NPASS Compound

Natural Product: NPC275802

Natural Product ID	NPC275802
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TZETVSMCLFVOIU-SIQIQTTRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5318160
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

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 87 91 0 0 0 0 0 0 0 0999 V2000 8.0004 2.2835 1.0020 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0243 1.2573 0.4983 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6023 1.7097 0.6097 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6915 0.6636 0.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1846 -0.4040 -0.3347 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3140 0.8012 0.0777 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4119 -0.1753 -0.4029 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4999 0.4746 -1.3252 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5199 -0.2244 -2.4499 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7098 -1.0278 -2.7985 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3084 -0.1810 -3.3260 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9499 0.2149 -2.6224 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8391 1.0266 -1.3879 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1895 0.3323 -0.0965 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8157 -1.1195 0.0310 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2934 -1.4219 0.9860 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0786 -1.0455 2.4223 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7285 -2.8602 0.8424 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2389 -3.8356 0.3416 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5859 -3.4007 -0.0932 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0206 -2.0016 0.3298 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2131 -2.7158 1.5625 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5441 -3.8707 0.7996 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1023 -1.6441 -0.4370 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3703 -2.0591 -0.5359 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7326 -2.9631 0.2060 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3906 -1.5124 -1.4801 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3134 -3.2163 2.0850 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5446 -0.6753 0.7209 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0739 -0.3404 1.7646 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5003 0.6220 0.3490 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8227 1.3767 1.4537 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8325 1.8159 2.0745 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1447 1.6828 1.9242 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3510 2.4558 3.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5795 2.7779 3.5525 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6923 2.3319 2.9134 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5641 1.5598 1.7779 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2993 1.2436 1.2957 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5847 1.6477 -1.2886 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6851 2.4898 -0.0706 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8944 2.5100 -2.4686 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5906 2.2021 -1.3816 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1863 -1.4815 -3.8770 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3869 0.8576 -0.7707 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0316 2.0896 0.6964 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9746 2.3185 2.1119 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7481 3.3115 0.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1279 0.3611 1.1745 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4471 2.6875 0.0696 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4136 1.9481 1.6802 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9597 -1.0376 -0.7599 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6692 -1.1242 -3.9270 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6528 -2.0905 -2.4605 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6587 -0.5316 -2.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5780 0.4471 -4.1991 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5029 0.8649 -3.3713 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5726 -0.7131 -2.5147 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5505 0.8466 0.6607 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4967 -1.4730 -0.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4470 -0.0885 2.7449 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1268 -0.7723 2.5540 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3241 -1.7778 3.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6292 -2.9223 0.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2984 -4.6618 1.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1639 -4.4324 -0.5395 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9147 -3.6884 -1.1308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0328 -2.4124 2.2586 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4027 -3.0891 2.1934 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0941 -0.5183 -1.8678 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3537 -1.4731 -0.9317 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5087 -2.2705 -2.2809 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8167 -4.0633 1.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4755 2.8190 3.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6465 3.3851 4.4452 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6625 2.5943 3.3121 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4569 1.2105 1.2774 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1825 0.6508 0.4227 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0768 2.0393 0.8275 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3555 3.3847 -0.2621 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3109 2.9720 0.1153 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1354 2.5854 -3.2374 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1406 3.5752 -2.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8357 2.1766 -3.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1771 2.9859 -1.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6148 -2.1506 -3.2926 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4558 -0.1243 -0.8703 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 6 24 25 1 0 25 26 2 0 25 27 1 0 18 28 1 0 16 29 1 0 29 30 2 0 14 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 13 40 1 0 40 41 1 0 40 42 1 0 13 43 1 6 11 44 1 0 2 45 1 0 29 7 1 0 39 34 1 0 40 8 1 0 21 15 1 0 23 20 1 0 1 46 1 0 1 47 1 0 1 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 7 52 1 6 10 53 1 0 10 54 1 0 10 55 1 0 11 56 1 6 12 57 1 0 12 58 1 0 14 59 1 1 15 60 1 6 17 61 1 0 17 62 1 0 17 63 1 0 18 64 1 6 19 65 1 0 19 66 1 0 20 67 1 6 22 68 1 0 22 69 1 0 27 70 1 0 27 71 1 0 27 72 1 0 28 73 1 0 35 74 1 0 36 75 1 0 37 76 1 0 38 77 1 0 39 78 1 0 41 79 1 0 41 80 1 0 41 81 1 0 42 82 1 0 42 83 1 0 42 84 1 0 43 85 1 0 44 86 1 0 45 87 1 0 M END

Standard InCHIKey	TZETVSMCLFVOIU-SIQIQTTRSA-N
Standard InCHI	InChI=1S/C33H42O12/c1-16(34)12-23(38)43-25-24-17(2)20(36)14-33(41,30(24,4)5)28(44-29(40)19-10-8-7-9-11-19)26-31(6,27(25)39)21(37)13-22-32(26,15-42-22)45-18(3)35/h7-11,16,20-22,25-26,28,34,36-37,41H,12-15H2,1-6H3/t16?,20-,21-,22+,25+,26-,28-,31+,32-,33+/m0/s1
SMILES	CC(CC(=O)O[C@@H]1C2=C(C)[C@H](C[C@@]([C@H]([C@H]3[C@@](C)([C@H](C[C@@H]4[C@]3(CO4)OC(=O)C)O)C1=O)OC(=O)c1ccccc1)(C2(C)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	630.27	Volume:	620.933 ? Van der Waals volume.
Dense:	1.015	LogP:	1.372 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.87 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.384 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	186.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.201	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.672	Fsp³:	0.636
MCE-18:	142.741 ? 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:	0.629	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.127 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.037	Promiscuous compounds:	0.42

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.464	MDCK Permeability:	-4.937
Pgp-inhibitor:	0.431	Pgp-substrate:	1.0
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):	0.002
20% Bioavailability (F20%):	0.998	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.998
Plasma Protein Binding (PPB):	86.087%	Volume Distribution (VD):	0.11
Fu:	13.496% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.622	BCRP inhibitor:	0.008
BSEP inhibitor:	0.933

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:	0.474	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.906
HLM stability:	0.372 ? 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):

6.963

Half-life (T1/2):

2.574

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.072
Human Hepatotoxicity (H-HT):	0.76	Drug-induced Liver Injury (DILI):	0.922
AMES Toxicity:	0.886	Rat Oral Acute Toxicity:	0.464
Maximum Recommended Daily Dose:	0.891	Skin Sensitization:	0.997
Carcinogencity:	0.419	Eye Corrosion:	0.0
Eye Irritation:	0.016	Respiratory Toxicity:	0.156
Drug-induced Neurotoxicity:	0.498	Ototoxicity:	0.876
Hematotoxicity:	0.893	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.354
A549 Cytotoxicity:	0.436	Hek293 Cytotoxicity:	0.271
BCF:	0.403 ? 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:	3.157 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.938 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.972 ? 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
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18951	Ligusticum sinense	Species	Apiaceae	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 NPC275802 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	10057
0.1-0.2	37202
0.2-0.3	2218
0.3-0.4	313
0.4-0.5	17
0.5-0.6	22
0.6-0.7	22
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC155329
0.92	High Similarity	NPC114357
0.7805	Intermediate Similarity	NPC259144
0.7317	Intermediate Similarity	NPC197037
0.7317	Intermediate Similarity	NPC229545
0.7317	Intermediate Similarity	NPC134685
0.663	Remote Similarity	NPC603140
0.6552	Remote Similarity	NPC11588
0.6535	Remote Similarity	NPC471606
0.6404	Remote Similarity	NPC219419
0.6316	Remote Similarity	NPC471493
0.6139	Remote Similarity	NPC471623
0.6139	Remote Similarity	NPC208553
0.6139	Remote Similarity	NPC181964
0.6139	Remote Similarity	NPC307628
0.6136	Remote Similarity	NPC91730
0.6136	Remote Similarity	NPC248265
0.61	Remote Similarity	NPC36607
0.6078	Remote Similarity	NPC33372
0.6078	Remote Similarity	NPC67246
0.6078	Remote Similarity	NPC324251
0.6078	Remote Similarity	NPC206211
0.6067	Remote Similarity	NPC217918
0.6019	Remote Similarity	NPC487360
0.6019	Remote Similarity	NPC479182
0.6019	Remote Similarity	NPC479180
0.6019	Remote Similarity	NPC471629
0.6019	Remote Similarity	NPC306001
0.598	Remote Similarity	NPC473400
0.598	Remote Similarity	NPC603171
0.5905	Remote Similarity	NPC275170
0.5889	Remote Similarity	NPC605573
0.5849	Remote Similarity	NPC486061
0.5849	Remote Similarity	NPC486060
0.5843	Remote Similarity	NPC38696
0.5794	Remote Similarity	NPC487361
0.5604	Remote Similarity	NPC609501
0.514	Remote Similarity	NPC321072
0.514	Remote Similarity	NPC215892
0.514	Remote Similarity	NPC242662
0.514	Remote Similarity	NPC102167
0.514	Remote Similarity	NPC488127
0.5106	Remote Similarity	NPC92867
0.5093	Remote Similarity	NPC453583
0.5093	Remote Similarity	NPC453588
0.5093	Remote Similarity	NPC191193
0.5047	Remote Similarity	NPC473300
0.5046	Remote Similarity	NPC471754
0.5046	Remote Similarity	NPC479183
0.5046	Remote Similarity	NPC479181

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC275802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3250
0.1-0.2	5773
0.2-0.3	114
0.3-0.4	2
0.4-0.5	4
0.5-0.6	5
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
0.6139	Remote Similarity	NPD8485	Phase 4
0.5619	Remote Similarity	NPD8368	Phase 2
0.5463	Remote Similarity	NPD8486	Phase 1
0.5299	Remote Similarity	NPD8462	Phase 2
0.514	Remote Similarity	NPD8360	Approved
0.514	Remote Similarity	NPD8361	Phase 4

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