Structure

Physi-Chem Properties

Molecular Weight:  348.23
Volume:  367.434
LogP:  4.488
LogD:  3.436
LogS:  -4.192
# Rotatable Bonds:  5
TPSA:  51.36
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.439
Synthetic Accessibility Score:  5.087
Fsp3:  0.857
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.85
MDCK Permeability:  3.6952525988454e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.079
30% Bioavailability (F30%):  0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.081
Plasma Protein Binding (PPB):  90.90258026123047%
Volume Distribution (VD):  1.773
Pgp-substrate:  5.828023433685303%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.926
CYP2C19-inhibitor:  0.149
CYP2C19-substrate:  0.893
CYP2C9-inhibitor:  0.207
CYP2C9-substrate:  0.054
CYP2D6-inhibitor:  0.021
CYP2D6-substrate:  0.379
CYP3A4-inhibitor:  0.567
CYP3A4-substrate:  0.504

ADMET: Excretion

Clearance (CL):  10.269
Half-life (T1/2):  0.093

ADMET: Toxicity

hERG Blockers:  0.051
Human Hepatotoxicity (H-HT):  0.579
Drug-inuced Liver Injury (DILI):  0.054
AMES Toxicity:  0.045
Rat Oral Acute Toxicity:  0.734
Maximum Recommended Daily Dose:  0.912
Skin Sensitization:  0.907
Carcinogencity:  0.845
Eye Corrosion:  0.071
Eye Irritation:  0.127
Respiratory Toxicity:  0.975

Download Data

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

  Natural Product: NPC476519

Natural Product ID:  NPC476519
Common Name*:   3-Deoxyaulacocarpin A
IUPAC Name:   methyl (E)-4-[(1R,2S,4aS,8aS)-5,5,8a-trimethylspiro[3,4,4a,6,7,8-hexahydro-1H-naphthalene-2,2'-oxirane]-1-yl]-2-(oxiran-2-yl)but-2-enoate
Synonyms:  
Standard InCHIKey:  ZLHMCXAVSLJKRX-SHUNQTBMSA-N
Standard InCHI:  InChI=1S/C21H32O4/c1-19(2)9-5-10-20(3)16(19)8-11-21(13-25-21)17(20)7-6-14(15-12-24-15)18(22)23-4/h6,15-17H,5,7-13H2,1-4H3/b14-6+/t15?,16-,17+,20-,21+/m0/s1
SMILES:  C[C@]12CCCC([C@@H]1CC[C@]3([C@@H]2C/C=C(\C4CO4)/C(=O)OC)CO3)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   49799799
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
NPO17019 Aframomum zambesiacum Species Zingiberaceae Eukaryota seeds n.a. n.a. PMID[19299148]
NPO17019 Aframomum zambesiacum Species Zingiberaceae 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
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 4970 nM PMID[19299148]

☑ 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 NPC476519 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
0.8681 High Similarity NPC93411
0.8454 Intermediate Similarity NPC72647
0.8454 Intermediate Similarity NPC107806
0.8438 Intermediate Similarity NPC209297
0.8438 Intermediate Similarity NPC475380
0.8421 Intermediate Similarity NPC470697
0.8351 Intermediate Similarity NPC100912
0.8351 Intermediate Similarity NPC475446
0.8351 Intermediate Similarity NPC73911
0.8351 Intermediate Similarity NPC311241
0.8229 Intermediate Similarity NPC140277
0.8211 Intermediate Similarity NPC72845
0.8081 Intermediate Similarity NPC316598
0.8081 Intermediate Similarity NPC159763
0.8081 Intermediate Similarity NPC124512
0.8081 Intermediate Similarity NPC278386
0.8061 Intermediate Similarity NPC194132
0.8043 Intermediate Similarity NPC306951
0.8041 Intermediate Similarity NPC38830
0.8021 Intermediate Similarity NPC49420
0.802 Intermediate Similarity NPC475038
0.802 Intermediate Similarity NPC476081
0.802 Intermediate Similarity NPC109195
0.798 Intermediate Similarity NPC2049
0.7979 Intermediate Similarity NPC475087
0.7959 Intermediate Similarity NPC276110
0.7957 Intermediate Similarity NPC474013
0.7944 Intermediate Similarity NPC122056
0.7941 Intermediate Similarity NPC471938
0.7925 Intermediate Similarity NPC470960
0.7917 Intermediate Similarity NPC161638
0.7917 Intermediate Similarity NPC78973
0.79 Intermediate Similarity NPC264378
0.79 Intermediate Similarity NPC473154
0.79 Intermediate Similarity NPC252295
0.7879 Intermediate Similarity NPC260796
0.7879 Intermediate Similarity NPC307164
0.7879 Intermediate Similarity NPC242848
0.7864 Intermediate Similarity NPC471937
0.7857 Intermediate Similarity NPC161998
0.7857 Intermediate Similarity NPC57117
0.7857 Intermediate Similarity NPC88326
0.7857 Intermediate Similarity NPC153700
0.7857 Intermediate Similarity NPC477130
0.7857 Intermediate Similarity NPC477129
0.7849 Intermediate Similarity NPC96055
0.7843 Intermediate Similarity NPC471914
0.783 Intermediate Similarity NPC253906
0.7826 Intermediate Similarity NPC471218
0.7822 Intermediate Similarity NPC476299
0.7822 Intermediate Similarity NPC470906
0.7822 Intermediate Similarity NPC474012
0.7818 Intermediate Similarity NPC50774
0.7818 Intermediate Similarity NPC709
0.7812 Intermediate Similarity NPC474396
0.7812 Intermediate Similarity NPC50488
0.781 Intermediate Similarity NPC322903
0.78 Intermediate Similarity NPC110937
0.78 Intermediate Similarity NPC84335
0.78 Intermediate Similarity NPC38530
0.7789 Intermediate Similarity NPC166857
0.7788 Intermediate Similarity NPC81630
0.7788 Intermediate Similarity NPC477090
0.7788 Intermediate Similarity NPC1679
0.7778 Intermediate Similarity NPC477126
0.7778 Intermediate Similarity NPC159333
0.7767 Intermediate Similarity NPC297617
0.7767 Intermediate Similarity NPC473283
0.7767 Intermediate Similarity NPC254202
0.7767 Intermediate Similarity NPC120321
0.7767 Intermediate Similarity NPC475526
0.7767 Intermediate Similarity NPC329345
0.7755 Intermediate Similarity NPC139692
0.7755 Intermediate Similarity NPC162615
0.7755 Intermediate Similarity NPC152778
0.7755 Intermediate Similarity NPC205034
0.7755 Intermediate Similarity NPC7349
0.7742 Intermediate Similarity NPC476927
0.7732 Intermediate Similarity NPC8062
0.7727 Intermediate Similarity NPC58662
0.7727 Intermediate Similarity NPC470493
0.7727 Intermediate Similarity NPC312824
0.7727 Intermediate Similarity NPC167606
0.7727 Intermediate Similarity NPC183580
0.7727 Intermediate Similarity NPC140055
0.7727 Intermediate Similarity NPC286528
0.7727 Intermediate Similarity NPC470492
0.7727 Intermediate Similarity NPC20302
0.7723 Intermediate Similarity NPC218107
0.7719 Intermediate Similarity NPC8374
0.7717 Intermediate Similarity NPC170303
0.7717 Intermediate Similarity NPC25554
0.7714 Intermediate Similarity NPC330011
0.7714 Intermediate Similarity NPC187435
0.7714 Intermediate Similarity NPC329048
0.7714 Intermediate Similarity NPC180744
0.7714 Intermediate Similarity NPC67321
0.7708 Intermediate Similarity NPC106332
0.7708 Intermediate Similarity NPC477128
0.7708 Intermediate Similarity NPC69713
0.7708 Intermediate Similarity NPC104560
0.77 Intermediate Similarity NPC114743
0.77 Intermediate Similarity NPC16967
0.77 Intermediate Similarity NPC195366
0.7692 Intermediate Similarity NPC477127
0.7692 Intermediate Similarity NPC283789
0.7692 Intermediate Similarity NPC470297
0.7685 Intermediate Similarity NPC269530
0.7685 Intermediate Similarity NPC4573
0.7685 Intermediate Similarity NPC277769
0.7684 Intermediate Similarity NPC131813
0.7679 Intermediate Similarity NPC474370
0.7677 Intermediate Similarity NPC105490
0.7677 Intermediate Similarity NPC191521
0.7677 Intermediate Similarity NPC84893
0.767 Intermediate Similarity NPC273668
0.767 Intermediate Similarity NPC320447
0.767 Intermediate Similarity NPC162973
0.767 Intermediate Similarity NPC40918
0.7664 Intermediate Similarity NPC473843
0.7664 Intermediate Similarity NPC473975
0.7664 Intermediate Similarity NPC474586
0.7664 Intermediate Similarity NPC473594
0.7658 Intermediate Similarity NPC186525
0.7653 Intermediate Similarity NPC473944
0.7647 Intermediate Similarity NPC476303
0.7647 Intermediate Similarity NPC38855
0.7647 Intermediate Similarity NPC471413
0.7647 Intermediate Similarity NPC47024
0.7647 Intermediate Similarity NPC16601
0.7642 Intermediate Similarity NPC473482
0.7642 Intermediate Similarity NPC475418
0.7642 Intermediate Similarity NPC318363
0.7634 Intermediate Similarity NPC256112
0.7634 Intermediate Similarity NPC2524
0.7629 Intermediate Similarity NPC469866
0.7629 Intermediate Similarity NPC314727
0.7629 Intermediate Similarity NPC82876
0.7629 Intermediate Similarity NPC471342
0.7629 Intermediate Similarity NPC177141
0.7629 Intermediate Similarity NPC73995
0.7624 Intermediate Similarity NPC474921
0.7624 Intermediate Similarity NPC287668
0.7619 Intermediate Similarity NPC34768
0.7611 Intermediate Similarity NPC67569
0.7609 Intermediate Similarity NPC469802
0.7604 Intermediate Similarity NPC102640
0.76 Intermediate Similarity NPC37603
0.76 Intermediate Similarity NPC183012
0.76 Intermediate Similarity NPC472441
0.76 Intermediate Similarity NPC33473
0.76 Intermediate Similarity NPC471786
0.76 Intermediate Similarity NPC111273
0.7596 Intermediate Similarity NPC176883
0.7596 Intermediate Similarity NPC476889
0.7596 Intermediate Similarity NPC165608
0.7596 Intermediate Similarity NPC72151
0.7596 Intermediate Similarity NPC476237
0.7596 Intermediate Similarity NPC180204
0.7596 Intermediate Similarity NPC112009
0.7593 Intermediate Similarity NPC194619
0.7593 Intermediate Similarity NPC317107
0.7589 Intermediate Similarity NPC475520
0.7589 Intermediate Similarity NPC264954
0.7579 Intermediate Similarity NPC30984
0.7579 Intermediate Similarity NPC476678
0.7576 Intermediate Similarity NPC474185
0.7576 Intermediate Similarity NPC53555
0.7576 Intermediate Similarity NPC472871
0.7573 Intermediate Similarity NPC93744
0.7573 Intermediate Similarity NPC471412
0.7573 Intermediate Similarity NPC282524
0.7573 Intermediate Similarity NPC473160
0.7573 Intermediate Similarity NPC476888
0.757 Intermediate Similarity NPC469370
0.757 Intermediate Similarity NPC475065
0.7568 Intermediate Similarity NPC243065
0.7553 Intermediate Similarity NPC12283
0.7553 Intermediate Similarity NPC79945
0.7553 Intermediate Similarity NPC474193
0.7551 Intermediate Similarity NPC302280
0.7551 Intermediate Similarity NPC310479
0.7551 Intermediate Similarity NPC475776
0.7551 Intermediate Similarity NPC152467
0.7549 Intermediate Similarity NPC57079
0.7549 Intermediate Similarity NPC478056
0.7549 Intermediate Similarity NPC174663
0.7549 Intermediate Similarity NPC108368
0.7549 Intermediate Similarity NPC278673
0.7549 Intermediate Similarity NPC176845
0.7547 Intermediate Similarity NPC471601
0.7547 Intermediate Similarity NPC475510
0.7547 Intermediate Similarity NPC475587
0.7545 Intermediate Similarity NPC147912
0.7545 Intermediate Similarity NPC67259
0.7544 Intermediate Similarity NPC470265
0.7544 Intermediate Similarity NPC23786
0.7527 Intermediate Similarity NPC159148
0.7527 Intermediate Similarity NPC476101
0.7526 Intermediate Similarity NPC473879

  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 NPC476519 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
0.8081 Intermediate Similarity NPD4225 Approved
0.7727 Intermediate Similarity NPD7115 Discovery
0.7547 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7476 Intermediate Similarity NPD6648 Approved
0.7447 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD5344 Discontinued
0.7379 Intermediate Similarity NPD7638 Approved
0.7339 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD7900 Approved
0.7327 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD7640 Approved
0.7308 Intermediate Similarity NPD7639 Approved
0.7248 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD1694 Approved
0.713 Intermediate Similarity NPD6008 Approved
0.7115 Intermediate Similarity NPD7902 Approved
0.699 Remote Similarity NPD7748 Approved
0.6961 Remote Similarity NPD7515 Phase 2
0.6931 Remote Similarity NPD6051 Approved
0.6923 Remote Similarity NPD6356 Clinical (unspecified phase)
0.69 Remote Similarity NPD3573 Approved
0.6893 Remote Similarity NPD6399 Phase 3
0.6847 Remote Similarity NPD6881 Approved
0.6847 Remote Similarity NPD6899 Approved
0.6818 Remote Similarity NPD5739 Approved
0.6818 Remote Similarity NPD6675 Approved
0.6818 Remote Similarity NPD7128 Approved
0.6818 Remote Similarity NPD6402 Approved
0.6814 Remote Similarity NPD6649 Approved
0.6814 Remote Similarity NPD6650 Approved
0.68 Remote Similarity NPD7146 Approved
0.68 Remote Similarity NPD6409 Approved
0.68 Remote Similarity NPD6684 Approved
0.68 Remote Similarity NPD7334 Approved
0.68 Remote Similarity NPD7521 Approved
0.68 Remote Similarity NPD5330 Approved
0.6786 Remote Similarity NPD6373 Approved
0.6786 Remote Similarity NPD6372 Approved
0.6757 Remote Similarity NPD5697 Approved
0.6735 Remote Similarity NPD5209 Approved
0.6726 Remote Similarity NPD7290 Approved
0.6726 Remote Similarity NPD6883 Approved
0.6726 Remote Similarity NPD7102 Approved
0.6699 Remote Similarity NPD5785 Approved
0.6697 Remote Similarity NPD7632 Discontinued
0.6696 Remote Similarity NPD7320 Approved
0.6696 Remote Similarity NPD6686 Approved
0.6667 Remote Similarity NPD6001 Approved
0.6667 Remote Similarity NPD6903 Approved
0.6667 Remote Similarity NPD8130 Phase 1
0.6667 Remote Similarity NPD6847 Approved
0.6667 Remote Similarity NPD5737 Approved
0.6667 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6672 Approved
0.6667 Remote Similarity NPD6869 Approved
0.6667 Remote Similarity NPD6617 Approved
0.6637 Remote Similarity NPD6012 Approved
0.6637 Remote Similarity NPD6013 Approved
0.6637 Remote Similarity NPD6014 Approved
0.6635 Remote Similarity NPD7637 Suspended
0.6635 Remote Similarity NPD5693 Phase 1
0.6634 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6634 Remote Similarity NPD3618 Phase 1
0.6629 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6609 Remote Similarity NPD6882 Approved
0.6609 Remote Similarity NPD8297 Approved
0.6607 Remote Similarity NPD5701 Approved
0.6604 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6579 Remote Similarity NPD6371 Approved
0.6549 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6549 Remote Similarity NPD6011 Approved
0.6545 Remote Similarity NPD5211 Phase 2
0.6538 Remote Similarity NPD7838 Discovery
0.6538 Remote Similarity NPD6698 Approved
0.6538 Remote Similarity NPD46 Approved
0.6531 Remote Similarity NPD7525 Registered
0.6514 Remote Similarity NPD5285 Approved
0.6514 Remote Similarity NPD5286 Approved
0.6514 Remote Similarity NPD4696 Approved
0.6481 Remote Similarity NPD4755 Approved
0.6481 Remote Similarity NPD6084 Phase 2
0.6481 Remote Similarity NPD6083 Phase 2
0.648 Remote Similarity NPD7319 Approved
0.6476 Remote Similarity NPD6079 Approved
0.6476 Remote Similarity NPD8034 Phase 2
0.6476 Remote Similarity NPD8035 Phase 2
0.6476 Remote Similarity NPD6411 Approved
0.6471 Remote Similarity NPD7328 Approved
0.6471 Remote Similarity NPD7327 Approved
0.6446 Remote Similarity NPD8033 Approved
0.6442 Remote Similarity NPD6673 Approved
0.6442 Remote Similarity NPD6904 Approved
0.6442 Remote Similarity NPD6080 Approved
0.6442 Remote Similarity NPD1695 Approved
0.6442 Remote Similarity NPD5328 Approved
0.6429 Remote Similarity NPD5141 Approved
0.6429 Remote Similarity NPD7645 Phase 2
0.6422 Remote Similarity NPD5696 Approved
0.6417 Remote Similarity NPD7516 Approved
0.6415 Remote Similarity NPD5779 Approved
0.6415 Remote Similarity NPD5778 Approved
0.6415 Remote Similarity NPD4202 Approved
0.6396 Remote Similarity NPD5226 Approved
0.6396 Remote Similarity NPD5225 Approved
0.6396 Remote Similarity NPD4633 Approved
0.6396 Remote Similarity NPD5224 Approved
0.6379 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6371 Remote Similarity NPD7507 Approved
0.6364 Remote Similarity NPD8377 Approved
0.6364 Remote Similarity NPD4700 Approved
0.6364 Remote Similarity NPD6319 Approved
0.6364 Remote Similarity NPD8294 Approved
0.6339 Remote Similarity NPD5175 Approved
0.6339 Remote Similarity NPD5174 Approved
0.6316 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6311 Remote Similarity NPD8379 Approved
0.6311 Remote Similarity NPD8296 Approved
0.6311 Remote Similarity NPD8380 Approved
0.6311 Remote Similarity NPD8335 Approved
0.6311 Remote Similarity NPD7503 Approved
0.6311 Remote Similarity NPD8378 Approved
0.6306 Remote Similarity NPD5223 Approved
0.6303 Remote Similarity NPD6274 Approved
0.6296 Remote Similarity NPD5695 Phase 3
0.6293 Remote Similarity NPD4634 Approved
0.629 Remote Similarity NPD7492 Approved
0.6286 Remote Similarity NPD6101 Approved
0.6286 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6281 Remote Similarity NPD7101 Approved
0.6281 Remote Similarity NPD7100 Approved
0.6275 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6275 Remote Similarity NPD3668 Phase 3
0.6275 Remote Similarity NPD4786 Approved
0.6273 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6271 Remote Similarity NPD4632 Approved
0.624 Remote Similarity NPD6616 Approved
0.6239 Remote Similarity NPD5222 Approved
0.6239 Remote Similarity NPD4697 Phase 3
0.6239 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6239 Remote Similarity NPD5221 Approved
0.6238 Remote Similarity NPD3667 Approved
0.623 Remote Similarity NPD6054 Approved
0.6214 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6214 Remote Similarity NPD5363 Approved
0.6214 Remote Similarity NPD1733 Clinical (unspecified phase)
0.621 Remote Similarity NPD8328 Phase 3
0.62 Remote Similarity NPD4695 Discontinued
0.6198 Remote Similarity NPD6335 Approved
0.619 Remote Similarity NPD5208 Approved
0.619 Remote Similarity NPD7078 Approved
0.6186 Remote Similarity NPD6053 Discontinued
0.6186 Remote Similarity NPD8039 Approved
0.6182 Remote Similarity NPD5173 Approved
0.6168 Remote Similarity NPD5281 Approved
0.6168 Remote Similarity NPD5284 Approved
0.6168 Remote Similarity NPD6050 Approved
0.6154 Remote Similarity NPD6098 Approved
0.6147 Remote Similarity NPD4629 Approved
0.6147 Remote Similarity NPD5210 Approved
0.6142 Remote Similarity NPD7736 Approved
0.6132 Remote Similarity NPD4753 Phase 2
0.6132 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6129 Remote Similarity NPD6370 Approved
0.6121 Remote Similarity NPD4729 Approved
0.6121 Remote Similarity NPD5128 Approved
0.6121 Remote Similarity NPD4730 Approved
0.6117 Remote Similarity NPD3666 Approved
0.6117 Remote Similarity NPD3133 Approved
0.6117 Remote Similarity NPD3665 Phase 1
0.6117 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6116 Remote Similarity NPD6317 Approved
0.6116 Remote Similarity NPD6009 Approved
0.6098 Remote Similarity NPD6059 Approved
0.6091 Remote Similarity NPD7732 Phase 3
0.6087 Remote Similarity NPD4767 Approved
0.6087 Remote Similarity NPD4768 Approved
0.608 Remote Similarity NPD7604 Phase 2
0.6075 Remote Similarity NPD5692 Phase 3
0.6075 Remote Similarity NPD5207 Approved
0.6075 Remote Similarity NPD3168 Discontinued
0.6066 Remote Similarity NPD6314 Approved
0.6066 Remote Similarity NPD6313 Approved
0.6063 Remote Similarity NPD8293 Discontinued
0.6058 Remote Similarity NPD1696 Phase 3
0.6058 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6055 Remote Similarity NPD5282 Discontinued
0.6053 Remote Similarity NPD4754 Approved
0.6048 Remote Similarity NPD6908 Approved
0.6048 Remote Similarity NPD6909 Approved
0.6048 Remote Similarity NPD6015 Approved
0.6048 Remote Similarity NPD6016 Approved
0.6048 Remote Similarity NPD6291 Clinical (unspecified phase)
0.604 Remote Similarity NPD4822 Approved
0.604 Remote Similarity NPD4821 Approved
0.604 Remote Similarity NPD4819 Approved
0.604 Remote Similarity NPD4820 Approved
0.6033 Remote Similarity NPD6868 Approved
0.602 Remote Similarity NPD6942 Approved
0.602 Remote Similarity NPD7339 Approved
0.6019 Remote Similarity NPD5694 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