):

2.254

Half-life (T1/2):

3.536

ADMET: Toxicity

hERG Blockers:	0.074	hERG Blockers (10um):	0.4
Human Hepatotoxicity (H-HT):	0.555	Drug-induced Liver Injury (DILI):	0.927
AMES Toxicity:	0.852	Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.575	Skin Sensitization:	0.995
Carcinogencity:	0.323	Eye Corrosion:	0.0
Eye Irritation:	0.4	Respiratory Toxicity:	0.028
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.635
Hematotoxicity:	0.039	Drug-induced Nephrotoxicity:	0.245
Genotoxicity:	0.956	RPMI-8226 Immunitoxicity:	0.125
A549 Cytotoxicity:	0.352	Hek293 Cytotoxicity:	0.906
BCF:	0.904 ? 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:	3.736 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.907 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.478 ? 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
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880314]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1294695]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104516]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	leaves and twigs	Taiwan	n.a.	PMID[1659612]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	aerial parts	Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China	2012-OCT	PMID[24955889]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	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
EC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1618	Individual protein	Peroxisome proliferator-activated receptor gamma	Mus musculus	EC50	>	100000	nM	PMID[24955889]

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 NPC477895 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	15052
0.1-0.2	29805
0.2-0.3	3796
0.3-0.4	736
0.4-0.5	252
0.5-0.6	146
0.6-0.7	38
0.7-0.8	0
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.883	High Similarity	NPC217520
0.8681	High Similarity	NPC85751
0.8681	High Similarity	NPC19240
0.8495	Intermediate Similarity	NPC223426
0.8081	Intermediate Similarity	NPC139571
0.8021	Intermediate Similarity	NPC214621
0.8021	Intermediate Similarity	NPC34267
0.7835	Intermediate Similarity	NPC81042
0.7629	Intermediate Similarity	NPC36138
0.7347	Intermediate Similarity	NPC477629
0.7129	Intermediate Similarity	NPC96605
0.7129	Intermediate Similarity	NPC280642
0.7113	Intermediate Similarity	NPC470125
0.7113	Intermediate Similarity	NPC153755
0.703	Intermediate Similarity	NPC218161
0.699	Remote Similarity	NPC470416
0.6916	Remote Similarity	NPC474093
0.6916	Remote Similarity	NPC104910
0.6701	Remote Similarity	NPC609888
0.6667	Remote Similarity	NPC129264
0.6667	Remote Similarity	NPC116864
0.6667	Remote Similarity	NPC244776
0.6637	Remote Similarity	NPC25946
0.6471	Remote Similarity	NPC104883
0.6471	Remote Similarity	NPC488679
0.6435	Remote Similarity	NPC21359
0.6435	Remote Similarity	NPC460984
0.6389	Remote Similarity	NPC470712
0.6372	Remote Similarity	NPC241781
0.6346	Remote Similarity	NPC80068
0.6346	Remote Similarity	NPC476472
0.6346	Remote Similarity	NPC294815
0.6346	Remote Similarity	NPC16194
0.6311	Remote Similarity	NPC473327
0.6283	Remote Similarity	NPC488079
0.6273	Remote Similarity	NPC470718
0.62	Remote Similarity	NPC471079
0.6195	Remote Similarity	NPC156785
0.6195	Remote Similarity	NPC162394
0.6186	Remote Similarity	NPC473554
0.6179	Remote Similarity	NPC475179
0.6154	Remote Similarity	NPC270448
0.614	Remote Similarity	NPC488078
0.6139	Remote Similarity	NPC173582
0.6139	Remote Similarity	NPC265885
0.6139	Remote Similarity	NPC181465
0.6139	Remote Similarity	NPC215710
0.6139	Remote Similarity	NPC473438
0.6139	Remote Similarity	NPC253788
0.6095	Remote Similarity	NPC270675
0.6095	Remote Similarity	NPC195685
0.6	Remote Similarity	NPC37668
0.6	Remote Similarity	NPC480796
0.5981	Remote Similarity	NPC260504
0.5981	Remote Similarity	NPC89809
0.598	Remote Similarity	NPC67326
0.5965	Remote Similarity	NPC470713
0.596	Remote Similarity	NPC223747
0.5943	Remote Similarity	NPC205824
0.5926	Remote Similarity	NPC483767
0.5926	Remote Similarity	NPC483769
0.5926	Remote Similarity	NPC470450
0.5926	Remote Similarity	NPC483768
0.5926	Remote Similarity	NPC483766
0.5922	Remote Similarity	NPC203259
0.5922	Remote Similarity	NPC33054
0.5922	Remote Similarity	NPC176740
0.5922	Remote Similarity	NPC471725
0.5922	Remote Similarity	NPC134532
0.5922	Remote Similarity	NPC156869
0.5922	Remote Similarity	NPC602582
0.5918	Remote Similarity	NPC175107
0.5918	Remote Similarity	NPC219904
0.5913	Remote Similarity	NPC474522
0.5902	Remote Similarity	NPC487502
0.59	Remote Similarity	NPC203050
0.59	Remote Similarity	NPC225434
0.5872	Remote Similarity	NPC478277
0.5872	Remote Similarity	NPC483765
0.5872	Remote Similarity	NPC478276
0.5872	Remote Similarity	NPC478275
0.5872	Remote Similarity	NPC92815
0.5859	Remote Similarity	NPC120099
0.5856	Remote Similarity	NPC472993
0.5816	Remote Similarity	NPC472459
0.5794	Remote Similarity	NPC221288
0.5794	Remote Similarity	NPC194836
0.5794	Remote Similarity	NPC91493
0.5794	Remote Similarity	NPC605081
0.578	Remote Similarity	NPC472994
0.5741	Remote Similarity	NPC471669
0.5729	Remote Similarity	NPC111929
0.5729	Remote Similarity	NPC320283
0.5729	Remote Similarity	NPC41121
0.5726	Remote Similarity	NPC249560
0.5714	Remote Similarity	NPC48984
0.5714	Remote Similarity	NPC10205
0.5676	Remote Similarity	NPC599948
0.5673	Remote Similarity	NPC39834
0.567	Remote Similarity	NPC77672
0.567	Remote Similarity	NPC133671
0.567	Remote Similarity	NPC135391
0.567	Remote Similarity	NPC78263
0.567	Remote Similarity	NPC250069
0.566	Remote Similarity	NPC296018
0.5648	Remote Similarity	NPC101399
0.5648	Remote Similarity	NPC217822
0.5648	Remote Similarity	NPC11847
0.5648	Remote Similarity	NPC198938
0.5625	Remote Similarity	NPC189564
0.5612	Remote Similarity	NPC64305
0.5612	Remote Similarity	NPC265530
0.56	Remote Similarity	NPC60735
0.56	Remote Similarity	NPC26230
0.5586	Remote Similarity	NPC603856
0.5579	Remote Similarity	NPC291153
0.5556	Remote Similarity	NPC476620
0.5547	Remote Similarity	NPC487501
0.5545	Remote Similarity	NPC609478
0.5536	Remote Similarity	NPC121703
0.5528	Remote Similarity	NPC275977
0.5528	Remote Similarity	NPC231787
0.5514	Remote Similarity	NPC154741
0.551	Remote Similarity	NPC127546
0.551	Remote Similarity	NPC57625
0.551	Remote Similarity	NPC173637
0.551	Remote Similarity	NPC317489
0.551	Remote Similarity	NPC223424
0.551	Remote Similarity	NPC600591
0.55	Remote Similarity	NPC325555
0.55	Remote Similarity	NPC226304
0.547	Remote Similarity	NPC488734
0.547	Remote Similarity	NPC488735
0.547	Remote Similarity	NPC488739
0.547	Remote Similarity	NPC488732
0.547	Remote Similarity	NPC488738
0.5455	Remote Similarity	NPC145038
0.5455	Remote Similarity	NPC56077
0.5455	Remote Similarity	NPC281131
0.5455	Remote Similarity	NPC470447
0.5455	Remote Similarity	NPC253662
0.5455	Remote Similarity	NPC179950
0.5455	Remote Similarity	NPC88789
0.5455	Remote Similarity	NPC491374
0.544	Remote Similarity	NPC30011
0.544	Remote Similarity	NPC72554
0.5439	Remote Similarity	NPC292019
0.5439	Remote Similarity	NPC202908
0.5439	Remote Similarity	NPC173837
0.5431	Remote Similarity	NPC470716
0.5421	Remote Similarity	NPC473571
0.5421	Remote Similarity	NPC110941
0.5417	Remote Similarity	NPC54802
0.5417	Remote Similarity	NPC197304
0.5398	Remote Similarity	NPC89052
0.5393	Remote Similarity	NPC603596
0.5391	Remote Similarity	NPC470715
0.5391	Remote Similarity	NPC164704
0.5378	Remote Similarity	NPC488740
0.5378	Remote Similarity	NPC488736
0.5378	Remote Similarity	NPC488733
0.537	Remote Similarity	NPC488074
0.5361	Remote Similarity	NPC288084
0.5349	Remote Similarity	NPC487500
0.534	Remote Similarity	NPC88023
0.534	Remote Similarity	NPC309025
0.5333	Remote Similarity	NPC470720
0.5294	Remote Similarity	NPC159579
0.5289	Remote Similarity	NPC488737
0.5271	Remote Similarity	NPC97817
0.5268	Remote Similarity	NPC470449
0.5268	Remote Similarity	NPC470445
0.5253	Remote Similarity	NPC135599
0.5253	Remote Similarity	NPC73855
0.5253	Remote Similarity	NPC113968
0.5253	Remote Similarity	NPC328940
0.5253	Remote Similarity	NPC277174
0.5253	Remote Similarity	NPC606877
0.5229	Remote Similarity	NPC488073
0.5229	Remote Similarity	NPC126784
0.5229	Remote Similarity	NPC241423
0.5204	Remote Similarity	NPC276222
0.5204	Remote Similarity	NPC274618
0.5204	Remote Similarity	NPC118284
0.5204	Remote Similarity	NPC608147
0.52	Remote Similarity	NPC19388
0.52	Remote Similarity	NPC240431
0.52	Remote Similarity	NPC55786
0.5192	Remote Similarity	NPC209023
0.5182	Remote Similarity	NPC12013
0.5182	Remote Similarity	NPC11432
0.5182	Remote Similarity	NPC477613
0.5175	Remote Similarity	NPC470455
0.5167	Remote Similarity	NPC480445
0.5152	Remote Similarity	NPC67037
0.5152	Remote Similarity	NPC255615
0.5149	Remote Similarity	NPC33083
0.514	Remote Similarity	NPC187379
0.513	Remote Similarity	NPC203145

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4179
0.1-0.2	4900
0.2-0.3	59
0.3-0.4	7
0.4-0.5	3
0.5-0.6	2
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
0.5922	Remote Similarity	NPD6797	Phase 2
0.5263	Remote Similarity	NPD7808	Phase 3

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