Structure

Physi-Chem Properties

Molecular Weight:  266.15
Volume:  272.215
LogP:  2.944
LogD:  2.399
LogS:  -3.239
# Rotatable Bonds:  0
TPSA:  73.83
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.674
Synthetic Accessibility Score:  4.384
Fsp3:  0.733
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:  -5.036
MDCK Permeability:  1.6041431081248447e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.229
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.266
Plasma Protein Binding (PPB):  92.0219955444336%
Volume Distribution (VD):  2.088
Pgp-substrate:  16.609310150146484%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.324
CYP2C19-inhibitor:  0.012
CYP2C19-substrate:  0.567
CYP2C9-inhibitor:  0.11
CYP2C9-substrate:  0.916
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.269
CYP3A4-inhibitor:  0.01
CYP3A4-substrate:  0.126

ADMET: Excretion

Clearance (CL):  10.04
Half-life (T1/2):  0.668

ADMET: Toxicity

hERG Blockers:  0.006
Human Hepatotoxicity (H-HT):  0.193
Drug-inuced Liver Injury (DILI):  0.307
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.973
Maximum Recommended Daily Dose:  0.964
Skin Sensitization:  0.57
Carcinogencity:  0.855
Eye Corrosion:  0.011
Eye Irritation:  0.439
Respiratory Toxicity:  0.963

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

  Natural Product: NPC474555

Natural Product ID:  NPC474555
Common Name*:   Dendocarbin L/Dendocarbin M
IUPAC Name:   (4R,5aS,9aS)-1,4-dihydroxy-6,6,9a-trimethyl-4,5,5a,7,8,9-hexahydro-1H-benzo[e][2]benzofuran-3-one
Synonyms:  
Standard InCHIKey:  FFDNVMGPKVVVOG-NSJIUELXSA-N
Standard InCHI:  InChI=1S/C15H22O4/c1-14(2)5-4-6-15(3)9(14)7-8(16)10-11(15)13(18)19-12(10)17/h8-9,13,16,18H,4-7H2,1-3H3/t8-,9+,13?,15+/m1/s1
SMILES:  CC1(CCCC2(C1CC(C3=C2C(OC3=O)O)O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL471892
PubChem CID:   44560019
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO8660 Dendrodoris carbunculosa Species Dendrodorididae Eukaryota n.a. Amatsu-kominato, Boso Peninsula, central Japan (35 07N, 140 11E) 1999-NOV PMID[11421732]
NPO8660 Dendrodoris carbunculosa Species Dendrodorididae 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
NPT168 Cell Line P388 Mus musculus IC50 > 25.0 ug.mL-1 PMID[512145]

☑ 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 NPC474555 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
0.9775 High Similarity NPC240673
0.9775 High Similarity NPC17578
0.9551 High Similarity NPC474554
0.9355 High Similarity NPC471075
0.9195 High Similarity NPC474062
0.9032 High Similarity NPC475709
0.8804 High Similarity NPC115021
0.8788 High Similarity NPC90946
0.8788 High Similarity NPC300614
0.87 High Similarity NPC31522
0.8681 High Similarity NPC470734
0.8587 High Similarity NPC477782
0.8587 High Similarity NPC232426
0.8587 High Similarity NPC281942
0.8539 High Similarity NPC71626
0.8526 High Similarity NPC242848
0.8495 Intermediate Similarity NPC477783
0.8495 Intermediate Similarity NPC472814
0.8495 Intermediate Similarity NPC141831
0.8495 Intermediate Similarity NPC177037
0.8454 Intermediate Similarity NPC476299
0.8454 Intermediate Similarity NPC474012
0.8438 Intermediate Similarity NPC53844
0.8431 Intermediate Similarity NPC235014
0.8416 Intermediate Similarity NPC325054
0.8409 Intermediate Similarity NPC282293
0.8384 Intermediate Similarity NPC159533
0.837 Intermediate Similarity NPC472810
0.837 Intermediate Similarity NPC472809
0.8333 Intermediate Similarity NPC476797
0.8316 Intermediate Similarity NPC104925
0.8316 Intermediate Similarity NPC298973
0.828 Intermediate Similarity NPC5509
0.828 Intermediate Similarity NPC251528
0.8261 Intermediate Similarity NPC312561
0.8242 Intermediate Similarity NPC473251
0.8242 Intermediate Similarity NPC42586
0.8235 Intermediate Similarity NPC476765
0.8211 Intermediate Similarity NPC271652
0.8211 Intermediate Similarity NPC166346
0.8211 Intermediate Similarity NPC139692
0.8211 Intermediate Similarity NPC472812
0.82 Intermediate Similarity NPC471208
0.8191 Intermediate Similarity NPC472307
0.8191 Intermediate Similarity NPC472642
0.8191 Intermediate Similarity NPC51486
0.8161 Intermediate Similarity NPC316500
0.8144 Intermediate Similarity NPC470801
0.8144 Intermediate Similarity NPC234993
0.8144 Intermediate Similarity NPC134072
0.8125 Intermediate Similarity NPC469697
0.8125 Intermediate Similarity NPC53685
0.8125 Intermediate Similarity NPC475572
0.8119 Intermediate Similarity NPC296950
0.8105 Intermediate Similarity NPC179517
0.8105 Intermediate Similarity NPC472811
0.8105 Intermediate Similarity NPC165904
0.81 Intermediate Similarity NPC295791
0.81 Intermediate Similarity NPC58329
0.8085 Intermediate Similarity NPC174342
0.8081 Intermediate Similarity NPC477720
0.8081 Intermediate Similarity NPC472644
0.8081 Intermediate Similarity NPC117685
0.8077 Intermediate Similarity NPC476766
0.8061 Intermediate Similarity NPC121402
0.8061 Intermediate Similarity NPC132753
0.8061 Intermediate Similarity NPC151681
0.8061 Intermediate Similarity NPC175351
0.8061 Intermediate Similarity NPC224356
0.8041 Intermediate Similarity NPC472441
0.8041 Intermediate Similarity NPC183012
0.8021 Intermediate Similarity NPC472641
0.8021 Intermediate Similarity NPC242069
0.8021 Intermediate Similarity NPC472640
0.8021 Intermediate Similarity NPC472303
0.8 Intermediate Similarity NPC161638
0.7981 Intermediate Similarity NPC476759
0.798 Intermediate Similarity NPC316598
0.7979 Intermediate Similarity NPC474629
0.7959 Intermediate Similarity NPC154526
0.7959 Intermediate Similarity NPC472363
0.7959 Intermediate Similarity NPC472362
0.7959 Intermediate Similarity NPC165632
0.7959 Intermediate Similarity NPC162346
0.7957 Intermediate Similarity NPC250981
0.7957 Intermediate Similarity NPC198761
0.7941 Intermediate Similarity NPC146731
0.7938 Intermediate Similarity NPC96541
0.7938 Intermediate Similarity NPC184870
0.7921 Intermediate Similarity NPC165250
0.7921 Intermediate Similarity NPC476890
0.7917 Intermediate Similarity NPC289479
0.7917 Intermediate Similarity NPC78594
0.7917 Intermediate Similarity NPC477122
0.7917 Intermediate Similarity NPC252433
0.79 Intermediate Similarity NPC54705
0.79 Intermediate Similarity NPC476767
0.79 Intermediate Similarity NPC469864
0.79 Intermediate Similarity NPC469872
0.7895 Intermediate Similarity NPC168131
0.7879 Intermediate Similarity NPC477719
0.7879 Intermediate Similarity NPC208094
0.7879 Intermediate Similarity NPC477718
0.7872 Intermediate Similarity NPC171722
0.7872 Intermediate Similarity NPC475678
0.7857 Intermediate Similarity NPC111273
0.7857 Intermediate Similarity NPC476487
0.7857 Intermediate Similarity NPC471915
0.7857 Intermediate Similarity NPC209355
0.7857 Intermediate Similarity NPC476488
0.7849 Intermediate Similarity NPC189311
0.7849 Intermediate Similarity NPC474860
0.7849 Intermediate Similarity NPC52628
0.7849 Intermediate Similarity NPC65661
0.7849 Intermediate Similarity NPC86316
0.7849 Intermediate Similarity NPC106416
0.7849 Intermediate Similarity NPC471300
0.7843 Intermediate Similarity NPC476889
0.7835 Intermediate Similarity NPC469939
0.7826 Intermediate Similarity NPC471297
0.7826 Intermediate Similarity NPC311070
0.7822 Intermediate Similarity NPC63249
0.7822 Intermediate Similarity NPC472643
0.7822 Intermediate Similarity NPC469657
0.7822 Intermediate Similarity NPC93744
0.7822 Intermediate Similarity NPC244456
0.7822 Intermediate Similarity NPC476888
0.7812 Intermediate Similarity NPC477149
0.7812 Intermediate Similarity NPC477147
0.7812 Intermediate Similarity NPC113393
0.7812 Intermediate Similarity NPC78973
0.7812 Intermediate Similarity NPC8062
0.78 Intermediate Similarity NPC474440
0.78 Intermediate Similarity NPC23364
0.7798 Intermediate Similarity NPC474483
0.7789 Intermediate Similarity NPC307298
0.7789 Intermediate Similarity NPC472378
0.7789 Intermediate Similarity NPC226863
0.7788 Intermediate Similarity NPC91034
0.7788 Intermediate Similarity NPC475570
0.7778 Intermediate Similarity NPC202833
0.7778 Intermediate Similarity NPC7124
0.7778 Intermediate Similarity NPC112654
0.7778 Intermediate Similarity NPC150646
0.7766 Intermediate Similarity NPC131813
0.7766 Intermediate Similarity NPC322159
0.7757 Intermediate Similarity NPC42658
0.7755 Intermediate Similarity NPC470255
0.7755 Intermediate Similarity NPC84893
0.7755 Intermediate Similarity NPC470697
0.7745 Intermediate Similarity NPC40918
0.7745 Intermediate Similarity NPC476081
0.7745 Intermediate Similarity NPC134077
0.7745 Intermediate Similarity NPC472815
0.7745 Intermediate Similarity NPC471914
0.7742 Intermediate Similarity NPC471302
0.7736 Intermediate Similarity NPC472666
0.7732 Intermediate Similarity NPC65513
0.7732 Intermediate Similarity NPC233345
0.7732 Intermediate Similarity NPC186363
0.7732 Intermediate Similarity NPC329842
0.7723 Intermediate Similarity NPC477721
0.7723 Intermediate Similarity NPC477716
0.7723 Intermediate Similarity NPC324841
0.7723 Intermediate Similarity NPC174314
0.7717 Intermediate Similarity NPC471298
0.7714 Intermediate Similarity NPC220155
0.7714 Intermediate Similarity NPC219900
0.7714 Intermediate Similarity NPC392
0.7714 Intermediate Similarity NPC177524
0.7714 Intermediate Similarity NPC473483
0.7708 Intermediate Similarity NPC214387
0.77 Intermediate Similarity NPC91695
0.77 Intermediate Similarity NPC121339
0.77 Intermediate Similarity NPC70145
0.77 Intermediate Similarity NPC253826
0.77 Intermediate Similarity NPC476253
0.7692 Intermediate Similarity NPC1679
0.7692 Intermediate Similarity NPC472645
0.7692 Intermediate Similarity NPC252296
0.7684 Intermediate Similarity NPC220930
0.7684 Intermediate Similarity NPC272039
0.7679 Intermediate Similarity NPC476204
0.7679 Intermediate Similarity NPC170084
0.7679 Intermediate Similarity NPC129434
0.7677 Intermediate Similarity NPC295347
0.767 Intermediate Similarity NPC132395
0.767 Intermediate Similarity NPC120321
0.767 Intermediate Similarity NPC475526
0.767 Intermediate Similarity NPC473283
0.767 Intermediate Similarity NPC329345
0.767 Intermediate Similarity NPC112009
0.767 Intermediate Similarity NPC471365
0.767 Intermediate Similarity NPC471938
0.767 Intermediate Similarity NPC471364
0.766 Intermediate Similarity NPC253604
0.766 Intermediate Similarity NPC472442
0.7647 Intermediate Similarity NPC471412
0.7647 Intermediate Similarity NPC303559
0.7647 Intermediate Similarity NPC477717

  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 NPC474555 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
0.7714 Intermediate Similarity NPD6686 Approved
0.7624 Intermediate Similarity NPD4225 Approved
0.7553 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD1694 Approved
0.7379 Intermediate Similarity NPD7640 Approved
0.7379 Intermediate Similarity NPD7639 Approved
0.7321 Intermediate Similarity NPD7115 Discovery
0.7282 Intermediate Similarity NPD7638 Approved
0.7248 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD7632 Discontinued
0.7083 Intermediate Similarity NPD7319 Approved
0.7059 Intermediate Similarity NPD7748 Approved
0.703 Intermediate Similarity NPD7515 Phase 2
0.7019 Intermediate Similarity NPD6083 Phase 2
0.7019 Intermediate Similarity NPD6084 Phase 2
0.699 Remote Similarity NPD5695 Phase 3
0.699 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6975 Remote Similarity NPD7507 Approved
0.6972 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6412 Phase 2
0.6961 Remote Similarity NPD5779 Approved
0.6961 Remote Similarity NPD5778 Approved
0.6931 Remote Similarity NPD5785 Approved
0.6881 Remote Similarity NPD5739 Approved
0.6881 Remote Similarity NPD6402 Approved
0.6881 Remote Similarity NPD6675 Approved
0.6881 Remote Similarity NPD7128 Approved
0.6869 Remote Similarity NPD7521 Approved
0.6869 Remote Similarity NPD3618 Phase 1
0.6869 Remote Similarity NPD5330 Approved
0.6869 Remote Similarity NPD6684 Approved
0.6869 Remote Similarity NPD6409 Approved
0.6869 Remote Similarity NPD7146 Approved
0.6869 Remote Similarity NPD7334 Approved
0.6863 Remote Similarity NPD6411 Approved
0.6857 Remote Similarity NPD7902 Approved
0.6847 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6837 Remote Similarity NPD3666 Approved
0.6837 Remote Similarity NPD3665 Phase 1
0.6837 Remote Similarity NPD3133 Approved
0.6818 Remote Similarity NPD5701 Approved
0.6818 Remote Similarity NPD5697 Approved
0.6814 Remote Similarity NPD6882 Approved
0.6796 Remote Similarity NPD6399 Phase 3
0.6792 Remote Similarity NPD5696 Approved
0.6757 Remote Similarity NPD7320 Approved
0.6757 Remote Similarity NPD6881 Approved
0.6757 Remote Similarity NPD6899 Approved
0.6733 Remote Similarity NPD5737 Approved
0.6733 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6733 Remote Similarity NPD6672 Approved
0.6733 Remote Similarity NPD6903 Approved
0.6724 Remote Similarity NPD8295 Clinical (unspecified phase)
0.67 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6699 Remote Similarity NPD7637 Suspended
0.6699 Remote Similarity NPD5693 Phase 1
0.6696 Remote Similarity NPD6012 Approved
0.6696 Remote Similarity NPD6372 Approved
0.6696 Remote Similarity NPD6373 Approved
0.6696 Remote Similarity NPD6013 Approved
0.6696 Remote Similarity NPD6014 Approved
0.6667 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4753 Phase 2
0.6667 Remote Similarity NPD6101 Approved
0.6667 Remote Similarity NPD7328 Approved
0.6667 Remote Similarity NPD7327 Approved
0.6667 Remote Similarity NPD8328 Phase 3
0.6667 Remote Similarity NPD5328 Approved
0.6639 Remote Similarity NPD8293 Discontinued
0.6637 Remote Similarity NPD7102 Approved
0.6637 Remote Similarity NPD7290 Approved
0.6637 Remote Similarity NPD6883 Approved
0.6633 Remote Similarity NPD3667 Approved
0.661 Remote Similarity NPD7516 Approved
0.6607 Remote Similarity NPD6011 Approved
0.6606 Remote Similarity NPD5211 Phase 2
0.6585 Remote Similarity NPD7736 Approved
0.6583 Remote Similarity NPD6370 Approved
0.6579 Remote Similarity NPD8130 Phase 1
0.6579 Remote Similarity NPD6847 Approved
0.6579 Remote Similarity NPD6650 Approved
0.6579 Remote Similarity NPD6869 Approved
0.6579 Remote Similarity NPD6649 Approved
0.6579 Remote Similarity NPD6617 Approved
0.6571 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6571 Remote Similarity NPD7900 Approved
0.6562 Remote Similarity NPD3617 Approved
0.6555 Remote Similarity NPD8294 Approved
0.6555 Remote Similarity NPD8377 Approved
0.6542 Remote Similarity NPD4755 Approved
0.6538 Remote Similarity NPD6079 Approved
0.6535 Remote Similarity NPD4519 Discontinued
0.6535 Remote Similarity NPD4623 Approved
0.6535 Remote Similarity NPD5279 Phase 3
0.6522 Remote Similarity NPD6053 Discontinued
0.6522 Remote Similarity NPD8297 Approved
0.65 Remote Similarity NPD7503 Approved
0.65 Remote Similarity NPD8380 Approved
0.65 Remote Similarity NPD8515 Approved
0.65 Remote Similarity NPD8033 Approved
0.65 Remote Similarity NPD8379 Approved
0.65 Remote Similarity NPD4786 Approved
0.65 Remote Similarity NPD8335 Approved
0.65 Remote Similarity NPD8516 Approved
0.65 Remote Similarity NPD8517 Approved
0.65 Remote Similarity NPD8513 Phase 3
0.65 Remote Similarity NPD8378 Approved
0.65 Remote Similarity NPD8296 Approved
0.6491 Remote Similarity NPD6371 Approved
0.6486 Remote Similarity NPD5141 Approved
0.6476 Remote Similarity NPD4202 Approved
0.6475 Remote Similarity NPD7492 Approved
0.6466 Remote Similarity NPD8133 Approved
0.6449 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6449 Remote Similarity NPD4697 Phase 3
0.6449 Remote Similarity NPD5221 Approved
0.6449 Remote Similarity NPD5222 Approved
0.6442 Remote Similarity NPD46 Approved
0.6442 Remote Similarity NPD6698 Approved
0.6436 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6436 Remote Similarity NPD5363 Approved
0.6435 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6423 Remote Similarity NPD6616 Approved
0.6422 Remote Similarity NPD4700 Approved
0.6422 Remote Similarity NPD5286 Approved
0.6422 Remote Similarity NPD5285 Approved
0.6422 Remote Similarity NPD4696 Approved
0.6417 Remote Similarity NPD6054 Approved
0.6417 Remote Similarity NPD6319 Approved
0.6417 Remote Similarity NPD6059 Approved
0.64 Remote Similarity NPD7154 Phase 3
0.6392 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6389 Remote Similarity NPD5173 Approved
0.6381 Remote Similarity NPD5284 Approved
0.6381 Remote Similarity NPD5281 Approved
0.6381 Remote Similarity NPD8035 Phase 2
0.6381 Remote Similarity NPD8034 Phase 2
0.6371 Remote Similarity NPD7078 Approved
0.6364 Remote Similarity NPD6016 Approved
0.6364 Remote Similarity NPD6015 Approved
0.6356 Remote Similarity NPD6274 Approved
0.6355 Remote Similarity NPD5210 Approved
0.6355 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6355 Remote Similarity NPD4629 Approved
0.6349 Remote Similarity NPD6914 Discontinued
0.6346 Remote Similarity NPD6904 Approved
0.6346 Remote Similarity NPD6080 Approved
0.6346 Remote Similarity NPD6051 Approved
0.6346 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6673 Approved
0.6316 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6311 Remote Similarity NPD5988 Approved
0.6311 Remote Similarity NPD3573 Approved
0.6306 Remote Similarity NPD5225 Approved
0.6306 Remote Similarity NPD4633 Approved
0.6306 Remote Similarity NPD5226 Approved
0.6306 Remote Similarity NPD5224 Approved
0.6303 Remote Similarity NPD6009 Approved
0.63 Remote Similarity NPD5209 Approved
0.63 Remote Similarity NPD4269 Approved
0.63 Remote Similarity NPD4223 Phase 3
0.63 Remote Similarity NPD4221 Approved
0.63 Remote Similarity NPD4270 Approved
0.6296 Remote Similarity NPD7839 Suspended
0.6286 Remote Similarity NPD5692 Phase 3
0.6263 Remote Similarity NPD4695 Discontinued
0.625 Remote Similarity NPD5174 Approved
0.625 Remote Similarity NPD8039 Approved
0.625 Remote Similarity NPD5208 Approved
0.625 Remote Similarity NPD5175 Approved
0.6238 Remote Similarity NPD5362 Discontinued
0.6226 Remote Similarity NPD6050 Approved
0.6226 Remote Similarity NPD5694 Approved
0.6218 Remote Similarity NPD6868 Approved
0.6216 Remote Similarity NPD5223 Approved
0.6214 Remote Similarity NPD5786 Approved
0.6207 Remote Similarity NPD4634 Approved
0.6198 Remote Similarity NPD7101 Approved
0.6198 Remote Similarity NPD7100 Approved
0.6186 Remote Similarity NPD6117 Approved
0.6186 Remote Similarity NPD4632 Approved
0.6176 Remote Similarity NPD4197 Approved
0.6176 Remote Similarity NPD3668 Phase 3
0.6167 Remote Similarity NPD6317 Approved
0.614 Remote Similarity NPD6008 Approved
0.614 Remote Similarity NPD4767 Approved
0.614 Remote Similarity NPD4768 Approved
0.6132 Remote Similarity NPD5207 Approved
0.6129 Remote Similarity NPD6067 Discontinued
0.6126 Remote Similarity NPD6404 Discontinued
0.6122 Remote Similarity NPD6116 Phase 1
0.6117 Remote Similarity NPD1696 Phase 3
0.6117 Remote Similarity NPD5329 Approved
0.6116 Remote Similarity NPD6314 Approved
0.6116 Remote Similarity NPD6335 Approved
0.6116 Remote Similarity NPD6313 Approved
0.6111 Remote Similarity NPD5282 Discontinued
0.6111 Remote Similarity NPD6001 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