Structure

Physi-Chem Properties

Molecular Weight:  204.19
Volume:  245.61
LogP:  4.913
LogD:  4.165
LogS:  -4.555
# Rotatable Bonds:  1
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.542
Synthetic Accessibility Score:  3.934
Fsp3:  0.733
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.574
MDCK Permeability:  1.4779381672269665e-05
Pgp-inhibitor:  0.03
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.94
30% Bioavailability (F30%):  0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.55
Plasma Protein Binding (PPB):  69.49620056152344%
Volume Distribution (VD):  1.669
Pgp-substrate:  26.23008155822754%

ADMET: Metabolism

CYP1A2-inhibitor:  0.32
CYP1A2-substrate:  0.609
CYP2C19-inhibitor:  0.185
CYP2C19-substrate:  0.886
CYP2C9-inhibitor:  0.169
CYP2C9-substrate:  0.27
CYP2D6-inhibitor:  0.044
CYP2D6-substrate:  0.811
CYP3A4-inhibitor:  0.491
CYP3A4-substrate:  0.333

ADMET: Excretion

Clearance (CL):  11.436
Half-life (T1/2):  0.116

ADMET: Toxicity

hERG Blockers:  0.054
Human Hepatotoxicity (H-HT):  0.333
Drug-inuced Liver Injury (DILI):  0.167
AMES Toxicity:  0.007
Rat Oral Acute Toxicity:  0.032
Maximum Recommended Daily Dose:  0.598
Skin Sensitization:  0.307
Carcinogencity:  0.41
Eye Corrosion:  0.868
Eye Irritation:  0.899
Respiratory Toxicity:  0.428

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC270463

Natural Product ID:  NPC270463
Common Name*:   YOVSPTNQHMDJAG-KKUMJFAQSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  YOVSPTNQHMDJAG-KKUMJFAQSA-N
Standard InCHI:  InChI=1S/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3/t13-,14-,15-/m0/s1
SMILES:  C=C(C)[C@H]1CC[C@]2(C)CCCC(=C)[C@@H]2C1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0000101] Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1002/ejlt.201100207]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1007/s11746-010-1670-2]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.foodcont.2016.09.002]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.jfca.2010.08.006]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2010.06.003]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2010.12.007]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2016.02.010]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.1016/j.supflu.2018.06.017]
NPO15351 Streptomyces prunicolor Species Streptomycetaceae Bacteria n.a. mycelium n.a. DOI[10.1021/np50098a008]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.12691/jfnr-2-5-9]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. DOI[10.5219/332]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[10336650]
NPO7193 Persicaria lapathifolia Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[11678656]
NPO6541 Scrophularia buergeriana Species Scrophulariaceae Eukaryota roots n.a. n.a. PMID[12444706]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. PMID[15217296]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[15679315]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[16252923]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. PMID[16499319]
NPO13478 Scorzonera pseudodivaricata Species Asteraceae Eukaryota n.a. Mongolian n.a. PMID[17542634]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[17624889]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. sand-covered bottom at -10 to -15 m at Hurghada, on the Egyptian Red Sea coast 2003-JUN PMID[18298079]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18611049]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[18768384]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. PMID[18942825]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[19476340]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[19628108]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. PMID[20405844]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[21912858]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. cone n.a. PMID[22111577]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. flower n.a. PMID[22166201]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[22538527]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[23790907]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[24811150]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[24948953]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[25564559]
NPO11898 Lobophora variegata Species Dictyotaceae Eukaryota n.a. at depths of 630 m at El Mdano (Tenerife, Canary Islands) n.a. PMID[26126835]
NPO5247 Elaphoglossum lindbergii Species Dryopteridaceae Eukaryota n.a. n.a. n.a. PMID[26689830]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[28274428]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. PMID[29154541]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[30236698]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds Guangzhou, China PMID[30563201]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[30583361]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[30599958]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[31159190]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota Seeds n.a. PMID[31861466]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12853 Leucocarpus perfoliatus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12633 Rapanea neurophylla Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10530 Aconitum subcuneatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6541 Scrophularia buergeriana Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1834 Atalantia racemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11206 Trifolium hybridum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10530 Aconitum subcuneatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12633 Rapanea neurophylla Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12853 Leucocarpus perfoliatus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7193 Persicaria lapathifolia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24390.1 Juniperus rigida var. conferta Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6541 Scrophularia buergeriana Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO10530 Aconitum subcuneatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6541 Scrophularia buergeriana Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6541 Scrophularia buergeriana Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2996 Pistacia atlantica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6541 Scrophularia buergeriana Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10053 Peperomia blanda Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12853 Leucocarpus perfoliatus Species Phrymaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7560 Tachardia acaciae n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO2207 Sphaerella rubella n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13879 Humulus lupulus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7193 Persicaria lapathifolia Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9606 Castanea dentata Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11518 Strophanthus sarmentosus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6360 Xenoacremonium recifei Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1044 Caiman crocodilus Species Alligatoridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5930 Crambe tatarica Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11848 Lemaireocereus griseus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13671 Ononis vaginalis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12196 Buphane fischeri n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10530 Aconitum subcuneatum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18489 Pinus serotina Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11206 Trifolium hybridum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24390.1 Juniperus rigida var. conferta Varieties Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8928 Pteris semipinnata Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9934 Mycobacterium leprae Species Mycobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO1834 Atalantia racemosa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9313 Fritillaria ningguoensis Species Liliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11898 Lobophora variegata Species Dictyotaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10783 Syncarpia hillii Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2398 Millettia erythrocalyx Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3223 Aristolochia esperanzae Species Aristolochiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13585 Rapanea lancifolia Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO999 Trigonostemon cherrieri Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15351 Streptomyces prunicolor Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12146 Stemodia maritima Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13478 Scorzonera pseudodivaricata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5714 Rogeria adenophylla Species Pedaliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13030 Artemisia dentata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11007 Ophiomastix annulosa Species Ophiocomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5247 Elaphoglossum lindbergii Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21830 Buddleja cordata Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23883 Penicillium abidjanum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO252 Hoffmannia strigillosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11639 Chlorogloeopsis fritschii Species Chlorogloeopsidaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12855 Alkanna cappadocica Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4815 Cladonia coccifera Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12700 Diospyros eriantha Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14578 Prorocentrum micans Species Prorocentraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1116 Periconia atropurpurea Species Periconiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13281 Salvia hispanica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12633 Rapanea neurophylla Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9363 Ferula ammoniacum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11527 Ibacus peronii Species Scyllaridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9810 Keteleeria davidiana Species Pinaceae 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 NP ID 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC270463 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC270463 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage

  Bioactivity similarity: Similar Natural Products in NPASS

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