NPASS Compound

Natural Product: NPC535595

Natural Product ID	NPC535595
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-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 64 67 0 0 0 0 0 0 0 0999 V2000 5.3790 -2.0030 -2.5053 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6947 -1.5625 -1.2098 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9073 -2.6044 -0.5411 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8649 -0.3427 -0.8298 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4087 0.4574 0.3023 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5887 -0.2564 1.2590 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1735 -1.1202 2.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5631 -1.3536 2.1480 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3545 -1.7464 3.0722 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9843 -1.5161 3.0843 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1736 -2.1559 4.0111 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4268 -0.6445 2.1677 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2082 0.0023 1.2392 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6958 0.8238 0.3724 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3822 1.1168 0.2956 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0066 2.0795 -0.7559 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8802 2.3195 -1.8108 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5664 3.2763 -2.7451 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5992 4.0172 -2.6731 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9170 4.9862 -3.6205 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4608 3.7787 -1.6286 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1371 2.8115 -0.6892 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4547 0.5122 1.1756 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8056 0.7467 1.1391 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7791 -0.0282 0.5072 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3989 0.6651 -0.4938 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4754 0.0163 -1.0637 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1386 -1.1830 -1.8805 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5701 -0.2642 -0.0348 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9997 0.9306 0.5188 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9885 -1.1401 1.0241 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7219 -2.4292 0.6227 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7594 -0.4661 1.5897 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1261 0.6153 2.3512 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0822 -0.3781 2.1246 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6648 -0.9261 2.9287 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7382 -3.0308 -2.4331 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2611 -1.3509 -2.6983 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6514 -1.9404 -3.3304 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5782 -3.1183 0.2082 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6977 -3.4624 -1.2756 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9458 -2.3110 -0.1316 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5290 0.2621 -1.5400 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2636 1.0083 0.7997 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8178 1.3269 -0.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1699 -0.5398 2.2317 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8163 -2.4292 3.7843 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9720 -1.6239 4.8713 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7746 1.7282 -1.8374 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2527 3.4699 -3.5797 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2675 5.8905 -3.4100 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3742 4.3511 -1.5614 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8578 2.7176 0.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3843 -0.9597 0.0561 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9443 0.7663 -1.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1878 -1.6656 -1.6700 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1817 -0.9767 -2.9727 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9371 -1.9524 -1.6650 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3908 -0.7638 -0.6018 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1956 1.6114 -0.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7136 -1.2032 1.8690 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1673 -3.1129 1.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2336 -1.2176 2.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9763 1.4919 1.8840 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 2 3 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 19 21 1 0 21 22 2 0 15 23 2 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 23 35 1 0 35 36 2 0 13 6 1 0 22 16 1 0 33 25 1 0 35 12 1 0 1 37 1 0 1 38 1 0 1 39 1 0 3 40 1 0 3 41 1 0 3 42 1 0 4 43 1 0 5 44 1 0 5 45 1 0 8 46 1 0 9 47 1 0 11 48 1 0 17 49 1 0 18 50 1 0 20 51 1 0 21 52 1 0 22 53 1 0 25 54 1 6 27 55 1 6 28 56 1 0 28 57 1 0 28 58 1 0 29 59 1 6 30 60 1 0 31 61 1 1 32 62 1 0 33 63 1 1 34 64 1 0 M END

Standard InCHIKey	RPLMLWBOUPDPQF-XXZNUWDDSA-N
Standard InCHI	InChI=1S/C26H28O10/c1-11(2)4-9-15-16(28)10-17(29)18-20(31)25(36-26-22(33)21(32)19(30)12(3)34-26)23(35-24(15)18)13-5-7-14(27)8-6-13/h4-8,10,12,19,21-22,26-30,32-33H,9H2,1-3H3/t12-,19-,21+,22-,26-/m0/s1
SMILES	CC(C)=CCC1=C(O)C=C(O)C2=C1OC(C1=CC=C(O)C=C1)=C(O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]1O)C2=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	500.17	Volume:	488.2 ? Van der Waals volume.
Dense:	1.025	LogP:	2.518 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.487 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.06 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	25.0
TPSA:	170.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.286	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.21	Fsp³:	0.346
MCE-18:	92.0 ? 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:	0.693	Fluc inhibitor:	0.283 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.964 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.945 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.091	Promiscuous compounds:	0.107

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.852	MDCK Permeability:	-4.977
Pgp-inhibitor:	0.041	Pgp-substrate:	0.619
PAMPA:	0.989 ? 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):	0.054
20% Bioavailability (F20%):	0.48	30% Bioavailability (F30%):	0.927
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.694
Plasma Protein Binding (PPB):	89.504%	Volume Distribution (VD):	0.187
Fu:	12.59% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.993
OATP1B3 inhibitor:	0.985	BCRP inhibitor:	0.863
BSEP inhibitor:	0.696

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.072	CYP2C19-substrate:	0.655
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.013
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

2.697

Half-life (T1/2):

2.761

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.325
Human Hepatotoxicity (H-HT):	0.624	Drug-induced Liver Injury (DILI):	0.939
AMES Toxicity:	0.883	Rat Oral Acute Toxicity:	0.282
Maximum Recommended Daily Dose:	0.236	Skin Sensitization:	0.997
Carcinogencity:	0.135	Eye Corrosion:	0.0
Eye Irritation:	0.395	Respiratory Toxicity:	0.597
Drug-induced Neurotoxicity:	0.024	Ototoxicity:	0.576
Hematotoxicity:	0.104	Drug-induced Nephrotoxicity:	0.371
Genotoxicity:	0.99	RPMI-8226 Immunitoxicity:	0.134
A549 Cytotoxicity:	0.74	Hek293 Cytotoxicity:	0.769
BCF:	1.468 ? 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:	4.306 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.543 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.096 ? 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
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	Species	Berberidaceae	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 NPC535595 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	14049
0.1-0.2	31433
0.2-0.3	3459
0.3-0.4	561
0.4-0.5	241
0.5-0.6	91
0.6-0.7	14
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC66087
0.8462	Intermediate Similarity	NPC278419
0.8462	Intermediate Similarity	NPC179198
0.6962	Remote Similarity	NPC111929
0.6962	Remote Similarity	NPC320283
0.6962	Remote Similarity	NPC41121
0.6463	Remote Similarity	NPC249281
0.631	Remote Similarity	NPC46420
0.6265	Remote Similarity	NPC127546
0.6265	Remote Similarity	NPC57625
0.6265	Remote Similarity	NPC173637
0.6265	Remote Similarity	NPC317489
0.6265	Remote Similarity	NPC223424
0.6265	Remote Similarity	NPC600591
0.617	Remote Similarity	NPC5319
0.6023	Remote Similarity	NPC116458
0.6023	Remote Similarity	NPC246943
0.5955	Remote Similarity	NPC276377
0.5882	Remote Similarity	NPC77672
0.5882	Remote Similarity	NPC133671
0.5882	Remote Similarity	NPC135391
0.5882	Remote Similarity	NPC78263
0.5882	Remote Similarity	NPC250069
0.587	Remote Similarity	NPC173582
0.587	Remote Similarity	NPC265885
0.587	Remote Similarity	NPC181465
0.587	Remote Similarity	NPC215710
0.587	Remote Similarity	NPC473438
0.587	Remote Similarity	NPC253788
0.5843	Remote Similarity	NPC223747
0.5814	Remote Similarity	NPC8573
0.5765	Remote Similarity	NPC135599
0.5765	Remote Similarity	NPC73855
0.5765	Remote Similarity	NPC113968
0.5765	Remote Similarity	NPC328940
0.5765	Remote Similarity	NPC277174
0.5765	Remote Similarity	NPC606877
0.5682	Remote Similarity	NPC59534
0.5638	Remote Similarity	NPC150164
0.5632	Remote Similarity	NPC265530
0.5618	Remote Similarity	NPC219904
0.5579	Remote Similarity	NPC186816
0.5568	Remote Similarity	NPC271692
0.5529	Remote Similarity	NPC288084
0.5505	Remote Similarity	NPC480443
0.5455	Remote Similarity	NPC297987
0.5435	Remote Similarity	NPC476215
0.5426	Remote Similarity	NPC139320
0.5408	Remote Similarity	NPC72016
0.5393	Remote Similarity	NPC305811
0.5393	Remote Similarity	NPC27640
0.5361	Remote Similarity	NPC470125
0.5354	Remote Similarity	NPC64755
0.5326	Remote Similarity	NPC605784
0.5316	Remote Similarity	NPC9117
0.5316	Remote Similarity	NPC220062
0.5312	Remote Similarity	NPC203259
0.5312	Remote Similarity	NPC65563
0.5312	Remote Similarity	NPC33054
0.5312	Remote Similarity	NPC470949
0.5312	Remote Similarity	NPC176740
0.5312	Remote Similarity	NPC471725
0.5312	Remote Similarity	NPC134532
0.5312	Remote Similarity	NPC602582
0.5281	Remote Similarity	NPC145038
0.5281	Remote Similarity	NPC56077
0.5281	Remote Similarity	NPC281131
0.5281	Remote Similarity	NPC253662
0.5281	Remote Similarity	NPC179950
0.5281	Remote Similarity	NPC88789
0.5281	Remote Similarity	NPC491374
0.5275	Remote Similarity	NPC159579
0.5263	Remote Similarity	NPC471079
0.5258	Remote Similarity	NPC129264
0.5258	Remote Similarity	NPC473571
0.5258	Remote Similarity	NPC110941
0.5253	Remote Similarity	NPC32641
0.5253	Remote Similarity	NPC256188
0.5253	Remote Similarity	NPC35119
0.5233	Remote Similarity	NPC54802
0.5233	Remote Similarity	NPC197304
0.5227	Remote Similarity	NPC331652
0.5222	Remote Similarity	NPC24043
0.5222	Remote Similarity	NPC488080
0.5222	Remote Similarity	NPC349108
0.5222	Remote Similarity	NPC169977
0.5213	Remote Similarity	NPC265115
0.5208	Remote Similarity	NPC163242
0.5208	Remote Similarity	NPC272068
0.5169	Remote Similarity	NPC476405
0.5169	Remote Similarity	NPC108831
0.5169	Remote Similarity	NPC182634
0.5155	Remote Similarity	NPC605592
0.5149	Remote Similarity	NPC85751
0.5149	Remote Similarity	NPC19240
0.513	Remote Similarity	NPC483159
0.513	Remote Similarity	NPC483160
0.5111	Remote Similarity	NPC64305
0.5111	Remote Similarity	NPC158674
0.5109	Remote Similarity	NPC175107
0.5109	Remote Similarity	NPC129217
0.5109	Remote Similarity	NPC611303
0.5104	Remote Similarity	NPC480466
0.51	Remote Similarity	NPC270448
0.5093	Remote Similarity	NPC483158
0.5093	Remote Similarity	NPC483157
0.5053	Remote Similarity	NPC116864
0.5053	Remote Similarity	NPC244776

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC535595 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4036
0.1-0.2	5052
0.2-0.3	53
0.3-0.4	4
0.4-0.5	3
0.5-0.6	1
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
0.617	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5312	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