Structure

Physi-Chem Properties

Molecular Weight:  676.36
Volume:  684.301
LogP:  5.979
LogD:  4.455
LogS:  -5.206
# Rotatable Bonds:  10
TPSA:  95.97
# H-Bond Aceptor:  7
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.216
Synthetic Accessibility Score:  5.301
Fsp3:  0.737
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.967
MDCK Permeability:  1.1321029887767509e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.12
30% Bioavailability (F30%):  0.887

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.962
Plasma Protein Binding (PPB):  76.77136993408203%
Volume Distribution (VD):  2.477
Pgp-substrate:  15.838130950927734%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.136
CYP2C19-inhibitor:  0.055
CYP2C19-substrate:  0.928
CYP2C9-inhibitor:  0.183
CYP2C9-substrate:  0.022
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.114
CYP3A4-inhibitor:  0.792
CYP3A4-substrate:  0.887

ADMET: Excretion

Clearance (CL):  6.244
Half-life (T1/2):  0.03

ADMET: Toxicity

hERG Blockers:  0.598
Human Hepatotoxicity (H-HT):  0.672
Drug-inuced Liver Injury (DILI):  0.361
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.645
Maximum Recommended Daily Dose:  0.848
Skin Sensitization:  0.586
Carcinogencity:  0.138
Eye Corrosion:  0.031
Eye Irritation:  0.027
Respiratory Toxicity:  0.974

Download Data

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

  Natural Product: NPC475404

Natural Product ID:  NPC475404
Common Name*:   (R)-((1S,2S,3S,4As,4Br,6As,10As,10Br,12S,12As)-12-Acetoxy-2-Acetyl-1-Formyl-4B,7,7,10A,12A-Pentamethyloctadecahydrochrysen-3-Yl) 3,3,3-Trifluoro-2-Methoxy-2-Phenylpropanoate
IUPAC Name:   [(1S,2S,3S,4aS,4bR,6aS,10aS,10bR,12S,12aS)-2-acetyl-12-acetyloxy-1-formyl-4b,7,7,10a,12a-pentamethyl-1,2,3,4,4a,5,6,6a,8,9,10,10b,11,12-tetradecahydrochrysen-3-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
Synonyms:  
Standard InCHIKey:  TWTYZDLWJXDDOI-XFTIWLLESA-N
Standard InCHI:  InChI=1S/C38H51F3O7/c1-22(43)31-25(21-42)36(7)29(19-26(31)48-32(45)37(46-8,38(39,40)41)24-13-10-9-11-14-24)35(6)18-15-27-33(3,4)16-12-17-34(27,5)28(35)20-30(36)47-23(2)44/h9-11,13-14,21,25-31H,12,15-20H2,1-8H3/t25-,26-,27-,28+,29-,30-,31-,34-,35+,36+,37+/m0/s1
SMILES:  O=C[C@H]1[C@H](C(=O)C)[C@H](C[C@@H]2[C@]1(C)[C@@H](OC(=O)C)C[C@H]1[C@@]2(C)CC[C@@H]2[C@]1(C)CCCC2(C)C)OC(=O)[C@@](C(F)(F)F)(c1ccccc1)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL504999
PubChem CID:   23246371
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001552] Sesterterpenoids
          • [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33404 phyllospongia sp. Species Thorectidae Eukaryota n.a. Indonesian n.a. PMID[12502324]

☑ 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
NPT91 Cell Line KB Homo sapiens Inhibition = 30.0 % PMID[495113]

☑ 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 NPC475404 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 NPC473677
0.8601 High Similarity NPC475651
0.8533 High Similarity NPC77719
0.8487 Intermediate Similarity NPC469771
0.8477 Intermediate Similarity NPC112523
0.8477 Intermediate Similarity NPC114410
0.8456 Intermediate Similarity NPC254558
0.8456 Intermediate Similarity NPC112216
0.8411 Intermediate Similarity NPC257213
0.8411 Intermediate Similarity NPC249471
0.8411 Intermediate Similarity NPC256142
0.8411 Intermediate Similarity NPC473414
0.8411 Intermediate Similarity NPC242262
0.8411 Intermediate Similarity NPC237549
0.8411 Intermediate Similarity NPC472022
0.8411 Intermediate Similarity NPC304876
0.8411 Intermediate Similarity NPC158333
0.8411 Intermediate Similarity NPC1173
0.8411 Intermediate Similarity NPC265395
0.8411 Intermediate Similarity NPC472005
0.8411 Intermediate Similarity NPC472030
0.8355 Intermediate Similarity NPC26033
0.8355 Intermediate Similarity NPC228204
0.8333 Intermediate Similarity NPC198455
0.8333 Intermediate Similarity NPC165260
0.8333 Intermediate Similarity NPC161239
0.8333 Intermediate Similarity NPC7095
0.8312 Intermediate Similarity NPC471102
0.8311 Intermediate Similarity NPC471107
0.8311 Intermediate Similarity NPC471100
0.8267 Intermediate Similarity NPC60509
0.8267 Intermediate Similarity NPC250046
0.8267 Intermediate Similarity NPC81698
0.8255 Intermediate Similarity NPC475552
0.8235 Intermediate Similarity NPC282239
0.8207 Intermediate Similarity NPC184109
0.8188 Intermediate Similarity NPC127857
0.8182 Intermediate Similarity NPC217091
0.8182 Intermediate Similarity NPC106895
0.8158 Intermediate Similarity NPC101043
0.8158 Intermediate Similarity NPC51602
0.8158 Intermediate Similarity NPC306799
0.8146 Intermediate Similarity NPC473403
0.8129 Intermediate Similarity NPC472393
0.8121 Intermediate Similarity NPC470231
0.8054 Intermediate Similarity NPC477468
0.8039 Intermediate Similarity NPC471103
0.8027 Intermediate Similarity NPC472371
0.8027 Intermediate Similarity NPC472395
0.8 Intermediate Similarity NPC473670
0.8 Intermediate Similarity NPC21410
0.8 Intermediate Similarity NPC472549
0.7987 Intermediate Similarity NPC477905
0.7987 Intermediate Similarity NPC182869
0.7986 Intermediate Similarity NPC469499
0.7933 Intermediate Similarity NPC139067
0.7933 Intermediate Similarity NPC191082
0.7933 Intermediate Similarity NPC246480
0.7933 Intermediate Similarity NPC475429
0.7933 Intermediate Similarity NPC270498
0.7933 Intermediate Similarity NPC147217
0.7933 Intermediate Similarity NPC177340
0.7933 Intermediate Similarity NPC473673
0.7919 Intermediate Similarity NPC213567
0.7908 Intermediate Similarity NPC473215
0.7905 Intermediate Similarity NPC214550
0.7905 Intermediate Similarity NPC210591
0.7905 Intermediate Similarity NPC475652
0.7887 Intermediate Similarity NPC473423
0.7881 Intermediate Similarity NPC471912
0.7881 Intermediate Similarity NPC51314
0.7881 Intermediate Similarity NPC67777
0.7881 Intermediate Similarity NPC80895
0.7875 Intermediate Similarity NPC329960
0.7875 Intermediate Similarity NPC295408
0.7875 Intermediate Similarity NPC150893
0.7871 Intermediate Similarity NPC472548
0.7862 Intermediate Similarity NPC472394
0.7857 Intermediate Similarity NPC470245
0.7857 Intermediate Similarity NPC473214
0.7852 Intermediate Similarity NPC476094
0.7852 Intermediate Similarity NPC473085
0.7852 Intermediate Similarity NPC184747
0.7852 Intermediate Similarity NPC473112
0.7852 Intermediate Similarity NPC473758
0.7852 Intermediate Similarity NPC147880
0.7852 Intermediate Similarity NPC473060
0.7852 Intermediate Similarity NPC473109
0.7852 Intermediate Similarity NPC211137
0.7852 Intermediate Similarity NPC477904
0.7852 Intermediate Similarity NPC473081
0.7852 Intermediate Similarity NPC43241
0.7852 Intermediate Similarity NPC200592
0.7852 Intermediate Similarity NPC183270
0.7852 Intermediate Similarity NPC4341
0.7852 Intermediate Similarity NPC473613
0.7852 Intermediate Similarity NPC48017
0.7838 Intermediate Similarity NPC283375
0.7838 Intermediate Similarity NPC183122
0.7829 Intermediate Similarity NPC301946
0.7829 Intermediate Similarity NPC277053
0.7823 Intermediate Similarity NPC477893
0.7821 Intermediate Similarity NPC219419
0.7808 Intermediate Similarity NPC472656
0.7808 Intermediate Similarity NPC472437
0.7806 Intermediate Similarity NPC470153
0.7805 Intermediate Similarity NPC302392
0.7793 Intermediate Similarity NPC472361
0.7792 Intermediate Similarity NPC476975
0.7771 Intermediate Similarity NPC114357
0.7771 Intermediate Similarity NPC259144
0.7771 Intermediate Similarity NPC155329
0.7762 Intermediate Similarity NPC470753
0.7762 Intermediate Similarity NPC473220
0.7762 Intermediate Similarity NPC253681
0.7755 Intermediate Similarity NPC329913
0.7755 Intermediate Similarity NPC474608
0.775 Intermediate Similarity NPC476077
0.7748 Intermediate Similarity NPC475135
0.7748 Intermediate Similarity NPC472546
0.7744 Intermediate Similarity NPC477471
0.7744 Intermediate Similarity NPC477473
0.7744 Intermediate Similarity NPC477466
0.7744 Intermediate Similarity NPC477469
0.774 Intermediate Similarity NPC471880
0.7733 Intermediate Similarity NPC475400
0.7733 Intermediate Similarity NPC79921
0.7727 Intermediate Similarity NPC281717
0.7724 Intermediate Similarity NPC147561
0.7718 Intermediate Similarity NPC475373
0.7707 Intermediate Similarity NPC134685
0.7707 Intermediate Similarity NPC229545
0.7707 Intermediate Similarity NPC248265
0.7707 Intermediate Similarity NPC11588
0.7703 Intermediate Similarity NPC477896
0.7703 Intermediate Similarity NPC17877
0.7703 Intermediate Similarity NPC195647
0.7703 Intermediate Similarity NPC291638
0.7703 Intermediate Similarity NPC471864
0.7703 Intermediate Similarity NPC66761
0.7703 Intermediate Similarity NPC472577
0.7702 Intermediate Similarity NPC55744
0.7697 Intermediate Similarity NPC477894
0.7692 Intermediate Similarity NPC470765
0.7692 Intermediate Similarity NPC329657
0.7687 Intermediate Similarity NPC476644
0.7683 Intermediate Similarity NPC102465
0.7682 Intermediate Similarity NPC224491
0.7677 Intermediate Similarity NPC301556
0.7677 Intermediate Similarity NPC471101
0.7677 Intermediate Similarity NPC92293
0.7677 Intermediate Similarity NPC266265
0.7677 Intermediate Similarity NPC270590
0.7676 Intermediate Similarity NPC307139
0.7676 Intermediate Similarity NPC469742
0.7658 Intermediate Similarity NPC473611
0.7647 Intermediate Similarity NPC125106
0.7647 Intermediate Similarity NPC95810
0.7647 Intermediate Similarity NPC476974
0.7647 Intermediate Similarity NPC25768
0.7647 Intermediate Similarity NPC472570
0.7647 Intermediate Similarity NPC95265
0.7647 Intermediate Similarity NPC57628
0.7647 Intermediate Similarity NPC472569
0.7647 Intermediate Similarity NPC163719
0.7647 Intermediate Similarity NPC475122
0.7647 Intermediate Similarity NPC472573
0.7647 Intermediate Similarity NPC70716
0.7647 Intermediate Similarity NPC188865
0.7647 Intermediate Similarity NPC11685
0.7643 Intermediate Similarity NPC473243
0.7643 Intermediate Similarity NPC327962
0.7639 Intermediate Similarity NPC5486
0.7635 Intermediate Similarity NPC48929
0.7635 Intermediate Similarity NPC126516
0.7632 Intermediate Similarity NPC172311
0.7628 Intermediate Similarity NPC91730
0.7625 Intermediate Similarity NPC472807
0.7619 Intermediate Similarity NPC209851
0.7607 Intermediate Similarity NPC471493
0.76 Intermediate Similarity NPC86772
0.76 Intermediate Similarity NPC262324
0.7597 Intermediate Similarity NPC96903
0.7597 Intermediate Similarity NPC472568
0.7597 Intermediate Similarity NPC174982
0.7597 Intermediate Similarity NPC472575
0.7597 Intermediate Similarity NPC472556
0.7597 Intermediate Similarity NPC476973
0.7597 Intermediate Similarity NPC200471
0.7597 Intermediate Similarity NPC472571
0.7597 Intermediate Similarity NPC473088
0.7597 Intermediate Similarity NPC469349
0.7597 Intermediate Similarity NPC158663
0.7597 Intermediate Similarity NPC177940
0.7597 Intermediate Similarity NPC471104
0.7597 Intermediate Similarity NPC29704
0.7597 Intermediate Similarity NPC171525
0.7597 Intermediate Similarity NPC470157
0.7597 Intermediate Similarity NPC470159
0.7597 Intermediate Similarity NPC70403

  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 NPC475404 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
0.7712 Intermediate Similarity NPD7236 Approved
0.7381 Intermediate Similarity NPD7799 Discontinued
0.7286 Intermediate Similarity NPD4198 Discontinued
0.725 Intermediate Similarity NPD7239 Suspended
0.7135 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD7008 Discontinued
0.711 Intermediate Similarity NPD8368 Discontinued
0.7102 Intermediate Similarity NPD8434 Phase 2
0.7092 Intermediate Similarity NPD2629 Approved
0.7042 Intermediate Similarity NPD3317 Approved
0.7039 Intermediate Similarity NPD7961 Discontinued
0.7025 Intermediate Similarity NPD8166 Discontinued
0.7022 Intermediate Similarity NPD8435 Approved
0.6993 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6989 Remote Similarity NPD8407 Phase 2
0.6978 Remote Similarity NPD8485 Approved
0.6927 Remote Similarity NPD8361 Approved
0.6927 Remote Similarity NPD8360 Approved
0.691 Remote Similarity NPD8424 Clinical (unspecified phase)
0.689 Remote Similarity NPD7458 Discontinued
0.6865 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6864 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7058 Phase 2
0.6845 Remote Similarity NPD7057 Phase 3
0.6818 Remote Similarity NPD6765 Approved
0.6818 Remote Similarity NPD6764 Approved
0.6816 Remote Similarity NPD8150 Discontinued
0.6803 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6797 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6747 Remote Similarity NPD6599 Discontinued
0.6726 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6719 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6719 Remote Similarity NPD7874 Approved
0.6713 Remote Similarity NPD7094 Approved
0.6713 Remote Similarity NPD6858 Approved
0.671 Remote Similarity NPD8032 Phase 2
0.6689 Remote Similarity NPD5667 Approved
0.6667 Remote Similarity NPD7435 Discontinued
0.6667 Remote Similarity NPD6010 Discontinued
0.6667 Remote Similarity NPD7741 Discontinued
0.6667 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6648 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6647 Remote Similarity NPD3787 Discontinued
0.6646 Remote Similarity NPD7097 Phase 1
0.6646 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6632 Remote Similarity NPD8320 Phase 1
0.6632 Remote Similarity NPD8319 Approved
0.6624 Remote Similarity NPD6355 Discontinued
0.662 Remote Similarity NPD2067 Discontinued
0.6608 Remote Similarity NPD7075 Discontinued
0.6605 Remote Similarity NPD4628 Phase 3
0.659 Remote Similarity NPD8127 Discontinued
0.6581 Remote Similarity NPD7095 Approved
0.6573 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6557 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6556 Remote Similarity NPD8312 Approved
0.6556 Remote Similarity NPD8313 Approved
0.6549 Remote Similarity NPD2182 Approved
0.6538 Remote Similarity NPD6798 Discontinued
0.6534 Remote Similarity NPD7473 Discontinued
0.6529 Remote Similarity NPD7819 Suspended
0.6507 Remote Similarity NPD690 Clinical (unspecified phase)
0.6503 Remote Similarity NPD7003 Approved
0.65 Remote Similarity NPD7033 Discontinued
0.6497 Remote Similarity NPD6663 Approved
0.6489 Remote Similarity NPD7699 Phase 2
0.6489 Remote Similarity NPD7700 Phase 2
0.6485 Remote Similarity NPD6799 Approved
0.6477 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6801 Discontinued
0.6467 Remote Similarity NPD17 Approved
0.6463 Remote Similarity NPD6190 Approved
0.646 Remote Similarity NPD2438 Suspended
0.6453 Remote Similarity NPD7768 Phase 2
0.6452 Remote Similarity NPD5736 Approved
0.6449 Remote Similarity NPD7798 Approved
0.6446 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6433 Remote Similarity NPD5760 Phase 2
0.6433 Remote Similarity NPD5761 Phase 2
0.6433 Remote Similarity NPD8455 Phase 2
0.6424 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6424 Remote Similarity NPD6652 Clinical (unspecified phase)
0.642 Remote Similarity NPD5763 Approved
0.642 Remote Similarity NPD1471 Phase 3
0.642 Remote Similarity NPD5762 Approved
0.642 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6417 Remote Similarity NPD6534 Approved
0.6417 Remote Similarity NPD6535 Approved
0.6414 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6407 Remote Similarity NPD6273 Approved
0.6404 Remote Similarity NPD3751 Discontinued
0.6398 Remote Similarity NPD7305 Phase 1
0.6395 Remote Similarity NPD3817 Phase 2
0.6395 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6393 Remote Similarity NPD6784 Approved
0.6393 Remote Similarity NPD6785 Approved
0.6392 Remote Similarity NPD7715 Approved
0.6392 Remote Similarity NPD7714 Approved
0.6391 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6391 Remote Similarity NPD3226 Approved
0.6387 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6387 Remote Similarity NPD6085 Phase 2
0.6382 Remote Similarity NPD4807 Approved
0.6382 Remote Similarity NPD4806 Approved
0.6382 Remote Similarity NPD6287 Discontinued
0.6373 Remote Similarity NPD7871 Phase 2
0.6373 Remote Similarity NPD7870 Phase 2
0.6369 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6232 Discontinued
0.6358 Remote Similarity NPD5305 Approved
0.6358 Remote Similarity NPD6100 Approved
0.6358 Remote Similarity NPD5306 Approved
0.6358 Remote Similarity NPD6099 Approved
0.6352 Remote Similarity NPD2979 Phase 3
0.6347 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6343 Remote Similarity NPD5494 Approved
0.6341 Remote Similarity NPD7421 Clinical (unspecified phase)
0.634 Remote Similarity NPD1608 Approved
0.6338 Remote Similarity NPD5048 Discontinued
0.6329 Remote Similarity NPD3764 Approved
0.6321 Remote Similarity NPD7696 Phase 3
0.6321 Remote Similarity NPD7698 Approved
0.6321 Remote Similarity NPD7697 Approved
0.6301 Remote Similarity NPD5402 Approved
0.6291 Remote Similarity NPD3024 Approved
0.6291 Remote Similarity NPD3025 Approved
0.6289 Remote Similarity NPD6233 Phase 2
0.6289 Remote Similarity NPD7713 Phase 3
0.6286 Remote Similarity NPD919 Approved
0.6284 Remote Similarity NPD5951 Approved
0.6283 Remote Similarity NPD8285 Discontinued
0.628 Remote Similarity NPD2897 Discontinued
0.6279 Remote Similarity NPD37 Approved
0.6275 Remote Similarity NPD1281 Approved
0.6272 Remote Similarity NPD5403 Approved
0.6268 Remote Similarity NPD164 Approved
0.6265 Remote Similarity NPD3887 Approved
0.6264 Remote Similarity NPD4966 Approved
0.6264 Remote Similarity NPD4965 Approved
0.6264 Remote Similarity NPD4967 Phase 2
0.6263 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6258 Remote Similarity NPD2796 Approved
0.625 Remote Similarity NPD6780 Approved
0.625 Remote Similarity NPD5126 Approved
0.625 Remote Similarity NPD6777 Approved
0.625 Remote Similarity NPD6782 Approved
0.625 Remote Similarity NPD6776 Approved
0.625 Remote Similarity NPD4060 Phase 1
0.625 Remote Similarity NPD6781 Approved
0.625 Remote Similarity NPD5401 Approved
0.625 Remote Similarity NPD7422 Clinical (unspecified phase)
0.625 Remote Similarity NPD6778 Approved
0.625 Remote Similarity NPD6779 Approved
0.625 Remote Similarity NPD5125 Phase 3
0.6236 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6232 Remote Similarity NPD1989 Approved
0.6226 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6222 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6222 Remote Similarity NPD7228 Approved
0.6221 Remote Similarity NPD6677 Suspended
0.6221 Remote Similarity NPD7411 Suspended
0.622 Remote Similarity NPD2346 Discontinued
0.6215 Remote Similarity NPD6959 Discontinued
0.6209 Remote Similarity NPD4136 Approved
0.6209 Remote Similarity NPD4135 Approved
0.6209 Remote Similarity NPD4106 Approved
0.6209 Remote Similarity NPD3026 Approved
0.6209 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6209 Remote Similarity NPD3023 Approved
0.6205 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6205 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6205 Remote Similarity NPD4110 Phase 3
0.6201 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6201 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6201 Remote Similarity NPD6166 Phase 2
0.6196 Remote Similarity NPD2971 Approved
0.6196 Remote Similarity NPD2799 Discontinued
0.6196 Remote Similarity NPD2968 Approved
0.6193 Remote Similarity NPD6234 Discontinued
0.6193 Remote Similarity NPD7701 Phase 2
0.619 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6188 Remote Similarity NPD8404 Phase 2
0.6188 Remote Similarity NPD5844 Phase 1
0.6182 Remote Similarity NPD4534 Discontinued
0.6181 Remote Similarity NPD7801 Approved
0.6163 Remote Similarity NPD4380 Phase 2
0.6159 Remote Similarity NPD2531 Phase 2
0.6159 Remote Similarity NPD5404 Approved
0.6159 Remote Similarity NPD5406 Approved
0.6159 Remote Similarity NPD7610 Discontinued
0.6159 Remote Similarity NPD5405 Approved
0.6159 Remote Similarity NPD5408 Approved
0.6154 Remote Similarity NPD2532 Approved
0.6154 Remote Similarity NPD1283 Approved
0.6154 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6154 Remote Similarity NPD2534 Approved
0.6154 Remote Similarity NPD2533 Approved
0.615 Remote Similarity NPD8462 Phase 1
0.6149 Remote Similarity NPD5119 Approved
0.6149 Remote Similarity NPD4140 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