Structure

Physi-Chem Properties

Molecular Weight:  658.2
Volume:  613.029
LogP:  2.122
LogD:  0.787
LogS:  -4.144
# Rotatable Bonds:  10
TPSA:  190.56
# H-Bond Aceptor:  14
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.146
Synthetic Accessibility Score:  6.371
Fsp3:  0.733
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.268
MDCK Permeability:  0.00018529818044044077
Pgp-inhibitor:  0.995
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.78
20% Bioavailability (F20%):  0.031
30% Bioavailability (F30%):  0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.07
Plasma Protein Binding (PPB):  44.87454605102539%
Volume Distribution (VD):  1.467
Pgp-substrate:  43.47086715698242%

ADMET: Metabolism

CYP1A2-inhibitor:  0.015
CYP1A2-substrate:  0.014
CYP2C19-inhibitor:  0.009
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.013
CYP2D6-inhibitor:  0.691
CYP2D6-substrate:  0.07
CYP3A4-inhibitor:  0.454
CYP3A4-substrate:  0.199

ADMET: Excretion

Clearance (CL):  2.572
Half-life (T1/2):  0.581

ADMET: Toxicity

hERG Blockers:  0.106
Human Hepatotoxicity (H-HT):  0.995
Drug-inuced Liver Injury (DILI):  0.933
AMES Toxicity:  0.158
Rat Oral Acute Toxicity:  0.264
Maximum Recommended Daily Dose:  0.031
Skin Sensitization:  0.148
Carcinogencity:  0.019
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.936

Download Data

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

  Natural Product: NPC140409

Natural Product ID:  NPC140409
Common Name*:   Gemmacolide A
IUPAC Name:   n.a.
Synonyms:   Gemmacolide A
Standard InCHIKey:  RVARBBKIGSFITE-BRDFTBFESA-N
Standard InCHI:  InChI=1S/C30H39ClO14/c1-12-9-10-19(40-14(3)32)28(8)22(26(44-18(7)36)30(38)13(2)27(37)45-23(30)20(12)31)29(11-39-29)25(43-17(6)35)21(41-15(4)33)24(28)42-16(5)34/h13,19-26,38H,1,9-11H2,2-8H3/t13-,19-,20-,21+,22+,23-,24-,25+,26-,28+,29-,30-/m0/s1
SMILES:  C=C1CC[C@@H]([C@]2(C)[C@@H]([C@@H]([C@@]3([C@@H](C)C(=O)O[C@H]3[C@H]1Cl)O)OC(=O)C)[C@@]1(CO1)[C@@H]([C@@H]([C@@H]2OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1923134
PubChem CID:   15060793
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO25525 Junceella juncea Species Ellisellidae Eukaryota n.a. n.a. n.a. PMID[11809065]
NPO25525 Junceella juncea Species Ellisellidae Eukaryota n.a. Taiwanese gorgonian n.a. PMID[12608873]
NPO25525 Junceella juncea Species Ellisellidae Eukaryota n.a. n.a. n.a. PMID[22071302]
NPO25525 Junceella juncea Species Ellisellidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25525 Junceella juncea Species Ellisellidae 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
NPT79 Organism Bacillus subtilis Bacillus subtilis IZ = 10.0 mm PMID[452725]
NPT2642 Organism Bacillus pumilus Bacillus pumilus IZ = 19.0 mm PMID[452725]
NPT766 Organism Proteus vulgaris Proteus vulgaris IZ = 12.0 mm PMID[452725]
NPT19 Organism Escherichia coli Escherichia coli IZ = 20.0 mm PMID[452725]
NPT21 Organism Aspergillus niger Aspergillus niger IZ = 10.0 mm PMID[452725]
NPT20 Organism Candida albicans Candida albicans IZ = 8.0 mm PMID[452725]

☑ 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 NPC140409 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 NPC156248
1.0 High Similarity NPC11491
0.9902 High Similarity NPC170294
0.9802 High Similarity NPC128210
0.9712 High Similarity NPC89018
0.9619 High Similarity NPC88867
0.9619 High Similarity NPC226608
0.9528 High Similarity NPC470466
0.9208 High Similarity NPC98225
0.885 High Similarity NPC310035
0.885 High Similarity NPC188222
0.885 High Similarity NPC282003
0.8796 High Similarity NPC470467
0.8772 High Similarity NPC303006
0.8716 High Similarity NPC470468
0.8661 High Similarity NPC476714
0.8611 High Similarity NPC475191
0.8264 Intermediate Similarity NPC470185
0.8182 Intermediate Similarity NPC94377
0.8113 Intermediate Similarity NPC152480
0.807 Intermediate Similarity NPC73314
0.7931 Intermediate Similarity NPC296822
0.7909 Intermediate Similarity NPC283850
0.7895 Intermediate Similarity NPC473877
0.787 Intermediate Similarity NPC477656
0.7845 Intermediate Similarity NPC474333
0.7826 Intermediate Similarity NPC477126
0.7818 Intermediate Similarity NPC61442
0.7818 Intermediate Similarity NPC99510
0.7797 Intermediate Similarity NPC470186
0.7788 Intermediate Similarity NPC42662
0.7706 Intermediate Similarity NPC477655
0.7692 Intermediate Similarity NPC253618
0.7692 Intermediate Similarity NPC329869
0.7692 Intermediate Similarity NPC77001
0.7658 Intermediate Similarity NPC72842
0.7652 Intermediate Similarity NPC157476
0.7652 Intermediate Similarity NPC194619
0.7611 Intermediate Similarity NPC475510
0.7611 Intermediate Similarity NPC475587
0.7583 Intermediate Similarity NPC475003
0.7568 Intermediate Similarity NPC183571
0.7565 Intermediate Similarity NPC473594
0.7565 Intermediate Similarity NPC474586
0.7565 Intermediate Similarity NPC473975
0.7565 Intermediate Similarity NPC473843
0.7561 Intermediate Similarity NPC470973
0.7544 Intermediate Similarity NPC473939
0.7544 Intermediate Similarity NPC273155
0.7544 Intermediate Similarity NPC473595
0.7523 Intermediate Similarity NPC474395
0.75 Intermediate Similarity NPC69171
0.75 Intermediate Similarity NPC474165
0.7479 Intermediate Similarity NPC476713
0.7479 Intermediate Similarity NPC476712
0.7478 Intermediate Similarity NPC154906
0.7478 Intermediate Similarity NPC475922
0.7477 Intermediate Similarity NPC308824
0.7456 Intermediate Similarity NPC166993
0.7453 Intermediate Similarity NPC312471
0.7453 Intermediate Similarity NPC471378
0.7431 Intermediate Similarity NPC473964
0.7431 Intermediate Similarity NPC256227
0.7414 Intermediate Similarity NPC115257
0.7414 Intermediate Similarity NPC281624
0.7414 Intermediate Similarity NPC161816
0.7404 Intermediate Similarity NPC246347
0.7395 Intermediate Similarity NPC476710
0.7395 Intermediate Similarity NPC476711
0.7391 Intermediate Similarity NPC112895
0.7391 Intermediate Similarity NPC37628
0.7391 Intermediate Similarity NPC218123
0.7391 Intermediate Similarity NPC231278
0.7383 Intermediate Similarity NPC122057
0.7383 Intermediate Similarity NPC91251
0.7377 Intermediate Similarity NPC477046
0.7377 Intermediate Similarity NPC102822
0.7368 Intermediate Similarity NPC474101
0.7368 Intermediate Similarity NPC200957
0.7368 Intermediate Similarity NPC138908
0.7364 Intermediate Similarity NPC111348
0.7364 Intermediate Similarity NPC473963
0.7364 Intermediate Similarity NPC136781
0.7345 Intermediate Similarity NPC156681
0.7333 Intermediate Similarity NPC122033
0.7333 Intermediate Similarity NPC470854
0.7333 Intermediate Similarity NPC287343
0.7333 Intermediate Similarity NPC470775
0.7333 Intermediate Similarity NPC471377
0.7333 Intermediate Similarity NPC176513
0.7333 Intermediate Similarity NPC474654
0.7333 Intermediate Similarity NPC97908
0.7328 Intermediate Similarity NPC16657
0.7328 Intermediate Similarity NPC204652
0.7321 Intermediate Similarity NPC475958
0.7308 Intermediate Similarity NPC93616
0.7304 Intermediate Similarity NPC216636
0.7304 Intermediate Similarity NPC78966
0.7304 Intermediate Similarity NPC284732
0.7295 Intermediate Similarity NPC317635
0.7295 Intermediate Similarity NPC329008
0.729 Intermediate Similarity NPC153853
0.7281 Intermediate Similarity NPC301787
0.7273 Intermediate Similarity NPC93245
0.7265 Intermediate Similarity NPC100908
0.7265 Intermediate Similarity NPC474567
0.7257 Intermediate Similarity NPC474709
0.7241 Intermediate Similarity NPC153587
0.7238 Intermediate Similarity NPC235196
0.7238 Intermediate Similarity NPC228593
0.7238 Intermediate Similarity NPC279260
0.7227 Intermediate Similarity NPC471252
0.7222 Intermediate Similarity NPC478207
0.7222 Intermediate Similarity NPC312805
0.7217 Intermediate Similarity NPC9303
0.7217 Intermediate Similarity NPC222833
0.7217 Intermediate Similarity NPC470587
0.7217 Intermediate Similarity NPC16313
0.7217 Intermediate Similarity NPC472655
0.7207 Intermediate Similarity NPC111187
0.7207 Intermediate Similarity NPC190080
0.7207 Intermediate Similarity NPC474921
0.7207 Intermediate Similarity NPC253586
0.7203 Intermediate Similarity NPC94650
0.7196 Intermediate Similarity NPC291875
0.7196 Intermediate Similarity NPC194642
0.7196 Intermediate Similarity NPC161560
0.7193 Intermediate Similarity NPC19239
0.7193 Intermediate Similarity NPC225238
0.7193 Intermediate Similarity NPC209298
0.7193 Intermediate Similarity NPC474166
0.7193 Intermediate Similarity NPC122811
0.7193 Intermediate Similarity NPC277074
0.719 Intermediate Similarity NPC469684
0.719 Intermediate Similarity NPC98249
0.719 Intermediate Similarity NPC58662
0.719 Intermediate Similarity NPC53396
0.7182 Intermediate Similarity NPC259042
0.7182 Intermediate Similarity NPC157686
0.7179 Intermediate Similarity NPC218853
0.7179 Intermediate Similarity NPC131903
0.7179 Intermediate Similarity NPC274827
0.7167 Intermediate Similarity NPC117712
0.7167 Intermediate Similarity NPC472400
0.7156 Intermediate Similarity NPC147272
0.7155 Intermediate Similarity NPC324327
0.7155 Intermediate Similarity NPC72813
0.7155 Intermediate Similarity NPC194620
0.7155 Intermediate Similarity NPC326994
0.7155 Intermediate Similarity NPC474421
0.7155 Intermediate Similarity NPC293512
0.7155 Intermediate Similarity NPC319438
0.7143 Intermediate Similarity NPC474927
0.7143 Intermediate Similarity NPC473397
0.7131 Intermediate Similarity NPC17772
0.7131 Intermediate Similarity NPC470776
0.7131 Intermediate Similarity NPC204552
0.7131 Intermediate Similarity NPC284707
0.7131 Intermediate Similarity NPC188667
0.713 Intermediate Similarity NPC65523
0.713 Intermediate Similarity NPC475036
0.7119 Intermediate Similarity NPC472214
0.7119 Intermediate Similarity NPC137104
0.7119 Intermediate Similarity NPC474786
0.7119 Intermediate Similarity NPC320383
0.7119 Intermediate Similarity NPC472215
0.7119 Intermediate Similarity NPC85391
0.7117 Intermediate Similarity NPC284518
0.7115 Intermediate Similarity NPC239308
0.7107 Intermediate Similarity NPC179626
0.7107 Intermediate Similarity NPC207217
0.7107 Intermediate Similarity NPC328374
0.7107 Intermediate Similarity NPC270478
0.7107 Intermediate Similarity NPC251236
0.7107 Intermediate Similarity NPC96312
0.7107 Intermediate Similarity NPC40632
0.7107 Intermediate Similarity NPC474734
0.7107 Intermediate Similarity NPC477509
0.7105 Intermediate Similarity NPC275990
0.7105 Intermediate Similarity NPC164551
0.7103 Intermediate Similarity NPC471221
0.7103 Intermediate Similarity NPC92370
0.7103 Intermediate Similarity NPC470260
0.7103 Intermediate Similarity NPC476379
0.7103 Intermediate Similarity NPC75443
0.7097 Intermediate Similarity NPC472401
0.7094 Intermediate Similarity NPC327286
0.7094 Intermediate Similarity NPC55972
0.7094 Intermediate Similarity NPC14862
0.7094 Intermediate Similarity NPC472439
0.7094 Intermediate Similarity NPC233379
0.7094 Intermediate Similarity NPC169888
0.7094 Intermediate Similarity NPC208461
0.7094 Intermediate Similarity NPC469916
0.7094 Intermediate Similarity NPC289702
0.7094 Intermediate Similarity NPC474664
0.7091 Intermediate Similarity NPC148000
0.7091 Intermediate Similarity NPC469596
0.7091 Intermediate Similarity NPC225474
0.7083 Intermediate Similarity NPC7921

  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 NPC140409 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
0.7094 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.6975 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6891 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6724 Remote Similarity NPD1700 Approved
0.6723 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3653 Clinical (unspecified phase)
0.6581 Remote Similarity NPD5344 Discontinued
0.6562 Remote Similarity NPD6921 Approved
0.6552 Remote Similarity NPD4225 Approved
0.6515 Remote Similarity NPD6033 Approved
0.6508 Remote Similarity NPD7115 Discovery
0.6475 Remote Similarity NPD8132 Clinical (unspecified phase)
0.646 Remote Similarity NPD8034 Phase 2
0.646 Remote Similarity NPD8035 Phase 2
0.6434 Remote Similarity NPD5983 Phase 2
0.64 Remote Similarity NPD8133 Approved
0.64 Remote Similarity NPD4632 Approved
0.6378 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6372 Remote Similarity NPD6698 Approved
0.6372 Remote Similarity NPD46 Approved
0.6364 Remote Similarity NPD6008 Approved
0.6364 Remote Similarity NPD6336 Discontinued
0.6357 Remote Similarity NPD6319 Approved
0.6356 Remote Similarity NPD6648 Approved
0.6311 Remote Similarity NPD7899 Clinical (unspecified phase)
0.629 Remote Similarity NPD6371 Approved
0.6279 Remote Similarity NPD7100 Approved
0.6261 Remote Similarity NPD6399 Phase 3
0.626 Remote Similarity NPD6686 Approved
0.6222 Remote Similarity NPD7319 Approved
0.6212 Remote Similarity NPD8328 Phase 3
0.6207 Remote Similarity NPD5282 Discontinued
0.6202 Remote Similarity NPD6335 Approved
0.6174 Remote Similarity NPD7983 Approved
0.6165 Remote Similarity NPD7492 Approved
0.6154 Remote Similarity NPD7101 Approved
0.6124 Remote Similarity NPD6009 Approved
0.6119 Remote Similarity NPD6616 Approved
0.6107 Remote Similarity NPD6059 Approved
0.6107 Remote Similarity NPD6054 Approved
0.6087 Remote Similarity NPD3168 Discontinued
0.608 Remote Similarity NPD6373 Approved
0.608 Remote Similarity NPD6372 Approved
0.6077 Remote Similarity NPD6313 Approved
0.6077 Remote Similarity NPD6314 Approved
0.6074 Remote Similarity NPD7078 Approved
0.6074 Remote Similarity NPD8293 Discontinued
0.6071 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6063 Remote Similarity NPD8297 Approved
0.6061 Remote Similarity NPD8513 Phase 3
0.6061 Remote Similarity NPD8517 Approved
0.6061 Remote Similarity NPD8515 Approved
0.6061 Remote Similarity NPD8516 Approved
0.6058 Remote Similarity NPD5956 Approved
0.605 Remote Similarity NPD7902 Approved
0.6034 Remote Similarity NPD6411 Approved
0.6031 Remote Similarity NPD7516 Approved
0.6029 Remote Similarity NPD7736 Approved
0.6015 Remote Similarity NPD6370 Approved
0.6 Remote Similarity NPD7638 Approved
0.6 Remote Similarity NPD7507 Approved
0.5984 Remote Similarity NPD6650 Approved
0.5984 Remote Similarity NPD6649 Approved
0.5983 Remote Similarity NPD5779 Approved
0.5983 Remote Similarity NPD5778 Approved
0.5968 Remote Similarity NPD7128 Approved
0.5968 Remote Similarity NPD6402 Approved
0.5968 Remote Similarity NPD6675 Approved
0.5968 Remote Similarity NPD5739 Approved
0.5954 Remote Similarity NPD7327 Approved
0.5954 Remote Similarity NPD7328 Approved
0.595 Remote Similarity NPD7639 Approved
0.595 Remote Similarity NPD7640 Approved
0.594 Remote Similarity NPD6016 Approved
0.594 Remote Similarity NPD6015 Approved
0.5932 Remote Similarity NPD7748 Approved
0.5929 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5923 Remote Similarity NPD6868 Approved
0.592 Remote Similarity NPD6412 Phase 2
0.5909 Remote Similarity NPD4522 Approved
0.5897 Remote Similarity NPD7637 Suspended
0.5896 Remote Similarity NPD5988 Approved
0.5873 Remote Similarity NPD6899 Approved
0.5873 Remote Similarity NPD7320 Approved
0.5873 Remote Similarity NPD6881 Approved
0.5862 Remote Similarity NPD6101 Approved
0.5862 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5859 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5859 Remote Similarity NPD5215 Approved
0.5852 Remote Similarity NPD7604 Phase 2
0.5839 Remote Similarity NPD8074 Phase 3
0.5826 Remote Similarity NPD7524 Approved
0.5814 Remote Similarity NPD6882 Approved
0.5812 Remote Similarity NPD7838 Discovery
0.581 Remote Similarity NPD7532 Clinical (unspecified phase)
0.5798 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5798 Remote Similarity NPD7900 Approved
0.5794 Remote Similarity NPD5701 Approved
0.5794 Remote Similarity NPD5697 Approved
0.5781 Remote Similarity NPD6883 Approved
0.5781 Remote Similarity NPD7290 Approved
0.5781 Remote Similarity NPD4634 Approved
0.5781 Remote Similarity NPD7102 Approved
0.5781 Remote Similarity NPD5169 Approved
0.5763 Remote Similarity NPD7515 Phase 2
0.575 Remote Similarity NPD1698 Clinical (unspecified phase)
0.575 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5736 Remote Similarity NPD5127 Approved
0.5736 Remote Similarity NPD6847 Approved
0.5736 Remote Similarity NPD6869 Approved
0.5736 Remote Similarity NPD5217 Approved
0.5736 Remote Similarity NPD5216 Approved
0.5736 Remote Similarity NPD8130 Phase 1
0.5736 Remote Similarity NPD6617 Approved
0.5727 Remote Similarity NPD6118 Approved
0.5727 Remote Similarity NPD6114 Approved
0.5727 Remote Similarity NPD6697 Approved
0.5727 Remote Similarity NPD6115 Approved
0.5726 Remote Similarity NPD1695 Approved
0.5725 Remote Similarity NPD5167 Approved
0.5714 Remote Similarity NPD5357 Phase 1
0.5714 Remote Similarity NPD5369 Approved
0.5704 Remote Similarity NPD8033 Approved
0.5704 Remote Similarity NPD8335 Approved
0.5704 Remote Similarity NPD8380 Approved
0.5704 Remote Similarity NPD8296 Approved
0.5704 Remote Similarity NPD8378 Approved
0.5704 Remote Similarity NPD8379 Approved
0.5703 Remote Similarity NPD6013 Approved
0.5703 Remote Similarity NPD6012 Approved
0.5703 Remote Similarity NPD6014 Approved
0.5656 Remote Similarity NPD6083 Phase 2
0.5656 Remote Similarity NPD6084 Phase 2
0.5636 Remote Similarity NPD6116 Phase 1
0.563 Remote Similarity NPD8294 Approved
0.563 Remote Similarity NPD8377 Approved
0.5625 Remote Similarity NPD6011 Approved
0.5625 Remote Similarity NPD5128 Approved
0.562 Remote Similarity NPD5695 Phase 3
0.5615 Remote Similarity NPD1719 Phase 1
0.5615 Remote Similarity NPD6401 Clinical (unspecified phase)
0.561 Remote Similarity NPD5696 Approved
0.5603 Remote Similarity NPD3618 Phase 1
0.56 Remote Similarity NPD7632 Discontinued

  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