Structure

Physi-Chem Properties

Molecular Weight:  394.27
Volume:  413.453
LogP:  3.87
LogD:  4.002
LogS:  -4.375
# Rotatable Bonds:  3
TPSA:  53.99
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.666
Synthetic Accessibility Score:  6.209
Fsp3:  0.957
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:  -4.764
MDCK Permeability:  6.933315307833254e-05
Pgp-inhibitor:  0.99
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.141

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.027
Plasma Protein Binding (PPB):  94.27994537353516%
Volume Distribution (VD):  1.788
Pgp-substrate:  3.4194464683532715%

ADMET: Metabolism

CYP1A2-inhibitor:  0.023
CYP1A2-substrate:  0.38
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.946
CYP2C9-inhibitor:  0.034
CYP2C9-substrate:  0.023
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.292
CYP3A4-inhibitor:  0.355
CYP3A4-substrate:  0.726

ADMET: Excretion

Clearance (CL):  7.374
Half-life (T1/2):  0.345

ADMET: Toxicity

hERG Blockers:  0.824
Human Hepatotoxicity (H-HT):  0.919
Drug-inuced Liver Injury (DILI):  0.926
AMES Toxicity:  0.107
Rat Oral Acute Toxicity:  0.485
Maximum Recommended Daily Dose:  0.023
Skin Sensitization:  0.119
Carcinogencity:  0.035
Eye Corrosion:  0.01
Eye Irritation:  0.02
Respiratory Toxicity:  0.897

Download Data

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

  Natural Product: NPC476718

Natural Product ID:  NPC476718
Common Name*:   [(2S,3R,4R,5R,8R,11S,14R,15R)-14-methoxy-5,8,11,15-tetramethyl-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadecan-4-yl] acetate
IUPAC Name:   [(2S,3R,4R,5R,8R,11S,14R,15R)-14-methoxy-5,8,11,15-tetramethyl-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadecan-4-yl] acetate
Synonyms:   Asbestinin-24
Standard InCHIKey:  MVCDLWCHVUYBCT-RTLILVSOSA-N
Standard InCHI:  InChI=1S/C23H38O5/c1-12-10-18-20-19-16(9-13(2)21(20)27-15(4)24)14(3)11-26-23(5,22(19)28-18)8-7-17(12)25-6/h12-14,16-22H,7-11H2,1-6H3/t12-,13-,14+,16?,17-,18?,19+,20+,21-,22?,23+/m1/s1
SMILES:  C[C@@H]1CC2[C@H](CO[C@]3(CC[C@H]([C@@H](CC4[C@H]([C@@H]1OC(=O)C)[C@H]2C3O4)C)OC)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   44566427
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001729] Oxepanes

*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
NPO33599 Briareum polyanthes Species Briareidae Eukaryota n.a. coral reef off Cabo Rojo, Puerto Rico, at a depth of 10-15 m 2000-OCT PMID[17190449]

☑ 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 16 ug/ml PMID[17190449]

☑ 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 NPC476718 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
0.9437 High Similarity NPC476719
0.942 High Similarity NPC123122
0.9028 High Similarity NPC136424
0.8784 High Similarity NPC252483
0.8784 High Similarity NPC191345
0.8784 High Similarity NPC43463
0.8701 High Similarity NPC476721
0.8553 High Similarity NPC186594
0.8481 Intermediate Similarity NPC476725
0.8481 Intermediate Similarity NPC476715
0.8442 Intermediate Similarity NPC119922
0.8442 Intermediate Similarity NPC211049
0.8442 Intermediate Similarity NPC116320
0.8333 Intermediate Similarity NPC216800
0.8228 Intermediate Similarity NPC127917
0.8228 Intermediate Similarity NPC470261
0.8171 Intermediate Similarity NPC476724
0.8171 Intermediate Similarity NPC476723
0.8148 Intermediate Similarity NPC214315
0.8077 Intermediate Similarity NPC472951
0.8077 Intermediate Similarity NPC471217
0.8077 Intermediate Similarity NPC472943
0.8077 Intermediate Similarity NPC471216
0.8025 Intermediate Similarity NPC93616
0.7975 Intermediate Similarity NPC71541
0.7975 Intermediate Similarity NPC470154
0.7949 Intermediate Similarity NPC477287
0.7927 Intermediate Similarity NPC279260
0.7927 Intermediate Similarity NPC246347
0.7927 Intermediate Similarity NPC475684
0.7927 Intermediate Similarity NPC476717
0.7927 Intermediate Similarity NPC228593
0.7927 Intermediate Similarity NPC235196
0.7875 Intermediate Similarity NPC477447
0.7875 Intermediate Similarity NPC477284
0.7875 Intermediate Similarity NPC477446
0.7875 Intermediate Similarity NPC470155
0.7831 Intermediate Similarity NPC44538
0.7831 Intermediate Similarity NPC471377
0.775 Intermediate Similarity NPC470156
0.7738 Intermediate Similarity NPC75443
0.7738 Intermediate Similarity NPC92370
0.7738 Intermediate Similarity NPC470260
0.7701 Intermediate Similarity NPC476722
0.7683 Intermediate Similarity NPC65133
0.7683 Intermediate Similarity NPC18953
0.7647 Intermediate Similarity NPC291875
0.7647 Intermediate Similarity NPC161560
0.7595 Intermediate Similarity NPC264610
0.759 Intermediate Similarity NPC471379
0.759 Intermediate Similarity NPC196911
0.7561 Intermediate Similarity NPC5958
0.7558 Intermediate Similarity NPC470262
0.7532 Intermediate Similarity NPC55508
0.7531 Intermediate Similarity NPC118116
0.75 Intermediate Similarity NPC471410
0.75 Intermediate Similarity NPC474008
0.75 Intermediate Similarity NPC155531
0.75 Intermediate Similarity NPC215968
0.75 Intermediate Similarity NPC476716
0.75 Intermediate Similarity NPC477283
0.75 Intermediate Similarity NPC471411
0.7471 Intermediate Similarity NPC165180
0.7471 Intermediate Similarity NPC41838
0.7471 Intermediate Similarity NPC312805
0.7471 Intermediate Similarity NPC91251
0.7439 Intermediate Similarity NPC477286
0.7439 Intermediate Similarity NPC286719
0.7436 Intermediate Similarity NPC472950
0.7436 Intermediate Similarity NPC472952
0.7416 Intermediate Similarity NPC476720
0.7412 Intermediate Similarity NPC110365
0.7412 Intermediate Similarity NPC45833
0.7412 Intermediate Similarity NPC213658
0.7412 Intermediate Similarity NPC62202
0.7407 Intermediate Similarity NPC474714
0.7407 Intermediate Similarity NPC475456
0.7356 Intermediate Similarity NPC312471
0.7356 Intermediate Similarity NPC471378
0.7349 Intermediate Similarity NPC111582
0.7349 Intermediate Similarity NPC29342
0.7349 Intermediate Similarity NPC2572
0.7349 Intermediate Similarity NPC477285
0.7349 Intermediate Similarity NPC239308
0.7326 Intermediate Similarity NPC221993
0.7326 Intermediate Similarity NPC471221
0.7326 Intermediate Similarity NPC470872
0.7324 Intermediate Similarity NPC204173
0.7317 Intermediate Similarity NPC476494
0.7317 Intermediate Similarity NPC190940
0.7317 Intermediate Similarity NPC77003
0.7294 Intermediate Similarity NPC64862
0.7284 Intermediate Similarity NPC476176
0.7273 Intermediate Similarity NPC122057
0.7229 Intermediate Similarity NPC103171
0.7229 Intermediate Similarity NPC208912
0.7229 Intermediate Similarity NPC154043
0.7229 Intermediate Similarity NPC60018
0.7229 Intermediate Similarity NPC202688
0.7229 Intermediate Similarity NPC2096
0.7215 Intermediate Similarity NPC186851
0.72 Intermediate Similarity NPC476928
0.7195 Intermediate Similarity NPC134227
0.7195 Intermediate Similarity NPC125366
0.7179 Intermediate Similarity NPC109510
0.7176 Intermediate Similarity NPC235402
0.7176 Intermediate Similarity NPC266651
0.7143 Intermediate Similarity NPC5209
0.7143 Intermediate Similarity NPC69953
0.7143 Intermediate Similarity NPC474284
0.7143 Intermediate Similarity NPC51956
0.7143 Intermediate Similarity NPC474253
0.7143 Intermediate Similarity NPC474346
0.7143 Intermediate Similarity NPC475820
0.7143 Intermediate Similarity NPC213737
0.7143 Intermediate Similarity NPC29005
0.7126 Intermediate Similarity NPC201607
0.7126 Intermediate Similarity NPC56777
0.7126 Intermediate Similarity NPC476435
0.7108 Intermediate Similarity NPC73515
0.7093 Intermediate Similarity NPC103782
0.7093 Intermediate Similarity NPC477441
0.7093 Intermediate Similarity NPC114378
0.7093 Intermediate Similarity NPC131365
0.7089 Intermediate Similarity NPC470151
0.7089 Intermediate Similarity NPC472944
0.7089 Intermediate Similarity NPC472945
0.7079 Intermediate Similarity NPC8729
0.7079 Intermediate Similarity NPC473066
0.7079 Intermediate Similarity NPC216137
0.7065 Intermediate Similarity NPC111348
0.7059 Intermediate Similarity NPC477434
0.7059 Intermediate Similarity NPC473299
0.7037 Intermediate Similarity NPC143250
0.7037 Intermediate Similarity NPC212453
0.7024 Intermediate Similarity NPC102156
0.7024 Intermediate Similarity NPC148740
0.7015 Intermediate Similarity NPC291724
0.7015 Intermediate Similarity NPC274261
0.7011 Intermediate Similarity NPC5943
0.7 Intermediate Similarity NPC475307
0.7 Intermediate Similarity NPC211845
0.7 Intermediate Similarity NPC35164
0.7 Intermediate Similarity NPC182740
0.7 Intermediate Similarity NPC474379
0.7 Intermediate Similarity NPC122083
0.7 Intermediate Similarity NPC256104
0.7 Intermediate Similarity NPC36479
0.6988 Remote Similarity NPC60568
0.6977 Remote Similarity NPC477445
0.6966 Remote Similarity NPC470114
0.6951 Remote Similarity NPC471045
0.6941 Remote Similarity NPC470070
0.6941 Remote Similarity NPC67158
0.6941 Remote Similarity NPC30102
0.6941 Remote Similarity NPC128816
0.6932 Remote Similarity NPC476379
0.6932 Remote Similarity NPC309656
0.6914 Remote Similarity NPC293223
0.6914 Remote Similarity NPC107963
0.6905 Remote Similarity NPC473257
0.6905 Remote Similarity NPC475743
0.6905 Remote Similarity NPC45256
0.6905 Remote Similarity NPC260977
0.6905 Remote Similarity NPC285480
0.6905 Remote Similarity NPC30443
0.6897 Remote Similarity NPC321812
0.6897 Remote Similarity NPC322922
0.6875 Remote Similarity NPC74639
0.6875 Remote Similarity NPC96759
0.6867 Remote Similarity NPC81074
0.6867 Remote Similarity NPC477282
0.6867 Remote Similarity NPC220379
0.6854 Remote Similarity NPC477440
0.6854 Remote Similarity NPC477443
0.6848 Remote Similarity NPC21897
0.6829 Remote Similarity NPC307865
0.6829 Remote Similarity NPC11907
0.6829 Remote Similarity NPC64081
0.6829 Remote Similarity NPC474574
0.6829 Remote Similarity NPC133596
0.6818 Remote Similarity NPC239938
0.6809 Remote Similarity NPC470066
0.6809 Remote Similarity NPC470067
0.679 Remote Similarity NPC478105
0.6786 Remote Similarity NPC186588
0.6778 Remote Similarity NPC477444
0.6778 Remote Similarity NPC50443
0.6778 Remote Similarity NPC477442
0.6778 Remote Similarity NPC477433
0.6778 Remote Similarity NPC18536
0.6774 Remote Similarity NPC238796
0.6774 Remote Similarity NPC116683
0.6774 Remote Similarity NPC156377
0.6774 Remote Similarity NPC237071
0.6774 Remote Similarity NPC145553
0.6774 Remote Similarity NPC235109
0.6774 Remote Similarity NPC203434
0.6761 Remote Similarity NPC170780
0.675 Remote Similarity NPC474755

  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 NPC476718 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
0.7143 Intermediate Similarity NPD2687 Approved
0.7143 Intermediate Similarity NPD2686 Approved
0.7143 Intermediate Similarity NPD2254 Approved
0.6941 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3669 Approved
0.6905 Remote Similarity NPD1780 Approved
0.6905 Remote Similarity NPD1779 Approved
0.6709 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1811 Approved
0.6667 Remote Similarity NPD1810 Approved
0.6579 Remote Similarity NPD371 Approved
0.6353 Remote Similarity NPD6115 Approved
0.6353 Remote Similarity NPD6118 Approved
0.6353 Remote Similarity NPD6697 Approved
0.6353 Remote Similarity NPD6114 Approved
0.6235 Remote Similarity NPD6116 Phase 1
0.6173 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6162 Remote Similarity NPD1700 Approved
0.6118 Remote Similarity NPD6117 Approved
0.6024 Remote Similarity NPD5777 Approved
0.6023 Remote Similarity NPD6928 Phase 2
0.5938 Remote Similarity NPD8171 Discontinued
0.59 Remote Similarity NPD6648 Approved
0.5882 Remote Similarity NPD6113 Clinical (unspecified phase)
0.5875 Remote Similarity NPD9496 Clinical (unspecified phase)
0.5865 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5854 Remote Similarity NPD229 Approved
0.5842 Remote Similarity NPD5344 Discontinued
0.581 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5769 Remote Similarity NPD1145 Discontinued
0.5755 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5701 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5682 Remote Similarity NPD8143 Approved
0.5682 Remote Similarity NPD8144 Approved
0.5673 Remote Similarity NPD8170 Clinical (unspecified phase)
0.567 Remote Similarity NPD8034 Phase 2
0.567 Remote Similarity NPD8035 Phase 2
0.5644 Remote Similarity NPD7638 Approved
0.5632 Remote Similarity NPD3703 Phase 2
0.5632 Remote Similarity NPD3702 Approved
0.5619 Remote Similarity NPD6008 Approved
0.5607 Remote Similarity NPD8132 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