NPASS Compound

Natural Product: NPC532498

Natural Product ID	NPC532498
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dihydroxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dihydroxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},5~{R},6~{R})-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]

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 71 75 0 0 0 0 0 0 0 0999 V2000 -4.6647 2.6847 2.0277 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6761 1.8567 0.7419 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6609 0.9426 0.7048 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0961 -0.3769 0.4242 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9539 -1.1255 0.3687 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6263 -1.6988 -0.8250 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4232 -0.6973 -1.9408 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4130 0.2029 -1.6579 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1708 -0.1172 -2.1087 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2248 -1.3722 -1.6589 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3469 -1.6774 -0.9117 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5613 -3.0036 -0.5814 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6477 -3.3982 0.1558 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5520 -2.4404 0.5788 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6530 -2.8140 1.3212 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8420 -4.0162 1.6181 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5261 -1.8212 1.7194 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3279 -0.5087 1.4029 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2379 0.5547 1.8147 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3637 0.3142 2.5415 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1799 1.3651 2.9013 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8865 2.6636 2.5431 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7481 3.6644 2.9373 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7390 2.8985 1.8033 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4851 4.2352 1.4638 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9174 1.8577 1.4387 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2481 -0.2074 0.6842 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3909 -1.1085 0.2816 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2687 -0.7576 -0.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1107 -0.0879 -3.6372 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4819 1.0774 -4.1138 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5272 -0.2475 -4.1402 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6031 -0.5625 -5.4789 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1419 -1.3420 -3.2608 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2860 -1.7941 -3.9045 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0192 -0.7357 1.5729 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3060 -0.6164 2.7679 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2320 0.1449 1.5183 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5138 0.5895 2.8149 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0509 1.2985 0.5759 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9611 2.3000 0.9598 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2057 3.6694 1.8756 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1123 2.1344 2.8383 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 2.8544 2.3975 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5190 2.6160 -0.0817 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6448 -0.3216 -0.5181 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6764 -2.2563 -0.6799 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3648 -2.4774 -1.1769 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3519 -0.0636 -2.0606 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5231 0.6972 -1.7838 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8628 -3.7850 -0.9014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8473 -4.4230 0.4321 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3905 -2.1274 2.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6440 -0.6684 2.8475 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0591 1.1561 3.4733 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6838 3.6509 2.5648 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6124 4.6276 1.8086 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0379 2.0771 0.8663 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1510 0.2879 -0.6993 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4420 -0.9998 -3.9872 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3719 1.1490 -3.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0637 0.6884 -3.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6970 -1.5529 -5.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3753 -2.1332 -3.1627 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4772 -2.7164 -3.5587 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3613 -1.7802 1.4017 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9572 -0.7214 3.5034 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1620 -0.4008 1.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3998 1.0425 2.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2899 1.0138 -0.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4631 2.6397 0.1652 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 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 1 0 24 26 2 0 18 27 1 0 27 28 1 0 28 29 2 0 9 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 4 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 40 2 1 0 34 7 1 0 29 11 1 0 28 14 1 0 26 19 1 0 1 42 1 0 1 43 1 0 1 44 1 0 2 45 1 6 4 46 1 6 6 47 1 0 6 48 1 0 7 49 1 6 9 50 1 1 12 51 1 0 13 52 1 0 17 53 1 0 20 54 1 0 21 55 1 0 23 56 1 0 25 57 1 0 26 58 1 0 29 59 1 0 30 60 1 6 31 61 1 0 32 62 1 6 33 63 1 0 34 64 1 1 35 65 1 0 36 66 1 6 37 67 1 0 38 68 1 6 39 69 1 0 40 70 1 6 41 71 1 0 M END

Standard InCHIKey	XEGFGSKULOVWMZ-BQFVCPKRSA-N
Standard InCHI	InChI=1S/C27H30O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-19-21(32)23(34)25(36)27(41-19)39-12-3-4-13-15(29)8-17(40-18(13)7-12)11-2-5-14(28)16(30)6-11/h2-8,10,19-28,30-36H,9H2,1H3/t10-,19-,20+,21-,22+,23+,24+,25-,26-,27-/m1/s1
SMILES	C[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=CC=C4C(=O)C=C(C5=CC=C(O)C(O)=C5)OC4=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.16	Volume:	534.737 ? Van der Waals volume.
Dense:	1.081	LogP:	0.128 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.594 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.564 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	228.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.162	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.582	Fsp³:	0.444
MCE-18:	115.923 ? 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:	0.619	Fluc inhibitor:	0.385 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.993 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.608 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.198	Promiscuous compounds:	0.259

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.455	MDCK Permeability:	-5.154
Pgp-inhibitor:	0.0	Pgp-substrate:	0.7
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):	0.061
20% Bioavailability (F20%):	0.758	30% Bioavailability (F30%):	0.916
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.35
Plasma Protein Binding (PPB):	80.448%	Volume Distribution (VD):	-0.072
Fu:	16.115% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.273
BSEP inhibitor:	0.711

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:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.529
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.165 ? 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):

1.216

Half-life (T1/2):

5.569

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.461
Human Hepatotoxicity (H-HT):	0.196	Drug-induced Liver Injury (DILI):	0.738
AMES Toxicity:	0.668	Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.111	Skin Sensitization:	0.783
Carcinogencity:	0.018	Eye Corrosion:	0.0
Eye Irritation:	0.301	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.967
Hematotoxicity:	0.063	Drug-induced Nephrotoxicity:	0.318
Genotoxicity:	0.627	RPMI-8226 Immunitoxicity:	0.091
A549 Cytotoxicity:	0.23	Hek293 Cytotoxicity:	0.179
BCF:	0.582 ? 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:	3.275 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.902 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.224 ? 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
NPO52226	Baptisia perfoliata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC532498 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	17093
0.1-0.2	28632
0.2-0.3	3194
0.3-0.4	571
0.4-0.5	266
0.5-0.6	75
0.6-0.7	24
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	Natural Product ID
0.7882	Intermediate Similarity	NPC210073
0.7195	Intermediate Similarity	NPC168822
0.6966	Remote Similarity	NPC44931
0.6778	Remote Similarity	NPC67105
0.6774	Remote Similarity	NPC209296
0.6703	Remote Similarity	NPC22062
0.6703	Remote Similarity	NPC473634
0.6703	Remote Similarity	NPC138811
0.663	Remote Similarity	NPC204693
0.6383	Remote Similarity	NPC475366
0.6374	Remote Similarity	NPC254540
0.6316	Remote Similarity	NPC65711
0.6279	Remote Similarity	NPC19709
0.617	Remote Similarity	NPC203259
0.617	Remote Similarity	NPC33054
0.617	Remote Similarity	NPC176740
0.617	Remote Similarity	NPC471725
0.617	Remote Similarity	NPC134532
0.617	Remote Similarity	NPC602582
0.6146	Remote Similarity	NPC470443
0.6122	Remote Similarity	NPC473073
0.6105	Remote Similarity	NPC186816
0.6064	Remote Similarity	NPC227508
0.6042	Remote Similarity	NPC126784
0.6042	Remote Similarity	NPC241423
0.6	Remote Similarity	NPC473512
0.5918	Remote Similarity	NPC229409
0.59	Remote Similarity	NPC101636
0.5833	Remote Similarity	NPC129827
0.5806	Remote Similarity	NPC190003
0.5729	Remote Similarity	NPC173582
0.5729	Remote Similarity	NPC265885
0.5729	Remote Similarity	NPC181465
0.5729	Remote Similarity	NPC215710
0.5729	Remote Similarity	NPC473438
0.5729	Remote Similarity	NPC253788
0.567	Remote Similarity	NPC65563
0.567	Remote Similarity	NPC470949
0.5625	Remote Similarity	NPC187379
0.5625	Remote Similarity	NPC473657
0.56	Remote Similarity	NPC473623
0.5588	Remote Similarity	NPC298171
0.5579	Remote Similarity	NPC172807
0.5567	Remote Similarity	NPC39834
0.5566	Remote Similarity	NPC480441
0.5545	Remote Similarity	NPC488089
0.5495	Remote Similarity	NPC189142
0.5495	Remote Similarity	NPC77660
0.5464	Remote Similarity	NPC295613
0.5455	Remote Similarity	NPC115674
0.5455	Remote Similarity	NPC473571
0.5455	Remote Similarity	NPC110941
0.5446	Remote Similarity	NPC483707
0.5444	Remote Similarity	NPC473043
0.5444	Remote Similarity	NPC331652
0.5429	Remote Similarity	NPC11468
0.5417	Remote Similarity	NPC211594
0.54	Remote Similarity	NPC475497
0.5385	Remote Similarity	NPC238376
0.5368	Remote Similarity	NPC99957
0.5354	Remote Similarity	NPC303913
0.5354	Remote Similarity	NPC156869
0.534	Remote Similarity	NPC476472
0.534	Remote Similarity	NPC294815
0.534	Remote Similarity	NPC16194
0.5294	Remote Similarity	NPC51326
0.5294	Remote Similarity	NPC473327
0.5269	Remote Similarity	NPC271692
0.5269	Remote Similarity	NPC45638
0.5263	Remote Similarity	NPC181616
0.5253	Remote Similarity	NPC67326
0.5253	Remote Similarity	NPC275454
0.5248	Remote Similarity	NPC488073
0.5248	Remote Similarity	NPC284277
0.5248	Remote Similarity	NPC64051
0.5213	Remote Similarity	NPC201292
0.52	Remote Similarity	NPC233994
0.5192	Remote Similarity	NPC231194
0.5192	Remote Similarity	NPC89127
0.5179	Remote Similarity	NPC298666
0.5179	Remote Similarity	NPC198199
0.5146	Remote Similarity	NPC122467
0.5138	Remote Similarity	NPC473644
0.5138	Remote Similarity	NPC25523
0.5106	Remote Similarity	NPC58716
0.5102	Remote Similarity	NPC116864
0.5102	Remote Similarity	NPC244776
0.51	Remote Similarity	NPC15358
0.5098	Remote Similarity	NPC488074
0.5096	Remote Similarity	NPC142142
0.5096	Remote Similarity	NPC270675
0.5096	Remote Similarity	NPC195685
0.5094	Remote Similarity	NPC470446
0.5091	Remote Similarity	NPC311850
0.5054	Remote Similarity	NPC211014
0.505	Remote Similarity	NPC218488
0.5049	Remote Similarity	NPC211532
0.5049	Remote Similarity	NPC488364
0.5046	Remote Similarity	NPC292019
0.5046	Remote Similarity	NPC202908
0.5043	Remote Similarity	NPC120952

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC532498 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4712
0.1-0.2	4339
0.2-0.3	86
0.3-0.4	7
0.4-0.5	1
0.5-0.6	1
0.6-0.7	4
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
0.6774	Remote Similarity	NPD7054	Phase 4
0.6364	Remote Similarity	NPD7472	Pre-clinical
0.6289	Remote Similarity	NPD7251	Phase 2
0.617	Remote Similarity	NPD6797	Phase 2
0.5429	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