NPASS Compound

Natural Product: NPC184344

Natural Product ID	NPC184344
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	QMCAKDVKAVSTQB-RIRREPTBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	72947651
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

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 57 61 0 0 0 0 0 0 0 0999 V2000 -4.0223 -1.6561 0.0476 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9316 -0.6947 0.5591 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 -1.2350 1.9220 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6116 0.6422 0.6431 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6182 1.7032 0.9394 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1917 1.2441 0.8699 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8833 0.4645 -0.4022 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5084 1.3306 -1.5171 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6254 0.6980 -1.9562 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3919 -0.6653 -1.8054 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7699 -0.7165 -0.4303 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6097 -1.1426 -2.8175 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5629 0.3159 -0.6586 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1274 -0.9557 -1.1293 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3960 -1.4558 -0.4918 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7244 -0.9653 0.8659 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5621 -0.1693 1.4917 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4470 0.8974 0.4688 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8520 1.1569 -0.0648 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7184 0.1989 0.7104 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9574 -0.2061 0.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9300 0.7384 1.9703 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8771 1.0007 -1.4148 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9603 2.2043 0.9168 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6988 3.1385 1.3528 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4062 2.4244 0.8545 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4591 -0.9151 -2.5200 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6103 -2.5366 -0.4416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5729 -2.0677 0.9508 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8192 -1.1165 -0.4967 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5049 -1.6094 1.9657 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7834 -0.5008 2.7445 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1565 -2.1317 2.2262 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2259 0.8128 -0.2648 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3747 0.5254 1.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8217 2.6439 0.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7837 2.0191 2.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 0.7115 1.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6048 2.3736 -1.2275 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7817 1.3411 -2.3855 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3666 -1.1536 -1.8987 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3164 -1.6976 -0.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9648 -1.9756 -3.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8388 1.0794 -1.4647 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4356 -1.8347 -1.1180 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4087 -2.5900 -0.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3110 -1.2791 -1.1382 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0882 -1.7139 1.5745 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8502 0.1496 2.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7340 -0.9235 1.4867 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2291 2.1721 0.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0847 -1.3256 0.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0453 0.1218 -1.0323 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8330 0.2027 0.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0547 1.7218 1.8425 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6200 1.4058 -1.8857 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9572 -0.2052 -2.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 8 9 1 0 9 10 1 0 10 11 1 0 10 12 1 0 7 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 20 22 1 1 19 23 1 0 18 24 1 1 24 25 2 0 24 26 1 0 14 27 1 0 11 2 1 0 18 13 1 0 26 6 1 0 11 7 1 0 20 16 1 0 1 28 1 0 1 29 1 0 1 30 1 0 3 31 1 0 3 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 5 36 1 0 5 37 1 0 6 38 1 1 8 39 1 0 8 40 1 0 10 41 1 1 11 42 1 6 12 43 1 0 13 44 1 6 14 45 1 6 15 46 1 0 15 47 1 0 16 48 1 1 17 49 1 0 17 50 1 0 19 51 1 6 21 52 1 0 21 53 1 0 21 54 1 0 22 55 1 0 23 56 1 0 27 57 1 0 M END

Standard InCHIKey	QMCAKDVKAVSTQB-RIRREPTBSA-N
Standard InCHI	InChI=1S/C20H30O7/c1-17(2)5-4-11-20(8-26-14(22)13(17)20)12-10(21)6-9-7-19(12,16(24)27-11)15(23)18(9,3)25/h9-15,21-23,25H,4-8H2,1-3H3/t9-,10+,11+,12-,13-,14-,15-,18+,19+,20+/m1/s1
SMILES	CC1(C)CC[C@H]2[C@@]3(CO[C@H]([C@H]13)O)[C@@H]1[C@H](C[C@@H]3C[C@]1([C@@H]([C@@]3(C)O)O)C(=O)O2)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	382.2	Volume:	370.589 ? Van der Waals volume.
Dense:	1.031	LogP:	0.857 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.501 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.783 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	24.0
TPSA:	116.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	7.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	7.0

MedChem Properties

QED Drug-Likeness Score:	0.442	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.904	Fsp³:	0.95
MCE-18:	133.718 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.386	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? 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:	0.189	Promiscuous compounds:	0.456

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.891	MDCK Permeability:	-4.799
Pgp-inhibitor:	0.0	Pgp-substrate:	0.901
PAMPA:	0.992 ? 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):	0.011
20% Bioavailability (F20%):	0.359	30% Bioavailability (F30%):	0.074
50% Bioavailability (F50%):	0.909

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.206	MRP1:	0.635
Plasma Protein Binding (PPB):	62.773%	Volume Distribution (VD):	0.059
Fu:	41.946% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.939
OATP1B3 inhibitor:	0.797	BCRP inhibitor:	0.017
BSEP inhibitor:	0.187

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.012
CYP3A4-inhibitor:	0.135	CYP3A4-substrate:	0.027
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.007
HLM stability:	0.033 ? 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):

5.079

Half-life (T1/2):

2.728

ADMET: Toxicity

hERG Blockers:	0.046	hERG Blockers (10um):	0.302
Human Hepatotoxicity (H-HT):	0.645	Drug-induced Liver Injury (DILI):	0.371
AMES Toxicity:	0.732	Rat Oral Acute Toxicity:	0.376
Maximum Recommended Daily Dose:	0.857	Skin Sensitization:	0.995
Carcinogencity:	0.761	Eye Corrosion:	0.019
Eye Irritation:	0.753	Respiratory Toxicity:	0.868
Drug-induced Neurotoxicity:	0.121	Ototoxicity:	0.709
Hematotoxicity:	0.206	Drug-induced Nephrotoxicity:	0.901
Genotoxicity:	0.807	RPMI-8226 Immunitoxicity:	0.202
A549 Cytotoxicity:	0.235	Hek293 Cytotoxicity:	0.285
BCF:	0.414 ? 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:	3.113 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.708 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.817 ? 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
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19099464]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19697926]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2421673]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	aerial parts	Muli County, Sichuan Province, China	2011-AUG	PMID[24219809]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9599286]
NPO17240	Crematogaster brevis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20336	Arctotheca calendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16021	Boletus bovinus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19889	Cereus stellatus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17508	Danae racemosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20470	Elaeagnus orientalis	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20115	Melampodium argophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19763	Meloidogyne incognita	Species	Meloidogynidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1558	Ozothamnus obcordatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20543	Psydrax livida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16409	Quercus pedunculata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21614	Urceolaria scruposa	Species	Trichodinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19768	Xylosalsola arbuscula	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16021	Boletus bovinus	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17508	Danae racemosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19768	Xylosalsola arbuscula	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19475	Isodon sculponeatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20336	Arctotheca calendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8991	Carcinus maenas	Species	Carcinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20470	Elaeagnus orientalis	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16409	Quercus pedunculata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1558	Ozothamnus obcordatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20543	Psydrax livida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21482	Crotalaria laburnifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17240	Crematogaster brevis	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20115	Melampodium argophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19889	Cereus stellatus	Species	Sagartiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19763	Meloidogyne incognita	Species	Meloidogynidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21139	Daphniphyllum calycinum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21614	Urceolaria scruposa	Species	Trichodinidae	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 NPC184344 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	19480
0.1-0.2	27496
0.2-0.3	2822
0.3-0.4	40
0.4-0.5	8
0.5-0.6	12
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	Natural Product ID
0.619	Remote Similarity	NPC483228
0.5909	Remote Similarity	NPC96333
0.5909	Remote Similarity	NPC88833
0.5909	Remote Similarity	NPC193785
0.5909	Remote Similarity	NPC483211
0.5735	Remote Similarity	NPC483222
0.5735	Remote Similarity	NPC483221
0.5692	Remote Similarity	NPC285927
0.5522	Remote Similarity	NPC42776
0.5441	Remote Similarity	NPC130302
0.5075	Remote Similarity	NPC483227
0.5075	Remote Similarity	NPC483225
0.5072	Remote Similarity	NPC88469

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC184344 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6453
0.1-0.2	2666
0.2-0.3	31
0.3-0.4	0
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