NPASS Compound

Natural Product: NPC558253

Natural Product ID	NPC558253
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-Octen-1-ol
IUPAC Name	oct-6-en-1-ol
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 25 24 0 0 0 0 0 0 0 0999 V2000 3.0223 1.2428 0.3900 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2754 -0.2042 0.1797 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3092 -1.1204 0.2444 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8928 -0.7902 0.5309 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0775 -1.2512 -0.6581 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3822 -0.9764 -0.4990 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6792 0.4996 -0.3314 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1856 0.7139 -0.1738 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4730 2.0681 -0.0187 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3703 1.4491 1.2624 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5615 1.6827 -0.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9879 1.7699 0.5119 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3080 -0.4892 -0.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5682 -2.1557 0.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5334 -1.3128 1.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8021 0.2812 0.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2117 -2.3461 -0.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4965 -0.8140 -1.5776 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8085 -1.5675 0.3053 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8834 -1.2879 -1.4423 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2114 0.8235 0.6168 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3177 1.0951 -1.1687 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4875 0.1329 0.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7258 0.3456 -1.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2627 2.2109 0.5851 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 1 10 1 0 1 11 1 0 1 12 1 0 2 13 1 0 3 14 1 0 4 15 1 0 4 16 1 0 5 17 1 0 5 18 1 0 6 19 1 0 6 20 1 0 7 21 1 0 7 22 1 0 8 23 1 0 8 24 1 0 9 25 1 0 M END

Standard InCHIKey	SHPVOXFREBUEHB-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C8H16O/c1-2-3-4-5-6-7-8-9/h2-3,9H,4-8H2,1H3
SMILES	CC=CCCCCCO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	128.12	Volume:	153.078 ? Van der Waals volume.
Dense:	0.837	LogP:	2.714 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.255 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.266 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	1.0
TPSA:	20.23 ? Topological Polar Surface Area.	H-Bond Acceptor:	1.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	1.0

MedChem Properties

QED Drug-Likeness Score:	0.444	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.304	Fsp³:	0.75
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:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.01	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:	1.0	Promiscuous compounds:	0.311

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.775	MDCK Permeability:	-4.731
Pgp-inhibitor:	0.627	Pgp-substrate:	0.33
PAMPA:	0.074 ? 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):	0.478
20% Bioavailability (F20%):	0.232	30% Bioavailability (F30%):	0.479
50% Bioavailability (F50%):	0.443

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.772	MRP1:	0.906
Plasma Protein Binding (PPB):	60.174%	Volume Distribution (VD):	-0.237
Fu:	41.717% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.055
OATP1B3 inhibitor:	0.174	BCRP inhibitor:	0.411
BSEP inhibitor:	0.888

ADMET: Metabolism

CYP1A2-inhibitor:	0.186	CYP1A2-substrate:	0.159
CYP2C19-inhibitor:	0.426	CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.979	CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.944	CYP2D6-substrate:	0.885
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.255
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.951
HLM stability:	0.979 ? 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):

9.391

Half-life (T1/2):

0.94

ADMET: Toxicity

hERG Blockers:	0.112	hERG Blockers (10um):	0.348
Human Hepatotoxicity (H-HT):	0.275	Drug-induced Liver Injury (DILI):	0.024
AMES Toxicity:	0.321	Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.042	Skin Sensitization:	0.971
Carcinogencity:	0.294	Eye Corrosion:	0.997
Eye Irritation:	0.999	Respiratory Toxicity:	0.454
Drug-induced Neurotoxicity:	0.068	Ototoxicity:	0.212
Hematotoxicity:	0.084	Drug-induced Nephrotoxicity:	0.351
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.059	Hek293 Cytotoxicity:	0.063
BCF:	1.031 ? 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:	3.22 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.41 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.843 ? 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
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	fruit	n.a.	PMID[18020353]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22934600]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23678820]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30543429]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30848923]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35108453]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36903935]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37047195]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37179510]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38263385]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38380569]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39592457]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[8864235]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15388	Eucalyptus globulus	Species	Myrtaceae	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 NPC558253 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	37338
0.1-0.2	11556
0.2-0.3	811
0.3-0.4	117
0.4-0.5	16
0.5-0.6	19
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
0.7619	Intermediate Similarity	NPC252978
0.7273	Intermediate Similarity	NPC76976
0.5556	Remote Similarity	NPC213764
0.55	Remote Similarity	NPC275462
0.5263	Remote Similarity	NPC152759
0.5263	Remote Similarity	NPC12231
0.5238	Remote Similarity	NPC126915
0.5238	Remote Similarity	NPC205141
0.5238	Remote Similarity	NPC24506
0.5238	Remote Similarity	NPC225783
0.5238	Remote Similarity	NPC279895
0.5238	Remote Similarity	NPC185538
0.5238	Remote Similarity	NPC181516
0.5238	Remote Similarity	NPC163556
0.5238	Remote Similarity	NPC139131
0.5238	Remote Similarity	NPC236797
0.5238	Remote Similarity	NPC291158
0.5238	Remote Similarity	NPC272998
0.5238	Remote Similarity	NPC112242
0.5238	Remote Similarity	NPC185041
0.5238	Remote Similarity	NPC147096

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC558253 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8215
0.1-0.2	884
0.2-0.3	44
0.3-0.4	5
0.4-0.5	0
0.5-0.6	2
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
0.5238	Remote Similarity	NPD2272	Phase 4
0.5238	Remote Similarity	NPD5383	Phase 4

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