Structure

Physi-Chem Properties

Molecular Weight:  238.19
Volume:  265.827
LogP:  3.516
LogD:  2.79
LogS:  -2.231
# Rotatable Bonds:  1
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.69
Synthetic Accessibility Score:  4.234
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.468
MDCK Permeability:  1.4476675460173283e-05
Pgp-inhibitor:  0.046
Pgp-substrate:  0.011
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.01
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.523
Plasma Protein Binding (PPB):  60.923255920410156%
Volume Distribution (VD):  1.14
Pgp-substrate:  34.11378860473633%

ADMET: Metabolism

CYP1A2-inhibitor:  0.029
CYP1A2-substrate:  0.411
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.857
CYP2C9-inhibitor:  0.024
CYP2C9-substrate:  0.115
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.197
CYP3A4-inhibitor:  0.256
CYP3A4-substrate:  0.514

ADMET: Excretion

Clearance (CL):  10.467
Half-life (T1/2):  0.268

ADMET: Toxicity

hERG Blockers:  0.044
Human Hepatotoxicity (H-HT):  0.408
Drug-inuced Liver Injury (DILI):  0.039
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.328
Maximum Recommended Daily Dose:  0.157
Skin Sensitization:  0.833
Carcinogencity:  0.848
Eye Corrosion:  0.984
Eye Irritation:  0.972
Respiratory Toxicity:  0.966

Download Data

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

  Natural Product: NPC310228

Natural Product ID:  NPC310228
Common Name*:   Guaidiol
IUPAC Name:   (1S,3aS,4S,7R,8aS)-1,4-dimethyl-7-prop-1-en-2-yl-2,3,3a,5,6,7,8,8a-octahydroazulene-1,4-diol
Synonyms:   Guaidiol; Guaidiol A
Standard InCHIKey:  RQHOQQOEZPFYTD-QTVXIADOSA-N
Standard InCHI:  InChI=1S/C15H26O2/c1-10(2)11-5-7-14(3,16)12-6-8-15(4,17)13(12)9-11/h11-13,16-17H,1,5-9H2,2-4H3/t11-,12+,13+,14+,15+/m1/s1
SMILES:  CC(=C)[C@@H]1CC[C@]([C@@H]2[C@H](C1)[C@@](C)(O)CC2)(C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463902
PubChem CID:   10633702
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0002874] Guaianes

*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
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)90945-1]
NPO7630 Cyperus longus Species Cyperaceae Eukaryota n.a. Egyptian herbal medicine n.a. PMID[15104485]
NPO17780 Curcuma heyneana Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23387824]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[24704449]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[26967731]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17780 Curcuma heyneana Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7630 Cyperus longus Species Cyperaceae 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
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 35.4 % PMID[546986]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 20.3 % PMID[546986]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 10.4 % PMID[546986]
NPT993 Cell Line Hepatocyte Mus musculus Inhibition = 2.6 % PMID[546986]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition < 65.0 % PMID[546987]

☑ 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 NPC310228 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
1.0 High Similarity NPC52431
0.8983 High Similarity NPC63111
0.8852 High Similarity NPC469326
0.8852 High Similarity NPC261782
0.8852 High Similarity NPC205618
0.8644 High Similarity NPC99480
0.8644 High Similarity NPC184049
0.8413 Intermediate Similarity NPC469328
0.8308 Intermediate Similarity NPC144647
0.8182 Intermediate Similarity NPC471781
0.8033 Intermediate Similarity NPC469321
0.8 Intermediate Similarity NPC278550
0.7966 Intermediate Similarity NPC45387
0.7778 Intermediate Similarity NPC15152
0.7705 Intermediate Similarity NPC119425
0.7647 Intermediate Similarity NPC470041
0.7619 Intermediate Similarity NPC162109
0.7619 Intermediate Similarity NPC252809
0.7536 Intermediate Similarity NPC41886
0.7536 Intermediate Similarity NPC471660
0.75 Intermediate Similarity NPC474900
0.746 Intermediate Similarity NPC5698
0.7424 Intermediate Similarity NPC300442
0.7397 Intermediate Similarity NPC469324
0.7391 Intermediate Similarity NPC133873
0.7385 Intermediate Similarity NPC474480
0.7361 Intermediate Similarity NPC141346
0.7361 Intermediate Similarity NPC473437
0.7361 Intermediate Similarity NPC124289
0.7361 Intermediate Similarity NPC115719
0.7361 Intermediate Similarity NPC126969
0.7361 Intermediate Similarity NPC142759
0.7361 Intermediate Similarity NPC25908
0.7344 Intermediate Similarity NPC323153
0.7333 Intermediate Similarity NPC192962
0.7324 Intermediate Similarity NPC471659
0.7286 Intermediate Similarity NPC469737
0.7273 Intermediate Similarity NPC219940
0.7258 Intermediate Similarity NPC274396
0.7206 Intermediate Similarity NPC136813
0.7206 Intermediate Similarity NPC472253
0.7206 Intermediate Similarity NPC472255
0.72 Intermediate Similarity NPC258965
0.72 Intermediate Similarity NPC156658
0.72 Intermediate Similarity NPC476625
0.7188 Intermediate Similarity NPC475968
0.7164 Intermediate Similarity NPC477009
0.7164 Intermediate Similarity NPC238352
0.7123 Intermediate Similarity NPC471658
0.7123 Intermediate Similarity NPC152017
0.7121 Intermediate Similarity NPC211291
0.7121 Intermediate Similarity NPC133368
0.7105 Intermediate Similarity NPC471661
0.7101 Intermediate Similarity NPC224532
0.7077 Intermediate Similarity NPC135648
0.7059 Intermediate Similarity NPC272125
0.7051 Intermediate Similarity NPC242016
0.6984 Remote Similarity NPC24443
0.6949 Remote Similarity NPC95969
0.6949 Remote Similarity NPC127997
0.6944 Remote Similarity NPC469320
0.6944 Remote Similarity NPC300940
0.6933 Remote Similarity NPC477817
0.6933 Remote Similarity NPC477819
0.6923 Remote Similarity NPC111409
0.6912 Remote Similarity NPC471200
0.6901 Remote Similarity NPC254845
0.6875 Remote Similarity NPC291147
0.6866 Remote Similarity NPC279200
0.6866 Remote Similarity NPC50435
0.6857 Remote Similarity NPC167527
0.6849 Remote Similarity NPC309178
0.6806 Remote Similarity NPC471662
0.68 Remote Similarity NPC471454
0.6795 Remote Similarity NPC133844
0.678 Remote Similarity NPC100445
0.6769 Remote Similarity NPC475830
0.6757 Remote Similarity NPC215215
0.6757 Remote Similarity NPC77501
0.6757 Remote Similarity NPC85831
0.6757 Remote Similarity NPC265921
0.6753 Remote Similarity NPC78545
0.6753 Remote Similarity NPC71535
0.6753 Remote Similarity NPC471656
0.6753 Remote Similarity NPC30675
0.675 Remote Similarity NPC284534
0.675 Remote Similarity NPC300082
0.675 Remote Similarity NPC204105
0.6724 Remote Similarity NPC87439
0.6719 Remote Similarity NPC264779
0.6719 Remote Similarity NPC39068
0.6716 Remote Similarity NPC210346
0.6716 Remote Similarity NPC147524
0.6714 Remote Similarity NPC477791
0.6714 Remote Similarity NPC308522
0.6714 Remote Similarity NPC74885
0.6712 Remote Similarity NPC310608
0.6712 Remote Similarity NPC234527
0.6712 Remote Similarity NPC14352
0.6711 Remote Similarity NPC475
0.6711 Remote Similarity NPC472502
0.6709 Remote Similarity NPC471340
0.6709 Remote Similarity NPC260852
0.6709 Remote Similarity NPC232023
0.6707 Remote Similarity NPC22376
0.6707 Remote Similarity NPC79549
0.6667 Remote Similarity NPC145245
0.6667 Remote Similarity NPC165069
0.6667 Remote Similarity NPC15162
0.6667 Remote Similarity NPC310643
0.6667 Remote Similarity NPC126248
0.6667 Remote Similarity NPC18543
0.6667 Remote Similarity NPC61503
0.6627 Remote Similarity NPC215556
0.6625 Remote Similarity NPC37005
0.6625 Remote Similarity NPC53011
0.6625 Remote Similarity NPC154893
0.6625 Remote Similarity NPC290052
0.6625 Remote Similarity NPC16887
0.6623 Remote Similarity NPC84185
0.6623 Remote Similarity NPC471890
0.6623 Remote Similarity NPC66677
0.6623 Remote Similarity NPC24504
0.6622 Remote Similarity NPC7382
0.6613 Remote Similarity NPC157781
0.6613 Remote Similarity NPC179169
0.6613 Remote Similarity NPC181255
0.6613 Remote Similarity NPC306195
0.6613 Remote Similarity NPC35519
0.6582 Remote Similarity NPC1272
0.6582 Remote Similarity NPC470614
0.6582 Remote Similarity NPC472465
0.6579 Remote Similarity NPC186109
0.6579 Remote Similarity NPC31037
0.6567 Remote Similarity NPC40206
0.6557 Remote Similarity NPC131623
0.6557 Remote Similarity NPC329773
0.6548 Remote Similarity NPC216284
0.6543 Remote Similarity NPC287015
0.6543 Remote Similarity NPC146850
0.6538 Remote Similarity NPC47149
0.6538 Remote Similarity NPC80622
0.6538 Remote Similarity NPC26117
0.6533 Remote Similarity NPC89374
0.6533 Remote Similarity NPC319090
0.6533 Remote Similarity NPC328104
0.6533 Remote Similarity NPC60818
0.6533 Remote Similarity NPC113639
0.6533 Remote Similarity NPC3403
0.6533 Remote Similarity NPC23231
0.6533 Remote Similarity NPC251435
0.6533 Remote Similarity NPC313185
0.6528 Remote Similarity NPC475952
0.6528 Remote Similarity NPC234511
0.6522 Remote Similarity NPC309300
0.6522 Remote Similarity NPC300593
0.6522 Remote Similarity NPC199937
0.6515 Remote Similarity NPC10017
0.6515 Remote Similarity NPC474769
0.6515 Remote Similarity NPC189290
0.65 Remote Similarity NPC128246
0.65 Remote Similarity NPC110778
0.65 Remote Similarity NPC477818
0.65 Remote Similarity NPC245665
0.6494 Remote Similarity NPC42853
0.6494 Remote Similarity NPC470944
0.6494 Remote Similarity NPC31828
0.6494 Remote Similarity NPC472499
0.6494 Remote Similarity NPC472500
0.6486 Remote Similarity NPC143576
0.6486 Remote Similarity NPC474140
0.6486 Remote Similarity NPC472506
0.6486 Remote Similarity NPC476709
0.6479 Remote Similarity NPC253303
0.6479 Remote Similarity NPC269077
0.6471 Remote Similarity NPC155215
0.6471 Remote Similarity NPC274704
0.6463 Remote Similarity NPC201273
0.6463 Remote Similarity NPC121981
0.6452 Remote Similarity NPC214584
0.6452 Remote Similarity NPC26906
0.6447 Remote Similarity NPC476317
0.6447 Remote Similarity NPC38141
0.6447 Remote Similarity NPC472472
0.6447 Remote Similarity NPC215481
0.6441 Remote Similarity NPC108441
0.6441 Remote Similarity NPC77550
0.6438 Remote Similarity NPC475728
0.642 Remote Similarity NPC116613
0.642 Remote Similarity NPC124172
0.642 Remote Similarity NPC255882
0.641 Remote Similarity NPC49627
0.641 Remote Similarity NPC476316
0.641 Remote Similarity NPC49599
0.6406 Remote Similarity NPC286752
0.64 Remote Similarity NPC476736
0.64 Remote Similarity NPC329090
0.64 Remote Similarity NPC27395
0.64 Remote Similarity NPC472503
0.64 Remote Similarity NPC308440

  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 NPC310228 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
0.6806 Remote Similarity NPD4243 Approved
0.6622 Remote Similarity NPD4784 Approved
0.6622 Remote Similarity NPD4785 Approved
0.6533 Remote Similarity NPD5275 Approved
0.6533 Remote Similarity NPD4190 Phase 3
0.6441 Remote Similarity NPD386 Approved
0.6441 Remote Similarity NPD388 Approved
0.641 Remote Similarity NPD4195 Approved
0.64 Remote Similarity NPD6926 Approved
0.64 Remote Similarity NPD6924 Approved
0.6329 Remote Similarity NPD6930 Phase 2
0.6329 Remote Similarity NPD6931 Approved
0.6234 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6234 Remote Similarity NPD6933 Approved
0.622 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6203 Remote Similarity NPD6929 Approved
0.619 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6173 Remote Similarity NPD4223 Phase 3
0.6173 Remote Similarity NPD4221 Approved
0.6154 Remote Similarity NPD6932 Approved
0.6125 Remote Similarity NPD7525 Registered
0.6098 Remote Similarity NPD6695 Phase 3
0.6098 Remote Similarity NPD4788 Approved
0.6024 Remote Similarity NPD4197 Approved
0.6 Remote Similarity NPD368 Approved
0.6 Remote Similarity NPD6683 Phase 2
0.5952 Remote Similarity NPD5329 Approved
0.5952 Remote Similarity NPD6893 Approved
0.5949 Remote Similarity NPD6925 Approved
0.5949 Remote Similarity NPD5776 Phase 2
0.5926 Remote Similarity NPD4820 Approved
0.5926 Remote Similarity NPD4822 Approved
0.5926 Remote Similarity NPD4819 Approved
0.5926 Remote Similarity NPD7514 Phase 3
0.5926 Remote Similarity NPD7509 Discontinued
0.5926 Remote Similarity NPD4821 Approved
0.5926 Remote Similarity NPD4748 Discontinued
0.5897 Remote Similarity NPD7339 Approved
0.5897 Remote Similarity NPD6942 Approved
0.5882 Remote Similarity NPD5690 Phase 2
0.5882 Remote Similarity NPD4688 Approved
0.5882 Remote Similarity NPD5205 Approved
0.5882 Remote Similarity NPD4138 Approved
0.5882 Remote Similarity NPD4689 Approved
0.5882 Remote Similarity NPD5280 Approved
0.5882 Remote Similarity NPD4690 Approved
0.5882 Remote Similarity NPD4693 Phase 3
0.5882 Remote Similarity NPD4694 Approved
0.5875 Remote Similarity NPD7145 Approved
0.5867 Remote Similarity NPD6923 Approved
0.5867 Remote Similarity NPD6922 Approved
0.5857 Remote Similarity NPD1145 Discontinued
0.5854 Remote Similarity NPD4692 Approved
0.5854 Remote Similarity NPD4139 Approved
0.5814 Remote Similarity NPD7750 Discontinued
0.5814 Remote Similarity NPD7524 Approved
0.5789 Remote Similarity NPD7143 Approved
0.5789 Remote Similarity NPD7144 Approved
0.5765 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5747 Remote Similarity NPD4518 Approved
0.5747 Remote Similarity NPD4722 Approved
0.5747 Remote Similarity NPD4723 Approved
0.5732 Remote Similarity NPD7332 Phase 2
0.5732 Remote Similarity NPD5368 Approved
0.573 Remote Similarity NPD5284 Approved
0.573 Remote Similarity NPD5281 Approved
0.5714 Remote Similarity NPD5331 Approved
0.5714 Remote Similarity NPD7152 Approved
0.5714 Remote Similarity NPD5332 Approved
0.5714 Remote Similarity NPD5362 Discontinued
0.5714 Remote Similarity NPD7151 Approved
0.5714 Remote Similarity NPD7150 Approved
0.5682 Remote Similarity NPD1695 Approved
0.5682 Remote Similarity NPD4753 Phase 2
0.5679 Remote Similarity NPD4271 Approved
0.5679 Remote Similarity NPD4268 Approved
0.5667 Remote Similarity NPD4202 Approved
0.5663 Remote Similarity NPD6898 Phase 1
0.5663 Remote Similarity NPD6902 Approved
0.5663 Remote Similarity NPD5369 Approved
0.5663 Remote Similarity NPD4790 Discontinued
0.5647 Remote Similarity NPD3666 Approved
0.5647 Remote Similarity NPD3133 Approved
0.5647 Remote Similarity NPD3665 Phase 1
0.5618 Remote Similarity NPD4001 Clinical (unspecified phase)
0.5618 Remote Similarity NPD4096 Approved

  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