Structure

Physi-Chem Properties

Molecular Weight:  306.26
Volume:  343.751
LogP:  5.405
LogD:  4.915
LogS:  -5.125
# Rotatable Bonds:  4
TPSA:  29.46
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.762
Synthetic Accessibility Score:  5.491
Fsp3:  0.9
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:  -4.674
MDCK Permeability:  1.7041853425325826e-05
Pgp-inhibitor:  0.507
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.043
30% Bioavailability (F30%):  0.371

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  94.87821960449219%
Volume Distribution (VD):  1.417
Pgp-substrate:  2.5036845207214355%

ADMET: Metabolism

CYP1A2-inhibitor:  0.124
CYP1A2-substrate:  0.567
CYP2C19-inhibitor:  0.135
CYP2C19-substrate:  0.942
CYP2C9-inhibitor:  0.231
CYP2C9-substrate:  0.327
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.277
CYP3A4-inhibitor:  0.577
CYP3A4-substrate:  0.575

ADMET: Excretion

Clearance (CL):  8.779
Half-life (T1/2):  0.28

ADMET: Toxicity

hERG Blockers:  0.067
Human Hepatotoxicity (H-HT):  0.808
Drug-inuced Liver Injury (DILI):  0.714
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.045
Maximum Recommended Daily Dose:  0.024
Skin Sensitization:  0.616
Carcinogencity:  0.07
Eye Corrosion:  0.046
Eye Irritation:  0.542
Respiratory Toxicity:  0.48

Download Data

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

  Natural Product: NPC477427

Natural Product ID:  NPC477427
Common Name*:   (1R,6S)-3-methyl-6-{(1R)-1-methyl-3-[(1R,2R,3R,4S)-1,3,4-trimethyl-7-oxabicyclo[2.2.1]hept-2-yl]propyl}cyclohex-2-en-1-ol
IUPAC Name:   (1R,6R)-3-methyl-6-[(2S)-4-[(1S,2R,3R,4R)-1,3,4-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]butan-2-yl]cyclohex-2-en-1-ol
Synonyms:  
Standard InCHIKey:  JTUWBMRONSWGPE-DJQWEKKZSA-N
Standard InCHI:  InChI=1S/C20H34O2/c1-13-6-8-16(18(21)12-13)14(2)7-9-17-15(3)19(4)10-11-20(17,5)22-19/h12,14-18,21H,6-11H2,1-5H3/t14-,15+,16+,17+,18-,19+,20-/m0/s1
SMILES:  C[C@@H]1[C@H]([C@@]2(CC[C@]1(O2)C)C)CC[C@H](C)[C@H]3CCC(=C[C@@H]3O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   44434922
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] 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
NPO22651 Laurencia intricata Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[15620241]
NPO22651 Laurencia intricata Species Rhodomelaceae Eukaryota n.a. n.a. n.a. PMID[18004798]
NPO22651 Laurencia intricata Species Rhodomelaceae 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
NPT211 Individual Protein Hypoxia-inducible factor 1 alpha Homo sapiens IC50 > 30000 nM PMID[18004798]

☑ 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 NPC477427 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 NPC477426
1.0 High Similarity NPC477425
1.0 High Similarity NPC474826
0.8608 High Similarity NPC155521
0.8514 High Similarity NPC23954
0.84 Intermediate Similarity NPC265485
0.84 Intermediate Similarity NPC220939
0.8312 Intermediate Similarity NPC265588
0.8289 Intermediate Similarity NPC476366
0.8289 Intermediate Similarity NPC201048
0.8205 Intermediate Similarity NPC470711
0.8205 Intermediate Similarity NPC470758
0.8171 Intermediate Similarity NPC474047
0.8148 Intermediate Similarity NPC87489
0.8133 Intermediate Similarity NPC34834
0.8095 Intermediate Similarity NPC476948
0.8077 Intermediate Similarity NPC470749
0.8026 Intermediate Similarity NPC167706
0.8 Intermediate Similarity NPC30986
0.8 Intermediate Similarity NPC209430
0.7975 Intermediate Similarity NPC91594
0.7973 Intermediate Similarity NPC114651
0.7955 Intermediate Similarity NPC144202
0.7952 Intermediate Similarity NPC231310
0.7952 Intermediate Similarity NPC470077
0.7949 Intermediate Similarity NPC32832
0.7927 Intermediate Similarity NPC202389
0.7927 Intermediate Similarity NPC122945
0.7927 Intermediate Similarity NPC218616
0.7927 Intermediate Similarity NPC49964
0.7927 Intermediate Similarity NPC296701
0.7927 Intermediate Similarity NPC109938
0.7927 Intermediate Similarity NPC470049
0.7927 Intermediate Similarity NPC471408
0.7901 Intermediate Similarity NPC295131
0.7901 Intermediate Similarity NPC206062
0.7887 Intermediate Similarity NPC66020
0.7882 Intermediate Similarity NPC166857
0.7875 Intermediate Similarity NPC476314
0.7875 Intermediate Similarity NPC11908
0.7867 Intermediate Similarity NPC96484
0.7857 Intermediate Similarity NPC274448
0.7841 Intermediate Similarity NPC27531
0.7838 Intermediate Similarity NPC326310
0.7838 Intermediate Similarity NPC202017
0.7831 Intermediate Similarity NPC475789
0.7821 Intermediate Similarity NPC306727
0.7805 Intermediate Similarity NPC264245
0.7805 Intermediate Similarity NPC249423
0.7805 Intermediate Similarity NPC476646
0.7792 Intermediate Similarity NPC242992
0.7792 Intermediate Similarity NPC164022
0.7792 Intermediate Similarity NPC477792
0.7792 Intermediate Similarity NPC471272
0.7778 Intermediate Similarity NPC47982
0.7778 Intermediate Similarity NPC84694
0.7778 Intermediate Similarity NPC28862
0.7778 Intermediate Similarity NPC143182
0.7778 Intermediate Similarity NPC321867
0.7778 Intermediate Similarity NPC81306
0.7778 Intermediate Similarity NPC207007
0.7778 Intermediate Similarity NPC68679
0.7778 Intermediate Similarity NPC109546
0.7765 Intermediate Similarity NPC261266
0.7765 Intermediate Similarity NPC6391
0.7763 Intermediate Similarity NPC471560
0.775 Intermediate Similarity NPC40049
0.775 Intermediate Similarity NPC214570
0.7738 Intermediate Similarity NPC205845
0.7738 Intermediate Similarity NPC238485
0.7722 Intermediate Similarity NPC313185
0.7711 Intermediate Similarity NPC256112
0.7711 Intermediate Similarity NPC101462
0.7711 Intermediate Similarity NPC304285
0.7701 Intermediate Similarity NPC477917
0.7692 Intermediate Similarity NPC182717
0.7692 Intermediate Similarity NPC130665
0.7683 Intermediate Similarity NPC209944
0.7683 Intermediate Similarity NPC96362
0.7683 Intermediate Similarity NPC241290
0.7683 Intermediate Similarity NPC164840
0.7683 Intermediate Similarity NPC234193
0.7674 Intermediate Similarity NPC149224
0.7674 Intermediate Similarity NPC245004
0.7662 Intermediate Similarity NPC92801
0.7654 Intermediate Similarity NPC474216
0.7654 Intermediate Similarity NPC167891
0.7654 Intermediate Similarity NPC285761
0.7654 Intermediate Similarity NPC83351
0.7654 Intermediate Similarity NPC275910
0.7647 Intermediate Similarity NPC318390
0.7647 Intermediate Similarity NPC157257
0.7647 Intermediate Similarity NPC470360
0.7647 Intermediate Similarity NPC266511
0.7639 Intermediate Similarity NPC240506
0.7632 Intermediate Similarity NPC471238
0.7632 Intermediate Similarity NPC208999
0.7625 Intermediate Similarity NPC73875
0.7625 Intermediate Similarity NPC244488
0.7625 Intermediate Similarity NPC202642
0.7625 Intermediate Similarity NPC247325
0.7625 Intermediate Similarity NPC46160
0.7625 Intermediate Similarity NPC189883
0.7625 Intermediate Similarity NPC253190
0.7619 Intermediate Similarity NPC317458
0.7619 Intermediate Similarity NPC470558
0.7619 Intermediate Similarity NPC132635
0.7619 Intermediate Similarity NPC476927
0.7619 Intermediate Similarity NPC474634
0.7619 Intermediate Similarity NPC82623
0.7614 Intermediate Similarity NPC295668
0.7614 Intermediate Similarity NPC77796
0.7614 Intermediate Similarity NPC92885
0.7614 Intermediate Similarity NPC476226
0.76 Intermediate Similarity NPC327815
0.76 Intermediate Similarity NPC267027
0.7595 Intermediate Similarity NPC469533
0.7595 Intermediate Similarity NPC100334
0.7595 Intermediate Similarity NPC91858
0.7595 Intermediate Similarity NPC469593
0.7595 Intermediate Similarity NPC477138
0.7595 Intermediate Similarity NPC469534
0.7595 Intermediate Similarity NPC243342
0.7595 Intermediate Similarity NPC309178
0.759 Intermediate Similarity NPC47761
0.759 Intermediate Similarity NPC7505
0.759 Intermediate Similarity NPC474731
0.759 Intermediate Similarity NPC474759
0.759 Intermediate Similarity NPC23852
0.759 Intermediate Similarity NPC209620
0.759 Intermediate Similarity NPC474752
0.759 Intermediate Similarity NPC474683
0.759 Intermediate Similarity NPC82986
0.7586 Intermediate Similarity NPC133588
0.7586 Intermediate Similarity NPC471952
0.7568 Intermediate Similarity NPC290367
0.7568 Intermediate Similarity NPC225415
0.7564 Intermediate Similarity NPC471271
0.7564 Intermediate Similarity NPC471268
0.7564 Intermediate Similarity NPC110799
0.7561 Intermediate Similarity NPC291379
0.7561 Intermediate Similarity NPC242767
0.7561 Intermediate Similarity NPC476701
0.7561 Intermediate Similarity NPC273410
0.7561 Intermediate Similarity NPC1319
0.7561 Intermediate Similarity NPC80530
0.7558 Intermediate Similarity NPC125399
0.7558 Intermediate Similarity NPC299068
0.7534 Intermediate Similarity NPC194208
0.7534 Intermediate Similarity NPC79576
0.7534 Intermediate Similarity NPC282694
0.7532 Intermediate Similarity NPC329989
0.7532 Intermediate Similarity NPC239373
0.7532 Intermediate Similarity NPC16964
0.7532 Intermediate Similarity NPC9942
0.7532 Intermediate Similarity NPC474248
0.7531 Intermediate Similarity NPC34177
0.7531 Intermediate Similarity NPC476703
0.7531 Intermediate Similarity NPC157996
0.7531 Intermediate Similarity NPC90979
0.7531 Intermediate Similarity NPC471798
0.7531 Intermediate Similarity NPC40394
0.7531 Intermediate Similarity NPC198968
0.7531 Intermediate Similarity NPC283619
0.7531 Intermediate Similarity NPC318495
0.7531 Intermediate Similarity NPC472805
0.7531 Intermediate Similarity NPC101475
0.7531 Intermediate Similarity NPC155986
0.7529 Intermediate Similarity NPC306951
0.7529 Intermediate Similarity NPC185568
0.7529 Intermediate Similarity NPC15534
0.7529 Intermediate Similarity NPC295799
0.7529 Intermediate Similarity NPC46320
0.75 Intermediate Similarity NPC475931
0.75 Intermediate Similarity NPC69649
0.75 Intermediate Similarity NPC189972
0.75 Intermediate Similarity NPC20946
0.75 Intermediate Similarity NPC122239
0.75 Intermediate Similarity NPC66566
0.75 Intermediate Similarity NPC470361
0.75 Intermediate Similarity NPC115607
0.75 Intermediate Similarity NPC12696
0.75 Intermediate Similarity NPC313179
0.75 Intermediate Similarity NPC50964
0.75 Intermediate Similarity NPC2524
0.75 Intermediate Similarity NPC30166
0.75 Intermediate Similarity NPC257347
0.75 Intermediate Similarity NPC171148
0.75 Intermediate Similarity NPC69383
0.75 Intermediate Similarity NPC121744
0.75 Intermediate Similarity NPC322353
0.75 Intermediate Similarity NPC291503
0.75 Intermediate Similarity NPC141071
0.75 Intermediate Similarity NPC477923
0.75 Intermediate Similarity NPC118508
0.75 Intermediate Similarity NPC259299
0.75 Intermediate Similarity NPC82337
0.75 Intermediate Similarity NPC68703
0.75 Intermediate Similarity NPC128066
0.75 Intermediate Similarity NPC471723

  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 NPC477427 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
0.7778 Intermediate Similarity NPD368 Approved
0.7561 Intermediate Similarity NPD7645 Phase 2
0.75 Intermediate Similarity NPD8264 Approved
0.747 Intermediate Similarity NPD7525 Registered
0.7284 Intermediate Similarity NPD7339 Approved
0.7284 Intermediate Similarity NPD6942 Approved
0.7195 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD342 Phase 1
0.7079 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6695 Phase 3
0.6951 Remote Similarity NPD6924 Approved
0.6951 Remote Similarity NPD6926 Approved
0.6932 Remote Similarity NPD7338 Clinical (unspecified phase)
0.686 Remote Similarity NPD6930 Phase 2
0.686 Remote Similarity NPD6931 Approved
0.6824 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6804 Remote Similarity NPD7640 Approved
0.6804 Remote Similarity NPD7639 Approved
0.6786 Remote Similarity NPD6933 Approved
0.6778 Remote Similarity NPD3618 Phase 1
0.6744 Remote Similarity NPD6929 Approved
0.6742 Remote Similarity NPD4786 Approved
0.6739 Remote Similarity NPD5328 Approved
0.6707 Remote Similarity NPD4243 Approved
0.6705 Remote Similarity NPD3667 Approved
0.6703 Remote Similarity NPD7750 Discontinued
0.6703 Remote Similarity NPD7524 Approved
0.6701 Remote Similarity NPD4225 Approved
0.6701 Remote Similarity NPD7638 Approved
0.6667 Remote Similarity NPD7509 Discontinued
0.6667 Remote Similarity NPD7514 Phase 3
0.6667 Remote Similarity NPD4748 Discontinued
0.6667 Remote Similarity NPD7332 Phase 2
0.6596 Remote Similarity NPD6079 Approved
0.6548 Remote Similarity NPD4785 Approved
0.6548 Remote Similarity NPD4784 Approved
0.6526 Remote Similarity NPD5778 Approved
0.6526 Remote Similarity NPD5779 Approved
0.6526 Remote Similarity NPD4202 Approved
0.6512 Remote Similarity NPD6925 Approved
0.6512 Remote Similarity NPD5776 Phase 2
0.6506 Remote Similarity NPD7151 Approved
0.6506 Remote Similarity NPD7152 Approved
0.6506 Remote Similarity NPD7150 Approved
0.6484 Remote Similarity NPD1696 Phase 3
0.6484 Remote Similarity NPD6893 Approved
0.6463 Remote Similarity NPD6922 Approved
0.6463 Remote Similarity NPD6923 Approved
0.6458 Remote Similarity NPD7748 Approved
0.6444 Remote Similarity NPD5362 Discontinued
0.6437 Remote Similarity NPD7145 Approved
0.6421 Remote Similarity NPD7515 Phase 2
0.6421 Remote Similarity NPD7087 Discontinued
0.6404 Remote Similarity NPD6898 Phase 1
0.6404 Remote Similarity NPD6902 Approved
0.64 Remote Similarity NPD5344 Discontinued
0.6386 Remote Similarity NPD7144 Approved
0.6386 Remote Similarity NPD7143 Approved
0.6383 Remote Similarity NPD6051 Approved
0.6374 Remote Similarity NPD3133 Approved
0.6374 Remote Similarity NPD3665 Phase 1
0.6374 Remote Similarity NPD3666 Approved
0.6354 Remote Similarity NPD6399 Phase 3
0.6346 Remote Similarity NPD7320 Approved
0.6337 Remote Similarity NPD5211 Phase 2
0.6322 Remote Similarity NPD6932 Approved
0.6311 Remote Similarity NPD5739 Approved
0.6311 Remote Similarity NPD6675 Approved
0.6311 Remote Similarity NPD6402 Approved
0.6311 Remote Similarity NPD7128 Approved
0.6304 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6292 Remote Similarity NPD4819 Approved
0.6292 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6292 Remote Similarity NPD4821 Approved
0.6292 Remote Similarity NPD4820 Approved
0.6292 Remote Similarity NPD4822 Approved
0.6282 Remote Similarity NPD1145 Discontinued
0.6279 Remote Similarity NPD4190 Phase 3
0.6279 Remote Similarity NPD5275 Approved
0.6264 Remote Similarity NPD7154 Phase 3
0.6264 Remote Similarity NPD5331 Approved
0.6264 Remote Similarity NPD5332 Approved
0.6263 Remote Similarity NPD4755 Approved
0.6263 Remote Similarity NPD7902 Approved
0.6238 Remote Similarity NPD4159 Approved
0.6237 Remote Similarity NPD4519 Discontinued
0.6237 Remote Similarity NPD4623 Approved
0.6222 Remote Similarity NPD4790 Discontinued
0.6214 Remote Similarity NPD5141 Approved
0.6211 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6211 Remote Similarity NPD6101 Approved
0.6196 Remote Similarity NPD6400 Clinical (unspecified phase)
0.619 Remote Similarity NPD6899 Approved
0.619 Remote Similarity NPD6881 Approved
0.6184 Remote Similarity NPD4219 Approved
0.6182 Remote Similarity NPD7115 Discovery
0.618 Remote Similarity NPD4195 Approved
0.618 Remote Similarity NPD6683 Phase 2
0.6176 Remote Similarity NPD7632 Discontinued
0.617 Remote Similarity NPD4250 Approved
0.617 Remote Similarity NPD4251 Approved
0.6162 Remote Similarity NPD4697 Phase 3
0.6162 Remote Similarity NPD5221 Approved
0.6162 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6162 Remote Similarity NPD5222 Approved
0.6139 Remote Similarity NPD5286 Approved
0.6139 Remote Similarity NPD6648 Approved
0.6139 Remote Similarity NPD5285 Approved
0.6139 Remote Similarity NPD4700 Approved
0.6139 Remote Similarity NPD4696 Approved
0.6132 Remote Similarity NPD6372 Approved
0.6132 Remote Similarity NPD6373 Approved
0.6129 Remote Similarity NPD1694 Approved
0.6129 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6105 Remote Similarity NPD6903 Approved
0.61 Remote Similarity NPD6083 Phase 2
0.61 Remote Similarity NPD5173 Approved
0.61 Remote Similarity NPD6084 Phase 2
0.6095 Remote Similarity NPD5701 Approved
0.6095 Remote Similarity NPD5697 Approved
0.6082 Remote Similarity NPD7637 Suspended
0.6082 Remote Similarity NPD6411 Approved
0.6078 Remote Similarity NPD5223 Approved
0.6075 Remote Similarity NPD7290 Approved
0.6075 Remote Similarity NPD7102 Approved
0.6075 Remote Similarity NPD6883 Approved
0.6067 Remote Similarity NPD4268 Approved
0.6067 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6067 Remote Similarity NPD4271 Approved
0.6064 Remote Similarity NPD7146 Approved
0.6064 Remote Similarity NPD7334 Approved
0.6064 Remote Similarity NPD5279 Phase 3
0.6064 Remote Similarity NPD5330 Approved
0.6064 Remote Similarity NPD4249 Approved
0.6064 Remote Similarity NPD7521 Approved
0.6064 Remote Similarity NPD6409 Approved
0.6064 Remote Similarity NPD6684 Approved
0.6061 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6042 Remote Similarity NPD4753 Phase 2
0.604 Remote Similarity NPD5290 Discontinued
0.6038 Remote Similarity NPD6011 Approved
0.6022 Remote Similarity NPD3668 Phase 3
0.602 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6019 Remote Similarity NPD6650 Approved
0.6019 Remote Similarity NPD5226 Approved
0.6019 Remote Similarity NPD4633 Approved
0.6019 Remote Similarity NPD8130 Phase 1
0.6019 Remote Similarity NPD5224 Approved
0.6019 Remote Similarity NPD6649 Approved
0.6019 Remote Similarity NPD6869 Approved
0.6019 Remote Similarity NPD6617 Approved
0.6019 Remote Similarity NPD6847 Approved
0.6019 Remote Similarity NPD5225 Approved
0.6019 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5982 Remote Similarity NPD7328 Approved
0.5982 Remote Similarity NPD7327 Approved
0.5981 Remote Similarity NPD6014 Approved
0.5981 Remote Similarity NPD6012 Approved
0.5981 Remote Similarity NPD6013 Approved
0.5979 Remote Similarity NPD3168 Discontinued
0.5978 Remote Similarity NPD4270 Approved
0.5978 Remote Similarity NPD4269 Approved
0.5978 Remote Similarity NPD4221 Approved
0.5978 Remote Similarity NPD4223 Phase 3
0.5976 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5963 Remote Similarity NPD6882 Approved
0.5963 Remote Similarity NPD6053 Discontinued
0.5963 Remote Similarity NPD8297 Approved
0.5962 Remote Similarity NPD5175 Approved
0.5962 Remote Similarity NPD4754 Approved
0.5962 Remote Similarity NPD5174 Approved
0.596 Remote Similarity NPD7900 Approved
0.596 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5957 Remote Similarity NPD5329 Approved
0.5938 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5929 Remote Similarity NPD7516 Approved
0.5918 Remote Similarity NPD8034 Phase 2
0.5918 Remote Similarity NPD8035 Phase 2
0.5915 Remote Similarity NPD4265 Approved
0.5904 Remote Similarity NPD7331 Phase 2
0.59 Remote Similarity NPD5695 Phase 3
0.5895 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5895 Remote Similarity NPD5786 Approved
0.5882 Remote Similarity NPD4267 Clinical (unspecified phase)
0.5877 Remote Similarity NPD8377 Approved
0.5877 Remote Similarity NPD8294 Approved
0.5877 Remote Similarity NPD6059 Approved
0.5877 Remote Similarity NPD6054 Approved
0.587 Remote Similarity NPD5369 Approved
0.5862 Remote Similarity NPD4732 Discontinued
0.5851 Remote Similarity NPD4197 Approved
0.5849 Remote Similarity NPD6008 Approved
0.5849 Remote Similarity NPD4767 Approved
0.5849 Remote Similarity NPD4768 Approved
0.5833 Remote Similarity NPD3573 Approved
0.5833 Remote Similarity NPD384 Approved
0.5833 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5833 Remote Similarity NPD385 Approved
0.5826 Remote Similarity NPD8380 Approved
0.5826 Remote Similarity NPD8033 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