Structure

Physi-Chem Properties

Molecular Weight:  318.22
Volume:  341.348
LogP:  1.874
LogD:  2.179
LogS:  -3.727
# Rotatable Bonds:  2
TPSA:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.792
Synthetic Accessibility Score:  5.832
Fsp3:  0.9
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.069
MDCK Permeability:  1.4473513147095218e-05
Pgp-inhibitor:  0.066
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.503
30% Bioavailability (F30%):  0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.902
Plasma Protein Binding (PPB):  61.32773971557617%
Volume Distribution (VD):  1.012
Pgp-substrate:  35.284793853759766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.721
CYP2C19-inhibitor:  0.022
CYP2C19-substrate:  0.782
CYP2C9-inhibitor:  0.069
CYP2C9-substrate:  0.051
CYP2D6-inhibitor:  0.229
CYP2D6-substrate:  0.094
CYP3A4-inhibitor:  0.897
CYP3A4-substrate:  0.428

ADMET: Excretion

Clearance (CL):  5.777
Half-life (T1/2):  0.769

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.319
Drug-inuced Liver Injury (DILI):  0.048
AMES Toxicity:  0.537
Rat Oral Acute Toxicity:  0.38
Maximum Recommended Daily Dose:  0.268
Skin Sensitization:  0.435
Carcinogencity:  0.327
Eye Corrosion:  0.252
Eye Irritation:  0.326
Respiratory Toxicity:  0.961

Download Data

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

  Natural Product: NPC476731

Natural Product ID:  NPC476731
Common Name*:   (1R,4S,5R,9S,10R,13R)-13-(hydroxymethyl)-5,9-dimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carbaldehyde
IUPAC Name:   (1R,4S,5R,9S,10R,13R)-13-(hydroxymethyl)-5,9-dimethyl-14-oxotetracyclo[11.2.1.01,10.04,9]hexadecane-5-carbaldehyde
Synonyms:  
Standard InCHIKey:  UMVIJKMALQMIIB-BOTNRJTISA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-17(12-21)6-3-7-18(2)14(17)4-8-19-10-16(23)20(11-19,13-22)9-5-15(18)19/h12,14-15,22H,3-11,13H2,1-2H3/t14-,15+,17+,18-,19+,20-/m1/s1
SMILES:  C[C@]1(CCC[C@@]2([C@@H]1CC[C@@]34[C@H]2CC[C@](C3)(C(=O)C4)CO)C)C=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   44584320
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids

*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
NPO33342 Bruguiera gymnorrhiza Species Rhizophoraceae Eukaryota stems Xiamen, China 2002-JUN PMID[15387677]
NPO33342 Bruguiera gymnorrhiza Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[16562850]

☑ 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
NPT1460 Cell Line L929 Mus musculus GI50 = 45.4 ug/ml PMID[15387677]
NPT111 Cell Line K562 Homo sapiens GI50 = 50 ug/ml PMID[15387677]
NPT165 Cell Line HeLa Homo sapiens CC50 = 37.7 ug/ml PMID[15387677]

☑ 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 NPC476731 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
0.9265 High Similarity NPC473267
0.8714 High Similarity NPC320549
0.8714 High Similarity NPC151018
0.8714 High Similarity NPC58057
0.8714 High Similarity NPC156277
0.8696 High Similarity NPC64466
0.8696 High Similarity NPC131892
0.8696 High Similarity NPC321732
0.8696 High Similarity NPC213178
0.8696 High Similarity NPC324607
0.8696 High Similarity NPC6120
0.8696 High Similarity NPC327728
0.8611 High Similarity NPC27349
0.8611 High Similarity NPC24014
0.8592 High Similarity NPC232112
0.8592 High Similarity NPC310766
0.8472 Intermediate Similarity NPC254340
0.8472 Intermediate Similarity NPC472854
0.8472 Intermediate Similarity NPC477930
0.8451 Intermediate Similarity NPC89310
0.8429 Intermediate Similarity NPC319671
0.8429 Intermediate Similarity NPC476734
0.8429 Intermediate Similarity NPC469941
0.8429 Intermediate Similarity NPC252032
0.84 Intermediate Similarity NPC52951
0.8378 Intermediate Similarity NPC477918
0.8356 Intermediate Similarity NPC174964
0.8356 Intermediate Similarity NPC472311
0.8356 Intermediate Similarity NPC21220
0.8356 Intermediate Similarity NPC97534
0.8356 Intermediate Similarity NPC195155
0.8356 Intermediate Similarity NPC273366
0.8356 Intermediate Similarity NPC125767
0.831 Intermediate Similarity NPC477850
0.831 Intermediate Similarity NPC477929
0.8286 Intermediate Similarity NPC260319
0.8286 Intermediate Similarity NPC474954
0.8286 Intermediate Similarity NPC180777
0.8286 Intermediate Similarity NPC103647
0.8286 Intermediate Similarity NPC2568
0.8286 Intermediate Similarity NPC473225
0.8243 Intermediate Similarity NPC477932
0.8243 Intermediate Similarity NPC472487
0.8243 Intermediate Similarity NPC475742
0.8243 Intermediate Similarity NPC472486
0.8243 Intermediate Similarity NPC5767
0.8243 Intermediate Similarity NPC477933
0.8219 Intermediate Similarity NPC280026
0.8219 Intermediate Similarity NPC167702
0.8219 Intermediate Similarity NPC133922
0.8133 Intermediate Similarity NPC264602
0.8133 Intermediate Similarity NPC221420
0.8133 Intermediate Similarity NPC475031
0.8133 Intermediate Similarity NPC106078
0.8133 Intermediate Similarity NPC23884
0.8108 Intermediate Similarity NPC477934
0.8108 Intermediate Similarity NPC159789
0.8108 Intermediate Similarity NPC212733
0.8077 Intermediate Similarity NPC46881
0.8077 Intermediate Similarity NPC110780
0.8056 Intermediate Similarity NPC108131
0.8028 Intermediate Similarity NPC478228
0.8026 Intermediate Similarity NPC185465
0.8 Intermediate Similarity NPC42060
0.8 Intermediate Similarity NPC4209
0.8 Intermediate Similarity NPC477931
0.8 Intermediate Similarity NPC268736
0.7975 Intermediate Similarity NPC175410
0.7975 Intermediate Similarity NPC217559
0.7975 Intermediate Similarity NPC471036
0.7975 Intermediate Similarity NPC291320
0.7975 Intermediate Similarity NPC268578
0.7975 Intermediate Similarity NPC292458
0.7971 Intermediate Similarity NPC128608
0.7945 Intermediate Similarity NPC290058
0.7945 Intermediate Similarity NPC469940
0.7945 Intermediate Similarity NPC472309
0.7922 Intermediate Similarity NPC472310
0.7922 Intermediate Similarity NPC201459
0.7922 Intermediate Similarity NPC320144
0.7917 Intermediate Similarity NPC196197
0.7917 Intermediate Similarity NPC474962
0.7895 Intermediate Similarity NPC317913
0.7895 Intermediate Similarity NPC180199
0.7895 Intermediate Similarity NPC143133
0.7895 Intermediate Similarity NPC207010
0.7895 Intermediate Similarity NPC477919
0.7895 Intermediate Similarity NPC298168
0.7887 Intermediate Similarity NPC474221
0.7887 Intermediate Similarity NPC130459
0.7887 Intermediate Similarity NPC478180
0.7875 Intermediate Similarity NPC471044
0.7875 Intermediate Similarity NPC50438
0.7875 Intermediate Similarity NPC473336
0.7848 Intermediate Similarity NPC477935
0.7848 Intermediate Similarity NPC268040
0.7838 Intermediate Similarity NPC81759
0.7838 Intermediate Similarity NPC68426
0.7838 Intermediate Similarity NPC282905
0.7838 Intermediate Similarity NPC477229
0.7821 Intermediate Similarity NPC470609
0.7792 Intermediate Similarity NPC476732
0.7792 Intermediate Similarity NPC224802
0.7792 Intermediate Similarity NPC34046
0.7792 Intermediate Similarity NPC80089
0.7792 Intermediate Similarity NPC171426
0.7792 Intermediate Similarity NPC324700
0.7792 Intermediate Similarity NPC199965
0.7778 Intermediate Similarity NPC190704
0.7778 Intermediate Similarity NPC201655
0.7778 Intermediate Similarity NPC471034
0.7778 Intermediate Similarity NPC102292
0.7761 Intermediate Similarity NPC476735
0.7733 Intermediate Similarity NPC130011
0.7733 Intermediate Similarity NPC159325
0.7733 Intermediate Similarity NPC168511
0.7722 Intermediate Similarity NPC469745
0.7722 Intermediate Similarity NPC474484
0.7722 Intermediate Similarity NPC164210
0.7722 Intermediate Similarity NPC103754
0.7722 Intermediate Similarity NPC50658
0.7703 Intermediate Similarity NPC126642
0.7692 Intermediate Similarity NPC201276
0.7692 Intermediate Similarity NPC245029
0.7692 Intermediate Similarity NPC80891
0.7692 Intermediate Similarity NPC31302
0.7662 Intermediate Similarity NPC474404
0.7654 Intermediate Similarity NPC319909
0.7654 Intermediate Similarity NPC74595
0.7654 Intermediate Similarity NPC264665
0.7639 Intermediate Similarity NPC472984
0.7632 Intermediate Similarity NPC267753
0.7632 Intermediate Similarity NPC132064
0.7632 Intermediate Similarity NPC179858
0.7625 Intermediate Similarity NPC289486
0.7625 Intermediate Similarity NPC328007
0.7625 Intermediate Similarity NPC317066
0.7625 Intermediate Similarity NPC30583
0.7625 Intermediate Similarity NPC145143
0.7625 Intermediate Similarity NPC477936
0.7625 Intermediate Similarity NPC477858
0.7625 Intermediate Similarity NPC61107
0.7619 Intermediate Similarity NPC116146
0.7619 Intermediate Similarity NPC24772
0.76 Intermediate Similarity NPC474123
0.7595 Intermediate Similarity NPC477851
0.7595 Intermediate Similarity NPC472853
0.759 Intermediate Similarity NPC259009
0.759 Intermediate Similarity NPC57469
0.759 Intermediate Similarity NPC263802
0.759 Intermediate Similarity NPC165895
0.7571 Intermediate Similarity NPC114891
0.7564 Intermediate Similarity NPC329117
0.7558 Intermediate Similarity NPC59350
0.7558 Intermediate Similarity NPC82138
0.7534 Intermediate Similarity NPC470956
0.7534 Intermediate Similarity NPC100917
0.7534 Intermediate Similarity NPC281203
0.7534 Intermediate Similarity NPC31187
0.7534 Intermediate Similarity NPC469724
0.7532 Intermediate Similarity NPC108840
0.7531 Intermediate Similarity NPC118800
0.7531 Intermediate Similarity NPC472743
0.7531 Intermediate Similarity NPC327451
0.7531 Intermediate Similarity NPC472498
0.7531 Intermediate Similarity NPC472744
0.7531 Intermediate Similarity NPC475726
0.7531 Intermediate Similarity NPC163616
0.7529 Intermediate Similarity NPC169933
0.75 Intermediate Similarity NPC58631
0.75 Intermediate Similarity NPC77311
0.75 Intermediate Similarity NPC12933
0.75 Intermediate Similarity NPC317212
0.75 Intermediate Similarity NPC472739
0.75 Intermediate Similarity NPC472483
0.747 Intermediate Similarity NPC302111
0.747 Intermediate Similarity NPC269396
0.747 Intermediate Similarity NPC98236
0.7463 Intermediate Similarity NPC143597
0.7463 Intermediate Similarity NPC151464
0.7439 Intermediate Similarity NPC25037
0.7439 Intermediate Similarity NPC474996
0.7439 Intermediate Similarity NPC475745
0.7439 Intermediate Similarity NPC474482
0.7439 Intermediate Similarity NPC34984
0.7439 Intermediate Similarity NPC474233
0.7439 Intermediate Similarity NPC146683
0.7436 Intermediate Similarity NPC169389
0.7436 Intermediate Similarity NPC472746
0.7436 Intermediate Similarity NPC476811
0.7436 Intermediate Similarity NPC471035
0.7436 Intermediate Similarity NPC149249
0.7436 Intermediate Similarity NPC212661
0.7432 Intermediate Similarity NPC295788
0.7429 Intermediate Similarity NPC218585
0.7429 Intermediate Similarity NPC148174
0.7429 Intermediate Similarity NPC71460
0.7424 Intermediate Similarity NPC288296
0.7424 Intermediate Similarity NPC53245
0.7412 Intermediate Similarity NPC61688

  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 NPC476731 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
0.8939 High Similarity NPD3171 Clinical (unspecified phase)
0.8841 High Similarity NPD4789 Approved
0.8714 High Similarity NPD4808 Clinical (unspecified phase)
0.8714 High Similarity NPD4809 Clinical (unspecified phase)
0.8696 High Similarity NPD3699 Clinical (unspecified phase)
0.8696 High Similarity NPD3698 Phase 2
0.8696 High Similarity NPD3700 Clinical (unspecified phase)
0.8571 High Similarity NPD4244 Approved
0.8571 High Similarity NPD4245 Approved
0.8529 High Similarity NPD4224 Phase 2
0.8286 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.8286 Intermediate Similarity NPD5360 Phase 3
0.8219 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.8108 Intermediate Similarity NPD3703 Phase 2
0.8 Intermediate Similarity NPD6117 Approved
0.7945 Intermediate Similarity NPD4758 Discontinued
0.7945 Intermediate Similarity NPD6081 Approved
0.7895 Intermediate Similarity NPD6116 Phase 1
0.7792 Intermediate Similarity NPD3671 Phase 1
0.7792 Intermediate Similarity NPD6118 Approved
0.7792 Intermediate Similarity NPD6115 Approved
0.7792 Intermediate Similarity NPD6114 Approved
0.7792 Intermediate Similarity NPD6697 Approved
0.7632 Intermediate Similarity NPD3702 Approved
0.7531 Intermediate Similarity NPD4788 Approved
0.7467 Intermediate Similarity NPD5777 Approved
0.7342 Intermediate Similarity NPD5364 Discontinued
0.7229 Intermediate Similarity NPD4786 Approved
0.7195 Intermediate Similarity NPD3667 Approved
0.7143 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD3666 Approved
0.7024 Intermediate Similarity NPD3133 Approved
0.7024 Intermediate Similarity NPD3665 Phase 1
0.6974 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6914 Remote Similarity NPD3617 Approved
0.6883 Remote Similarity NPD4787 Phase 1
0.686 Remote Similarity NPD3618 Phase 1
0.6818 Remote Similarity NPD5328 Approved
0.6818 Remote Similarity NPD4753 Phase 2
0.6786 Remote Similarity NPD4223 Phase 3
0.6786 Remote Similarity NPD4221 Approved
0.6739 Remote Similarity NPD4697 Phase 3
0.6667 Remote Similarity NPD5279 Phase 3
0.6667 Remote Similarity NPD4139 Approved
0.6667 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4692 Approved
0.6667 Remote Similarity NPD6079 Approved
0.6628 Remote Similarity NPD4197 Approved
0.6593 Remote Similarity NPD4202 Approved
0.6552 Remote Similarity NPD5329 Approved
0.6484 Remote Similarity NPD8034 Phase 2
0.6484 Remote Similarity NPD8035 Phase 2
0.6477 Remote Similarity NPD4688 Approved
0.6477 Remote Similarity NPD4138 Approved
0.6477 Remote Similarity NPD4689 Approved
0.6477 Remote Similarity NPD5205 Approved
0.6477 Remote Similarity NPD4693 Phase 3
0.6477 Remote Similarity NPD4690 Approved
0.6452 Remote Similarity NPD4629 Approved
0.6452 Remote Similarity NPD5210 Approved
0.6438 Remote Similarity NPD3198 Approved
0.6437 Remote Similarity NPD3668 Phase 3
0.6429 Remote Similarity NPD615 Clinical (unspecified phase)
0.6413 Remote Similarity NPD6399 Phase 3
0.641 Remote Similarity NPD6705 Phase 1
0.6383 Remote Similarity NPD5222 Approved
0.6383 Remote Similarity NPD5221 Approved
0.6383 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6316 Remote Similarity NPD5173 Approved
0.6316 Remote Similarity NPD6084 Phase 2
0.6316 Remote Similarity NPD4755 Approved
0.6316 Remote Similarity NPD6083 Phase 2
0.6304 Remote Similarity NPD7515 Phase 2
0.6292 Remote Similarity NPD5690 Phase 2
0.6292 Remote Similarity NPD4694 Approved
0.6292 Remote Similarity NPD5280 Approved
0.6197 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6186 Remote Similarity NPD5286 Approved
0.6186 Remote Similarity NPD5285 Approved
0.6186 Remote Similarity NPD8418 Phase 2
0.6186 Remote Similarity NPD4700 Approved
0.6186 Remote Similarity NPD4696 Approved
0.6163 Remote Similarity NPD4695 Discontinued
0.6163 Remote Similarity NPD6928 Phase 2
0.6163 Remote Similarity NPD7525 Registered
0.6154 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5737 Approved
0.6154 Remote Similarity NPD6672 Approved
0.6145 Remote Similarity NPD7339 Approved
0.6145 Remote Similarity NPD6942 Approved
0.6122 Remote Similarity NPD5223 Approved
0.6111 Remote Similarity NPD6409 Approved
0.6111 Remote Similarity NPD4623 Approved
0.6111 Remote Similarity NPD4519 Discontinued
0.6111 Remote Similarity NPD7146 Approved
0.6111 Remote Similarity NPD7334 Approved
0.6111 Remote Similarity NPD5330 Approved
0.6111 Remote Similarity NPD6684 Approved
0.6111 Remote Similarity NPD7521 Approved
0.6105 Remote Similarity NPD5695 Phase 3
0.61 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6082 Remote Similarity NPD5696 Approved
0.6071 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6061 Remote Similarity NPD4633 Approved
0.6061 Remote Similarity NPD5224 Approved
0.6061 Remote Similarity NPD5225 Approved
0.6061 Remote Similarity NPD5226 Approved
0.6061 Remote Similarity NPD5211 Phase 2
0.6049 Remote Similarity NPD4747 Approved
0.6047 Remote Similarity NPD4195 Approved
0.604 Remote Similarity NPD6920 Discontinued
0.6 Remote Similarity NPD4754 Approved
0.6 Remote Similarity NPD5175 Approved
0.6 Remote Similarity NPD5174 Approved
0.6 Remote Similarity NPD7748 Approved
0.5978 Remote Similarity NPD6903 Approved
0.5962 Remote Similarity NPD4634 Approved
0.5957 Remote Similarity NPD5281 Approved
0.5957 Remote Similarity NPD5284 Approved
0.5941 Remote Similarity NPD5141 Approved
0.5934 Remote Similarity NPD6098 Approved
0.593 Remote Similarity NPD4776 Phase 2
0.593 Remote Similarity NPD4238 Approved
0.593 Remote Similarity NPD4802 Phase 2
0.593 Remote Similarity NPD4777 Suspended
0.5926 Remote Similarity NPD4137 Phase 3
0.5922 Remote Similarity NPD6415 Discontinued
0.5914 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5895 Remote Similarity NPD5133 Approved
0.5882 Remote Similarity NPD344 Approved
0.5882 Remote Similarity NPD7128 Approved
0.5882 Remote Similarity NPD345 Approved
0.5882 Remote Similarity NPD6675 Approved
0.5882 Remote Similarity NPD4767 Approved
0.5882 Remote Similarity NPD5739 Approved
0.5882 Remote Similarity NPD384 Approved
0.5882 Remote Similarity NPD4768 Approved
0.5882 Remote Similarity NPD385 Approved
0.5882 Remote Similarity NPD6402 Approved
0.5882 Remote Similarity NPD343 Approved
0.5854 Remote Similarity NPD4691 Approved
0.5851 Remote Similarity NPD4096 Approved
0.5833 Remote Similarity NPD6924 Approved
0.5833 Remote Similarity NPD6926 Approved
0.5825 Remote Similarity NPD5701 Approved
0.5825 Remote Similarity NPD5697 Approved
0.5816 Remote Similarity NPD7902 Approved
0.5806 Remote Similarity NPD5208 Approved
0.5802 Remote Similarity NPD3621 Clinical (unspecified phase)
0.5795 Remote Similarity NPD4748 Discontinued
0.5783 Remote Similarity NPD4243 Approved
0.5769 Remote Similarity NPD5128 Approved
0.5769 Remote Similarity NPD6881 Approved
0.5769 Remote Similarity NPD5168 Approved
0.5769 Remote Similarity NPD7320 Approved
0.5769 Remote Similarity NPD6899 Approved
0.5769 Remote Similarity NPD6011 Approved
0.5769 Remote Similarity NPD4729 Approved
0.5769 Remote Similarity NPD4730 Approved
0.5758 Remote Similarity NPD7638 Approved
0.5747 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5745 Remote Similarity NPD6904 Approved
0.5745 Remote Similarity NPD6080 Approved
0.5745 Remote Similarity NPD6673 Approved
0.5735 Remote Similarity NPD634 Phase 3
0.5714 Remote Similarity NPD6014 Approved
0.5714 Remote Similarity NPD6373 Approved
0.5714 Remote Similarity NPD6372 Approved
0.5714 Remote Similarity NPD6013 Approved
0.5714 Remote Similarity NPD6012 Approved
0.57 Remote Similarity NPD7640 Approved
0.57 Remote Similarity NPD7639 Approved
0.5698 Remote Similarity NPD6933 Approved
0.5696 Remote Similarity NPD7909 Approved
0.5682 Remote Similarity NPD7645 Phase 2
0.5673 Remote Similarity NPD6412 Phase 2
0.566 Remote Similarity NPD5249 Phase 3
0.566 Remote Similarity NPD5247 Approved
0.566 Remote Similarity NPD5248 Approved
0.566 Remote Similarity NPD6883 Approved
0.566 Remote Similarity NPD7102 Approved
0.566 Remote Similarity NPD7290 Approved
0.566 Remote Similarity NPD5251 Approved
0.566 Remote Similarity NPD5134 Clinical (unspecified phase)
0.566 Remote Similarity NPD5169 Approved
0.566 Remote Similarity NPD5135 Approved
0.566 Remote Similarity NPD5250 Approved
0.5647 Remote Similarity NPD4784 Approved
0.5647 Remote Similarity NPD4687 Approved
0.5647 Remote Similarity NPD4785 Approved
0.5647 Remote Similarity NPD5733 Approved
0.5647 Remote Similarity NPD4058 Approved
0.5638 Remote Similarity NPD4518 Approved
0.5636 Remote Similarity NPD7115 Discovery
0.5625 Remote Similarity NPD5693 Phase 1
0.5625 Remote Similarity NPD6411 Approved
0.5619 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5612 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5607 Remote Similarity NPD6649 Approved
0.5607 Remote Similarity NPD6869 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