NPASS Compound

Natural Product: NPC138974

Natural Product ID	NPC138974
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FYNMKNFAKCHMLL-PPXWZDJSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL480662
PubChem CID	10789345
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

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 78 83 0 0 0 0 0 0 0 0999 V2000 7.7504 -2.5863 0.9243 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5190 -1.9654 1.0181 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6812 -0.4420 0.9672 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3283 0.1481 1.1712 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3663 -0.2069 0.0575 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3293 -1.7283 -0.0897 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6744 -2.3450 -0.1605 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5656 -2.2515 0.9212 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3199 -1.9259 0.9404 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0156 -0.8754 0.0304 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9682 0.2226 0.4009 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6006 1.5784 -0.0689 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1904 1.8767 0.4400 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2240 0.9121 -0.2133 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6485 -0.4774 0.2412 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4430 -1.3011 -0.3848 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6520 -0.4982 0.1249 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1421 0.9106 0.3715 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1318 1.8876 -0.0772 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4470 1.7063 0.6529 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6035 2.5710 0.3759 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6336 1.1438 -0.1357 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5173 0.1657 0.5620 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6513 -0.3228 -0.3082 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4696 -1.3013 0.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1773 -1.0310 -1.5392 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8304 -1.0282 1.1393 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7519 3.3373 -0.0183 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2986 1.1125 -1.6872 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3233 -1.5118 -1.3021 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5803 -1.9597 -1.3745 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8716 0.4502 -1.2090 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6211 -3.4844 0.5198 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0269 -2.2480 1.9680 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3289 -0.1220 1.8018 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1399 -0.1540 0.0133 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4206 1.2622 1.2096 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9235 -0.2197 2.1442 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2174 -2.0201 -1.0740 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5718 -3.4288 -0.1809 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9424 0.2709 1.5335 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7421 1.7968 -1.1212 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2571 2.3070 0.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2200 1.7933 1.5329 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9949 2.9304 0.1502 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4273 -0.4853 1.3517 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4812 -1.2501 -1.4763 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4243 -2.3156 0.0256 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4892 -0.5465 -0.5669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9402 -1.0095 1.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9960 0.9929 1.4706 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3739 1.7006 -1.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3190 1.3245 1.7017 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6211 3.3999 -0.3473 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2978 2.7434 1.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4702 0.9555 -1.2182 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0090 0.7013 1.4154 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3431 0.5037 -0.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5187 -1.3775 0.1132 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5892 -0.9606 1.5631 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0688 -2.3400 0.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1075 -1.2525 -1.4471 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7576 -1.9771 -1.7462 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3415 -0.3797 -2.4230 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5887 -1.6550 1.6705 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1443 -0.6661 1.9360 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3566 -1.6912 0.4033 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2888 3.7211 -0.9526 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7031 3.9096 0.0505 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1823 3.6021 0.8927 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4774 0.6264 -2.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2760 0.7672 -2.0844 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3437 2.2286 -1.8636 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6029 -1.5951 -2.1030 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0137 -2.4312 -2.2446 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0930 1.5103 -0.9523 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1202 0.3369 -1.9958 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8007 -0.0391 -1.5295 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 1 0 5 6 1 0 6 7 1 6 6 8 1 0 8 9 1 0 10 9 1 1 10 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 0 17 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 24 26 1 0 23 27 1 0 19 28 1 0 14 29 1 6 10 30 1 0 30 31 2 0 5 32 1 6 7 2 1 0 15 10 1 0 22 20 1 0 11 5 1 0 18 14 1 0 31 6 1 0 1 33 1 0 2 34 1 1 3 35 1 0 3 36 1 0 4 37 1 0 4 38 1 0 7 39 1 0 7 40 1 0 11 41 1 1 12 42 1 0 12 43 1 0 13 44 1 0 13 45 1 0 15 46 1 1 16 47 1 0 16 48 1 0 17 49 1 0 17 50 1 0 18 51 1 1 19 52 1 6 20 53 1 1 21 54 1 0 21 55 1 0 22 56 1 6 23 57 1 1 24 58 1 0 25 59 1 0 25 60 1 0 25 61 1 0 26 62 1 0 26 63 1 0 26 64 1 0 27 65 1 0 27 66 1 0 27 67 1 0 28 68 1 0 28 69 1 0 28 70 1 0 29 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 31 75 1 0 32 76 1 0 32 77 1 0 32 78 1 0 M END

Standard InCHIKey	FYNMKNFAKCHMLL-PPXWZDJSSA-N
Standard InCHI	InChI=1S/C29H46O3/c1-17(2)18(3)21-15-22(21)19(4)23-7-8-24-26(23,5)11-10-25-27(6)12-9-20(30)16-28(27)13-14-29(24,25)32-31-28/h13-14,17-25,30H,7-12,15-16H2,1-6H3/t18-,19-,20+,21-,22-,23-,24-,25-,26-,27-,28-,29+/m1/s1
SMILES	O[C@H]1CC[C@]2([C@@]3(C1)OO[C@@]1([C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H]([C@H]1C[C@@H]1[C@@H](C(C)C)C)C)C)C=C3)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	442.34	Volume:	482.535 ? Van der Waals volume.
Dense:	0.917	LogP:	4.905 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.016 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.024 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	26.0
TPSA:	38.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	7.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.396	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.968	Fsp³:	0.931
MCE-18:	142.071 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.854	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.237	Promiscuous compounds:	0.211

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.382	MDCK Permeability:	-5.139
Pgp-inhibitor:	0.984	Pgp-substrate:	0.003
PAMPA:	0.005 ? 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%):	0.277	30% Bioavailability (F30%):	0.581
50% Bioavailability (F50%):	0.948

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159	MRP1:	0.351
Plasma Protein Binding (PPB):	97.294%	Volume Distribution (VD):	-0.086
Fu:	2.745% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.159
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.006
CYP2C19-inhibitor:	0.839	CYP2C19-substrate:	0.229
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.671
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.944
HLM stability:	0.963 ? 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):

15.612

Half-life (T1/2):

1.309

ADMET: Toxicity

hERG Blockers:	0.135	hERG Blockers (10um):	0.429
Human Hepatotoxicity (H-HT):	0.517	Drug-induced Liver Injury (DILI):	0.067
AMES Toxicity:	0.215	Rat Oral Acute Toxicity:	0.435
Maximum Recommended Daily Dose:	0.702	Skin Sensitization:	0.994
Carcinogencity:	0.925	Eye Corrosion:	0.063
Eye Irritation:	0.709	Respiratory Toxicity:	0.788
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.725
Hematotoxicity:	0.078	Drug-induced Nephrotoxicity:	0.496
Genotoxicity:	0.056	RPMI-8226 Immunitoxicity:	0.135
A549 Cytotoxicity:	0.105	Hek293 Cytotoxicity:	0.563
BCF:	2.944 ? 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:	4.364 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.957 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.02 ? 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
NPO29933	Sinularia	Genus	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650100]
NPO4638	Cynoglossum gansuense	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1860	Ceratium reticulatum	Species	Ceratiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO943	Carex nigra	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6518	Aspilia laevissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5562	Armillaria novae-zelandiae	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2783	Lobophytum sarcophytoides	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29	Laburnum alpinum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO943	Carex nigra	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1860	Ceratium reticulatum	Species	Ceratiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4638	Cynoglossum gansuense	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2783	Lobophytum sarcophytoides	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6518	Aspilia laevissima	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5562	Armillaria novae-zelandiae	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29	Laburnum alpinum	Species	Fabaceae	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
ED50	4

Activity Type	# Activity
Cell line	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
NPT168	Cell line	P388	Mus musculus	ED50	=	0.4	ug ml-1	PMID[10650100]
NPT91	Cell line	KB	Homo sapiens	ED50	=	2.1	ug ml-1	PMID[10650100]
NPT81	Cell line	A549	Homo sapiens	ED50	=	2.7	ug ml-1	PMID[10650100]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	1.4	ug ml-1	PMID[10650100]

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 NPC138974 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	27062
0.1-0.2	21905
0.2-0.3	854
0.3-0.4	24
0.4-0.5	7
0.5-0.6	0
0.6-0.7	3
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
0.75	Intermediate Similarity	NPC4574
0.7241	Intermediate Similarity	NPC212596
0.7069	Intermediate Similarity	NPC304083
0.6721	Remote Similarity	NPC101886
0.661	Remote Similarity	NPC479824
0.6406	Remote Similarity	NPC475605

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC138974 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7745
0.1-0.2	1347
0.2-0.3	55
0.3-0.4	3
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