NPASS Compound

Natural Product: NPC513428

Natural Product ID	NPC513428
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3,5-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	3,5-dihydroxy-2-(3-hydroxy-4-methoxy-phenyl)-7-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{S},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]

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 11.2866 1.8396 -1.5291 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1439 0.8664 -0.5317 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8739 0.4257 -0.1887 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7135 0.9080 -0.7897 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4742 0.4441 -0.4226 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3270 -0.5287 0.5676 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9606 -0.9630 0.9235 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6622 -1.9698 1.7974 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6556 -2.6832 2.4324 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3372 -2.3292 2.0914 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0510 -3.2421 2.8853 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3043 -1.6347 1.4696 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9830 -1.9432 1.7201 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6685 -2.9572 2.6003 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0035 -1.2043 1.0617 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3072 -0.1966 0.1869 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3663 0.5448 -0.4691 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0083 0.4088 -0.2304 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4929 -0.3894 -1.2683 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9060 -0.4278 -1.3176 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4827 -1.1189 -0.1440 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7856 -1.2766 -0.1098 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7784 -0.4307 -0.0313 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5656 -0.7752 1.1211 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4846 0.2580 1.3448 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8246 1.5933 1.5371 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4732 0.3637 0.2053 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4089 -0.6483 0.3185 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8103 0.3519 -1.1431 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8401 0.0717 -2.0716 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7650 -0.7275 -1.1887 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3681 -1.9366 -0.8688 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4398 0.9552 -1.5124 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6715 1.5782 -2.5516 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0916 1.7392 -0.2713 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6459 3.0198 -0.2838 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5740 1.7994 -0.2133 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1321 2.4260 0.9458 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6655 0.0630 -0.0206 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6773 -0.6357 0.6028 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9368 -0.3526 0.3738 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4684 -0.9848 1.1411 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7306 -0.5262 0.7808 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8659 -1.0372 1.4093 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6717 1.5963 -2.4175 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3452 1.9638 -1.8562 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9250 2.8364 -1.1810 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8309 1.6598 -1.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5591 0.8068 -0.8827 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5621 -3.6541 2.7279 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3713 -3.8518 2.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0083 -1.4952 1.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1583 -0.0640 0.7466 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1474 -1.0091 -2.2309 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0392 -0.7226 0.8319 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0131 -2.1779 -0.1610 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6603 0.6451 0.0407 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0489 -0.0044 2.2590 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7791 1.5036 1.9116 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8734 2.2461 0.6377 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3782 2.1378 2.3329 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9963 1.3381 0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4101 -0.9654 1.2572 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3401 1.3106 -1.4220 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8999 -0.8934 -2.2723 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2347 -0.7740 -2.1541 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1240 -2.2807 0.0285 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4722 0.9312 -1.8112 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8468 0.9786 -3.3316 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4523 1.2601 0.6664 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0784 3.6462 -0.7661 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2497 2.3567 -1.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6859 3.2859 0.6938 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9007 0.8524 -0.7074 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4460 -1.7277 1.9153 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3709 -0.4722 2.0902 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 8 9 1 0 8 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 13 15 1 0 15 16 2 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 25 26 1 0 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 20 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 16 39 1 0 39 40 2 0 40 41 1 0 6 42 1 0 42 43 2 0 43 44 1 0 43 3 1 0 41 7 1 0 40 12 1 0 37 18 1 0 31 23 1 0 1 45 1 0 1 46 1 0 1 47 1 0 4 48 1 0 5 49 1 0 9 50 1 0 14 51 1 0 15 52 1 0 18 53 1 1 20 54 1 6 21 55 1 0 21 56 1 0 23 57 1 1 25 58 1 1 26 59 1 0 26 60 1 0 26 61 1 0 27 62 1 1 28 63 1 0 29 64 1 6 30 65 1 0 31 66 1 6 32 67 1 0 33 68 1 6 34 69 1 0 35 70 1 1 36 71 1 0 37 72 1 6 38 73 1 0 39 74 1 0 42 75 1 0 44 76 1 0 M END

Standard InCHIKey	FMZXFFXOKZSIMV-MHRZETSCSA-N
Standard InCHI	InChI=1S/C28H32O16/c1-9-18(31)21(34)24(37)27(41-9)40-8-16-19(32)22(35)25(38)28(44-16)42-11-6-13(30)17-15(7-11)43-26(23(36)20(17)33)10-3-4-14(39-2)12(29)5-10/h3-7,9,16,18-19,21-22,24-25,27-32,34-38H,8H2,1-2H3/t9-,16-,18-,19-,21-,22-,24-,25+,27+,28+/m0/s1
SMILES	COC1=CC=C(C2=C(O)C(=O)C3=C(O)C=C(O[C@@H]4O[C@@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@H](O)[C@@H]5O)[C@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	624.17	Volume:	569.614 ? Van der Waals volume.
Dense:	1.096	LogP:	-0.094 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.747 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.882 ? 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:	0.147	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.765	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:	0
Colloidal aggregators:	0.639	Fluc inhibitor:	0.342 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.882 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.712 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.086	Promiscuous compounds:	0.526

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.405	MDCK Permeability:	-5.296
Pgp-inhibitor:	0.0	Pgp-substrate:	0.891
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%):	0.672	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.499
Plasma Protein Binding (PPB):	81.797%	Volume Distribution (VD):	-0.352
Fu:	17.557% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.55
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.076	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.572
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.789
HLM stability:	0.959 ? 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):

1.285

Half-life (T1/2):

3.343

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.115
Human Hepatotoxicity (H-HT):	0.552	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.977	Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.037	Skin Sensitization:	0.999
Carcinogencity:	0.284	Eye Corrosion:	0.0
Eye Irritation:	0.426	Respiratory Toxicity:	0.07
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.844
Hematotoxicity:	0.504	Drug-induced Nephrotoxicity:	0.677
Genotoxicity:	0.95	RPMI-8226 Immunitoxicity:	0.319
A549 Cytotoxicity:	0.921	Hek293 Cytotoxicity:	0.615
BCF:	0.442 ? 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:	3.102 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.614 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.801 ? 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
NPO4324	Verbascum phlomoides	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16142	Verbascum thapsiforme	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4324	Verbascum phlomoides	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4324	Verbascum phlomoides	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16142	Verbascum thapsiforme	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4324	Verbascum phlomoides	Species	Scrophulariaceae	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 NPC513428 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	16067
0.1-0.2	29316
0.2-0.3	3457
0.3-0.4	601
0.4-0.5	274
0.5-0.6	104
0.6-0.7	23
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC67105
0.8276	Intermediate Similarity	NPC209296
0.8118	Intermediate Similarity	NPC227508
0.7416	Intermediate Similarity	NPC22062
0.7416	Intermediate Similarity	NPC473634
0.7416	Intermediate Similarity	NPC138811
0.7191	Intermediate Similarity	NPC187379
0.7158	Intermediate Similarity	NPC135358
0.7111	Intermediate Similarity	NPC275454
0.7011	Intermediate Similarity	NPC486578
0.6915	Remote Similarity	NPC473327
0.6897	Remote Similarity	NPC285197
0.6848	Remote Similarity	NPC210073
0.6824	Remote Similarity	NPC238376
0.6774	Remote Similarity	NPC186816
0.6739	Remote Similarity	NPC44931
0.6705	Remote Similarity	NPC611303
0.6628	Remote Similarity	NPC108831
0.6628	Remote Similarity	NPC182634
0.6476	Remote Similarity	NPC198199
0.6296	Remote Similarity	NPC120952
0.625	Remote Similarity	NPC204693
0.6224	Remote Similarity	NPC473623
0.6214	Remote Similarity	NPC480796
0.6176	Remote Similarity	NPC11468
0.6162	Remote Similarity	NPC488089
0.6146	Remote Similarity	NPC303913
0.61	Remote Similarity	NPC80068
0.6076	Remote Similarity	NPC200740
0.6061	Remote Similarity	NPC606657
0.6	Remote Similarity	NPC142142
0.6	Remote Similarity	NPC277205
0.6	Remote Similarity	NPC37919
0.596	Remote Similarity	NPC470443
0.5957	Remote Similarity	NPC601586
0.5941	Remote Similarity	NPC476472
0.5941	Remote Similarity	NPC294815
0.5941	Remote Similarity	NPC16194
0.5914	Remote Similarity	NPC22832
0.5882	Remote Similarity	NPC287889
0.5859	Remote Similarity	NPC126784
0.5859	Remote Similarity	NPC241423
0.5859	Remote Similarity	NPC475366
0.5849	Remote Similarity	NPC480441
0.5849	Remote Similarity	NPC473644
0.5849	Remote Similarity	NPC25523
0.5833	Remote Similarity	NPC251417
0.5824	Remote Similarity	NPC323593
0.5824	Remote Similarity	NPC203500
0.5794	Remote Similarity	NPC311850
0.5769	Remote Similarity	NPC244875
0.5758	Remote Similarity	NPC473571
0.5758	Remote Similarity	NPC110941
0.5728	Remote Similarity	NPC101636
0.5714	Remote Similarity	NPC173582
0.5714	Remote Similarity	NPC265885
0.5714	Remote Similarity	NPC181465
0.5714	Remote Similarity	NPC215710
0.5714	Remote Similarity	NPC473438
0.5714	Remote Similarity	NPC253788
0.5657	Remote Similarity	NPC233994
0.5657	Remote Similarity	NPC203259
0.5657	Remote Similarity	NPC33054
0.5657	Remote Similarity	NPC176740
0.5657	Remote Similarity	NPC471725
0.5657	Remote Similarity	NPC134532
0.5657	Remote Similarity	NPC602582
0.5644	Remote Similarity	NPC65711
0.5636	Remote Similarity	NPC68592
0.5591	Remote Similarity	NPC46420
0.5591	Remote Similarity	NPC271692
0.5567	Remote Similarity	NPC477848
0.5556	Remote Similarity	NPC39834
0.5545	Remote Similarity	NPC46202
0.5532	Remote Similarity	NPC21100
0.549	Remote Similarity	NPC211532
0.549	Remote Similarity	NPC488364
0.5484	Remote Similarity	NPC158674
0.5474	Remote Similarity	NPC219904
0.5437	Remote Similarity	NPC483707
0.5376	Remote Similarity	NPC249281
0.5376	Remote Similarity	NPC19709
0.5357	Remote Similarity	NPC488086
0.5347	Remote Similarity	NPC479405
0.5347	Remote Similarity	NPC65563
0.5347	Remote Similarity	NPC470949
0.5345	Remote Similarity	NPC262222
0.5333	Remote Similarity	NPC475382
0.5333	Remote Similarity	NPC473073
0.5315	Remote Similarity	NPC488087
0.5312	Remote Similarity	NPC307938
0.531	Remote Similarity	NPC298666
0.5306	Remote Similarity	NPC276377
0.5294	Remote Similarity	NPC479404
0.5288	Remote Similarity	NPC51326
0.5283	Remote Similarity	NPC298171
0.5269	Remote Similarity	NPC473043
0.5269	Remote Similarity	NPC331652
0.5263	Remote Similarity	NPC181712
0.5213	Remote Similarity	NPC254306
0.5213	Remote Similarity	NPC476405
0.5204	Remote Similarity	NPC99957
0.5196	Remote Similarity	NPC475155
0.5192	Remote Similarity	NPC479403
0.5189	Remote Similarity	NPC195257
0.5185	Remote Similarity	NPC14187
0.5182	Remote Similarity	NPC472993
0.5182	Remote Similarity	NPC173837
0.5179	Remote Similarity	NPC488083
0.5172	Remote Similarity	NPC469622
0.5158	Remote Similarity	NPC95090
0.5158	Remote Similarity	NPC27408
0.5143	Remote Similarity	NPC32641
0.5143	Remote Similarity	NPC256188
0.5143	Remote Similarity	NPC139060
0.5143	Remote Similarity	NPC229409
0.514	Remote Similarity	NPC235575
0.5138	Remote Similarity	NPC89052
0.5138	Remote Similarity	NPC121703
0.5102	Remote Similarity	NPC243930
0.5102	Remote Similarity	NPC181616
0.51	Remote Similarity	NPC211594
0.5096	Remote Similarity	NPC488073
0.5096	Remote Similarity	NPC240306
0.5096	Remote Similarity	NPC64051
0.5094	Remote Similarity	NPC270675
0.5094	Remote Similarity	NPC195685
0.5094	Remote Similarity	NPC486577
0.5089	Remote Similarity	NPC277532
0.5055	Remote Similarity	NPC473241
0.5053	Remote Similarity	NPC289667
0.5051	Remote Similarity	NPC116458
0.5051	Remote Similarity	NPC246943
0.5051	Remote Similarity	NPC605784
0.5051	Remote Similarity	NPC607707
0.5049	Remote Similarity	NPC150164
0.5046	Remote Similarity	NPC603856

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC513428 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4543
0.1-0.2	4528
0.2-0.3	66
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
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	Drug ID	Developmental Stage
0.8276	Intermediate Similarity	NPD7054	Phase 4
0.65	Remote Similarity	NPD7472	Pre-clinical
0.65	Remote Similarity	NPD7808	Phase 3
0.6263	Remote Similarity	NPD7251	Phase 2
0.5657	Remote Similarity	NPD6797	Phase 2

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