NPASS Compound

Natural Product: NPC596431

Natural Product ID	NPC596431
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)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 [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 76 80 0 0 0 0 0 0 0 0999 V2000 6.7718 2.0412 -1.8737 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9995 1.7914 -1.2148 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0239 0.9981 -0.0834 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8707 0.4472 0.4080 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8798 -0.3492 1.5402 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6254 -0.9310 2.0458 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5634 -1.7305 3.1602 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3562 -2.2627 3.6067 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2800 -2.9953 4.6229 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1916 -1.9851 2.9190 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9675 -2.4898 3.3213 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8697 -3.3028 4.4448 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8333 -2.1989 2.6217 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9317 -1.3811 1.4912 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2402 -1.1274 0.8345 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4414 -0.3489 -0.3007 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3772 0.6600 -0.1107 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0707 0.9337 -1.2772 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8649 2.1903 -1.1874 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8240 2.2006 -0.2248 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8306 1.2900 -0.3004 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0507 1.9275 -0.5846 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9752 1.0311 -1.0931 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2043 1.8249 -1.5006 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7369 2.4835 -0.4062 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3820 0.1238 0.0770 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3213 -0.7641 -0.3901 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1195 -0.6051 0.4834 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4384 -1.4030 1.5866 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0460 0.4054 0.8737 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9372 -0.3215 1.2474 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1314 0.9780 -2.4736 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0207 1.7589 -2.2636 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7454 -0.4882 -2.7175 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5124 -1.0352 -3.7365 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8617 -1.2914 -1.4370 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0432 -2.3659 -1.4410 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1577 -0.8867 1.1041 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3336 -1.1742 1.8089 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4857 -0.6910 1.4180 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0793 -0.5752 2.1628 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2743 -0.0236 1.6807 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2246 0.7511 0.5691 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3619 1.3319 0.0312 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4184 1.1174 -2.3751 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9081 2.8297 -2.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0012 2.3801 -1.1507 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9158 0.6140 -0.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4470 -1.9708 3.7235 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3211 -4.1466 4.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1188 -2.5937 2.9375 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4871 0.1281 -0.6718 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7391 0.0818 -1.4625 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2211 2.4935 -2.1945 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1274 3.0039 -0.9125 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6574 0.6408 -1.2040 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5504 0.4683 -1.9221 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9505 2.5829 -2.2684 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9667 1.1245 -1.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7191 2.6631 -0.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7443 0.7925 0.8731 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2482 -0.4303 -0.3138 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8069 -1.2069 -0.3946 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1313 -2.0559 1.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4499 1.0013 1.7143 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4175 0.0901 1.9912 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6976 1.3078 -3.3462 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2054 2.7052 -2.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3293 -0.4676 -2.9916 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4206 -1.1980 -3.3873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8516 -1.7337 -1.2747 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9310 -2.0918 -1.7891 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2541 -0.2554 0.2384 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1550 -1.1913 3.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2235 -0.2164 2.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6396 1.0926 -0.9269 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 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 23 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 18 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 14 38 1 0 38 39 2 0 39 40 1 0 5 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 43 3 1 0 40 6 1 0 39 10 1 0 36 16 1 0 30 21 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 7 49 1 0 12 50 1 0 13 51 1 0 16 52 1 6 18 53 1 6 19 54 1 0 19 55 1 0 21 56 1 6 23 57 1 6 24 58 1 0 24 59 1 0 25 60 1 0 26 61 1 1 27 62 1 0 28 63 1 6 29 64 1 0 30 65 1 1 31 66 1 0 32 67 1 6 33 68 1 0 34 69 1 6 35 70 1 0 36 71 1 1 37 72 1 0 38 73 1 0 41 74 1 0 42 75 1 0 44 76 1 0 M END

Standard InCHIKey	VBQHDIZHOUCBIA-XEOMBDOUSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-39-16-4-10(2-3-12(16)30)15-7-14(32)20-13(31)5-11(6-17(20)42-15)41-28-26(38)24(36)22(34)19(44-28)9-40-27-25(37)23(35)21(33)18(8-29)43-27/h2-7,18-19,21-31,33-38H,8-9H2,1H3/t18-,19+,21-,22-,23+,24+,25-,26-,27-,28-/m1/s1
SMILES	COC1=CC(C2=CC(=O)C3=C(O)C=C(O[C@@H]4O[C@@H](CO[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)=CC=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	0.389 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.017 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.712 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	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:	0.13	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.688	Fsp³:	0.464
MCE-18:	118.585 ? 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:	0.633	Fluc inhibitor:	0.299 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.977 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.643 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.08	Promiscuous compounds:	0.361

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.465	MDCK Permeability:	-5.155
Pgp-inhibitor:	0.0	Pgp-substrate:	0.76
PAMPA:	0.999 ? 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):	0.797
20% Bioavailability (F20%):	0.208	30% Bioavailability (F30%):	0.985
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.187
Plasma Protein Binding (PPB):	80.848%	Volume Distribution (VD):	-0.089
Fu:	17.16% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.841
BSEP inhibitor:	0.002

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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.192
HLM stability:	0.001 ? 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):

1.802

Half-life (T1/2):

4.248

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.07
Human Hepatotoxicity (H-HT):	0.591	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.956	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.016	Skin Sensitization:	0.999
Carcinogencity:	0.178	Eye Corrosion:	0.0
Eye Irritation:	0.102	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.963
Hematotoxicity:	0.148	Drug-induced Nephrotoxicity:	0.587
Genotoxicity:	0.795	RPMI-8226 Immunitoxicity:	0.151
A549 Cytotoxicity:	0.529	Hek293 Cytotoxicity:	0.409
BCF:	0.348 ? 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:	2.84 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.368 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.46 ? 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
NPO18450	Oxytropis campestris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18450	Oxytropis campestris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18450	Oxytropis campestris	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 NPC596431 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	23902
0.1-0.2	21459
0.2-0.3	3227
0.3-0.4	813
0.4-0.5	284
0.5-0.6	115
0.6-0.7	40
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
0.8415	Intermediate Similarity	NPC311830
0.7857	Intermediate Similarity	NPC601144
0.7333	Intermediate Similarity	NPC44931
0.7312	Intermediate Similarity	NPC209296
0.7253	Intermediate Similarity	NPC22062
0.7253	Intermediate Similarity	NPC473634
0.7253	Intermediate Similarity	NPC210073
0.7253	Intermediate Similarity	NPC138811
0.6979	Remote Similarity	NPC195257
0.686	Remote Similarity	NPC39360
0.686	Remote Similarity	NPC29763
0.686	Remote Similarity	NPC210003
0.6854	Remote Similarity	NPC22832
0.6854	Remote Similarity	NPC243930
0.6842	Remote Similarity	NPC65711
0.6782	Remote Similarity	NPC95090
0.6782	Remote Similarity	NPC27408
0.6782	Remote Similarity	NPC189142
0.6782	Remote Similarity	NPC77660
0.6778	Remote Similarity	NPC602805
0.6778	Remote Similarity	NPC607707
0.6771	Remote Similarity	NPC473623
0.6701	Remote Similarity	NPC488089
0.6522	Remote Similarity	NPC601586
0.6421	Remote Similarity	NPC275454
0.6408	Remote Similarity	NPC472993
0.64	Remote Similarity	NPC101636
0.6392	Remote Similarity	NPC46202
0.6392	Remote Similarity	NPC64051
0.6355	Remote Similarity	NPC198199
0.6304	Remote Similarity	NPC601710
0.6292	Remote Similarity	NPC261866
0.6286	Remote Similarity	NPC311850
0.6263	Remote Similarity	NPC229409
0.6226	Remote Similarity	NPC488083
0.62	Remote Similarity	NPC270675
0.62	Remote Similarity	NPC195685
0.6182	Remote Similarity	NPC120952
0.6173	Remote Similarity	NPC137062
0.6111	Remote Similarity	NPC68592
0.6087	Remote Similarity	NPC27942
0.6082	Remote Similarity	NPC67105
0.6078	Remote Similarity	NPC298171
0.6055	Remote Similarity	NPC298666
0.6042	Remote Similarity	NPC8856
0.602	Remote Similarity	NPC479405
0.6019	Remote Similarity	NPC472994
0.6	Remote Similarity	NPC331652
0.5978	Remote Similarity	NPC181712
0.596	Remote Similarity	NPC204693
0.596	Remote Similarity	NPC479404
0.596	Remote Similarity	NPC186816
0.5934	Remote Similarity	NPC19709
0.5905	Remote Similarity	NPC11468
0.5865	Remote Similarity	NPC135358
0.5859	Remote Similarity	NPC473512
0.5859	Remote Similarity	NPC129827
0.5842	Remote Similarity	NPC479403
0.5833	Remote Similarity	NPC190003
0.5825	Remote Similarity	NPC476472
0.5825	Remote Similarity	NPC294815
0.5825	Remote Similarity	NPC475382
0.5825	Remote Similarity	NPC16194
0.5806	Remote Similarity	NPC84362
0.5789	Remote Similarity	NPC262222
0.5743	Remote Similarity	NPC488073
0.5741	Remote Similarity	NPC480441
0.5741	Remote Similarity	NPC25523
0.57	Remote Similarity	NPC65003
0.5699	Remote Similarity	NPC93337
0.5699	Remote Similarity	NPC277205
0.5699	Remote Similarity	NPC37919
0.5699	Remote Similarity	NPC323593
0.5699	Remote Similarity	NPC203500
0.5644	Remote Similarity	NPC115674
0.5638	Remote Similarity	NPC105025
0.5638	Remote Similarity	NPC45638
0.5636	Remote Similarity	NPC488087
0.5631	Remote Similarity	NPC483707
0.5625	Remote Similarity	NPC486578
0.5612	Remote Similarity	NPC4390
0.5612	Remote Similarity	NPC172807
0.56	Remote Similarity	NPC227508
0.5596	Remote Similarity	NPC473644
0.5591	Remote Similarity	NPC58053
0.5588	Remote Similarity	NPC475366
0.5579	Remote Similarity	NPC201292
0.5575	Remote Similarity	NPC471030
0.5556	Remote Similarity	NPC35924
0.5556	Remote Similarity	NPC254540
0.5545	Remote Similarity	NPC102028
0.5545	Remote Similarity	NPC156869
0.5532	Remote Similarity	NPC297987
0.5532	Remote Similarity	NPC146792
0.5532	Remote Similarity	NPC136042
0.5521	Remote Similarity	NPC285197
0.5521	Remote Similarity	NPC609451
0.551	Remote Similarity	NPC488072
0.5484	Remote Similarity	NPC473043
0.5474	Remote Similarity	NPC186807
0.5474	Remote Similarity	NPC58716
0.5474	Remote Similarity	NPC610763
0.5464	Remote Similarity	NPC80188
0.5464	Remote Similarity	NPC605067
0.5455	Remote Similarity	NPC211594
0.5437	Remote Similarity	NPC284277
0.5437	Remote Similarity	NPC475497
0.5408	Remote Similarity	NPC88023
0.5408	Remote Similarity	NPC309025
0.5405	Remote Similarity	NPC277532
0.5398	Remote Similarity	NPC488086
0.5364	Remote Similarity	NPC480796
0.5354	Remote Similarity	NPC203050
0.5354	Remote Similarity	NPC469931
0.5354	Remote Similarity	NPC225434
0.5347	Remote Similarity	NPC295613
0.5347	Remote Similarity	NPC473657
0.5341	Remote Similarity	NPC37074
0.534	Remote Similarity	NPC122809
0.5321	Remote Similarity	NPC121703
0.5306	Remote Similarity	NPC101026
0.5306	Remote Similarity	NPC284960
0.5306	Remote Similarity	NPC488077
0.5306	Remote Similarity	NPC606560
0.5294	Remote Similarity	NPC15358
0.5288	Remote Similarity	NPC153755
0.5281	Remote Similarity	NPC287780
0.5281	Remote Similarity	NPC60982
0.5263	Remote Similarity	NPC289667
0.5263	Remote Similarity	NPC45618
0.5263	Remote Similarity	NPC143851
0.5259	Remote Similarity	NPC488079
0.5253	Remote Similarity	NPC116458
0.5253	Remote Similarity	NPC246943
0.5253	Remote Similarity	NPC220169
0.5253	Remote Similarity	NPC605784
0.5243	Remote Similarity	NPC303913
0.5238	Remote Similarity	NPC470443
0.5234	Remote Similarity	NPC80068
0.5234	Remote Similarity	NPC231194
0.5208	Remote Similarity	NPC168822
0.5204	Remote Similarity	NPC191306
0.5204	Remote Similarity	NPC307938
0.5165	Remote Similarity	NPC191154
0.5152	Remote Similarity	NPC197285
0.5146	Remote Similarity	NPC47923
0.514	Remote Similarity	NPC142142
0.5138	Remote Similarity	NPC253685
0.5102	Remote Similarity	NPC222936
0.5102	Remote Similarity	NPC182045
0.51	Remote Similarity	NPC206123
0.5098	Remote Similarity	NPC251417
0.5098	Remote Similarity	NPC606546
0.5096	Remote Similarity	NPC218488
0.5091	Remote Similarity	NPC14187
0.5057	Remote Similarity	NPC189589
0.505	Remote Similarity	NPC61791
0.5048	Remote Similarity	NPC473571
0.5048	Remote Similarity	NPC213052
0.5048	Remote Similarity	NPC110941
0.5047	Remote Similarity	NPC35119
0.5043	Remote Similarity	NPC488088
0.5042	Remote Similarity	NPC192539

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC596431 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5802
0.1-0.2	3276
0.2-0.3	58
0.3-0.4	8
0.4-0.5	2
0.5-0.6	3
0.6-0.7	0
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
0.7312	Intermediate Similarity	NPD7054	Phase 4
0.5673	Remote Similarity	NPD7251	Phase 2
0.5607	Remote Similarity	NPD7472	Pre-clinical
0.5321	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