NPASS Compound

Natural Product: NPC583873

Natural Product ID	NPC583873
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	12-docosenoic acid
IUPAC Name	docos-12-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 66 65 0 0 0 0 0 0 0 0999 V2000 8.7527 2.2246 -1.4780 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0950 0.8578 -1.3559 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3775 0.8242 -0.0256 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6845 -0.5036 0.1953 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6682 -0.7795 -0.8651 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5915 0.2532 -0.9320 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8735 0.2928 0.4084 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7710 1.3101 0.4130 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0597 1.3001 1.7202 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3012 0.0681 1.9614 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1161 -0.9359 1.1532 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3035 -2.1423 1.5668 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8639 -2.2374 0.5779 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6323 -0.9596 0.7101 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8285 -0.8660 -0.2022 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7780 -1.9701 0.1005 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0155 -1.9425 -0.7789 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7369 -0.6485 -0.5724 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9920 -0.5502 -1.4165 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7062 0.7542 -1.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1304 0.9449 0.2354 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8289 2.2498 0.3796 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2381 2.5259 1.5581 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0416 3.1288 -0.6560 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3416 2.2916 -2.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9530 2.9683 -1.4186 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4141 2.3491 -0.5945 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4248 0.7304 -2.2176 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8931 0.0720 -1.4139 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1400 0.9534 0.7594 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6567 1.6576 -0.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2997 -0.5249 1.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4495 -1.3075 0.1367 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2363 -1.7886 -0.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1877 -0.8474 -1.8403 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8360 -0.0199 -1.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0045 1.2375 -1.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6596 0.6651 1.1396 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5585 -0.7001 0.6980 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1594 2.3390 0.2320 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0296 1.0479 -0.3820 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8526 1.4638 2.5074 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3806 2.1985 1.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8240 -0.0158 2.9649 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4778 -0.9845 0.1395 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8970 -3.0502 1.4557 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0610 -1.9796 2.5917 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4567 -3.1465 0.7732 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4104 -2.3613 -0.4184 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8990 -0.7197 1.7572 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9374 -0.1391 0.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4354 -0.8944 -1.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3102 0.1070 0.0303 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1426 -1.8256 1.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 -2.9729 0.0469 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7201 -2.0262 -1.8569 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6503 -2.8260 -0.5696 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0676 0.1690 -0.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9695 -0.5245 0.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 -0.6867 -2.4916 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7007 -1.3652 -1.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6228 0.8295 -1.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0004 1.5645 -1.4496 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2626 0.9865 0.9375 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8683 0.1671 0.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8695 3.7095 -0.6095 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 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 3 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 2 0 22 24 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 0 2 29 1 0 3 30 1 0 3 31 1 0 4 32 1 0 4 33 1 0 5 34 1 0 5 35 1 0 6 36 1 0 6 37 1 0 7 38 1 0 7 39 1 0 8 40 1 0 8 41 1 0 9 42 1 0 9 43 1 0 10 44 1 0 11 45 1 0 12 46 1 0 12 47 1 0 13 48 1 0 13 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 15 53 1 0 16 54 1 0 16 55 1 0 17 56 1 0 17 57 1 0 18 58 1 0 18 59 1 0 19 60 1 0 19 61 1 0 20 62 1 0 20 63 1 0 21 64 1 0 21 65 1 0 24 66 1 0 M END

Standard InCHIKey	XMABYTBFOIFDNU-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C22H42O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h10-11H,2-9,12-21H2,1H3,(H,23,24)
SMILES	CCCCCCCCCC=CCCCCCCCCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	338.32	Volume:	401.376 ? Van der Waals volume.
Dense:	0.843	LogP:	8.656 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.347 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.603 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	2.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.194	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.099	Fsp³:	0.864
MCE-18:	0.0 ? 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:	0.525	Fluc inhibitor:	0.28 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.016 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.993	Promiscuous compounds:	0.872

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.101	MDCK Permeability:	-4.761
Pgp-inhibitor:	0.0	Pgp-substrate:	0.006
PAMPA:	0.013 ? 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):	0.914
20% Bioavailability (F20%):	0.85	30% Bioavailability (F30%):	0.979
50% Bioavailability (F50%):	0.62

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.992
Plasma Protein Binding (PPB):	97.944%	Volume Distribution (VD):	0.203
Fu:	1.069% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.286
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.286
BSEP inhibitor:	0.296

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.995
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.017
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.215
CYP2D6-inhibitor:	0.958	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.985	CYP2C8-inhibitor:	1.0
HLM stability:	0.001 ? 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):

3.875

Half-life (T1/2):

0.999

ADMET: Toxicity

hERG Blockers:	0.214	hERG Blockers (10um):	0.437
Human Hepatotoxicity (H-HT):	0.254	Drug-induced Liver Injury (DILI):	0.009
AMES Toxicity:	0.047	Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.154	Skin Sensitization:	0.999
Carcinogencity:	0.147	Eye Corrosion:	0.998
Eye Irritation:	0.998	Respiratory Toxicity:	0.883
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.187
Hematotoxicity:	0.052	Drug-induced Nephrotoxicity:	0.259
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.036
A549 Cytotoxicity:	0.313	Hek293 Cytotoxicity:	0.059
BCF:	0.557 ? 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:	3.943 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.742 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.433 ? 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
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25333853]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2953	Ostericum grosseserratum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2392	Hansenia weberbaueriana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24644	Hansenia forbesii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2953	Ostericum grosseserratum	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 NPC583873 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	37587
0.1-0.2	10305
0.2-0.3	1474
0.3-0.4	269
0.4-0.5	93
0.5-0.6	49
0.6-0.7	32
0.7-0.8	5
0.8-0.85	1
0.85-0.9	8
0.9-0.95	1
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC424
1.0	High Similarity	NPC36061
1.0	High Similarity	NPC69510
1.0	High Similarity	NPC77272
1.0	High Similarity	NPC290563
1.0	High Similarity	NPC139029
1.0	High Similarity	NPC281972
1.0	High Similarity	NPC261831
1.0	High Similarity	NPC87564
0.9615	High Similarity	NPC281245
0.9259	High Similarity	NPC92114
0.8966	High Similarity	NPC154245
0.8966	High Similarity	NPC85813
0.8966	High Similarity	NPC223697
0.8966	High Similarity	NPC6095
0.8929	High Similarity	NPC95145
0.8929	High Similarity	NPC325642
0.8929	High Similarity	NPC65174
0.8621	High Similarity	NPC321062
0.8	Intermediate Similarity	NPC5413
0.7742	Intermediate Similarity	NPC52955
0.7742	Intermediate Similarity	NPC88966
0.7742	Intermediate Similarity	NPC25417
0.7742	Intermediate Similarity	NPC1813
0.7742	Intermediate Similarity	NPC59051
0.7692	Intermediate Similarity	NPC171736
0.7692	Intermediate Similarity	NPC301585
0.7692	Intermediate Similarity	NPC261080
0.7692	Intermediate Similarity	NPC132565
0.7692	Intermediate Similarity	NPC209970
0.7692	Intermediate Similarity	NPC216630
0.7692	Intermediate Similarity	NPC201844
0.7692	Intermediate Similarity	NPC301696
0.7692	Intermediate Similarity	NPC196924
0.7692	Intermediate Similarity	NPC307783
0.7692	Intermediate Similarity	NPC154186
0.7692	Intermediate Similarity	NPC149184
0.7692	Intermediate Similarity	NPC279026
0.7692	Intermediate Similarity	NPC113928
0.7692	Intermediate Similarity	NPC14227
0.7429	Intermediate Similarity	NPC477201
0.7419	Intermediate Similarity	NPC91495
0.7419	Intermediate Similarity	NPC70387
0.7308	Intermediate Similarity	NPC155263
0.7027	Intermediate Similarity	NPC243532
0.6944	Remote Similarity	NPC106851
0.6944	Remote Similarity	NPC282788
0.6944	Remote Similarity	NPC274927
0.6897	Remote Similarity	NPC180534
0.6897	Remote Similarity	NPC611531
0.6857	Remote Similarity	NPC606120
0.6842	Remote Similarity	NPC68343
0.6842	Remote Similarity	NPC328089
0.6757	Remote Similarity	NPC179764
0.6579	Remote Similarity	NPC251042
0.6579	Remote Similarity	NPC255863
0.6579	Remote Similarity	NPC473863
0.6579	Remote Similarity	NPC174447
0.6579	Remote Similarity	NPC136164
0.6579	Remote Similarity	NPC122521
0.6579	Remote Similarity	NPC245947
0.6562	Remote Similarity	NPC149821
0.6538	Remote Similarity	NPC214610
0.6538	Remote Similarity	NPC118968
0.6538	Remote Similarity	NPC183424
0.6538	Remote Similarity	NPC294085
0.6452	Remote Similarity	NPC34416
0.641	Remote Similarity	NPC318420
0.641	Remote Similarity	NPC326268
0.6389	Remote Similarity	NPC487561
0.6389	Remote Similarity	NPC225929
0.6296	Remote Similarity	NPC175342
0.625	Remote Similarity	NPC8219
0.6154	Remote Similarity	NPC268826
0.6061	Remote Similarity	NPC18712
0.6061	Remote Similarity	NPC74845
0.6061	Remote Similarity	NPC207292
0.5938	Remote Similarity	NPC262968
0.5882	Remote Similarity	NPC87394
0.5882	Remote Similarity	NPC48162
0.5882	Remote Similarity	NPC324004
0.5882	Remote Similarity	NPC328497
0.5882	Remote Similarity	NPC602547
0.5854	Remote Similarity	NPC320642
0.5854	Remote Similarity	NPC329550
0.5833	Remote Similarity	NPC40082
0.5806	Remote Similarity	NPC55023
0.5806	Remote Similarity	NPC21844
0.5769	Remote Similarity	NPC174368
0.5758	Remote Similarity	NPC129972
0.5758	Remote Similarity	NPC301528
0.5758	Remote Similarity	NPC71317
0.5758	Remote Similarity	NPC163746
0.5758	Remote Similarity	NPC103286
0.575	Remote Similarity	NPC323597
0.575	Remote Similarity	NPC187777
0.575	Remote Similarity	NPC211752
0.575	Remote Similarity	NPC318814
0.575	Remote Similarity	NPC320669
0.575	Remote Similarity	NPC323498
0.5714	Remote Similarity	NPC323045
0.5714	Remote Similarity	NPC49863
0.5714	Remote Similarity	NPC317881
0.5714	Remote Similarity	NPC174560
0.5714	Remote Similarity	NPC125312
0.5667	Remote Similarity	NPC604140
0.561	Remote Similarity	NPC317583
0.5581	Remote Similarity	NPC322461
0.5556	Remote Similarity	NPC134782
0.55	Remote Similarity	NPC274290
0.5455	Remote Similarity	NPC314679
0.5455	Remote Similarity	NPC117572
0.5455	Remote Similarity	NPC605544
0.5455	Remote Similarity	NPC607260
0.5429	Remote Similarity	NPC224227
0.5366	Remote Similarity	NPC99619
0.5333	Remote Similarity	NPC329249
0.5333	Remote Similarity	NPC92558
0.525	Remote Similarity	NPC28205
0.5161	Remote Similarity	NPC202716
0.5152	Remote Similarity	NPC50457
0.5152	Remote Similarity	NPC604910
0.5116	Remote Similarity	NPC325977
0.5116	Remote Similarity	NPC470320
0.5116	Remote Similarity	NPC327112
0.5116	Remote Similarity	NPC235242

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC583873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6682
0.1-0.2	2174
0.2-0.3	220
0.3-0.4	43
0.4-0.5	12
0.5-0.6	7
0.6-0.7	3
0.7-0.8	5
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD3195	Phase 2
1.0	High Similarity	NPD3196	Approved
0.8966	High Similarity	NPD4266	Phase 2
0.8	Intermediate Similarity	NPD3173	Phase 4
0.7879	Intermediate Similarity	NPD3194	Phase 4
0.7742	Intermediate Similarity	NPD3172	Approved
0.7692	Intermediate Similarity	NPD2270	Pre-clinical
0.7692	Intermediate Similarity	NPD633	Phase 3
0.7692	Intermediate Similarity	NPD9448	Phase 2
0.6897	Remote Similarity	NPD622	Pre-clinical
0.6842	Remote Similarity	NPD39	Phase 4
0.6538	Remote Similarity	NPD9655	Phase 4
0.5938	Remote Similarity	NPD28	Approved
0.5938	Remote Similarity	NPD29	Phase 4
0.5882	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5455	Remote Similarity	NPD4222	Phase 3
0.5429	Remote Similarity	NPD3197	Phase 1
0.5116	Remote Similarity	NPD4246	Phase 2

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