Structure

Physi-Chem Properties

Molecular Weight:  254.19
Volume:  274.618
LogP:  2.465
LogD:  2.327
LogS:  -3.671
# Rotatable Bonds:  1
TPSA:  52.99
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.557
Synthetic Accessibility Score:  4.883
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.505
MDCK Permeability:  1.3731069884670433e-05
Pgp-inhibitor:  0.067
Pgp-substrate:  0.349
Human Intestinal Absorption (HIA):  0.045
20% Bioavailability (F20%):  0.019
30% Bioavailability (F30%):  0.122

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.868
Plasma Protein Binding (PPB):  88.18012237548828%
Volume Distribution (VD):  1.687
Pgp-substrate:  10.99283504486084%

ADMET: Metabolism

CYP1A2-inhibitor:  0.043
CYP1A2-substrate:  0.193
CYP2C19-inhibitor:  0.022
CYP2C19-substrate:  0.846
CYP2C9-inhibitor:  0.045
CYP2C9-substrate:  0.203
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.141
CYP3A4-inhibitor:  0.069
CYP3A4-substrate:  0.332

ADMET: Excretion

Clearance (CL):  9.798
Half-life (T1/2):  0.336

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.553
Drug-inuced Liver Injury (DILI):  0.063
AMES Toxicity:  0.06
Rat Oral Acute Toxicity:  0.161
Maximum Recommended Daily Dose:  0.683
Skin Sensitization:  0.199
Carcinogencity:  0.047
Eye Corrosion:  0.142
Eye Irritation:  0.439
Respiratory Toxicity:  0.794

Download Data

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

  Natural Product: NPC190859

Natural Product ID:  NPC190859
Common Name*:   SIRCULICGXIYIW-KAKCHQBASA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SIRCULICGXIYIW-KAKCHQBASA-N
Standard InCHI:  InChI=1S/C15H26O3/c1-9(2)12-6-5-10(3)7-11(16)8-15(4)14(18-15)13(12)17/h7,9,11-14,16-17H,5-6,8H2,1-4H3/b10-7+/t11-,12-,13+,14-,15-/m0/s1
SMILES:  CC(C)[C@@H]1CC/C(=C/[C@@H](C[C@@]2(C)[C@H]([C@@H]1O)O2)O)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464156
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:0002456] Germacrane 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
NPO29822 Santolina insularis Species Asteraceae Eukaryota aerial parts n.a. n.a. PMID[15974607]
NPO29822 Santolina insularis Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[15974607]

☑ 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
NPT27 Others Unspecified IC50 >= 10.0 ug.mL-1 PMID[495761]

☑ 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 NPC190859 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
0.9714 High Similarity NPC170148
0.9041 High Similarity NPC476703
0.875 High Similarity NPC476709
0.8696 High Similarity NPC311736
0.8667 High Similarity NPC477089
0.859 High Similarity NPC231601
0.8571 High Similarity NPC163290
0.8406 Intermediate Similarity NPC300593
0.8333 Intermediate Similarity NPC304690
0.8333 Intermediate Similarity NPC239373
0.8333 Intermediate Similarity NPC329989
0.8333 Intermediate Similarity NPC74722
0.831 Intermediate Similarity NPC259299
0.8261 Intermediate Similarity NPC473508
0.8194 Intermediate Similarity NPC305698
0.8158 Intermediate Similarity NPC236228
0.8158 Intermediate Similarity NPC256720
0.8133 Intermediate Similarity NPC471525
0.8077 Intermediate Similarity NPC476701
0.8049 Intermediate Similarity NPC255143
0.8028 Intermediate Similarity NPC61503
0.8028 Intermediate Similarity NPC471200
0.7973 Intermediate Similarity NPC129630
0.7971 Intermediate Similarity NPC99487
0.7949 Intermediate Similarity NPC68119
0.7949 Intermediate Similarity NPC13823
0.7917 Intermediate Similarity NPC267027
0.7848 Intermediate Similarity NPC86971
0.7808 Intermediate Similarity NPC82337
0.7792 Intermediate Similarity NPC93213
0.7765 Intermediate Similarity NPC49783
0.7763 Intermediate Similarity NPC329763
0.775 Intermediate Similarity NPC474739
0.7722 Intermediate Similarity NPC475980
0.7711 Intermediate Similarity NPC298595
0.7692 Intermediate Similarity NPC268111
0.7681 Intermediate Similarity NPC155025
0.7654 Intermediate Similarity NPC474894
0.7619 Intermediate Similarity NPC281316
0.7606 Intermediate Similarity NPC225342
0.76 Intermediate Similarity NPC16964
0.7595 Intermediate Similarity NPC40049
0.7586 Intermediate Similarity NPC476705
0.7571 Intermediate Similarity NPC475931
0.7568 Intermediate Similarity NPC161612
0.7568 Intermediate Similarity NPC73603
0.7568 Intermediate Similarity NPC33583
0.7561 Intermediate Similarity NPC477390
0.7561 Intermediate Similarity NPC477385
0.7534 Intermediate Similarity NPC250836
0.7534 Intermediate Similarity NPC308844
0.7532 Intermediate Similarity NPC143576
0.7471 Intermediate Similarity NPC197107
0.7471 Intermediate Similarity NPC191323
0.7468 Intermediate Similarity NPC126969
0.7467 Intermediate Similarity NPC272961
0.7465 Intermediate Similarity NPC66020
0.7465 Intermediate Similarity NPC258788
0.7439 Intermediate Similarity NPC246621
0.7436 Intermediate Similarity NPC227814
0.7436 Intermediate Similarity NPC144995
0.7436 Intermediate Similarity NPC24590
0.7432 Intermediate Similarity NPC326310
0.7391 Intermediate Similarity NPC24443
0.7381 Intermediate Similarity NPC83702
0.7375 Intermediate Similarity NPC471454
0.7375 Intermediate Similarity NPC84360
0.7368 Intermediate Similarity NPC472947
0.7361 Intermediate Similarity NPC321867
0.7361 Intermediate Similarity NPC207007
0.7361 Intermediate Similarity NPC68679
0.7356 Intermediate Similarity NPC299527
0.7349 Intermediate Similarity NPC259858
0.7342 Intermediate Similarity NPC12696
0.7333 Intermediate Similarity NPC220221
0.7324 Intermediate Similarity NPC122239
0.7317 Intermediate Similarity NPC471266
0.7317 Intermediate Similarity NPC95124
0.7303 Intermediate Similarity NPC119379
0.7297 Intermediate Similarity NPC473722
0.7273 Intermediate Similarity NPC470041
0.7273 Intermediate Similarity NPC3952
0.7273 Intermediate Similarity NPC471781
0.7262 Intermediate Similarity NPC260852
0.726 Intermediate Similarity NPC50435
0.7253 Intermediate Similarity NPC210717
0.7253 Intermediate Similarity NPC57664
0.7253 Intermediate Similarity NPC103165
0.7253 Intermediate Similarity NPC279621
0.725 Intermediate Similarity NPC329626
0.7246 Intermediate Similarity NPC227135
0.7241 Intermediate Similarity NPC476707
0.7241 Intermediate Similarity NPC476704
0.7241 Intermediate Similarity NPC476706
0.7237 Intermediate Similarity NPC167527
0.7229 Intermediate Similarity NPC471270
0.7222 Intermediate Similarity NPC57405
0.7222 Intermediate Similarity NPC240506
0.7222 Intermediate Similarity NPC303942
0.7209 Intermediate Similarity NPC311163
0.7209 Intermediate Similarity NPC477389
0.7209 Intermediate Similarity NPC477387
0.7195 Intermediate Similarity NPC471537
0.7195 Intermediate Similarity NPC325869
0.7191 Intermediate Similarity NPC302584
0.7191 Intermediate Similarity NPC158061
0.7183 Intermediate Similarity NPC181872
0.7183 Intermediate Similarity NPC226848
0.7179 Intermediate Similarity NPC472254
0.7179 Intermediate Similarity NPC23954
0.7179 Intermediate Similarity NPC306085
0.7176 Intermediate Similarity NPC78673
0.7176 Intermediate Similarity NPC160517
0.7176 Intermediate Similarity NPC186155
0.7174 Intermediate Similarity NPC261807
0.7159 Intermediate Similarity NPC115607
0.7159 Intermediate Similarity NPC128066
0.7143 Intermediate Similarity NPC473893
0.7143 Intermediate Similarity NPC270013
0.7143 Intermediate Similarity NPC14961
0.7126 Intermediate Similarity NPC477388
0.7126 Intermediate Similarity NPC476948
0.7126 Intermediate Similarity NPC477386
0.7125 Intermediate Similarity NPC23231
0.7125 Intermediate Similarity NPC60818
0.7123 Intermediate Similarity NPC172622
0.7111 Intermediate Similarity NPC125674
0.7111 Intermediate Similarity NPC475838
0.7111 Intermediate Similarity NPC228451
0.7108 Intermediate Similarity NPC236707
0.7108 Intermediate Similarity NPC470946
0.7108 Intermediate Similarity NPC470945
0.7108 Intermediate Similarity NPC470947
0.7108 Intermediate Similarity NPC100697
0.7108 Intermediate Similarity NPC474592
0.7105 Intermediate Similarity NPC477791
0.7105 Intermediate Similarity NPC136813
0.7097 Intermediate Similarity NPC473326
0.7089 Intermediate Similarity NPC265485
0.7089 Intermediate Similarity NPC220939
0.7079 Intermediate Similarity NPC473448
0.7073 Intermediate Similarity NPC181838
0.7073 Intermediate Similarity NPC3852
0.7073 Intermediate Similarity NPC52755
0.7073 Intermediate Similarity NPC137345
0.7059 Intermediate Similarity NPC471340
0.7059 Intermediate Similarity NPC185605
0.7045 Intermediate Similarity NPC248312
0.7042 Intermediate Similarity NPC52012
0.7037 Intermediate Similarity NPC293223
0.7037 Intermediate Similarity NPC301525
0.7037 Intermediate Similarity NPC271070
0.7033 Intermediate Similarity NPC81386
0.7033 Intermediate Similarity NPC474035
0.7033 Intermediate Similarity NPC474247
0.7027 Intermediate Similarity NPC474155
0.7027 Intermediate Similarity NPC473759
0.7024 Intermediate Similarity NPC207188
0.7021 Intermediate Similarity NPC288876
0.7013 Intermediate Similarity NPC224532
0.7013 Intermediate Similarity NPC471238
0.7011 Intermediate Similarity NPC61527
0.7 Intermediate Similarity NPC223604
0.7 Intermediate Similarity NPC114389
0.7 Intermediate Similarity NPC306727
0.7 Intermediate Similarity NPC475441
0.6989 Remote Similarity NPC205143
0.6989 Remote Similarity NPC182811
0.6988 Remote Similarity NPC89128
0.6988 Remote Similarity NPC233295
0.6986 Remote Similarity NPC469694
0.6974 Remote Similarity NPC202017
0.6974 Remote Similarity NPC469328
0.6966 Remote Similarity NPC473564
0.6966 Remote Similarity NPC97103
0.6962 Remote Similarity NPC471272
0.6962 Remote Similarity NPC41886
0.6962 Remote Similarity NPC471662
0.6962 Remote Similarity NPC471271
0.6962 Remote Similarity NPC471268
0.6957 Remote Similarity NPC240838
0.6951 Remote Similarity NPC477425
0.6951 Remote Similarity NPC477427
0.6951 Remote Similarity NPC477426
0.6951 Remote Similarity NPC474826
0.6951 Remote Similarity NPC476439
0.6947 Remote Similarity NPC476896
0.6941 Remote Similarity NPC472465
0.6933 Remote Similarity NPC309300
0.6932 Remote Similarity NPC474765
0.6923 Remote Similarity NPC471560
0.6923 Remote Similarity NPC474900
0.6923 Remote Similarity NPC329656
0.6923 Remote Similarity NPC269841
0.6923 Remote Similarity NPC234511
0.6923 Remote Similarity NPC137461
0.6923 Remote Similarity NPC475912
0.6923 Remote Similarity NPC212486
0.6915 Remote Similarity NPC274458
0.6914 Remote Similarity NPC36479

  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 NPC190859 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
0.7361 Intermediate Similarity NPD368 Approved
0.7126 Intermediate Similarity NPD7524 Approved
0.7079 Intermediate Similarity NPD7838 Discovery
0.6977 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6947 Remote Similarity NPD5344 Discontinued
0.6889 Remote Similarity NPD46 Approved
0.6889 Remote Similarity NPD6698 Approved
0.686 Remote Similarity NPD6695 Phase 3
0.6761 Remote Similarity NPD342 Phase 1
0.6706 Remote Similarity NPD6931 Approved
0.6706 Remote Similarity NPD6930 Phase 2
0.663 Remote Similarity NPD7983 Approved
0.6588 Remote Similarity NPD6929 Approved
0.6556 Remote Similarity NPD7750 Discontinued
0.6522 Remote Similarity NPD3168 Discontinued
0.6517 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6512 Remote Similarity NPD7514 Phase 3
0.6512 Remote Similarity NPD7332 Phase 2
0.6495 Remote Similarity NPD6648 Approved
0.6437 Remote Similarity NPD6902 Approved
0.6429 Remote Similarity NPD6933 Approved
0.641 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6353 Remote Similarity NPD5776 Phase 2
0.6353 Remote Similarity NPD6925 Approved
0.6333 Remote Similarity NPD6893 Approved
0.6322 Remote Similarity NPD4820 Approved
0.6322 Remote Similarity NPD4819 Approved
0.6322 Remote Similarity NPD4821 Approved
0.6322 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6322 Remote Similarity NPD4822 Approved
0.6282 Remote Similarity NPD371 Approved
0.6279 Remote Similarity NPD7145 Approved
0.6277 Remote Similarity NPD7087 Discontinued
0.6267 Remote Similarity NPD585 Clinical (unspecified phase)
0.6265 Remote Similarity NPD4732 Discontinued
0.6264 Remote Similarity NPD4249 Approved
0.625 Remote Similarity NPD6371 Approved
0.625 Remote Similarity NPD6898 Phase 1
0.6211 Remote Similarity NPD5778 Approved
0.6211 Remote Similarity NPD5779 Approved
0.6196 Remote Similarity NPD4251 Approved
0.6196 Remote Similarity NPD4250 Approved
0.6196 Remote Similarity NPD4751 Clinical (unspecified phase)
0.619 Remote Similarity NPD6926 Approved
0.619 Remote Similarity NPD6924 Approved
0.6163 Remote Similarity NPD6932 Approved
0.6118 Remote Similarity NPD8264 Approved
0.6111 Remote Similarity NPD7154 Phase 3
0.6111 Remote Similarity NPD6110 Phase 1
0.6092 Remote Similarity NPD4271 Approved
0.6092 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6092 Remote Similarity NPD4268 Approved
0.6064 Remote Similarity NPD1695 Approved
0.6061 Remote Similarity NPD4225 Approved
0.6061 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6023 Remote Similarity NPD7645 Phase 2
0.6023 Remote Similarity NPD6683 Phase 2
0.5978 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5962 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5955 Remote Similarity NPD7525 Registered
0.5955 Remote Similarity NPD7509 Discontinued
0.5938 Remote Similarity NPD7637 Suspended
0.5934 Remote Similarity NPD5362 Discontinued
0.5905 Remote Similarity NPD6686 Approved
0.5897 Remote Similarity NPD1145 Discontinued
0.5888 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5882 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5865 Remote Similarity NPD5357 Phase 1
0.5865 Remote Similarity NPD6640 Phase 3
0.5862 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5849 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5824 Remote Similarity NPD6435 Approved
0.5816 Remote Similarity NPD5282 Discontinued
0.5784 Remote Similarity NPD4159 Approved
0.5761 Remote Similarity NPD5332 Approved
0.5761 Remote Similarity NPD5331 Approved
0.5747 Remote Similarity NPD6942 Approved
0.5747 Remote Similarity NPD7339 Approved
0.573 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6922 Approved
0.5714 Remote Similarity NPD4265 Approved
0.5714 Remote Similarity NPD6923 Approved
0.5714 Remote Similarity NPD4790 Discontinued
0.57 Remote Similarity NPD7839 Suspended
0.5686 Remote Similarity NPD7639 Approved
0.5686 Remote Similarity NPD7640 Approved
0.566 Remote Similarity NPD6412 Phase 2
0.5652 Remote Similarity NPD4269 Approved
0.5652 Remote Similarity NPD4270 Approved
0.5647 Remote Similarity NPD7144 Approved
0.5647 Remote Similarity NPD7143 Approved
0.5625 Remote Similarity NPD7115 Discovery
0.5604 Remote Similarity NPD5368 Approved
0.56 Remote Similarity NPD1698 Clinical (unspecified phase)

  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