NPASS Compound

Natural Product: NPC512597

Natural Product ID	NPC512597
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Luteolin 7-glucuronide-3'-glucoside
IUPAC Name	(3~{S},4~{S},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-[4-hydroxy-3-[(2~{S},4~{S},5~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 72 76 0 0 0 0 0 0 0 0999 V2000 10.1679 -1.8809 1.3010 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1685 -1.1788 1.5512 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6604 -1.1486 2.8309 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5382 -0.3907 0.4908 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4368 0.3345 0.9372 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6320 0.5516 -0.2183 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3587 0.9245 0.0992 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2165 0.2261 -0.2089 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2459 -0.9586 -0.8909 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0370 -1.6000 -1.1609 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0586 -2.8099 -1.8567 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8247 -1.0786 -0.7636 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6275 -1.7118 -1.0298 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6501 -2.7870 -1.6484 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5549 -1.1075 -0.5873 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5406 0.0878 0.0973 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7720 0.7380 0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6193 1.9471 1.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6952 2.6255 1.7275 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9371 2.0873 1.5200 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0276 2.7797 2.0059 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1425 0.8770 0.8428 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4348 0.4592 0.7085 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8646 -0.7032 0.0767 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6762 -0.4529 -1.0301 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8266 0.2365 -0.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8194 0.0259 -1.8452 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0133 0.6937 -1.5882 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4960 -0.2947 0.5456 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8708 -0.2939 0.4697 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0142 -1.7249 0.7255 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6872 -2.2965 1.8006 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5414 -1.6523 1.0504 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9866 -2.9130 1.0495 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0173 0.2302 0.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6266 0.6314 0.3145 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7791 0.1150 -0.0752 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9666 0.7466 0.1909 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3679 1.5698 -1.0810 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2714 1.1996 -2.4128 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7595 1.8410 -0.6206 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7769 2.8436 0.3463 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4830 0.5962 -0.1570 C 0 0 2 0 0 0 0 0 0 0 0 0 10.1461 -0.0551 -1.1831 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8432 -1.8755 3.5282 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1846 -1.0662 -0.3342 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6890 -0.3979 -0.7692 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1475 -1.4278 -1.2331 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4740 -2.8176 -2.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4788 -1.6213 -0.8071 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6258 2.3532 1.4029 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5221 3.5571 2.2476 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7084 3.1864 1.3879 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9949 -1.2565 -0.3141 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7025 1.3127 -0.5910 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9916 -1.0663 -2.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4320 0.4292 -2.8017 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1968 1.4354 -2.1894 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1400 0.2941 1.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2713 0.4825 0.9491 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1933 -2.2418 -0.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1986 -3.1167 1.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4277 -1.2180 2.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0202 -3.2815 1.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1204 -0.7015 -0.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9734 1.6838 0.7280 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7893 2.5305 -0.9828 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3033 1.3344 -2.6669 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3388 2.2354 -1.4891 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6025 2.4800 1.2567 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2259 0.8895 0.6190 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1906 0.5558 -1.9586 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 10 12 2 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 20 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 26 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 22 35 2 0 16 36 1 0 36 37 1 0 37 38 2 0 6 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 4 1 0 38 8 1 0 37 12 1 0 35 17 1 0 33 24 1 0 3 45 1 0 4 46 1 0 6 47 1 6 9 48 1 0 11 49 1 0 15 50 1 0 18 51 1 0 19 52 1 0 21 53 1 0 24 54 1 6 26 55 1 0 27 56 1 0 27 57 1 0 28 58 1 0 29 59 1 1 30 60 1 0 31 61 1 6 32 62 1 0 33 63 1 0 34 64 1 0 35 65 1 0 38 66 1 0 39 67 1 0 40 68 1 0 41 69 1 6 42 70 1 0 43 71 1 1 44 72 1 0 M END

Standard InCHIKey	RISDMLSLRAZUPQ-ZXJFBCABSA-N
Standard InCHI	InChI=1S/C27H28O17/c28-7-16-18(32)19(33)22(36)27(43-16)42-14-3-8(1-2-10(14)29)13-6-12(31)17-11(30)4-9(5-15(17)41-13)40-26-23(37)20(34)21(35)24(44-26)25(38)39/h1-6,16,18-24,26-30,32-37H,7H2,(H,38,39)/t16?,18-,19+,20+,21+,22?,23?,24?,26-,27-/m1/s1
SMILES	O=C(O)C1O[C@@H](OC2=CC(O)=C3C(=O)C=C(C4=CC=C(O)C(O[C@@H]5OC(CO)[C@@H](O)[C@H](O)C5O)=C4)OC3=C2)C(O)[C@@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.13	Volume:	558.471 ? Van der Waals volume.
Dense:	1.118	LogP:	-0.647 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.506 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.886 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	31.0
TPSA:	286.5 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.128	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.759	Fsp³:	0.407
MCE-18:	123.421 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.469	Fluc inhibitor:	0.24 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.982 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.954 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.349	Promiscuous compounds:	0.328

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.526	MDCK Permeability:	-5.016
Pgp-inhibitor:	0.0	Pgp-substrate:	0.967
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):	0.997
20% Bioavailability (F20%):	0.857	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.923
Plasma Protein Binding (PPB):	79.885%	Volume Distribution (VD):	-0.049
Fu:	17.708% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.511
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.096
BSEP inhibitor:	0.0

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:	0.073
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.579
HLM stability:	0.0 ? 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):

1.349

Half-life (T1/2):

4.996

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.047
Human Hepatotoxicity (H-HT):	0.453	Drug-induced Liver Injury (DILI):	0.969
AMES Toxicity:	0.611	Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.104	Skin Sensitization:	0.656
Carcinogencity:	0.018	Eye Corrosion:	0.0
Eye Irritation:	0.02	Respiratory Toxicity:	0.011
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.985
Hematotoxicity:	0.026	Drug-induced Nephrotoxicity:	0.454
Genotoxicity:	0.695	RPMI-8226 Immunitoxicity:	0.096
A549 Cytotoxicity:	0.075	Hek293 Cytotoxicity:	0.195
BCF:	0.198 ? 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:	2.572 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.237 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.278 ? 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
NPO23222	Salvia triloba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38474654]
NPO23222	Salvia triloba	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23222	Salvia triloba	Species	Lamiaceae	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 NPC512597 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	25720
0.1-0.2	21214
0.2-0.3	2051
0.3-0.4	584
0.4-0.5	193
0.5-0.6	67
0.6-0.7	18
0.7-0.8	0
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
0.8313	Intermediate Similarity	NPC601144
0.7791	Intermediate Similarity	NPC311830
0.7356	Intermediate Similarity	NPC282169
0.7356	Intermediate Similarity	NPC20505
0.7011	Intermediate Similarity	NPC189142
0.7011	Intermediate Similarity	NPC77660
0.6897	Remote Similarity	NPC39360
0.6897	Remote Similarity	NPC29763
0.6897	Remote Similarity	NPC210003
0.6889	Remote Similarity	NPC608742
0.6703	Remote Similarity	NPC601710
0.67	Remote Similarity	NPC253685
0.6522	Remote Similarity	NPC22832
0.6522	Remote Similarity	NPC243930
0.6444	Remote Similarity	NPC95090
0.6444	Remote Similarity	NPC27408
0.6383	Remote Similarity	NPC601586
0.6333	Remote Similarity	NPC261866
0.6277	Remote Similarity	NPC602805
0.6277	Remote Similarity	NPC607707
0.617	Remote Similarity	NPC43211
0.6139	Remote Similarity	NPC229409
0.61	Remote Similarity	NPC64051
0.6019	Remote Similarity	NPC195257
0.5978	Remote Similarity	NPC19709
0.5895	Remote Similarity	NPC237435
0.587	Remote Similarity	NPC331652
0.5851	Remote Similarity	NPC58716
0.5816	Remote Similarity	NPC600989
0.5784	Remote Similarity	NPC46202
0.5758	Remote Similarity	NPC8856
0.5758	Remote Similarity	NPC606546
0.5745	Remote Similarity	NPC146792
0.5745	Remote Similarity	NPC277205
0.5745	Remote Similarity	NPC37919
0.5745	Remote Similarity	NPC136042
0.5684	Remote Similarity	NPC84362
0.567	Remote Similarity	NPC115760
0.5625	Remote Similarity	NPC27942
0.5579	Remote Similarity	NPC297987
0.5579	Remote Similarity	NPC323593
0.5579	Remote Similarity	NPC203500
0.5567	Remote Similarity	NPC135277
0.5567	Remote Similarity	NPC210094
0.5567	Remote Similarity	NPC285197
0.5556	Remote Similarity	NPC469931
0.5556	Remote Similarity	NPC190003
0.5532	Remote Similarity	NPC473043
0.5521	Remote Similarity	NPC45638
0.55	Remote Similarity	NPC4390
0.5474	Remote Similarity	NPC45618
0.5464	Remote Similarity	NPC201292
0.5455	Remote Similarity	NPC605784
0.5417	Remote Similarity	NPC93337
0.5417	Remote Similarity	NPC168822
0.5408	Remote Similarity	NPC191306
0.5385	Remote Similarity	NPC115674
0.5361	Remote Similarity	NPC181712
0.5361	Remote Similarity	NPC105025
0.5361	Remote Similarity	NPC610763
0.5354	Remote Similarity	NPC197285
0.5354	Remote Similarity	NPC486578
0.5354	Remote Similarity	NPC605067
0.5312	Remote Similarity	NPC289667
0.5312	Remote Similarity	NPC58053
0.5312	Remote Similarity	NPC143851
0.5306	Remote Similarity	NPC101191
0.53	Remote Similarity	NPC116458
0.53	Remote Similarity	NPC246943
0.5294	Remote Similarity	NPC251417
0.5288	Remote Similarity	NPC65003
0.5288	Remote Similarity	NPC210073
0.5287	Remote Similarity	NPC137062
0.5283	Remote Similarity	NPC65711
0.5253	Remote Similarity	NPC307938
0.5253	Remote Similarity	NPC609451
0.5217	Remote Similarity	NPC191154
0.5204	Remote Similarity	NPC186807
0.52	Remote Similarity	NPC610187
0.5192	Remote Similarity	NPC44931
0.5185	Remote Similarity	NPC270675
0.5185	Remote Similarity	NPC195685
0.5149	Remote Similarity	NPC88023
0.5149	Remote Similarity	NPC309025
0.5135	Remote Similarity	NPC14187
0.5133	Remote Similarity	NPC472993
0.5098	Remote Similarity	NPC488072
0.505	Remote Similarity	NPC284960
0.5047	Remote Similarity	NPC64425
0.5045	Remote Similarity	NPC472994
0.5043	Remote Similarity	NPC277532

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC512597 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5107
0.1-0.2	3969
0.2-0.3	60
0.3-0.4	10
0.4-0.5	3
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5895	Remote Similarity	NPD4338	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