NPASS Compound

Natural Product: NPC473088

Natural Product ID	NPC473088
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HHEBRZYAUOCPFH-KPNXULIBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3609596
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

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 82 86 0 0 0 0 0 0 0 0999 V2000 -1.5194 1.8121 4.8160 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1374 1.5412 3.4862 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1650 2.1264 3.0917 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5559 0.6106 2.6579 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0505 0.2685 1.3738 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1202 -0.7736 0.8325 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2566 -0.1772 0.7367 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2090 1.1746 0.5255 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7118 2.1743 1.3278 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2647 1.6964 2.3430 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6081 3.5920 1.0254 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1324 4.5425 1.8698 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0447 5.8998 1.6006 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4139 6.3065 0.4538 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1197 5.3720 -0.4084 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0200 4.0153 -0.1180 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0536 -1.0025 -0.2235 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3446 -0.4835 -0.4690 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5247 -1.0561 -0.1096 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5019 -2.1491 0.5007 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7889 -0.4072 -0.4302 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9654 -1.0149 -0.0513 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2068 -0.4527 -0.3243 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2789 0.7501 -0.9942 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1168 1.3753 -1.3823 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8757 0.7932 -1.0983 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3853 -1.2334 -1.5538 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0295 -0.6198 -1.5663 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5782 -1.4155 -0.4452 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9589 -2.6898 -0.5171 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0815 -2.7021 -1.5600 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0734 -3.6327 -1.1849 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5900 -3.1239 -2.8845 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0359 -1.6998 -0.4554 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4599 -2.4091 0.7921 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5672 -2.4443 1.9434 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1797 -1.9219 1.8266 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6913 -1.4542 3.0474 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1598 -1.7691 3.0437 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9174 -0.5320 -0.8236 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6621 -0.9167 -2.7605 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2042 0.0061 -3.6376 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1298 1.2138 -3.3514 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8711 -0.3982 -4.9079 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8744 1.0872 5.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6549 2.8589 5.1364 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4228 1.6351 4.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9470 1.2381 0.7937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0837 -0.0297 1.4944 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7372 -0.3269 1.7282 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6224 4.1956 2.7631 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4808 6.6194 2.3090 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3484 7.3802 0.2477 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6052 5.7398 -1.2954 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4453 3.3290 -0.8102 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2504 -1.9615 0.3034 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9502 -1.9553 0.4738 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1353 -0.9262 -0.0287 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2496 1.2147 -1.2216 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1871 2.3165 -1.9061 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9748 1.2878 -1.4048 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9662 -0.9711 -2.4223 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0024 0.4590 -1.3824 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0574 -3.9311 -0.1240 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0336 -3.2522 -1.5287 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9305 -4.6086 -1.7411 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6847 -3.2407 -2.9780 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1818 -2.4560 -3.7002 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1848 -4.1404 -3.1740 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1813 -2.4394 -1.3061 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7883 -3.4719 0.5631 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4540 -1.9401 1.0771 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4477 -3.4977 2.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5225 -2.7219 1.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5082 -2.2645 3.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1461 -1.9156 2.9779 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7981 -0.4326 -0.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4294 -0.6634 -1.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3682 0.4197 -0.9393 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9507 -0.1463 -4.8093 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7237 -1.4812 -5.1152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4712 0.2019 -5.7548 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 6 5 1 1 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 7 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 17 27 1 0 27 28 1 0 28 29 1 0 29 30 1 6 30 31 1 0 31 32 1 0 31 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 34 40 1 0 28 41 1 0 41 42 1 0 42 43 2 0 42 44 1 0 37 6 1 0 29 6 1 0 16 11 1 0 26 21 1 0 31 27 1 0 1 45 1 0 1 46 1 0 1 47 1 0 5 48 1 0 5 49 1 0 7 50 1 1 12 51 1 0 13 52 1 0 14 53 1 0 15 54 1 0 16 55 1 0 17 56 1 1 22 57 1 0 23 58 1 0 24 59 1 0 25 60 1 0 26 61 1 0 27 62 1 6 28 63 1 1 32 64 1 0 32 65 1 0 32 66 1 0 33 67 1 0 33 68 1 0 33 69 1 0 34 70 1 6 35 71 1 0 35 72 1 0 36 73 1 1 37 74 1 6 38 75 1 0 39 76 1 0 40 77 1 0 40 78 1 0 40 79 1 0 44 80 1 0 44 81 1 0 44 82 1 0 M END

Standard InCHIKey	HHEBRZYAUOCPFH-KPNXULIBSA-N
Standard InCHI	InChI=1S/C33H38O11/c1-18-16-23(36)26(37)32(17-40-19(2)34)28(43-30(39)22-14-10-7-11-15-22)25(42-29(38)21-12-8-6-9-13-21)24-27(41-20(3)35)33(18,32)44-31(24,4)5/h6-15,18,23-28,36-37H,16-17H2,1-5H3/t18-,23+,24-,25-,26+,27-,28-,32+,33-/m1/s1
SMILES	CC(=O)OC[C@@]12[C@H](OC(=O)c3ccccc3)[C@H](OC(=O)c3ccccc3)[C@@H]3[C@H]([C@]2(OC3(C)C)[C@@H](C[C@@H]([C@@H]1O)O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.24	Volume:	606.87 ? Van der Waals volume.
Dense:	1.006	LogP:	2.95 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.986 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.512 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	30.0
TPSA:	154.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.351	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.843	Fsp³:	0.515
MCE-18:	164.28 ? 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:	0.554	Fluc inhibitor:	0.018 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.053 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.049	Promiscuous compounds:	0.095

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.728	MDCK Permeability:	-5.105
Pgp-inhibitor:	0.732	Pgp-substrate:	0.092
PAMPA:	0.424 ? 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):	0.0
20% Bioavailability (F20%):	0.056	30% Bioavailability (F30%):	0.154
50% Bioavailability (F50%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977	MRP1:	0.999
Plasma Protein Binding (PPB):	81.896%	Volume Distribution (VD):	-0.534
Fu:	18.552% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	0.934	BCRP inhibitor:	0.002
BSEP inhibitor:	0.791

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.043
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.112	CYP3A4-substrate:	0.266
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.98 ? 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):

1.603

Half-life (T1/2):

1.421

ADMET: Toxicity

hERG Blockers:	0.047	hERG Blockers (10um):	0.378
Human Hepatotoxicity (H-HT):	0.043	Drug-induced Liver Injury (DILI):	0.872
AMES Toxicity:	0.91	Rat Oral Acute Toxicity:	0.162
Maximum Recommended Daily Dose:	0.204	Skin Sensitization:	0.999
Carcinogencity:	0.785	Eye Corrosion:	0.0
Eye Irritation:	0.545	Respiratory Toxicity:	0.155
Drug-induced Neurotoxicity:	0.747	Ototoxicity:	0.233
Hematotoxicity:	0.249	Drug-induced Nephrotoxicity:	0.736
Genotoxicity:	0.12	RPMI-8226 Immunitoxicity:	0.181
A549 Cytotoxicity:	0.816	Hek293 Cytotoxicity:	0.811
BCF:	0.576 ? 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:	3.461 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.795 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.299 ? 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
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/S0031-9422(99)00216-2]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	seeds and root bark	Henan, China	n.a.	PMID[26295746]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25272	Celastrus angulatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25272	Celastrus angulatus	Species	Celastraceae	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

Activity Type	# Activity
Activity	8

Activity Type	# Activity
Cell line	1
Organism	3
Others	4

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Activity	=	31.6	%	PMID[17685651]
NPT2	Others	Unspecified	n.a.	Activity	=	2.0	%	PMID[25906329]
NPT2	Others	Unspecified	n.a.	Activity	=	72.1	%	PMID[19318257]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[20573514]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	60.0	%	PMID[15974609]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	90.0	%	PMID[15921441]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	5.3	n.a.	PubChem BioAssay data set

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 NPC473088 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	8568
0.1-0.2	37777
0.2-0.3	2807
0.3-0.4	540
0.4-0.5	122
0.5-0.6	31
0.6-0.7	10
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	Natural Product ID
0.7846	Intermediate Similarity	NPC241951
0.6944	Remote Similarity	NPC252314
0.662	Remote Similarity	NPC483845
0.6479	Remote Similarity	NPC51314
0.6389	Remote Similarity	NPC147880
0.6301	Remote Similarity	NPC137718
0.6301	Remote Similarity	NPC148062
0.6164	Remote Similarity	NPC90257
0.6164	Remote Similarity	NPC69357
0.6027	Remote Similarity	NPC473060
0.6026	Remote Similarity	NPC483849
0.5921	Remote Similarity	NPC483844
0.589	Remote Similarity	NPC90614
0.5867	Remote Similarity	NPC147217
0.5844	Remote Similarity	NPC479043
0.5844	Remote Similarity	NPC11685
0.5833	Remote Similarity	NPC475429
0.5833	Remote Similarity	NPC211137
0.5696	Remote Similarity	NPC483848
0.5676	Remote Similarity	NPC483862
0.561	Remote Similarity	NPC479040
0.5488	Remote Similarity	NPC603877
0.5455	Remote Similarity	NPC27377
0.5443	Remote Similarity	NPC57628
0.5443	Remote Similarity	NPC472569
0.5443	Remote Similarity	NPC16912
0.5405	Remote Similarity	NPC481047
0.5405	Remote Similarity	NPC66761
0.5405	Remote Similarity	NPC483843
0.5405	Remote Similarity	NPC481045
0.5405	Remote Similarity	NPC476094
0.5395	Remote Similarity	NPC281717
0.5316	Remote Similarity	NPC41481
0.5316	Remote Similarity	NPC471103
0.525	Remote Similarity	NPC472570
0.5233	Remote Similarity	NPC473115
0.519	Remote Similarity	NPC473758
0.519	Remote Similarity	NPC471104
0.5181	Remote Similarity	NPC481486
0.5063	Remote Similarity	NPC483846
0.506	Remote Similarity	NPC481050
0.506	Remote Similarity	NPC481489

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473088 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2764
0.1-0.2	6143
0.2-0.3	241
0.3-0.4	2
0.4-0.5	0
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