NPASS Compound

Natural Product: NPC532857

Natural Product ID	NPC532857
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	12-hydroxy-6,10-dimethyl-2-(4-methylpent-3-enyl)dodeca-2,6,10-trienoic acid
IUPAC Name	12-hydroxy-6,10-dimethyl-2-(4-methylpent-3-enyl)dodeca-2,6,10-trienoic 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 55 54 0 0 0 0 0 0 0 0999 V2000 7.2396 -0.3712 -2.0261 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2191 0.2135 -1.1197 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 1.5815 -1.3876 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7459 -0.4459 -0.0699 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7189 0.1599 0.8305 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5076 -0.7686 0.7699 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3894 -0.3239 1.5993 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2050 -0.0225 1.1025 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9149 -0.1063 -0.3201 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0292 -1.2625 -0.6512 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 -1.1605 0.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4516 -1.2820 1.5132 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3384 -1.0174 -0.7210 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6747 -0.9035 -0.1208 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2353 0.4388 -0.6016 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5692 0.6053 -0.0323 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6453 0.6112 1.4927 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6881 0.7473 -0.6559 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9819 0.7873 -2.0999 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9134 0.6546 -2.9405 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6314 -0.2259 3.0510 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7216 -0.5017 3.5475 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5909 0.1939 3.8955 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2067 0.1450 -1.8292 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9316 -0.2710 -3.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3877 -1.4504 -1.8465 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5931 1.5589 -1.5401 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8892 2.2239 -0.4992 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1588 2.0413 -2.2741 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0991 -1.4397 0.1518 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4596 1.1679 0.5025 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1249 0.2019 1.8550 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2854 -0.9390 -0.2900 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9291 -1.7541 1.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4380 0.3413 1.8199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2646 0.8168 -0.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7926 -0.0312 -1.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5237 -2.2386 -0.3776 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1491 -1.3550 -1.7540 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2594 -2.0434 1.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5225 -1.6913 1.9628 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7833 -0.3580 1.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2855 -0.9784 -1.8104 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7289 -0.9911 0.9624 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2999 -1.7270 -0.5461 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 1.1993 -0.1826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1321 0.4364 -1.6760 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3224 1.4772 1.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1480 -0.3053 1.8017 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6624 0.7793 1.9414 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6121 0.8623 -0.0286 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7029 -0.0746 -2.2775 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5342 1.7519 -2.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9948 -0.0578 -3.6134 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7246 0.1394 4.9012 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 2 3 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 3 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 2 3 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 16 18 2 3 18 19 1 0 19 20 1 0 7 21 1 0 21 22 2 0 21 23 1 0 1 24 1 0 1 25 1 0 1 26 1 0 3 27 1 0 3 28 1 0 3 29 1 0 4 30 1 0 5 31 1 0 5 32 1 0 6 33 1 0 6 34 1 0 8 35 1 0 9 36 1 0 9 37 1 0 10 38 1 0 10 39 1 0 12 40 1 0 12 41 1 0 12 42 1 0 13 43 1 0 14 44 1 0 14 45 1 0 15 46 1 0 15 47 1 0 17 48 1 0 17 49 1 0 17 50 1 0 18 51 1 0 19 52 1 0 19 53 1 0 20 54 1 0 23 55 1 0 M END

Standard InCHIKey	USXGDFAHMRCBBX-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C20H32O3/c1-16(2)8-5-12-19(20(22)23)13-7-11-17(3)9-6-10-18(4)14-15-21/h8-9,13-14,21H,5-7,10-12,15H2,1-4H3,(H,22,23)
SMILES	CC(C)=CCCC(=CCCC(C)=CCCC(C)=CCO)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	320.24	Volume:	367.665 ? Van der Waals volume.
Dense:	0.871	LogP:	5.506 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.256 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.104 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	5.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.407	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.109	Fsp³:	0.55
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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.166	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.781	Promiscuous compounds:	0.137

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.792	MDCK Permeability:	-4.777
Pgp-inhibitor:	0.046	Pgp-substrate:	0.02
PAMPA:	0.942 ? 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):	0.286
20% Bioavailability (F20%):	0.052	30% Bioavailability (F30%):	0.054
50% Bioavailability (F50%):	0.501

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.111	MRP1:	0.988
Plasma Protein Binding (PPB):	86.195%	Volume Distribution (VD):	-0.51
Fu:	9.58% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.965
OATP1B3 inhibitor:	0.841	BCRP inhibitor:	0.011
BSEP inhibitor:	0.519

ADMET: Metabolism

CYP1A2-inhibitor:	0.019	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.592	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.99	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.321	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.006
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.027
HLM stability:	0.058 ? 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):

6.399

Half-life (T1/2):

0.986

ADMET: Toxicity

hERG Blockers:	0.05	hERG Blockers (10um):	0.158
Human Hepatotoxicity (H-HT):	0.51	Drug-induced Liver Injury (DILI):	0.093
AMES Toxicity:	0.049	Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.034	Skin Sensitization:	0.998
Carcinogencity:	0.154	Eye Corrosion:	0.968
Eye Irritation:	0.992	Respiratory Toxicity:	0.62
Drug-induced Neurotoxicity:	0.22	Ototoxicity:	0.549
Hematotoxicity:	0.305	Drug-induced Nephrotoxicity:	0.41
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.009
BCF:	1.496 ? 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:	4.42 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.785 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.019 ? 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
NPO23728	Favolaschia tonkinensis	Species	Favolaschiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20329738]
NPO17318	Streptomyces cyaneus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21462031]
NPO14339	Fevillea trilobata	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23590	Woodsia scopulina	Species	Woodsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17251	Aniba firmula	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5124	Aconitum ibukiense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3705	Anacardium humile	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50387	Calocedrus macropepis var.formosana	Genus	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO59238	Calocedrus microlepic var. formosana	Genus	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17500	Candelaria vitellina	Species	Candelariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23401	Castilleja integra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13361	Clerodendrum tomentosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24081	Conocephalum supradecompositum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23728	Favolaschia tonkinensis	Species	Favolaschiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15612	Glaucium oxylobum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12311	Graphis handelii	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14653	Haliotis diversicolor	Species	Haliotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23636	Liparis condylobulbon	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25141	Mycetinis alliaceus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23446	Rumex pulcher	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24166	Spongia lamellosa	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17318	Streptomyces cyaneus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23174	Tortrix viridana	Species	Tortricidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17158	Trichocereus bridgesii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15612	Glaucium oxylobum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15612	Glaucium oxylobum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15612	Glaucium oxylobum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17158	Trichocereus bridgesii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12311	Graphis handelii	Species	Graphidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14653	Haliotis diversicolor	Species	Haliotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14339	Fevillea trilobata	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25141	Mycetinis alliaceus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15612	Glaucium oxylobum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17251	Aniba firmula	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3705	Anacardium humile	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23401	Castilleja integra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13361	Clerodendrum tomentosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17318	Streptomyces cyaneus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5124	Aconitum ibukiense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23636	Liparis condylobulbon	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24166	Spongia lamellosa	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23728	Favolaschia tonkinensis	Species	Favolaschiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17500	Candelaria vitellina	Species	Candelariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23174	Tortrix viridana	Species	Tortricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23590	Woodsia scopulina	Species	Woodsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24081	Conocephalum supradecompositum	Species	Conocephalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23446	Rumex pulcher	Species	Polygonaceae	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 NPC532857 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	21978
0.1-0.2	25214
0.2-0.3	2445
0.3-0.4	180
0.4-0.5	27
0.5-0.6	15
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	Natural Product ID
0.5789	Remote Similarity	NPC29091
0.5789	Remote Similarity	NPC103213
0.5789	Remote Similarity	NPC300623
0.5789	Remote Similarity	NPC213538
0.5789	Remote Similarity	NPC269823
0.5789	Remote Similarity	NPC39222
0.5789	Remote Similarity	NPC9860
0.5745	Remote Similarity	NPC142423
0.5745	Remote Similarity	NPC308294
0.5263	Remote Similarity	NPC182840
0.5263	Remote Similarity	NPC255042
0.5246	Remote Similarity	NPC114918
0.52	Remote Similarity	NPC68110
0.5122	Remote Similarity	NPC116934
0.5116	Remote Similarity	NPC140501

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC532857 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5985
0.1-0.2	3054
0.2-0.3	99
0.3-0.4	10
0.4-0.5	1
0.5-0.6	1
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
0.5116	Remote Similarity	NPD4265	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