Structure

Physi-Chem Properties

Molecular Weight:  937.35
Volume:  934.941
LogP:  4.388
LogD:  2.296
LogS:  -4.354
# Rotatable Bonds:  19
TPSA:  233.43
# H-Bond Aceptor:  17
# H-Bond Donor:  2
# Rings:  7
# Heavy Atoms:  17

MedChem Properties

QED Drug-Likeness Score:  0.14
Synthetic Accessibility Score:  6.146
Fsp3:  0.451
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.381
MDCK Permeability:  0.00011298355093458667
Pgp-inhibitor:  1.0
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.069
20% Bioavailability (F20%):  0.998
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.086
Plasma Protein Binding (PPB):  88.05130004882812%
Volume Distribution (VD):  2.245
Pgp-substrate:  8.064356803894043%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.012
CYP2C19-inhibitor:  0.077
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.531
CYP2C9-substrate:  0.017
CYP2D6-inhibitor:  0.021
CYP2D6-substrate:  0.041
CYP3A4-inhibitor:  0.694
CYP3A4-substrate:  0.744

ADMET: Excretion

Clearance (CL):  4.409
Half-life (T1/2):  0.005

ADMET: Toxicity

hERG Blockers:  0.182
Human Hepatotoxicity (H-HT):  0.995
Drug-inuced Liver Injury (DILI):  0.992
AMES Toxicity:  0.08
Rat Oral Acute Toxicity:  0.869
Maximum Recommended Daily Dose:  0.843
Skin Sensitization:  0.234
Carcinogencity:  0.046
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.959

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

  Natural Product: NPC473490

Natural Product ID:  NPC473490
Common Name*:   WQUSBTYBTBXULJ-YUHJQDCISA-N
IUPAC Name:   n.a.
Synonyms:   2',7-Diacetyltaxol
Standard InCHIKey:  WQUSBTYBTBXULJ-YUHJQDCISA-N
Standard InCHI:  InChI=1S/C51H55NO16/c1-27-35(66-47(60)41(65-30(4)55)39(32-18-12-9-13-19-32)52-45(58)33-20-14-10-15-21-33)25-51(61)44(67-46(59)34-22-16-11-17-23-34)42-49(8,43(57)40(64-29(3)54)38(27)48(51,6)7)36(63-28(2)53)24-37-50(42,26-62-37)68-31(5)56/h9-23,35-37,39-42,44,61H,24-26H2,1-8H3,(H,52,58)/t35-,36-,37+,39-,40+,41+,42-,44-,49+,50-,51+/m0/s1
SMILES:  CC(=O)O[C@H]([C@H](c1ccccc1)N=C(c1ccccc1)O)C(=O)O[C@H]1C[C@@]2(O)[C@@H](OC(=O)c3ccccc3)[C@@H]3[C@@]4(CO[C@@H]4C[C@@H]([C@]3(C(=O)[C@@H](C(=C1C)C2(C)C)OC(=O)C)C)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL443371
PubChem CID:   44593344
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0000676] Taxanes and derivatives

*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
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[1955887]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[2878063]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[7130988]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota bark n.a. n.a. PMID[7623034]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27064 Taxus brevifolia Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27064 Taxus brevifolia Species Taxaceae 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
NPT91 Cell Line KB Homo sapiens ED50 = 2.0 10'-1 ug/ml PMID[500923]
NPT168 Cell Line P388 Mus musculus T/C = 100.0 % PMID[500923]
NPT168 Cell Line P388 Mus musculus T/C = 105.0 % PMID[500923]
NPT168 Cell Line P388 Mus musculus T/C = 104.0 % PMID[500923]
NPT91 Cell Line KB Homo sapiens ED50 = 3.0 10'-2 ug/ml PMID[500924]
NPT91 Cell Line KB Homo sapiens Activity = 16.0 % PMID[500925]
NPT2 Others Unspecified ED50 = 0.03 ug ml-1 PMID[500925]

☑ 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 NPC473490 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
0.9886 High Similarity NPC473558
0.983 High Similarity NPC208553
0.983 High Similarity NPC471606
0.983 High Similarity NPC181964
0.9773 High Similarity NPC242662
0.9773 High Similarity NPC191193
0.9773 High Similarity NPC321072
0.9773 High Similarity NPC215892
0.9602 High Similarity NPC33372
0.9602 High Similarity NPC67246
0.956 High Similarity NPC116862
0.9545 High Similarity NPC453583
0.9545 High Similarity NPC473300
0.9545 High Similarity NPC475336
0.9505 High Similarity NPC289383
0.9435 High Similarity NPC324251
0.9435 High Similarity NPC473400
0.9435 High Similarity NPC306001
0.9435 High Similarity NPC471754
0.9435 High Similarity NPC317882
0.9435 High Similarity NPC471629
0.9435 High Similarity NPC206211
0.9435 High Similarity NPC275170
0.9432 High Similarity NPC327699
0.9396 High Similarity NPC472391
0.9341 High Similarity NPC472392
0.927 High Similarity NPC471623
0.9235 High Similarity NPC472375
0.8763 High Similarity NPC36607
0.8136 Intermediate Similarity NPC472393
0.8125 Intermediate Similarity NPC155329
0.8125 Intermediate Similarity NPC259144
0.8125 Intermediate Similarity NPC114357
0.809 Intermediate Similarity NPC471102
0.8079 Intermediate Similarity NPC217091
0.8068 Intermediate Similarity NPC219419
0.8068 Intermediate Similarity NPC11588
0.8068 Intermediate Similarity NPC229545
0.8068 Intermediate Similarity NPC248265
0.8068 Intermediate Similarity NPC134685
0.8023 Intermediate Similarity NPC282239
0.8023 Intermediate Similarity NPC228204
0.8023 Intermediate Similarity NPC26033
0.7978 Intermediate Similarity NPC106895
0.7967 Intermediate Similarity NPC471493
0.7966 Intermediate Similarity NPC473414
0.7966 Intermediate Similarity NPC158333
0.7966 Intermediate Similarity NPC256142
0.7966 Intermediate Similarity NPC265395
0.7966 Intermediate Similarity NPC472030
0.7966 Intermediate Similarity NPC77719
0.7966 Intermediate Similarity NPC249471
0.7966 Intermediate Similarity NPC257213
0.7966 Intermediate Similarity NPC1173
0.7966 Intermediate Similarity NPC472022
0.7966 Intermediate Similarity NPC304876
0.7966 Intermediate Similarity NPC237549
0.7966 Intermediate Similarity NPC472005
0.7966 Intermediate Similarity NPC242262
0.7955 Intermediate Similarity NPC197037
0.7921 Intermediate Similarity NPC112523
0.7921 Intermediate Similarity NPC473670
0.7921 Intermediate Similarity NPC21410
0.7921 Intermediate Similarity NPC114410
0.7901 Intermediate Similarity NPC476077
0.7898 Intermediate Similarity NPC7095
0.7898 Intermediate Similarity NPC112216
0.7898 Intermediate Similarity NPC91730
0.7853 Intermediate Similarity NPC306799
0.7853 Intermediate Similarity NPC51602
0.7853 Intermediate Similarity NPC101043
0.7841 Intermediate Similarity NPC60509
0.7841 Intermediate Similarity NPC250046
0.7841 Intermediate Similarity NPC81698
0.7833 Intermediate Similarity NPC469771
0.7821 Intermediate Similarity NPC472549
0.7797 Intermediate Similarity NPC165260
0.7797 Intermediate Similarity NPC254558
0.7797 Intermediate Similarity NPC161239
0.7797 Intermediate Similarity NPC198455
0.7784 Intermediate Similarity NPC217918
0.7771 Intermediate Similarity NPC127857
0.7753 Intermediate Similarity NPC471103
0.7753 Intermediate Similarity NPC470153
0.7722 Intermediate Similarity NPC473611
0.7709 Intermediate Similarity NPC472548
0.7709 Intermediate Similarity NPC477905
0.7697 Intermediate Similarity NPC470245
0.7697 Intermediate Similarity NPC473214
0.764 Intermediate Similarity NPC473215
0.764 Intermediate Similarity NPC476975
0.7627 Intermediate Similarity NPC474935
0.7624 Intermediate Similarity NPC132599
0.7624 Intermediate Similarity NPC469730
0.7624 Intermediate Similarity NPC473632
0.7614 Intermediate Similarity NPC38696
0.7584 Intermediate Similarity NPC281717
0.7571 Intermediate Similarity NPC471107
0.7571 Intermediate Similarity NPC471100
0.7553 Intermediate Similarity NPC102465
0.7542 Intermediate Similarity NPC270590
0.7542 Intermediate Similarity NPC92293
0.7542 Intermediate Similarity NPC301556
0.7542 Intermediate Similarity NPC471101
0.7542 Intermediate Similarity NPC266265
0.754 Intermediate Similarity NPC30171
0.7527 Intermediate Similarity NPC295408
0.7527 Intermediate Similarity NPC150893
0.7527 Intermediate Similarity NPC329960
0.7514 Intermediate Similarity NPC472573
0.7514 Intermediate Similarity NPC95265
0.7514 Intermediate Similarity NPC80895
0.7514 Intermediate Similarity NPC188865
0.7514 Intermediate Similarity NPC471912
0.7514 Intermediate Similarity NPC25768
0.7514 Intermediate Similarity NPC470231
0.7514 Intermediate Similarity NPC11685
0.7514 Intermediate Similarity NPC472569
0.7514 Intermediate Similarity NPC70716
0.7514 Intermediate Similarity NPC125106
0.7514 Intermediate Similarity NPC95810
0.7514 Intermediate Similarity NPC476974
0.7514 Intermediate Similarity NPC57628
0.7514 Intermediate Similarity NPC163719
0.7514 Intermediate Similarity NPC472570
0.7513 Intermediate Similarity NPC477466
0.7513 Intermediate Similarity NPC477471
0.7513 Intermediate Similarity NPC278272
0.7513 Intermediate Similarity NPC120667
0.7513 Intermediate Similarity NPC477469
0.7513 Intermediate Similarity NPC477473
0.7512 Intermediate Similarity NPC315889
0.75 Intermediate Similarity NPC34012
0.75 Intermediate Similarity NPC182869
0.7472 Intermediate Similarity NPC184817
0.7472 Intermediate Similarity NPC473088
0.7472 Intermediate Similarity NPC171525
0.7472 Intermediate Similarity NPC472568
0.7472 Intermediate Similarity NPC476973
0.7472 Intermediate Similarity NPC472575
0.7472 Intermediate Similarity NPC301946
0.7472 Intermediate Similarity NPC96903
0.7472 Intermediate Similarity NPC177940
0.7472 Intermediate Similarity NPC472571
0.7472 Intermediate Similarity NPC200471
0.7472 Intermediate Similarity NPC472556
0.7472 Intermediate Similarity NPC174982
0.7472 Intermediate Similarity NPC277053
0.7472 Intermediate Similarity NPC471104
0.7472 Intermediate Similarity NPC470159
0.7472 Intermediate Similarity NPC70403
0.7472 Intermediate Similarity NPC470157
0.7472 Intermediate Similarity NPC158663
0.7472 Intermediate Similarity NPC29704
0.7472 Intermediate Similarity NPC472572
0.7472 Intermediate Similarity NPC469349
0.7461 Intermediate Similarity NPC475649
0.7451 Intermediate Similarity NPC314941
0.7444 Intermediate Similarity NPC475648
0.7443 Intermediate Similarity NPC213567
0.7429 Intermediate Similarity NPC472371
0.7429 Intermediate Similarity NPC472395
0.7416 Intermediate Similarity NPC470152
0.7416 Intermediate Similarity NPC241951
0.7416 Intermediate Similarity NPC475759
0.7416 Intermediate Similarity NPC475122
0.7409 Intermediate Similarity NPC475345
0.7405 Intermediate Similarity NPC469399
0.7403 Intermediate Similarity NPC31829
0.7401 Intermediate Similarity NPC472546
0.7396 Intermediate Similarity NPC469421
0.7394 Intermediate Similarity NPC471134
0.7391 Intermediate Similarity NPC11410
0.7385 Intermediate Similarity NPC96801
0.7385 Intermediate Similarity NPC150698
0.738 Intermediate Similarity NPC253738
0.738 Intermediate Similarity NPC55744
0.7374 Intermediate Similarity NPC473541
0.7368 Intermediate Similarity NPC469420
0.736 Intermediate Similarity NPC477894
0.736 Intermediate Similarity NPC191082
0.736 Intermediate Similarity NPC177340
0.736 Intermediate Similarity NPC147217
0.736 Intermediate Similarity NPC246480
0.736 Intermediate Similarity NPC473673
0.736 Intermediate Similarity NPC475429
0.736 Intermediate Similarity NPC270498
0.736 Intermediate Similarity NPC139067
0.736 Intermediate Similarity NPC163087
0.7351 Intermediate Similarity NPC469417
0.7345 Intermediate Similarity NPC224491
0.7345 Intermediate Similarity NPC16912
0.734 Intermediate Similarity NPC66193
0.7337 Intermediate Similarity NPC251139
0.7333 Intermediate Similarity NPC94602
0.7327 Intermediate Similarity NPC475601
0.7318 Intermediate Similarity NPC67777
0.7318 Intermediate Similarity NPC260194
0.7318 Intermediate Similarity NPC51314
0.7309 Intermediate Similarity NPC253482

  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 NPC473490 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
0.983 High Similarity NPD8485 Approved
0.9665 High Similarity NPD8486 Clinical (unspecified phase)
0.927 High Similarity NPD8360 Approved
0.927 High Similarity NPD8361 Approved
0.927 High Similarity NPD8435 Approved
0.8944 High Similarity NPD8424 Clinical (unspecified phase)
0.8771 High Similarity NPD8368 Discontinued
0.8729 High Similarity NPD8407 Phase 2
0.8297 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.8168 Intermediate Similarity NPD8404 Phase 2
0.815 Intermediate Similarity NPD8462 Phase 1
0.7487 Intermediate Similarity NPD8150 Discontinued
0.7451 Intermediate Similarity NPD8320 Phase 1
0.7451 Intermediate Similarity NPD8319 Approved
0.744 Intermediate Similarity NPD7874 Approved
0.744 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7398 Intermediate Similarity NPD8434 Phase 2
0.7336 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD7801 Approved
0.7241 Intermediate Similarity NPD7699 Phase 2
0.7241 Intermediate Similarity NPD7700 Phase 2
0.7225 Intermediate Similarity NPD8151 Discontinued
0.7178 Intermediate Similarity NPD6535 Approved
0.7178 Intermediate Similarity NPD6534 Approved
0.7115 Intermediate Similarity NPD7871 Phase 2
0.7115 Intermediate Similarity NPD7870 Phase 2
0.7095 Intermediate Similarity NPD7701 Phase 2
0.7067 Intermediate Similarity NPD7696 Phase 3
0.7067 Intermediate Similarity NPD7697 Approved
0.7067 Intermediate Similarity NPD7698 Approved
0.7026 Intermediate Similarity NPD7799 Discontinued
0.7019 Intermediate Similarity NPD6823 Phase 2
0.7005 Intermediate Similarity NPD6777 Approved
0.7005 Intermediate Similarity NPD6779 Approved
0.7005 Intermediate Similarity NPD6776 Approved
0.7005 Intermediate Similarity NPD6781 Approved
0.7005 Intermediate Similarity NPD6782 Approved
0.7005 Intermediate Similarity NPD6780 Approved
0.7005 Intermediate Similarity NPD6778 Approved
0.6986 Remote Similarity NPD7435 Discontinued
0.697 Remote Similarity NPD5030 Phase 2
0.694 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6935 Remote Similarity NPD5034 Approved
0.6935 Remote Similarity NPD5028 Approved
0.6935 Remote Similarity NPD4955 Approved
0.6935 Remote Similarity NPD36 Approved
0.6935 Remote Similarity NPD5026 Approved
0.6935 Remote Similarity NPD4954 Approved
0.6926 Remote Similarity NPD8468 Phase 2
0.6915 Remote Similarity NPD5036 Approved
0.6902 Remote Similarity NPD7236 Approved
0.6898 Remote Similarity NPD7239 Suspended
0.6881 Remote Similarity NPD5037 Approved
0.6881 Remote Similarity NPD5038 Approved
0.684 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6834 Remote Similarity NPD3823 Discontinued
0.6829 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6825 Remote Similarity NPD7497 Discontinued
0.6759 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6759 Remote Similarity NPD7783 Phase 2
0.6721 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6716 Remote Similarity NPD5029 Approved
0.6716 Remote Similarity NPD5031 Approved
0.6716 Remote Similarity NPD5027 Approved
0.6711 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6711 Remote Similarity NPD8059 Phase 3
0.6699 Remote Similarity NPD7282 Approved
0.6667 Remote Similarity NPD5968 Phase 3
0.665 Remote Similarity NPD6836 Approved
0.665 Remote Similarity NPD5035 Approved
0.6649 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7907 Approved
0.6585 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6583 Remote Similarity NPD7997 Clinical (unspecified phase)
0.6574 Remote Similarity NPD6973 Clinical (unspecified phase)
0.657 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6557 Remote Similarity NPD8285 Discontinued
0.6555 Remote Similarity NPD6212 Phase 3
0.6555 Remote Similarity NPD6213 Phase 3
0.6555 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6546 Remote Similarity NPD7972 Discontinued
0.6507 Remote Similarity NPD8146 Phase 2
0.6507 Remote Similarity NPD3819 Phase 2
0.6488 Remote Similarity NPD8312 Approved
0.6488 Remote Similarity NPD8313 Approved
0.648 Remote Similarity NPD7058 Phase 2
0.648 Remote Similarity NPD7057 Phase 3
0.6479 Remote Similarity NPD7811 Phase 3
0.6479 Remote Similarity NPD7810 Phase 3
0.6479 Remote Similarity NPD7565 Approved
0.6478 Remote Similarity NPD8067 Phase 3
0.6465 Remote Similarity NPD6746 Phase 2
0.645 Remote Similarity NPD5242 Approved
0.6449 Remote Similarity NPD4914 Approved
0.6447 Remote Similarity NPD7075 Discontinued
0.6439 Remote Similarity NPD5032 Approved
0.6436 Remote Similarity NPD2575 Approved
0.6425 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6422 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6418 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6416 Remote Similarity NPD8366 Approved
0.6402 Remote Similarity NPD6190 Approved
0.64 Remote Similarity NPD4665 Approved
0.6398 Remote Similarity NPD4466 Phase 1
0.6386 Remote Similarity NPD7473 Discontinued
0.6378 Remote Similarity NPD7460 Discontinued
0.6378 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6376 Remote Similarity NPD8491 Approved
0.6368 Remote Similarity NPD3300 Phase 2
0.636 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6355 Remote Similarity NPD7177 Discontinued
0.6349 Remote Similarity NPD8166 Discontinued
0.6343 Remote Similarity NPD3452 Approved
0.6343 Remote Similarity NPD3450 Approved
0.6343 Remote Similarity NPD2494 Approved
0.6343 Remote Similarity NPD2493 Approved
0.6339 Remote Similarity NPD7713 Phase 3
0.633 Remote Similarity NPD4583 Approved
0.633 Remote Similarity NPD4582 Approved
0.6327 Remote Similarity NPD4111 Phase 1
0.6327 Remote Similarity NPD7029 Discontinued
0.6326 Remote Similarity NPD5544 Approved
0.632 Remote Similarity NPD7654 Discontinued
0.6313 Remote Similarity NPD4386 Approved
0.6313 Remote Similarity NPD4387 Approved
0.6308 Remote Similarity NPD6599 Discontinued
0.6308 Remote Similarity NPD2973 Approved
0.6308 Remote Similarity NPD2975 Approved
0.6308 Remote Similarity NPD2974 Approved
0.6304 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6296 Remote Similarity NPD4580 Approved
0.6295 Remote Similarity NPD7930 Approved
0.6293 Remote Similarity NPD5441 Clinical (unspecified phase)
0.6284 Remote Similarity NPD4004 Approved
0.6284 Remote Similarity NPD4002 Approved
0.6276 Remote Similarity NPD6385 Approved
0.6276 Remote Similarity NPD6386 Approved
0.6275 Remote Similarity NPD3751 Discontinued
0.6273 Remote Similarity NPD7583 Approved
0.6271 Remote Similarity NPD7048 Phase 3
0.6264 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6263 Remote Similarity NPD5402 Approved
0.6262 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6256 Remote Similarity NPD7458 Discontinued
0.6256 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6256 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6256 Remote Similarity NPD6166 Phase 2
0.6256 Remote Similarity NPD3455 Phase 2
0.625 Remote Similarity NPD7715 Approved
0.625 Remote Similarity NPD7961 Discontinued
0.625 Remote Similarity NPD7546 Discontinued
0.625 Remote Similarity NPD7237 Clinical (unspecified phase)
0.625 Remote Similarity NPD7714 Approved
0.6245 Remote Similarity NPD6997 Phase 2
0.6244 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6244 Remote Similarity NPD6801 Discontinued
0.6244 Remote Similarity NPD7585 Approved
0.6244 Remote Similarity NPD5844 Phase 1
0.6238 Remote Similarity NPD7315 Approved
0.6238 Remote Similarity NPD6232 Discontinued
0.6237 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6236 Remote Similarity NPD6287 Discontinued
0.6232 Remote Similarity NPD8014 Clinical (unspecified phase)
0.6231 Remote Similarity NPD4868 Clinical (unspecified phase)
0.623 Remote Similarity NPD5952 Clinical (unspecified phase)
0.623 Remote Similarity NPD7008 Discontinued
0.6227 Remote Similarity NPD7999 Approved
0.6224 Remote Similarity NPD6502 Phase 2
0.6216 Remote Similarity NPD5119 Approved
0.6216 Remote Similarity NPD5121 Approved
0.6216 Remote Similarity NPD5120 Approved
0.6215 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6212 Remote Similarity NPD7819 Suspended
0.6209 Remote Similarity NPD7693 Approved
0.6204 Remote Similarity NPD4975 Approved
0.6204 Remote Similarity NPD4974 Approved
0.6202 Remote Similarity NPD7808 Phase 3
0.6202 Remote Similarity NPD7962 Phase 2
0.62 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6199 Remote Similarity NPD7584 Approved
0.6193 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6184 Remote Similarity NPD7959 Clinical (unspecified phase)
0.6181 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6181 Remote Similarity NPD3817 Phase 2
0.6178 Remote Similarity NPD3400 Discontinued
0.6178 Remote Similarity NPD4628 Phase 3
0.6176 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6176 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6176 Remote Similarity NPD6894 Phase 1
0.6176 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6175 Remote Similarity NPD5201 Approved
0.6175 Remote Similarity NPD5608 Approved
0.6175 Remote Similarity NPD5609 Approved
0.6175 Remote Similarity NPD5203 Approved
0.6175 Remote Similarity NPD4617 Approved
0.6175 Remote Similarity NPD4620 Approved
0.6175 Remote Similarity NPD6874 Approved
0.6172 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6169 Remote Similarity NPD7793 Clinical (unspecified phase)
0.6164 Remote Similarity NPD3057 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