NPASS Compound

Natural Product: NPC135107

Natural Product ID	NPC135107
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PMQDVDNUZOVYCU-ASMIUSRBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	24094147
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0000507] Isoflavonoid O-glycosides

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 75 79 0 0 0 0 0 0 0 0999 V2000 -11.6175 0.0970 -1.4163 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0083 0.0206 -0.1600 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6225 0.0097 -0.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8672 0.0751 -1.2105 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4908 0.0646 -1.1186 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8712 -0.0104 0.1096 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4950 -0.0170 0.1375 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9245 -0.0854 1.2571 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7375 0.0486 -1.0129 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4436 0.1216 -2.2022 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7541 0.1277 -2.2268 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2751 0.0421 -0.9857 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5672 -0.7471 -1.8649 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1971 -0.7886 -1.8806 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4476 -0.0177 -0.9887 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1735 0.7623 -0.1204 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5628 0.8082 -0.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9162 -0.1071 -1.0592 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8051 0.5857 -0.2462 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5833 -0.4245 0.5527 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4798 0.3517 1.4831 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0950 1.5372 0.8022 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8855 1.6014 -0.6501 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7804 0.8425 -1.5732 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0963 0.8600 -1.4487 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8436 0.3794 -0.4743 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9935 -0.5235 -0.9270 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8022 -0.5378 0.3693 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2627 -0.8220 0.0907 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9069 -0.8302 1.3311 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5694 0.8448 0.8781 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6229 1.4434 0.0560 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2320 -1.4872 1.1822 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5950 -1.8126 -1.1726 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5598 1.4095 -1.0372 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5229 2.7313 1.3696 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3749 -0.4756 2.1328 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6433 -1.0906 1.3715 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6558 -0.0746 1.2426 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0307 -0.0666 1.1924 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8672 -0.1285 2.2916 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2693 -1.4126 2.7400 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0458 -0.1492 2.4651 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.7183 -0.0610 -1.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4026 1.0630 -1.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1938 -0.7195 -2.0552 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3373 0.1338 -2.1720 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8781 0.1748 -3.1341 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1561 -1.3579 -2.5712 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6667 -1.4254 -2.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6558 1.3819 0.5942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0997 1.4356 0.5996 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2622 1.2080 0.4847 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0745 -1.2064 -0.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7969 0.7416 2.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1464 1.6199 1.0937 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0640 2.6955 -0.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5581 1.3145 -2.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3546 -0.1991 -1.7665 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4061 -0.1347 0.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6297 -0.0616 -1.6791 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7088 -0.1008 -0.5934 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3952 -1.8316 -0.3469 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1089 -1.7548 1.6213 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2729 0.8176 1.9446 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5045 1.4754 0.8291 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5078 -2.0095 0.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4198 -2.3892 -1.0844 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7834 3.4421 0.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0672 -0.7811 3.0225 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0333 -1.8848 1.7966 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6684 -2.2245 2.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1435 -1.5037 3.8485 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3280 -1.6050 2.4373 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4926 0.5911 2.8818 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 7 9 1 0 9 10 2 0 10 11 1 0 9 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 15 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 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 31 32 1 0 28 33 1 1 27 34 1 0 23 35 1 0 22 36 1 0 21 37 1 0 20 38 1 0 6 39 1 0 39 40 2 0 40 41 1 0 41 42 1 0 39 43 1 0 40 3 1 0 11 5 1 0 17 12 1 0 35 19 1 0 32 26 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 10 48 1 0 13 49 1 0 14 50 1 0 16 51 1 0 17 52 1 0 19 53 1 1 20 54 1 6 21 55 1 1 22 56 1 6 23 57 1 6 24 58 1 0 24 59 1 0 26 60 1 1 27 61 1 6 29 62 1 0 29 63 1 0 30 64 1 0 31 65 1 0 31 66 1 0 33 67 1 0 34 68 1 0 36 69 1 0 37 70 1 0 38 71 1 0 42 72 1 0 42 73 1 0 42 74 1 0 43 75 1 0 M END

Standard InCHIKey	PMQDVDNUZOVYCU-ASMIUSRBSA-N
Standard InCHI	InChI=1S/C28H32O15/c1-37-16-7-15-18(21(32)24(16)38-2)19(30)14(8-39-15)12-3-5-13(6-4-12)42-26-23(34)22(33)20(31)17(43-26)9-40-27-25(35)28(36,10-29)11-41-27/h3-8,17,20,22-23,25-27,29,31-36H,9-11H2,1-2H3/t17-,20-,22+,23-,25+,26-,27-,28-/m1/s1
SMILES	COc1cc2c(c(=O)c(co2)c2ccc(cc2)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]3[C@@H]([C@@](CO)(CO3)O)O)O2)O)O)O)c(c1OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	0.971 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.421 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.013 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	29.0
TPSA:	227.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.152	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.679	Fsp³:	0.464
MCE-18:	116.927 ? 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:	0.516	Fluc inhibitor:	0.264 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.679 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.519 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.03	Promiscuous compounds:	0.246

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.278	MDCK Permeability:	-5.334
Pgp-inhibitor:	0.0	Pgp-substrate:	0.407
PAMPA:	0.99 ? 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):	0.805
20% Bioavailability (F20%):	0.056	30% Bioavailability (F30%):	0.889
50% Bioavailability (F50%):	0.972

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012	MRP1:	0.343
Plasma Protein Binding (PPB):	83.182%	Volume Distribution (VD):	-0.34
Fu:	14.81% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.125
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:	0.19
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.16
HLM stability:	0.0 ? 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):

1.801

Half-life (T1/2):

2.933

ADMET: Toxicity

hERG Blockers:	0.043	hERG Blockers (10um):	0.084
Human Hepatotoxicity (H-HT):	0.802	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.961	Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.081	Skin Sensitization:	0.983
Carcinogencity:	0.369	Eye Corrosion:	0.0
Eye Irritation:	0.079	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.045	Ototoxicity:	0.964
Hematotoxicity:	0.294	Drug-induced Nephrotoxicity:	0.858
Genotoxicity:	0.888	RPMI-8226 Immunitoxicity:	0.257
A549 Cytotoxicity:	0.628	Hek293 Cytotoxicity:	0.501
BCF:	0.425 ? 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:	3.196 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.741 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.869 ? 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
NPO26331	Plumbago auriculata	Species	Plumbaginaceae	Eukaryota	n.a.	flower	n.a.	PMID[22260638]
NPO20876	Arnica longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO23269	Spodoptera exigua	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26331	Plumbago auriculata	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20876	Arnica longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17889	Clerodendrum indicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23821	Rubus rigidus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23821	Rubus rigidus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6173	Senegalia caesia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23821	Rubus rigidus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26331	Plumbago auriculata	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20876	Arnica longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22848	Kaempferia galanga	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20888	Paraderris canarensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23269	Spodoptera exigua	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17889	Clerodendrum indicum	Species	Lamiaceae	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 NPC135107 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	18344
0.1-0.2	28005
0.2-0.3	2705
0.3-0.4	631
0.4-0.5	137
0.5-0.6	26
0.6-0.7	5
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
0.8068	Intermediate Similarity	NPC257714
0.7234	Intermediate Similarity	NPC235575
0.6292	Remote Similarity	NPC73511
0.6146	Remote Similarity	NPC479405
0.6082	Remote Similarity	NPC479404
0.6044	Remote Similarity	NPC205076
0.6022	Remote Similarity	NPC307518
0.5979	Remote Similarity	NPC475155
0.5979	Remote Similarity	NPC303913
0.59	Remote Similarity	NPC51326
0.5778	Remote Similarity	NPC160515
0.5638	Remote Similarity	NPC224462
0.5631	Remote Similarity	NPC231194
0.5625	Remote Similarity	NPC48773
0.5543	Remote Similarity	NPC476442
0.5543	Remote Similarity	NPC215512
0.549	Remote Similarity	NPC479403
0.5484	Remote Similarity	NPC156457
0.5476	Remote Similarity	NPC171533
0.5446	Remote Similarity	NPC204693
0.5385	Remote Similarity	NPC600130
0.5354	Remote Similarity	NPC487212
0.534	Remote Similarity	NPC65711
0.5288	Remote Similarity	NPC483707
0.5269	Remote Similarity	NPC45165
0.5269	Remote Similarity	NPC135345
0.5253	Remote Similarity	NPC211594
0.5185	Remote Similarity	NPC475261
0.5158	Remote Similarity	NPC197896
0.5158	Remote Similarity	NPC313163
0.5109	Remote Similarity	NPC25547
0.5056	Remote Similarity	NPC287429
0.5053	Remote Similarity	NPC348541

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC135107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4754
0.1-0.2	4330
0.2-0.3	52
0.3-0.4	9
0.4-0.5	5
0.5-0.6	0
0.6-0.7	0
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
		NPD

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