NPASS Compound

Natural Product: NPC475039

Natural Product ID	NPC475039
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Orbiculin B
IUPAC Name	n.a.
Synonyms	Orbiculin B
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL493856
PubChem CID	10697040
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 71 75 0 0 0 0 0 0 0 0999 V2000 -4.4919 -1.7870 -1.7080 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3320 -1.9591 -0.7617 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4818 -2.3442 0.4281 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0400 -1.7007 -1.1662 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8873 -1.8446 -0.3441 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1009 -3.0446 -0.8587 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2050 -3.1565 -0.2053 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0372 -1.8858 -0.2305 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2623 -0.7389 0.2949 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1273 -0.5673 -0.3621 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1156 -0.2898 -1.8692 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8052 0.6225 0.2078 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2034 0.6263 0.2277 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0270 1.4657 -0.4565 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4111 2.2897 -1.1832 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4643 1.5221 -0.4456 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2228 0.7118 0.3685 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6001 0.7608 0.3754 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2417 1.6442 -0.4539 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5189 2.4872 -1.2978 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1280 2.3960 -1.2646 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2465 1.1786 1.5017 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2239 0.9997 1.7142 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8613 0.5611 0.3778 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1433 0.8721 0.1884 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8520 1.7342 -0.5306 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1271 2.4466 -1.2143 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2961 1.8956 -0.5757 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0418 2.7870 -1.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3802 2.6012 -1.0616 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3991 1.5607 -0.1339 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1838 1.1894 0.1137 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3458 -0.2950 2.5237 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9031 -1.1855 1.6022 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4324 -0.2674 3.7364 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7171 -0.5181 3.0538 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7267 -1.7608 -1.5210 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4338 -1.8917 -1.1510 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4487 -2.5928 -2.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4194 -0.8064 -2.2448 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1143 -2.1320 0.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7244 -3.9271 -0.5649 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0866 -3.0931 -1.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8190 -3.9282 -0.7392 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0738 -3.5468 0.8289 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8059 -2.1245 0.5680 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7333 0.5845 -2.0457 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8973 -0.0146 -2.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4182 -1.1756 -2.4082 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5923 1.4911 -0.5005 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6921 0.0229 1.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1626 0.1236 1.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3234 1.6872 -0.4527 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0393 3.1804 -1.9477 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6073 3.0726 -1.9397 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4320 2.2743 1.5906 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8627 0.7485 2.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7447 1.8373 2.1648 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3866 1.2990 -0.3110 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6100 3.5094 -1.9911 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2070 3.1453 -1.4896 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3334 1.1818 0.2672 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8911 -0.7604 4.6216 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2258 0.7796 4.0685 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5088 -0.8373 3.5517 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8782 -1.6355 3.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5181 -0.0179 2.4847 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8509 -0.1939 4.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7308 -0.7356 -1.9667 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8097 -2.0023 -1.3974 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3849 -2.5287 -2.2789 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 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 12 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 23 33 1 0 33 34 1 0 33 35 1 0 33 36 1 0 8 37 1 0 10 5 1 0 21 16 1 0 32 28 1 0 9 34 1 1 24 9 1 0 1 38 1 0 1 39 1 0 1 40 1 0 5 41 1 1 6 42 1 0 6 43 1 0 7 44 1 0 7 45 1 0 8 46 1 1 11 47 1 0 11 48 1 0 11 49 1 0 12 50 1 6 17 51 1 0 18 52 1 0 19 53 1 0 20 54 1 0 21 55 1 0 22 56 1 0 22 57 1 0 23 58 1 1 24 59 1 6 29 60 1 0 30 61 1 0 31 62 1 0 35 63 1 0 35 64 1 0 35 65 1 0 36 66 1 0 36 67 1 0 36 68 1 0 37 69 1 0 37 70 1 0 37 71 1 0 M END

Standard InCHIKey	YGASMTNLTDWIAV-SHTGXHFHSA-N
Standard InCHI	InChI=1S/C29H34O8/c1-17-13-14-22(34-18(2)30)28(5)23(35-25(31)19-10-7-6-8-11-19)16-20-24(29(17,28)37-27(20,3)4)36-26(32)21-12-9-15-33-21/h6-12,15,17,20,22-24H,13-14,16H2,1-5H3/t17-,20-,22+,23+,24-,28+,29-/m1/s1
SMILES	CC(=O)O[C@H]1CC[C@H]([C@@]23[C@]1(C)[C@@H](OC(=O)c1ccccc1)C[C@H]([C@H]3OC(=O)c1ccco1)C(O2)(C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	510.23	Volume:	516.588 ? Van der Waals volume.
Dense:	0.988	LogP:	3.901 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.534 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.936 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	28.0
TPSA:	101.27 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.411	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.565	Fsp³:	0.552
MCE-18:	152.622 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.27	Fluc inhibitor:	0.445 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.015 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.248	Promiscuous compounds:	0.073

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.111	MDCK Permeability:	-4.707
Pgp-inhibitor:	0.973	Pgp-substrate:	0.185
PAMPA:	0.23 ? 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%):	0.271	30% Bioavailability (F30%):	0.23
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803	MRP1:	0.997
Plasma Protein Binding (PPB):	97.232%	Volume Distribution (VD):	-0.351
Fu:	2.895% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.944	BCRP inhibitor:	0.301
BSEP inhibitor:	0.976

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.998
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.933
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.844	CYP3A4-substrate:	0.979
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.989 ? 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):

6.124

Half-life (T1/2):

0.466

ADMET: Toxicity

hERG Blockers:	0.082	hERG Blockers (10um):	0.514
Human Hepatotoxicity (H-HT):	0.168	Drug-induced Liver Injury (DILI):	0.954
AMES Toxicity:	0.674	Rat Oral Acute Toxicity:	0.422
Maximum Recommended Daily Dose:	0.354	Skin Sensitization:	0.967
Carcinogencity:	0.896	Eye Corrosion:	0.004
Eye Irritation:	0.714	Respiratory Toxicity:	0.158
Drug-induced Neurotoxicity:	0.391	Ototoxicity:	0.17
Hematotoxicity:	0.063	Drug-induced Nephrotoxicity:	0.467
Genotoxicity:	0.9	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.358	Hek293 Cytotoxicity:	0.507
BCF:	0.861 ? 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:	3.761 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.143 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.784 ? 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
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[10346948]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170672]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[11809076]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[18507472]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23421714]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27791375]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461657]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6349	Celastrus orbiculatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6349	Celastrus orbiculatus	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
IC50	3
Ratio IC50	1

Activity Type	# Activity
Non-molecular	3
Others	1

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	268000.0	nM	PMID[10346948]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	246000.0	nM	PMID[10346948]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	19600.0	nM	PMID[10346948]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	12.5	n.a.	PMID[19183048]

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 NPC475039 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	15269
0.1-0.2	32649
0.2-0.3	1610
0.3-0.4	206
0.4-0.5	81
0.5-0.6	27
0.6-0.7	7
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC476035
0.8209	Intermediate Similarity	NPC1408
0.7733	Intermediate Similarity	NPC88593
0.7733	Intermediate Similarity	NPC14499
0.7612	Intermediate Similarity	NPC283375
0.7353	Intermediate Similarity	NPC474608
0.7101	Intermediate Similarity	NPC183122
0.64	Remote Similarity	NPC163087
0.6329	Remote Similarity	NPC210591
0.625	Remote Similarity	NPC475652
0.6184	Remote Similarity	NPC159520
0.6118	Remote Similarity	NPC483870
0.6104	Remote Similarity	NPC246480
0.6104	Remote Similarity	NPC246841
0.5897	Remote Similarity	NPC48017
0.5769	Remote Similarity	NPC17877
0.5714	Remote Similarity	NPC483875
0.5658	Remote Similarity	NPC200592
0.5658	Remote Similarity	NPC270498
0.5658	Remote Similarity	NPC610542
0.5632	Remote Similarity	NPC483874
0.5618	Remote Similarity	NPC483869
0.5517	Remote Similarity	NPC483872
0.5465	Remote Similarity	NPC4421
0.5455	Remote Similarity	NPC473081
0.5455	Remote Similarity	NPC195647
0.5443	Remote Similarity	NPC483847
0.5435	Remote Similarity	NPC483868
0.5393	Remote Similarity	NPC483871
0.5385	Remote Similarity	NPC211137
0.5385	Remote Similarity	NPC66761
0.5385	Remote Similarity	NPC483843
0.5287	Remote Similarity	NPC212768
0.525	Remote Similarity	NPC475759
0.525	Remote Similarity	NPC470152
0.5195	Remote Similarity	NPC147561
0.519	Remote Similarity	NPC475429
0.519	Remote Similarity	NPC476094
0.5063	Remote Similarity	NPC100913
0.5062	Remote Similarity	NPC311175
0.5055	Remote Similarity	NPC483864

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3052
0.1-0.2	5910
0.2-0.3	186
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