Structure

Physi-Chem Properties

Molecular Weight:  440.4
Volume:  514.023
LogP:  7.468
LogD:  5.999
LogS:  -6.644
# Rotatable Bonds:  5
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.424
Synthetic Accessibility Score:  4.652
Fsp3:  0.871
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.952
MDCK Permeability:  9.930500709742773e-06
Pgp-inhibitor:  0.868
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.975
30% Bioavailability (F30%):  0.868

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.032
Plasma Protein Binding (PPB):  94.13733673095703%
Volume Distribution (VD):  1.321
Pgp-substrate:  1.6956502199172974%

ADMET: Metabolism

CYP1A2-inhibitor:  0.038
CYP1A2-substrate:  0.604
CYP2C19-inhibitor:  0.108
CYP2C19-substrate:  0.979
CYP2C9-inhibitor:  0.155
CYP2C9-substrate:  0.636
CYP2D6-inhibitor:  0.07
CYP2D6-substrate:  0.869
CYP3A4-inhibitor:  0.564
CYP3A4-substrate:  0.852

ADMET: Excretion

Clearance (CL):  6.791
Half-life (T1/2):  0.03

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.038
Drug-inuced Liver Injury (DILI):  0.049
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.199
Maximum Recommended Daily Dose:  0.869
Skin Sensitization:  0.121
Carcinogencity:  0.017
Eye Corrosion:  0.338
Eye Irritation:  0.72
Respiratory Toxicity:  0.348

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  Natural Product: NPC82183

Natural Product ID:  NPC82183
Common Name*:   XJLZCPIILZRCPS-ANMPWZFDSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  XJLZCPIILZRCPS-ANMPWZFDSA-N
Standard InCHI:  InChI=1S/C31H52O/c1-20(2)21(3)10-11-22(4)23-14-18-31(9)25-12-13-26-28(5,6)27(32)16-17-29(26,7)24(25)15-19-30(23,31)8/h20,22-23,26-27,32H,3,10-19H2,1-2,4-9H3/t22-,23-,26+,27+,29-,30-,31+/m1/s1
SMILES:  CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   9803310
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Anhui province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Gansu province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Henan province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shandong province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Shanxi province, China DOI[10.1016/j.foodres.2020.109416]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. DOI[10.2174/092986712800229032]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. fruit body n.a. PMID[15095145]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[17559265]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. mycelium n.a. PMID[17932820]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. PMID[19402674]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19721258]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[19772486]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[20806783]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. fruit body n.a. PMID[21028898]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota fruiting body n.a. n.a. PMID[21028898]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota fruiting body n.a. n.a. PMID[21115251]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21782011]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. root n.a. PMID[21954959]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota roots Whitessence Srl, Viterbo, Italy 2005-OCT PMID[21954959]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[22190295]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. seed n.a. PMID[23497864]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[23517145]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[26838074]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27313650]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. root n.a. PMID[27429639]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[29741372]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[31891260]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds DingXi, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds LanZhou, GanSu, China early autumn (from August to the beginning of September PMID[32545196]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds HeZe, ShanDong, China early autumn (from August to the beginning of September PMID[32545196]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Roots n.a. n.a. PMID[32951423]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota Seeds Xinjiang,China PMID[33063333]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China Maturation PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 80 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 90 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China Maturation PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 20 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 30 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 40 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 50 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 60 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Fruits Yangling, Shaanxi, China 10 days after pollination PMID[33131958]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota Seeds Yangling, Shaanxi, China 70 days after pollination PMID[33131958]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. fruit body n.a. PMID[8594142]
NPO15630 Manduca sexta Species Sphingidae Eukaryota n.a. n.a. n.a. PMID[8748375]
NPO6926 Colubrina asiatica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4176 Mosla scabra Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3354 Fomes officinalis Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4176 Mosla scabra Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4789 Adiantum caudatum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4095 Hedysarum multijugum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3354 Fomes officinalis Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11787 Orthosiphon wulfenioides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6926 Colubrina asiatica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4789 Adiantum caudatum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4176 Mosla scabra Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17660 Podocarpus lawrencei Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9798 Paeonia lactiflora Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8037 Bryum rutilans Species Bryaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13627 Sphaeria macula n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15265 Paeonia rockii Species Paeoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6988 Diploschistes cretaceus Species Graphidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25603 Lycoris x chejuensis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6815 Streptomyces sclerotialus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO3354 Fomes officinalis Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6926 Colubrina asiatica Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14403 Taiwanofungus camphoratus Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6533 Dipterocarpus pilosus Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11557 Echinus miliaris Species Echinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27240 Alcyonium grandis Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11787 Orthosiphon wulfenioides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4789 Adiantum caudatum Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4909 Hilliardiella oligocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29200 Moquiniastrum paniculatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4095 Hedysarum multijugum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15630 Manduca sexta Species Sphingidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6429 Phlomis regelii Species Lamiaceae 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
NPO15265 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 83.30 ± 1.06 n.a. n.a. mg/kg PMID[32545196]
NPO15265 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 76.56 ± 0.68 n.a. n.a. mg/kg PMID[32545196]
NPO30287 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 92.16 ±7.45 n.a. n.a. mg/kg PMID[32545196]
NPO30287 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 41.72 ± 0.59 n.a. n.a. mg/kg PMID[32545196]
NPO30287 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 68.66 ± 0.47 n.a. n.a. mg/kg PMID[32545196]
NPO30287 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 88.64 ± 2.15 n.a. n.a. mg/kg PMID[32545196]
NPO30287 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 40.98 ± 3.06 n.a. n.a. mg/kg PMID[32545196]
NPO30287 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 67.16 ± 3.44 n.a. n.a. mg/kg PMID[32545196]
NPO30287 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 88.48 ± 1.95 n.a. n.a. mg/kg PMID[32545196]
NPO30287 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 49.46 ± 4.73 n.a. n.a. mg/kg PMID[32545196]
NPO9798 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 21.53 ± 0.18 n.a. n.a. mg/kg PMID[32545196]
NPO9798 NPC82183 Naturally dried; extract seed oils with Soxhlet extractor Seeds 32.41 ± 0.87 n.a. n.a. mg/kg PMID[32545196]

☑ 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 NPC82183 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 NPC82183 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