NPASS Compound

Natural Product: NPC586662

Natural Product ID	NPC586662
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[2-acetoxy-4-[5-hydroxy-4-oxo-3,7-bis[[(3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy]chromen-2-yl]phenyl] acetate
IUPAC Name	[2-acetoxy-4-[5-hydroxy-4-oxo-3,7-bis[[(3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy]chromen-2-yl]phenyl] acetate
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 84 88 0 0 0 0 0 0 0 0999 V2000 -7.6455 -4.5372 -0.4174 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4530 -3.6288 -0.3021 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2666 -2.9596 0.7470 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5403 -3.5020 -1.3250 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4538 -2.6563 -1.1840 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5490 -1.3127 -1.5065 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4687 -0.4560 -1.3707 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2903 -0.9530 -0.9074 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1065 -0.1607 -0.6629 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0766 1.1758 -0.5013 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2229 1.9508 -0.5366 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9619 2.2651 0.6275 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2377 1.7687 0.6548 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2598 2.5528 0.2402 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4922 2.6004 -1.2573 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5695 3.4555 -1.4826 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2755 3.9364 0.8425 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3441 3.8208 2.2110 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9517 4.5727 0.4719 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7975 4.8321 -0.8631 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8872 3.6941 1.0775 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1766 3.6835 2.4695 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1264 1.8698 -0.2739 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1437 3.1151 -0.1330 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2857 1.1223 -0.2161 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4872 1.7658 0.0081 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5860 3.1207 0.1758 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6742 1.0193 0.0704 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6350 -0.3399 -0.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7516 -1.1283 -0.0426 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0271 -0.7112 0.1846 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8199 -0.9345 -0.9856 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7695 0.0842 -0.9793 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7046 -0.0907 -2.1542 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6659 0.8977 -2.1845 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4819 0.0237 0.3451 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1851 1.1273 1.1568 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2297 -1.2834 1.0667 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8185 -2.2943 0.3044 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7496 -1.5074 1.2633 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3505 -0.9779 2.4843 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3838 -0.9455 -0.3165 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2111 -0.2430 -0.3824 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0542 -0.8236 -0.5939 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2046 -2.3333 -0.5808 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2641 -3.1861 -0.7121 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1606 -4.5486 -0.3839 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3621 -5.0454 0.8835 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2614 -6.4667 1.2595 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6585 -4.2271 1.8113 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4383 -4.0974 -1.0556 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3466 -5.5398 -0.7832 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0614 -4.6762 0.5882 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4625 -0.8753 -1.8762 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5327 0.5821 -1.6497 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4257 1.6966 1.4625 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2098 2.0679 0.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7797 1.5451 -1.5444 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6183 2.8884 -1.8405 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2893 4.2817 -1.9741 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1428 4.5046 0.4547 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7814 4.6523 2.5857 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9168 5.5505 1.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2492 5.6470 -1.0293 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9294 4.1441 0.9729 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7953 4.5147 2.8944 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1764 3.5205 1.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6132 1.5123 0.2416 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0863 0.3565 0.4391 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2300 1.0518 -1.0225 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2045 -1.0753 -2.1155 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0603 -0.0923 -3.0677 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7836 1.1708 -3.1174 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5756 0.1014 0.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9344 1.9101 0.5754 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7701 -1.2369 2.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5873 -3.2006 0.5997 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4953 -2.5885 1.1680 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8753 -0.2165 2.7788 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3675 -2.0126 -0.4411 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2776 -2.7590 -0.2100 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9648 -6.5561 2.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5021 -6.9781 0.6415 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2393 -6.9952 1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 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 14 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 10 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 29 42 1 0 42 43 2 0 43 44 1 0 8 45 1 0 45 46 2 0 46 47 1 0 47 48 1 0 48 49 1 0 48 50 2 0 46 5 1 0 44 9 1 0 21 12 1 0 43 25 1 0 40 31 1 0 1 51 1 0 1 52 1 0 1 53 1 0 6 54 1 0 7 55 1 0 12 56 1 0 14 57 1 1 15 58 1 0 15 59 1 0 16 60 1 0 17 61 1 6 18 62 1 0 19 63 1 1 20 64 1 0 21 65 1 1 22 66 1 0 27 67 1 0 28 68 1 0 31 69 1 0 33 70 1 6 34 71 1 0 34 72 1 0 35 73 1 0 36 74 1 6 37 75 1 0 38 76 1 1 39 77 1 0 40 78 1 1 41 79 1 0 42 80 1 0 45 81 1 0 49 82 1 0 49 83 1 0 49 84 1 0 M END

Standard InCHIKey	JVJQREGRJQFQQU-CPGGPPNLSA-N
Standard InCHI	InChI=1S/C31H34O19/c1-10(34)44-15-4-3-12(5-16(15)45-11(2)35)28-29(50-31-27(43)25(41)22(38)19(9-33)49-31)23(39)20-14(36)6-13(7-17(20)47-28)46-30-26(42)24(40)21(37)18(8-32)48-30/h3-7,18-19,21-22,24-27,30-33,36-38,40-43H,8-9H2,1-2H3/t18-,19-,21-,22-,24+,25+,26-,27-,30?,31?/m1/s1
SMILES	CC(=O)OC1=CC=C(C2=C(OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=O)C3=C(O)C=C(OC4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1OC(C)=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	710.17	Volume:	642.599 ? Van der Waals volume.
Dense:	1.105	LogP:	-0.791 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.266 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.806 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	32.0
TPSA:	301.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.081	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.895	Fsp³:	0.452
MCE-18:	127.444 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.593	Fluc inhibitor:	0.272 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.928 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.66 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.131	Promiscuous compounds:	0.158

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.546	MDCK Permeability:	-4.991
Pgp-inhibitor:	0.0	Pgp-substrate:	0.506
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):	0.315
20% Bioavailability (F20%):	0.001	30% Bioavailability (F30%):	0.974
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.013
Plasma Protein Binding (PPB):	65.789%	Volume Distribution (VD):	-0.351
Fu:	33.356% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.066
BSEP inhibitor:	0.005

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:	0.325
HLM stability:	0.354 ? 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):

1.068

Half-life (T1/2):

4.732

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.554	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.93	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	0.999
Carcinogencity:	0.069	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.977
Hematotoxicity:	0.268	Drug-induced Nephrotoxicity:	0.397
Genotoxicity:	0.747	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.711	Hek293 Cytotoxicity:	0.16
BCF:	0.363 ? 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:	2.954 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.768 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.73 ? 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
NPO49172	Ifloga spicata	Species	Asteraceae	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 NPC586662 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	18112
0.1-0.2	27999
0.2-0.3	2590
0.3-0.4	666
0.4-0.5	329
0.5-0.6	114
0.6-0.7	38
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
0.8026	Intermediate Similarity	NPC289667
0.7468	Intermediate Similarity	NPC297987
0.7468	Intermediate Similarity	NPC136042
0.7381	Intermediate Similarity	NPC251417
0.7229	Intermediate Similarity	NPC116458
0.7229	Intermediate Similarity	NPC246943
0.7229	Intermediate Similarity	NPC605784
0.6966	Remote Similarity	NPC64425
0.6951	Remote Similarity	NPC84362
0.6706	Remote Similarity	NPC243930
0.6588	Remote Similarity	NPC611303
0.6506	Remote Similarity	NPC249281
0.6437	Remote Similarity	NPC607707
0.6429	Remote Similarity	NPC64305
0.6395	Remote Similarity	NPC285197
0.6289	Remote Similarity	NPC14187
0.6279	Remote Similarity	NPC472459
0.6277	Remote Similarity	NPC35119
0.6235	Remote Similarity	NPC95090
0.6235	Remote Similarity	NPC277205
0.6235	Remote Similarity	NPC27408
0.6235	Remote Similarity	NPC37919
0.618	Remote Similarity	NPC276377
0.6163	Remote Similarity	NPC46420
0.6163	Remote Similarity	NPC271692
0.6139	Remote Similarity	NPC277532
0.6136	Remote Similarity	NPC22832
0.6136	Remote Similarity	NPC486578
0.6105	Remote Similarity	NPC32641
0.6105	Remote Similarity	NPC256188
0.6078	Remote Similarity	NPC470716
0.6047	Remote Similarity	NPC158674
0.6047	Remote Similarity	NPC323593
0.6047	Remote Similarity	NPC203500
0.6047	Remote Similarity	NPC189142
0.6047	Remote Similarity	NPC77660
0.604	Remote Similarity	NPC480441
0.604	Remote Similarity	NPC470715
0.604	Remote Similarity	NPC25523
0.604	Remote Similarity	NPC164704
0.6023	Remote Similarity	NPC60735
0.6023	Remote Similarity	NPC26230
0.6023	Remote Similarity	NPC488071
0.6022	Remote Similarity	NPC150164
0.6	Remote Similarity	NPC488072
0.5977	Remote Similarity	NPC24043
0.5955	Remote Similarity	NPC120099
0.5955	Remote Similarity	NPC21666
0.5938	Remote Similarity	NPC606657
0.593	Remote Similarity	NPC261866
0.593	Remote Similarity	NPC39360
0.593	Remote Similarity	NPC77672
0.593	Remote Similarity	NPC133671
0.593	Remote Similarity	NPC135391
0.593	Remote Similarity	NPC29763
0.593	Remote Similarity	NPC78263
0.593	Remote Similarity	NPC210003
0.593	Remote Similarity	NPC250069
0.5862	Remote Similarity	NPC145038
0.5862	Remote Similarity	NPC56077
0.5862	Remote Similarity	NPC281131
0.5862	Remote Similarity	NPC253662
0.5862	Remote Similarity	NPC179950
0.5862	Remote Similarity	NPC88789
0.5862	Remote Similarity	NPC491374
0.5824	Remote Similarity	NPC203050
0.5824	Remote Similarity	NPC225434
0.581	Remote Similarity	NPC295625
0.5794	Remote Similarity	NPC470720
0.5789	Remote Similarity	NPC186816
0.5778	Remote Similarity	NPC601144
0.5773	Remote Similarity	NPC72016
0.5747	Remote Similarity	NPC19388
0.5747	Remote Similarity	NPC240431
0.5747	Remote Similarity	NPC55786
0.573	Remote Similarity	NPC325555
0.573	Remote Similarity	NPC226304
0.5714	Remote Similarity	NPC311830
0.5701	Remote Similarity	NPC470719
0.5701	Remote Similarity	NPC470717
0.5667	Remote Similarity	NPC307938
0.5652	Remote Similarity	NPC601586
0.5638	Remote Similarity	NPC480466
0.5631	Remote Similarity	NPC48984
0.5618	Remote Similarity	NPC603655
0.5604	Remote Similarity	NPC101026
0.5604	Remote Similarity	NPC488077
0.5604	Remote Similarity	NPC609478
0.5567	Remote Similarity	NPC240306
0.5556	Remote Similarity	NPC42773
0.5556	Remote Similarity	NPC45522
0.5556	Remote Similarity	NPC599850
0.5532	Remote Similarity	NPC480463
0.5506	Remote Similarity	NPC234739
0.5495	Remote Similarity	NPC609451
0.5444	Remote Similarity	NPC488080
0.5444	Remote Similarity	NPC169977
0.5443	Remote Similarity	NPC236769
0.5437	Remote Similarity	NPC121703
0.5426	Remote Similarity	NPC265115
0.5417	Remote Similarity	NPC275454
0.5412	Remote Similarity	NPC134819
0.54	Remote Similarity	NPC5319
0.5393	Remote Similarity	NPC58053
0.5393	Remote Similarity	NPC238376
0.5347	Remote Similarity	NPC76831
0.5345	Remote Similarity	NPC223860
0.5333	Remote Similarity	NPC8573
0.5333	Remote Similarity	NPC197896
0.5333	Remote Similarity	NPC313163
0.5319	Remote Similarity	NPC355481
0.5316	Remote Similarity	NPC153758
0.5294	Remote Similarity	NPC191154
0.5275	Remote Similarity	NPC186807
0.5275	Remote Similarity	NPC27640
0.5275	Remote Similarity	NPC181712
0.5275	Remote Similarity	NPC73511
0.5269	Remote Similarity	NPC148710
0.5248	Remote Similarity	NPC486577
0.5243	Remote Similarity	NPC135358
0.5227	Remote Similarity	NPC288084
0.5222	Remote Similarity	NPC108831
0.5222	Remote Similarity	NPC19709
0.5222	Remote Similarity	NPC182634
0.5217	Remote Similarity	NPC182045
0.5213	Remote Similarity	NPC88023
0.5213	Remote Similarity	NPC206123
0.5213	Remote Similarity	NPC309025
0.5204	Remote Similarity	NPC156869
0.5169	Remote Similarity	NPC67037
0.5169	Remote Similarity	NPC255615
0.5161	Remote Similarity	NPC219904
0.5161	Remote Similarity	NPC80140
0.5158	Remote Similarity	NPC190003
0.5155	Remote Similarity	NPC139320
0.5119	Remote Similarity	NPC99671
0.5111	Remote Similarity	NPC111929
0.5111	Remote Similarity	NPC320283
0.5111	Remote Similarity	NPC473043
0.5111	Remote Similarity	NPC331652
0.5111	Remote Similarity	NPC41121
0.5106	Remote Similarity	NPC284960
0.5106	Remote Similarity	NPC605067
0.5102	Remote Similarity	NPC471748
0.5056	Remote Similarity	NPC34531
0.5055	Remote Similarity	NPC127546
0.5055	Remote Similarity	NPC57625
0.5055	Remote Similarity	NPC173637
0.5055	Remote Similarity	NPC317489
0.5055	Remote Similarity	NPC223424
0.5055	Remote Similarity	NPC143851
0.5055	Remote Similarity	NPC600591
0.5054	Remote Similarity	NPC21100
0.5054	Remote Similarity	NPC27942
0.5054	Remote Similarity	NPC117260
0.5053	Remote Similarity	NPC223747
0.5052	Remote Similarity	NPC8856
0.505	Remote Similarity	NPC483414
0.5047	Remote Similarity	NPC219043

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC586662 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4978
0.1-0.2	4092
0.2-0.3	65
0.3-0.4	9
0.4-0.5	3
0.5-0.6	2
0.6-0.7	1
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
0.6392	Remote Similarity	NPD7808	Phase 3
0.55	Remote Similarity	NPD7251	Phase 2
0.54	Remote Similarity	NPD7804	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