Structure

Physi-Chem Properties

Molecular Weight:  614.37
Volume:  619.222
LogP:  1.904
LogD:  2.192
LogS:  -3.791
# Rotatable Bonds:  9
TPSA:  178.53
# H-Bond Aceptor:  11
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.185
Synthetic Accessibility Score:  5.5
Fsp3:  0.875
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:  -5.68
MDCK Permeability:  7.742695743218064e-05
Pgp-inhibitor:  0.989
Pgp-substrate:  0.963
Human Intestinal Absorption (HIA):  0.978
20% Bioavailability (F20%):  0.051
30% Bioavailability (F30%):  0.88

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.059
Plasma Protein Binding (PPB):  88.14763641357422%
Volume Distribution (VD):  0.583
Pgp-substrate:  10.777185440063477%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.117
CYP2C19-inhibitor:  0.004
CYP2C19-substrate:  0.285
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.036
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.078
CYP3A4-inhibitor:  0.022
CYP3A4-substrate:  0.06

ADMET: Excretion

Clearance (CL):  0.946
Half-life (T1/2):  0.838

ADMET: Toxicity

hERG Blockers:  0.031
Human Hepatotoxicity (H-HT):  0.097
Drug-inuced Liver Injury (DILI):  0.011
AMES Toxicity:  0.072
Rat Oral Acute Toxicity:  0.105
Maximum Recommended Daily Dose:  0.01
Skin Sensitization:  0.939
Carcinogencity:  0.019
Eye Corrosion:  0.004
Eye Irritation:  0.038
Respiratory Toxicity:  0.798

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

  Natural Product: NPC64348

Natural Product ID:  NPC64348
Common Name*:   6-O-[Beta-D-Glucopyranosyl]-(1->4)-Alpha-L-Rhamnopyranosyl-(13E)-Cleroda-3,13-Dien-15-Ol
IUPAC Name:   (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5R,6R)-6-[[(1S,3R,4S,4aR,8aR)-4-[(E)-5-hydroxy-3-methylpent-3-enyl]-3,4,8,8a-tetramethyl-1,2,3,4a,5,6-hexahydronaphthalen-1-yl]oxy]-4,5-dihydroxy-2-methyloxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  BGZWGOQCGUPNJK-FULVCJEYSA-N
Standard InCHI:  InChI=1S/C32H54O11/c1-16(11-13-33)10-12-31(5)18(3)14-22(32(6)17(2)8-7-9-21(31)32)42-29-27(39)25(37)28(19(4)40-29)43-30-26(38)24(36)23(35)20(15-34)41-30/h8,11,18-30,33-39H,7,9-10,12-15H2,1-6H3/b16-11+/t18-,19+,20-,21-,22+,23-,24+,25+,26-,27-,28+,29+,30+,31+,32+/m1/s1
SMILES:  OC/C=C(/CC[C@@]1(C)[C@H](C)C[C@@H]([C@@]2([C@@H]1CCC=C2C)C)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL376213
PubChem CID:   16109823
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001755] Diterpene glycosides

*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
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[11032480]
NPO32662 dicranopteris dichotoma Species Gleicheniaceae Eukaryota n.a. n.a. n.a. PMID[17315963]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[6821187]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6671 Ulva conglobata Species Ulvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8186 Ocotea minarum Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2384 Ircinia ramosa Species Irciniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7705 Navanax inermis Species Aglajidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7925 Asparagus officinalis Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6938 Astragalus dissectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6671 Ulva conglobata Species Ulvaceae 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
NPT1452 Cell Line C8166 Homo sapiens CC50 = 325330.0 nM PMID[534591]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 85060.0 nM PMID[534591]
NPT2 Others Unspecified Ratio CC50/EC50 > 3.82 n.a. PMID[534591]

☑ 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 NPC64348 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
0.9583 High Similarity NPC470768
0.9479 High Similarity NPC162354
0.9381 High Similarity NPC75608
0.9362 High Similarity NPC240372
0.9286 High Similarity NPC470763
0.9286 High Similarity NPC470767
0.9255 High Similarity NPC90583
0.9247 High Similarity NPC477927
0.9247 High Similarity NPC72817
0.9184 High Similarity NPC203354
0.9184 High Similarity NPC110656
0.9184 High Similarity NPC473127
0.9091 High Similarity NPC472898
0.9091 High Similarity NPC472899
0.9091 High Similarity NPC472900
0.9082 High Similarity NPC473123
0.9082 High Similarity NPC473198
0.9082 High Similarity NPC473124
0.9072 High Similarity NPC470434
0.9072 High Similarity NPC117714
0.9072 High Similarity NPC263756
0.9043 High Similarity NPC305160
0.9032 High Similarity NPC302584
0.9 High Similarity NPC281939
0.9 High Similarity NPC231340
0.899 High Similarity NPC93352
0.899 High Similarity NPC109792
0.899 High Similarity NPC187400
0.899 High Similarity NPC221562
0.899 High Similarity NPC54521
0.899 High Similarity NPC57065
0.899 High Similarity NPC470885
0.898 High Similarity NPC76497
0.898 High Similarity NPC256133
0.898 High Similarity NPC30289
0.898 High Similarity NPC213674
0.8969 High Similarity NPC469942
0.8911 High Similarity NPC472897
0.8911 High Similarity NPC472896
0.89 High Similarity NPC242748
0.8889 High Similarity NPC99627
0.8889 High Similarity NPC123796
0.8889 High Similarity NPC473129
0.8866 High Similarity NPC477928
0.8824 High Similarity NPC157530
0.8824 High Similarity NPC14630
0.8824 High Similarity NPC250089
0.8812 High Similarity NPC257964
0.8812 High Similarity NPC78034
0.8812 High Similarity NPC33053
0.8812 High Similarity NPC472390
0.8812 High Similarity NPC190395
0.88 High Similarity NPC473734
0.88 High Similarity NPC471434
0.88 High Similarity NPC148603
0.88 High Similarity NPC173583
0.88 High Similarity NPC471435
0.88 High Similarity NPC230948
0.8788 High Similarity NPC312553
0.8788 High Similarity NPC159036
0.8788 High Similarity NPC272015
0.8788 High Similarity NPC136816
0.8788 High Similarity NPC288694
0.8776 High Similarity NPC7341
0.8776 High Similarity NPC473200
0.8763 High Similarity NPC243728
0.8763 High Similarity NPC473890
0.8738 High Similarity NPC141433
0.8725 High Similarity NPC126147
0.8713 High Similarity NPC473923
0.8713 High Similarity NPC138057
0.8713 High Similarity NPC309448
0.8713 High Similarity NPC473476
0.8713 High Similarity NPC173859
0.8713 High Similarity NPC470512
0.87 High Similarity NPC211879
0.87 High Similarity NPC189852
0.87 High Similarity NPC8039
0.87 High Similarity NPC157659
0.87 High Similarity NPC31907
0.87 High Similarity NPC245280
0.87 High Similarity NPC155010
0.87 High Similarity NPC16573
0.87 High Similarity NPC473020
0.87 High Similarity NPC16520
0.87 High Similarity NPC286969
0.87 High Similarity NPC472252
0.87 High Similarity NPC114874
0.87 High Similarity NPC131479
0.87 High Similarity NPC120123
0.8687 High Similarity NPC129372
0.8687 High Similarity NPC4831
0.8687 High Similarity NPC160734
0.8687 High Similarity NPC472023
0.8687 High Similarity NPC309425
0.8687 High Similarity NPC47566
0.8687 High Similarity NPC88000
0.8679 High Similarity NPC146652
0.8673 High Similarity NPC234287
0.8673 High Similarity NPC158088
0.8673 High Similarity NPC280825
0.8667 High Similarity NPC307642
0.8654 High Similarity NPC473021
0.8654 High Similarity NPC472987
0.8641 High Similarity NPC195116
0.8641 High Similarity NPC221110
0.8641 High Similarity NPC180459
0.8641 High Similarity NPC285253
0.8641 High Similarity NPC302057
0.8641 High Similarity NPC472901
0.8627 High Similarity NPC473469
0.8614 High Similarity NPC165033
0.8614 High Similarity NPC273879
0.8586 High Similarity NPC91497
0.8586 High Similarity NPC473790
0.8586 High Similarity NPC282669
0.8586 High Similarity NPC471242
0.8571 High Similarity NPC216595
0.8571 High Similarity NPC473567
0.8558 High Similarity NPC65155
0.8558 High Similarity NPC191439
0.8558 High Similarity NPC472717
0.8558 High Similarity NPC103627
0.8558 High Similarity NPC170974
0.8557 High Similarity NPC476894
0.8544 High Similarity NPC7213
0.8544 High Similarity NPC235824
0.8544 High Similarity NPC476541
0.8544 High Similarity NPC476538
0.8544 High Similarity NPC476539
0.8544 High Similarity NPC476540
0.8544 High Similarity NPC38376
0.8544 High Similarity NPC80210
0.8542 High Similarity NPC91654
0.8542 High Similarity NPC474792
0.8542 High Similarity NPC67398
0.8529 High Similarity NPC208594
0.8529 High Similarity NPC152584
0.8529 High Similarity NPC474569
0.8529 High Similarity NPC269627
0.8529 High Similarity NPC181845
0.8529 High Similarity NPC160816
0.8529 High Similarity NPC194842
0.8529 High Similarity NPC208477
0.8529 High Similarity NPC127801
0.8529 High Similarity NPC69737
0.8515 High Similarity NPC213190
0.85 High Similarity NPC21568
0.85 High Similarity NPC285231
0.85 High Similarity NPC267510
0.8491 Intermediate Similarity NPC51154
0.8485 Intermediate Similarity NPC476895
0.8476 Intermediate Similarity NPC157474
0.8476 Intermediate Similarity NPC13190
0.8476 Intermediate Similarity NPC235841
0.8476 Intermediate Similarity NPC297208
0.8476 Intermediate Similarity NPC108748
0.8476 Intermediate Similarity NPC30397
0.8476 Intermediate Similarity NPC114188
0.8476 Intermediate Similarity NPC110494
0.8476 Intermediate Similarity NPC472715
0.8476 Intermediate Similarity NPC211798
0.8476 Intermediate Similarity NPC197231
0.8476 Intermediate Similarity NPC473481
0.8469 Intermediate Similarity NPC207617
0.8462 Intermediate Similarity NPC306131
0.8462 Intermediate Similarity NPC473318
0.8462 Intermediate Similarity NPC473328
0.8462 Intermediate Similarity NPC28844
0.8462 Intermediate Similarity NPC477027
0.8462 Intermediate Similarity NPC477026
0.8462 Intermediate Similarity NPC475670
0.8462 Intermediate Similarity NPC70204
0.8454 Intermediate Similarity NPC96736
0.8454 Intermediate Similarity NPC178949
0.8454 Intermediate Similarity NPC211238
0.8447 Intermediate Similarity NPC94272
0.8447 Intermediate Similarity NPC305423
0.8447 Intermediate Similarity NPC14946
0.8447 Intermediate Similarity NPC230507
0.8447 Intermediate Similarity NPC161676
0.8447 Intermediate Similarity NPC208650
0.8447 Intermediate Similarity NPC234160
0.8447 Intermediate Similarity NPC470432
0.8447 Intermediate Similarity NPC226642
0.8447 Intermediate Similarity NPC113044
0.8447 Intermediate Similarity NPC283829
0.8447 Intermediate Similarity NPC181467
0.8447 Intermediate Similarity NPC476594
0.8447 Intermediate Similarity NPC14704
0.8447 Intermediate Similarity NPC63368
0.8431 Intermediate Similarity NPC152966
0.8426 Intermediate Similarity NPC471547
0.8421 Intermediate Similarity NPC477917
0.8416 Intermediate Similarity NPC470571
0.8396 Intermediate Similarity NPC477050
0.8396 Intermediate Similarity NPC472716
0.8396 Intermediate Similarity NPC174836
0.8396 Intermediate Similarity NPC476305
0.8396 Intermediate Similarity NPC231797

  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 NPC64348 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
0.7965 Intermediate Similarity NPD8033 Approved
0.7876 Intermediate Similarity NPD8377 Approved
0.7876 Intermediate Similarity NPD8294 Approved
0.7807 Intermediate Similarity NPD8378 Approved
0.7807 Intermediate Similarity NPD8380 Approved
0.7807 Intermediate Similarity NPD8379 Approved
0.7807 Intermediate Similarity NPD8296 Approved
0.7807 Intermediate Similarity NPD8335 Approved
0.7778 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7699 Intermediate Similarity NPD7327 Approved
0.7699 Intermediate Similarity NPD7328 Approved
0.7632 Intermediate Similarity NPD7516 Approved
0.7611 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD6412 Phase 2
0.7523 Intermediate Similarity NPD6686 Approved
0.7521 Intermediate Similarity NPD8328 Phase 3
0.75 Intermediate Similarity NPD7503 Approved
0.735 Intermediate Similarity NPD8515 Approved
0.735 Intermediate Similarity NPD8513 Phase 3
0.735 Intermediate Similarity NPD8516 Approved
0.735 Intermediate Similarity NPD8517 Approved
0.7345 Intermediate Similarity NPD8133 Approved
0.725 Intermediate Similarity NPD7507 Approved
0.7188 Intermediate Similarity NPD7645 Phase 2
0.7115 Intermediate Similarity NPD8171 Discontinued
0.7073 Intermediate Similarity NPD7319 Approved
0.6961 Remote Similarity NPD7524 Approved
0.6905 Remote Similarity NPD8449 Approved
0.6881 Remote Similarity NPD7640 Approved
0.6881 Remote Similarity NPD7639 Approved
0.687 Remote Similarity NPD8413 Clinical (unspecified phase)
0.685 Remote Similarity NPD8450 Suspended
0.6832 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5344 Discontinued
0.6789 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6789 Remote Similarity NPD4225 Approved
0.6789 Remote Similarity NPD7638 Approved
0.6771 Remote Similarity NPD8264 Approved
0.6768 Remote Similarity NPD7525 Registered
0.6733 Remote Similarity NPD6695 Phase 3
0.6721 Remote Similarity NPD6370 Approved
0.672 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD1811 Approved
0.6667 Remote Similarity NPD1810 Approved
0.664 Remote Similarity NPD8293 Discontinued
0.664 Remote Similarity NPD8074 Phase 3
0.6635 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6635 Remote Similarity NPD7750 Discontinued
0.6604 Remote Similarity NPD3168 Discontinued
0.6598 Remote Similarity NPD7339 Approved
0.6598 Remote Similarity NPD6942 Approved
0.6583 Remote Similarity NPD7115 Discovery
0.6574 Remote Similarity NPD7748 Approved
0.6557 Remote Similarity NPD6054 Approved
0.6557 Remote Similarity NPD6059 Approved
0.6552 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6545 Remote Similarity NPD7902 Approved
0.6532 Remote Similarity NPD6067 Discontinued
0.6531 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6430 Approved
0.6525 Remote Similarity NPD6429 Approved
0.6505 Remote Similarity NPD6400 Clinical (unspecified phase)
0.65 Remote Similarity NPD6929 Approved
0.6491 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6698 Approved
0.6449 Remote Similarity NPD46 Approved
0.6449 Remote Similarity NPD7838 Discovery
0.6436 Remote Similarity NPD6931 Approved
0.6436 Remote Similarity NPD6930 Phase 2
0.6429 Remote Similarity NPD6648 Approved
0.6389 Remote Similarity NPD7515 Phase 2
0.6389 Remote Similarity NPD7983 Approved
0.6387 Remote Similarity NPD8297 Approved
0.6387 Remote Similarity NPD6882 Approved
0.6371 Remote Similarity NPD6015 Approved
0.6371 Remote Similarity NPD6016 Approved
0.6356 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6354 Remote Similarity NPD2254 Approved
0.6354 Remote Similarity NPD2686 Approved
0.6354 Remote Similarity NPD2687 Approved
0.6349 Remote Similarity NPD7492 Approved
0.633 Remote Similarity NPD6399 Phase 3
0.633 Remote Similarity NPD5778 Approved
0.633 Remote Similarity NPD5779 Approved
0.6325 Remote Similarity NPD5345 Clinical (unspecified phase)
0.632 Remote Similarity NPD5988 Approved
0.6316 Remote Similarity NPD7632 Discontinued
0.6311 Remote Similarity NPD6009 Approved
0.63 Remote Similarity NPD5776 Phase 2
0.63 Remote Similarity NPD6925 Approved
0.6299 Remote Similarity NPD6616 Approved
0.6296 Remote Similarity NPD8522 Clinical (unspecified phase)
0.629 Remote Similarity NPD6319 Approved
0.6275 Remote Similarity NPD7514 Phase 3
0.6275 Remote Similarity NPD6928 Phase 2
0.6275 Remote Similarity NPD7332 Phase 2
0.6273 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6273 Remote Similarity NPD7900 Approved
0.6259 Remote Similarity NPD7625 Phase 1
0.625 Remote Similarity NPD7078 Approved
0.625 Remote Similarity NPD3670 Clinical (unspecified phase)
0.625 Remote Similarity NPD3669 Approved
0.6239 Remote Similarity NPD7087 Discontinued
0.6239 Remote Similarity NPD7637 Suspended
0.6239 Remote Similarity NPD6411 Approved
0.6238 Remote Similarity NPD7145 Approved
0.6228 Remote Similarity NPD4159 Approved
0.6214 Remote Similarity NPD6902 Approved
0.62 Remote Similarity NPD6933 Approved
0.6198 Remote Similarity NPD4632 Approved
0.619 Remote Similarity NPD4786 Approved
0.6186 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5357 Phase 1
0.6154 Remote Similarity NPD6402 Approved
0.6154 Remote Similarity NPD3667 Approved
0.6154 Remote Similarity NPD5739 Approved
0.6154 Remote Similarity NPD7128 Approved
0.6154 Remote Similarity NPD6675 Approved
0.6134 Remote Similarity NPD6372 Approved
0.6134 Remote Similarity NPD6373 Approved
0.6132 Remote Similarity NPD6893 Approved
0.6102 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6094 Remote Similarity NPD8341 Approved
0.6094 Remote Similarity NPD8342 Approved
0.6094 Remote Similarity NPD8340 Approved
0.6094 Remote Similarity NPD8299 Approved
0.6091 Remote Similarity NPD8034 Phase 2
0.6091 Remote Similarity NPD8035 Phase 2
0.6077 Remote Similarity NPD6033 Approved
0.6075 Remote Similarity NPD3618 Phase 1
0.6063 Remote Similarity NPD5125 Phase 3
0.6063 Remote Similarity NPD5126 Approved
0.6058 Remote Similarity NPD6898 Phase 1
0.6055 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6055 Remote Similarity NPD6101 Approved
0.6055 Remote Similarity NPD5328 Approved
0.605 Remote Similarity NPD6881 Approved
0.605 Remote Similarity NPD6899 Approved
0.605 Remote Similarity NPD7320 Approved
0.6034 Remote Similarity NPD5211 Phase 2
0.6033 Remote Similarity NPD8130 Phase 1
0.6033 Remote Similarity NPD6650 Approved
0.6033 Remote Similarity NPD6649 Approved
0.6022 Remote Similarity NPD368 Approved
0.6018 Remote Similarity NPD7839 Suspended
0.6017 Remote Similarity NPD6640 Phase 3
0.6 Remote Similarity NPD6924 Approved
0.6 Remote Similarity NPD6926 Approved
0.598 Remote Similarity NPD6932 Approved
0.5966 Remote Similarity NPD5701 Approved
0.5966 Remote Similarity NPD5697 Approved
0.5965 Remote Similarity NPD4755 Approved
0.5962 Remote Similarity NPD7509 Discontinued
0.5962 Remote Similarity NPD4748 Discontinued
0.5957 Remote Similarity NPD6674 Discontinued
0.595 Remote Similarity NPD6883 Approved
0.595 Remote Similarity NPD7290 Approved
0.595 Remote Similarity NPD7102 Approved
0.595 Remote Similarity NPD4634 Approved
0.5946 Remote Similarity NPD6079 Approved
0.5932 Remote Similarity NPD5141 Approved
0.5923 Remote Similarity NPD8451 Approved
0.5922 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5909 Remote Similarity NPD6051 Approved
0.5902 Remote Similarity NPD6617 Approved
0.5902 Remote Similarity NPD6847 Approved
0.5902 Remote Similarity NPD6869 Approved
0.5895 Remote Similarity NPD371 Approved
0.5893 Remote Similarity NPD4202 Approved
0.5891 Remote Similarity NPD7829 Approved
0.5891 Remote Similarity NPD7604 Phase 2
0.5891 Remote Similarity NPD7830 Approved
0.5882 Remote Similarity NPD6008 Approved
0.5878 Remote Similarity NPD8448 Approved
0.5868 Remote Similarity NPD6012 Approved
0.5868 Remote Similarity NPD6014 Approved
0.5868 Remote Similarity NPD6013 Approved
0.5865 Remote Similarity NPD6683 Phase 2
0.5865 Remote Similarity NPD8392 Approved
0.5865 Remote Similarity NPD8391 Approved
0.5865 Remote Similarity NPD6914 Discontinued
0.5865 Remote Similarity NPD8390 Approved
0.5862 Remote Similarity NPD5286 Approved
0.5862 Remote Similarity NPD4696 Approved
0.5862 Remote Similarity NPD5285 Approved
0.5862 Remote Similarity NPD4700 Approved
0.5859 Remote Similarity NPD6921 Approved
0.5859 Remote Similarity NPD5983 Phase 2
0.5854 Remote Similarity NPD6053 Discontinued
0.5842 Remote Similarity NPD4784 Approved
0.5842 Remote Similarity NPD4785 Approved
0.5833 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5826 Remote Similarity NPD6083 Phase 2
0.5826 Remote Similarity NPD6084 Phase 2
0.582 Remote Similarity NPD6371 Approved
0.5802 Remote Similarity NPD6336 Discontinued
0.58 Remote Similarity NPD7151 Approved
0.58 Remote Similarity NPD4243 Approved
0.58 Remote Similarity NPD7152 Approved
0.58 Remote Similarity NPD7150 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