NPASS Compound

Natural Product: NPC511432

Natural Product ID	NPC511432
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DTXSID001111355
IUPAC Name	7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-[[(2~{R},3~{R},4~{R})-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)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 8.5251 -4.0049 2.6005 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8786 -3.2047 1.5134 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9976 -2.3166 0.9009 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6949 -2.1541 1.3240 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8304 -1.2712 0.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2533 -0.5032 -0.3754 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2922 0.4208 -0.9930 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6313 1.2150 -2.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7138 2.0912 -2.6466 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9772 2.8261 -3.6139 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4502 2.1169 -2.0904 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4573 2.9504 -2.5895 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8089 3.7480 -3.6700 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2207 2.9521 -2.0186 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8658 2.1445 -0.9251 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4114 2.2455 -0.4499 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9348 1.5296 0.6179 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9666 0.6900 0.2046 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2107 1.2589 0.1856 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9293 0.8726 -1.0736 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1176 -0.4783 -1.2454 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8600 -1.0835 -0.2666 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1303 -2.1018 0.3224 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0641 -2.8322 1.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3381 -2.8372 0.2155 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3902 -2.5347 1.0673 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6092 -4.1874 -0.4121 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7171 -5.1861 0.5390 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0949 -1.7773 -0.8124 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1440 -0.8524 -0.7196 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1679 2.7929 0.1984 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4652 3.2479 0.0375 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6072 3.1721 1.5452 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4999 4.5303 1.7225 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3462 2.4139 1.7775 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3192 1.7017 2.9684 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8634 1.3352 -0.4560 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1445 1.3098 -1.0201 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0671 0.5176 -0.5364 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5454 -0.6636 -0.7960 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4177 -1.5596 -0.1702 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4072 -4.6499 2.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3041 -3.3557 3.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6343 -4.6088 2.3388 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3920 -2.7631 2.1689 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8033 -1.1551 1.0579 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6161 1.1789 -2.4788 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3521 4.5785 -3.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4652 3.6142 -2.4301 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1570 0.8588 1.0264 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7340 0.9780 1.1199 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3878 1.3347 -1.9160 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9598 1.3364 -1.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1561 -0.3092 0.4767 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2091 -2.3883 2.0335 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7044 -3.8697 1.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5637 -1.5606 1.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7575 -4.4383 -1.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5125 -4.1688 -1.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6950 -4.8512 1.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9525 -2.1552 -1.8345 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1636 -0.2173 -1.4622 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5698 3.1125 -0.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8466 3.6624 0.8409 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3566 2.8040 2.3044 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6612 4.8269 2.6659 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5199 3.1793 1.8662 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4047 1.5622 3.3072 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6843 0.6837 0.3775 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9050 -0.0890 -1.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4369 -1.6650 -0.5253 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 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 12 14 1 0 14 15 2 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 25 26 1 1 25 27 1 0 27 28 1 0 25 29 1 0 29 30 1 0 19 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 15 37 1 0 37 38 2 0 38 39 1 0 6 40 1 0 40 41 2 0 41 3 1 0 39 7 1 0 38 11 1 0 35 17 1 0 29 22 1 0 1 42 1 0 1 43 1 0 1 44 1 0 4 45 1 0 5 46 1 0 8 47 1 0 13 48 1 0 14 49 1 0 17 50 1 1 19 51 1 1 20 52 1 0 20 53 1 0 22 54 1 1 24 55 1 0 24 56 1 0 26 57 1 0 27 58 1 0 27 59 1 0 28 60 1 0 29 61 1 6 30 62 1 0 31 63 1 6 32 64 1 0 33 65 1 1 34 66 1 0 35 67 1 1 36 68 1 0 37 69 1 0 40 70 1 0 41 71 1 0 M END

Standard InCHIKey	FSUVCZVLSOYPAU-MFYRMPRMSA-N
Standard InCHI	InChI=1S/C27H30O14/c1-36-13-4-2-12(3-5-13)17-8-16(30)20-15(29)6-14(7-18(20)40-17)39-25-23(33)22(32)21(31)19(41-25)9-37-26-24(34)27(35,10-28)11-38-26/h2-8,19,21-26,28-29,31-35H,9-11H2,1H3/t19-,21-,22+,23-,24+,25-,26-,27-/m1/s1
SMILES	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[C@@H]4O[C@H](CO[C@@H]5OC[C@](O)(CO)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.16	Volume:	534.737 ? Van der Waals volume.
Dense:	1.081	LogP:	1.608 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.014 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.28 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	29.0
TPSA:	217.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.167	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.577	Fsp³:	0.444
MCE-18:	114.231 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.595	Fluc inhibitor:	0.305 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.948 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.641 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.053	Promiscuous compounds:	0.309

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.21	MDCK Permeability:	-5.139
Pgp-inhibitor:	0.0	Pgp-substrate:	0.68
PAMPA:	0.992 ? 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):	0.949
20% Bioavailability (F20%):	0.367	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.427
Plasma Protein Binding (PPB):	84.245%	Volume Distribution (VD):	-0.199
Fu:	15.34% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.497
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:	0.007
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.992
HLM stability:	0.006 ? 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):

1.815

Half-life (T1/2):

3.085

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.072
Human Hepatotoxicity (H-HT):	0.666	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.979	Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.118	Skin Sensitization:	0.989
Carcinogencity:	0.521	Eye Corrosion:	0.0
Eye Irritation:	0.336	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.868
Hematotoxicity:	0.142	Drug-induced Nephrotoxicity:	0.614
Genotoxicity:	0.954	RPMI-8226 Immunitoxicity:	0.193
A549 Cytotoxicity:	0.57	Hek293 Cytotoxicity:	0.651
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:	3.112 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.644 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.773 ? 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
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22060189]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	flower	n.a.	PMID[22723874]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23371463]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Flowers	Lasa, China	n.a.	PMID[24621197]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27748595]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39732883]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Bud	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18311	Carthamus tinctorius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18311	Carthamus tinctorius	Species	Asteraceae	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 NPC511432 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	19239
0.1-0.2	26900
0.2-0.3	2676
0.3-0.4	691
0.4-0.5	241
0.5-0.6	63
0.6-0.7	30
0.7-0.8	1
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8372	Intermediate Similarity	NPC65711
0.8023	Intermediate Similarity	NPC22062
0.8023	Intermediate Similarity	NPC473634
0.8023	Intermediate Similarity	NPC138811
0.7667	Intermediate Similarity	NPC473623
0.7582	Intermediate Similarity	NPC488089
0.7253	Intermediate Similarity	NPC46202
0.7143	Intermediate Similarity	NPC95090
0.7143	Intermediate Similarity	NPC27408
0.7097	Intermediate Similarity	NPC209296
0.7059	Intermediate Similarity	NPC181712
0.6923	Remote Similarity	NPC44931
0.6667	Remote Similarity	NPC210073
0.6596	Remote Similarity	NPC204693
0.6531	Remote Similarity	NPC101636
0.65	Remote Similarity	NPC11468
0.6413	Remote Similarity	NPC211594
0.6392	Remote Similarity	NPC483707
0.6354	Remote Similarity	NPC64051
0.6277	Remote Similarity	NPC295613
0.6277	Remote Similarity	NPC473657
0.6264	Remote Similarity	NPC22832
0.6264	Remote Similarity	NPC243930
0.625	Remote Similarity	NPC122809
0.625	Remote Similarity	NPC311850
0.6224	Remote Similarity	NPC229409
0.6222	Remote Similarity	NPC27942
0.62	Remote Similarity	NPC298171
0.6196	Remote Similarity	NPC607707
0.619	Remote Similarity	NPC488087
0.619	Remote Similarity	NPC488083
0.6162	Remote Similarity	NPC270675
0.6162	Remote Similarity	NPC195685
0.6154	Remote Similarity	NPC473644
0.61	Remote Similarity	NPC475382
0.6075	Remote Similarity	NPC488086
0.6075	Remote Similarity	NPC68592
0.6067	Remote Similarity	NPC39360
0.6067	Remote Similarity	NPC29763
0.6067	Remote Similarity	NPC210003
0.6058	Remote Similarity	NPC472993
0.598	Remote Similarity	NPC472994
0.5955	Remote Similarity	NPC331652
0.5914	Remote Similarity	NPC80188
0.5882	Remote Similarity	NPC235575
0.5851	Remote Similarity	NPC311830
0.5851	Remote Similarity	NPC220169
0.5825	Remote Similarity	NPC135358
0.5824	Remote Similarity	NPC189142
0.5824	Remote Similarity	NPC77660
0.5816	Remote Similarity	NPC473512
0.5816	Remote Similarity	NPC129827
0.5789	Remote Similarity	NPC190003
0.5761	Remote Similarity	NPC186807
0.5752	Remote Similarity	NPC262222
0.5745	Remote Similarity	NPC608742
0.5729	Remote Similarity	NPC172807
0.5714	Remote Similarity	NPC58053
0.5714	Remote Similarity	NPC261866
0.5714	Remote Similarity	NPC19709
0.5714	Remote Similarity	NPC275454
0.5714	Remote Similarity	NPC67105
0.5696	Remote Similarity	NPC29353
0.5688	Remote Similarity	NPC488088
0.5686	Remote Similarity	NPC479766
0.5631	Remote Similarity	NPC479765
0.5604	Remote Similarity	NPC473043
0.5586	Remote Similarity	NPC198199
0.5579	Remote Similarity	NPC601144
0.5556	Remote Similarity	NPC227508
0.5545	Remote Similarity	NPC284277
0.5545	Remote Similarity	NPC475497
0.5543	Remote Similarity	NPC476442
0.5543	Remote Similarity	NPC215512
0.551	Remote Similarity	NPC254540
0.5446	Remote Similarity	NPC298666
0.5446	Remote Similarity	NPC186816
0.5439	Remote Similarity	NPC120952
0.5437	Remote Similarity	NPC257714
0.5392	Remote Similarity	NPC475366
0.5385	Remote Similarity	NPC600130
0.5376	Remote Similarity	NPC143851
0.5347	Remote Similarity	NPC479405
0.5347	Remote Similarity	NPC150164
0.5333	Remote Similarity	NPC477629
0.5294	Remote Similarity	NPC479404
0.5258	Remote Similarity	NPC486578
0.5248	Remote Similarity	NPC15358
0.5225	Remote Similarity	NPC277532
0.5213	Remote Similarity	NPC289667
0.52	Remote Similarity	NPC8856
0.5196	Remote Similarity	NPC65003
0.5196	Remote Similarity	NPC303913
0.5192	Remote Similarity	NPC479403
0.5189	Remote Similarity	NPC80068
0.5155	Remote Similarity	NPC212748
0.5155	Remote Similarity	NPC285197
0.5149	Remote Similarity	NPC187379
0.5138	Remote Similarity	NPC121703
0.5116	Remote Similarity	NPC171533
0.5094	Remote Similarity	NPC486577
0.5054	Remote Similarity	NPC34965
0.5047	Remote Similarity	NPC195257
0.5045	Remote Similarity	NPC480796

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC511432 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5129
0.1-0.2	3943
0.2-0.3	64
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
0.7097	Intermediate Similarity	NPD7054	Phase 4
0.5421	Remote Similarity	NPD7472	Pre-clinical
0.5278	Remote Similarity	NPD7808	Phase 3
0.5189	Remote Similarity	NPD7251	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