NPASS Compound

Natural Product: NPC592383

Natural Product ID	NPC592383
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Nitensoside B
IUPAC Name	2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
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

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 1.4264 -3.5763 -0.2640 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9167 -2.2715 -0.4401 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8234 -1.2173 -0.4319 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1688 -1.4214 -0.2597 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0626 -0.3741 -0.2524 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5779 0.9319 -0.4261 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2472 1.1558 -0.5984 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7629 2.4356 -0.7696 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3723 0.1049 -0.6033 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0311 0.2630 -0.7710 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9421 0.4629 0.2045 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7122 -0.7279 0.2327 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4969 -0.7737 1.3774 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4363 -1.9219 1.3097 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2587 -2.0957 0.2845 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1887 -1.2568 -0.1485 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5065 -1.7890 -0.0193 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4121 -0.7611 -0.0414 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4609 -0.0452 1.3157 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2771 0.1961 -1.1594 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3492 0.0739 -2.0755 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9981 0.2110 -1.8999 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2221 1.3654 -1.6726 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1192 -0.9803 -1.6596 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8437 -0.8348 -2.1218 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9530 0.4956 1.9528 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4117 0.6836 3.2700 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7594 1.7390 1.1535 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9498 2.4229 0.9129 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9136 1.5578 -0.0857 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3052 2.7467 -0.4753 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4632 1.9809 -0.4200 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0734 3.1532 -0.5706 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8129 1.6815 -0.2387 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2525 0.3928 -0.0717 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6665 0.0937 0.1169 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0438 -1.2464 0.2795 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3629 -1.6030 0.4629 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3698 -0.6647 0.4953 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7053 -1.0036 0.6791 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0087 0.6562 0.3362 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9927 1.6413 0.3616 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6686 1.0253 0.1493 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3471 -0.5561 -0.0891 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8818 -3.7102 0.7486 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2016 -3.8421 -0.9905 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5485 -4.2592 -0.2901 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5471 -2.4165 -0.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7713 3.1370 -0.0353 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4764 0.5037 1.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6978 -1.1506 2.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7725 -2.8640 1.3515 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9781 -2.0354 2.3239 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2236 -0.3126 0.3726 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4318 -1.2441 -0.1252 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4525 0.4969 1.3008 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6492 0.6691 1.4417 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5045 -0.8472 2.0730 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4254 1.2343 -0.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5859 0.9413 -2.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1930 0.2300 -3.0027 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7558 2.0688 -1.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5975 -1.8623 -2.1826 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6887 -0.0519 -2.6910 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0571 0.4225 2.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6304 1.3143 3.1932 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1615 2.4596 1.7948 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8054 3.4003 0.8622 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5253 1.2475 -0.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0156 2.6678 -1.4174 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5120 2.5160 -0.2346 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2411 -1.9844 0.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6278 -2.6402 0.5855 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1572 -0.7602 1.5602 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0749 2.2439 1.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4243 2.0778 0.0275 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 1 0 7 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 13 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 6 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 39 41 1 0 41 42 1 0 41 43 2 0 35 44 1 0 9 3 1 0 30 11 1 0 43 36 1 0 44 5 1 0 24 16 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 8 49 1 0 11 50 1 1 13 51 1 1 14 52 1 0 14 53 1 0 16 54 1 1 18 55 1 6 19 56 1 0 19 57 1 0 19 58 1 0 20 59 1 1 21 60 1 0 22 61 1 6 23 62 1 0 24 63 1 6 25 64 1 0 26 65 1 1 27 66 1 0 28 67 1 1 29 68 1 0 30 69 1 6 31 70 1 0 34 71 1 0 37 72 1 0 38 73 1 0 40 74 1 0 42 75 1 0 43 76 1 0 M END

Standard InCHIKey	MTUPEWBIUKFRBD-PCIFUKDKSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-19(32)22(35)24(37)27(41-9)40-8-17-20(33)23(36)25(38)28(43-17)44-26-16(39-2)7-15-18(21(26)34)13(31)6-14(42-15)10-3-4-11(29)12(30)5-10/h3-7,9,17,19-20,22-25,27-30,32-38H,8H2,1-2H3/t9-,17+,19-,20+,22+,23-,24+,25+,27+,28-/m0/s1
SMILES	COC1=CC2=C(C(O)=C1O[C@@H]1O[C@H](CO[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]1O)C(=O)C=C(C1=CC=C(O)C(O)=C1)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.258 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.817 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.429 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	258.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.137	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.782	Fsp³:	0.464
MCE-18:	122.073 ? 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:	0.608	Fluc inhibitor:	0.268 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.934 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.695 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.075	Promiscuous compounds:	0.465

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.306	MDCK Permeability:	-5.332
Pgp-inhibitor:	0.0	Pgp-substrate:	0.5
PAMPA:	0.998 ? 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):	0.428
20% Bioavailability (F20%):	0.768	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.546
Plasma Protein Binding (PPB):	82.705%	Volume Distribution (VD):	-0.031
Fu:	14.938% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.376
BSEP inhibitor:	0.003

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:	0.005
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.071
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.904
HLM stability:	0.028 ? 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):

1.96

Half-life (T1/2):

4.729

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.249
Human Hepatotoxicity (H-HT):	0.253	Drug-induced Liver Injury (DILI):	0.857
AMES Toxicity:	0.799	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.038	Skin Sensitization:	0.987
Carcinogencity:	0.03	Eye Corrosion:	0.0
Eye Irritation:	0.147	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.972
Hematotoxicity:	0.052	Drug-induced Nephrotoxicity:	0.12
Genotoxicity:	0.565	RPMI-8226 Immunitoxicity:	0.071
A549 Cytotoxicity:	0.528	Hek293 Cytotoxicity:	0.28
BCF:	0.438 ? 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:	3.052 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.635 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.784 ? 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
NPO10824	Pterogyne nitens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159272]
NPO10824	Pterogyne nitens	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19159272]
NPO10824	Pterogyne nitens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10824	Pterogyne nitens	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

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 NPC592383 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	19788
0.1-0.2	26087
0.2-0.3	2933
0.3-0.4	644
0.4-0.5	274
0.5-0.6	89
0.6-0.7	25
0.7-0.8	1
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8293	Intermediate Similarity	NPC254540
0.8	Intermediate Similarity	NPC210073
0.7907	Intermediate Similarity	NPC204693
0.7326	Intermediate Similarity	NPC172807
0.7229	Intermediate Similarity	NPC45638
0.7079	Intermediate Similarity	NPC44931
0.7065	Intermediate Similarity	NPC209296
0.7	Intermediate Similarity	NPC22062
0.7	Intermediate Similarity	NPC473634
0.7	Intermediate Similarity	NPC138811
0.6915	Remote Similarity	NPC473073
0.6774	Remote Similarity	NPC470443
0.6744	Remote Similarity	NPC201292
0.6703	Remote Similarity	NPC67105
0.6667	Remote Similarity	NPC126784
0.6667	Remote Similarity	NPC241423
0.6556	Remote Similarity	NPC211594
0.6526	Remote Similarity	NPC483707
0.6517	Remote Similarity	NPC99957
0.6421	Remote Similarity	NPC65711
0.6395	Remote Similarity	NPC19709
0.6322	Remote Similarity	NPC93337
0.6316	Remote Similarity	NPC475366
0.6277	Remote Similarity	NPC203259
0.6277	Remote Similarity	NPC33054
0.6277	Remote Similarity	NPC176740
0.6277	Remote Similarity	NPC471725
0.6277	Remote Similarity	NPC134532
0.6277	Remote Similarity	NPC602582
0.625	Remote Similarity	NPC27640
0.6105	Remote Similarity	NPC233994
0.6042	Remote Similarity	NPC473571
0.6042	Remote Similarity	NPC110941
0.6042	Remote Similarity	NPC186816
0.6	Remote Similarity	NPC227508
0.5938	Remote Similarity	NPC473512
0.5918	Remote Similarity	NPC211532
0.5918	Remote Similarity	NPC488364
0.5897	Remote Similarity	NPC25270
0.5889	Remote Similarity	NPC105025
0.587	Remote Similarity	NPC605067
0.5859	Remote Similarity	NPC473623
0.5859	Remote Similarity	NPC229409
0.5843	Remote Similarity	NPC58053
0.5842	Remote Similarity	NPC101636
0.5833	Remote Similarity	NPC173582
0.5833	Remote Similarity	NPC265885
0.5833	Remote Similarity	NPC181465
0.5833	Remote Similarity	NPC215710
0.5833	Remote Similarity	NPC473438
0.5833	Remote Similarity	NPC253788
0.5816	Remote Similarity	NPC488073
0.58	Remote Similarity	NPC488089
0.5773	Remote Similarity	NPC129827
0.5773	Remote Similarity	NPC65563
0.5773	Remote Similarity	NPC470949
0.5761	Remote Similarity	NPC609451
0.5745	Remote Similarity	NPC190003
0.5743	Remote Similarity	NPC476472
0.5743	Remote Similarity	NPC294815
0.5743	Remote Similarity	NPC16194
0.5673	Remote Similarity	NPC11468
0.567	Remote Similarity	NPC39834
0.5657	Remote Similarity	NPC488074
0.5638	Remote Similarity	NPC602805
0.5604	Remote Similarity	NPC189142
0.5604	Remote Similarity	NPC77660
0.5556	Remote Similarity	NPC473043
0.5556	Remote Similarity	NPC115674
0.5556	Remote Similarity	NPC331652
0.5545	Remote Similarity	NPC473327
0.5543	Remote Similarity	NPC186807
0.5543	Remote Similarity	NPC58716
0.5543	Remote Similarity	NPC271692
0.5514	Remote Similarity	NPC480441
0.5484	Remote Similarity	NPC117260
0.5481	Remote Similarity	NPC470446
0.5455	Remote Similarity	NPC156869
0.5446	Remote Similarity	NPC483414
0.5446	Remote Similarity	NPC483415
0.5408	Remote Similarity	NPC187379
0.5408	Remote Similarity	NPC473657
0.5405	Remote Similarity	NPC198199
0.5392	Remote Similarity	NPC483416
0.5385	Remote Similarity	NPC298171
0.5385	Remote Similarity	NPC470445
0.537	Remote Similarity	NPC473644
0.5368	Remote Similarity	NPC181616
0.5354	Remote Similarity	NPC15358
0.5354	Remote Similarity	NPC67326
0.5347	Remote Similarity	NPC475497
0.534	Remote Similarity	NPC142142
0.5326	Remote Similarity	NPC238376
0.5321	Remote Similarity	NPC311850
0.53	Remote Similarity	NPC218488
0.5294	Remote Similarity	NPC469622
0.5269	Remote Similarity	NPC168822
0.5263	Remote Similarity	NPC120952
0.5263	Remote Similarity	NPC488071
0.5253	Remote Similarity	NPC295613
0.5243	Remote Similarity	NPC122467
0.5217	Remote Similarity	NPC114740
0.5213	Remote Similarity	NPC305811
0.52	Remote Similarity	NPC275454
0.5196	Remote Similarity	NPC46202
0.5196	Remote Similarity	NPC284277
0.5196	Remote Similarity	NPC64051
0.5179	Remote Similarity	NPC68592
0.5149	Remote Similarity	NPC303913
0.5143	Remote Similarity	NPC89127
0.5138	Remote Similarity	NPC292019
0.5138	Remote Similarity	NPC202908
0.5133	Remote Similarity	NPC298666
0.5096	Remote Similarity	NPC150767
0.5091	Remote Similarity	NPC25523
0.5053	Remote Similarity	NPC46420
0.5052	Remote Similarity	NPC606560
0.5051	Remote Similarity	NPC294629
0.5051	Remote Similarity	NPC116864
0.5051	Remote Similarity	NPC244776
0.5051	Remote Similarity	NPC131407
0.5048	Remote Similarity	NPC270675
0.5048	Remote Similarity	NPC195685
0.5048	Remote Similarity	NPC486577

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC592383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5201
0.1-0.2	3888
0.2-0.3	50
0.3-0.4	6
0.4-0.5	0
0.5-0.6	1
0.6-0.7	3
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
0.7065	Intermediate Similarity	NPD7054	Phase 4
0.6277	Remote Similarity	NPD6797	Phase 2
0.6224	Remote Similarity	NPD7251	Phase 2
0.6139	Remote Similarity	NPD7472	Pre-clinical
0.5377	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