Structure

Physi-Chem Properties

Molecular Weight:  326.16
Volume:  329.58
LogP:  2.558
LogD:  2.182
LogS:  -2.893
# Rotatable Bonds:  1
TPSA:  43.7
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.754
Synthetic Accessibility Score:  4.651
Fsp3:  0.526
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.953
MDCK Permeability:  4.395373980514705e-05
Pgp-inhibitor:  0.211
Pgp-substrate:  0.261
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.744
30% Bioavailability (F30%):  0.69

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.988
Plasma Protein Binding (PPB):  72.70375061035156%
Volume Distribution (VD):  1.901
Pgp-substrate:  26.9714298248291%

ADMET: Metabolism

CYP1A2-inhibitor:  0.784
CYP1A2-substrate:  0.847
CYP2C19-inhibitor:  0.263
CYP2C19-substrate:  0.949
CYP2C9-inhibitor:  0.075
CYP2C9-substrate:  0.793
CYP2D6-inhibitor:  0.774
CYP2D6-substrate:  0.915
CYP3A4-inhibitor:  0.216
CYP3A4-substrate:  0.903

ADMET: Excretion

Clearance (CL):  10.455
Half-life (T1/2):  0.125

ADMET: Toxicity

hERG Blockers:  0.102
Human Hepatotoxicity (H-HT):  0.412
Drug-inuced Liver Injury (DILI):  0.481
AMES Toxicity:  0.488
Rat Oral Acute Toxicity:  0.626
Maximum Recommended Daily Dose:  0.988
Skin Sensitization:  0.149
Carcinogencity:  0.654
Eye Corrosion:  0.004
Eye Irritation:  0.045
Respiratory Toxicity:  0.952

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

  Natural Product: NPC472098

Natural Product ID:  NPC472098
Common Name*:   QBWRCKLMBISIJV-JHNDHUHGSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  QBWRCKLMBISIJV-JHNDHUHGSA-N
Standard InCHI:  InChI=1S/C19H22N2O3/c1-20-16-7-12-11-6-10(23-3)4-5-15(11)21(2)18(12)17(20)8-13-14(16)9-24-19(13)22/h4-6,13-14,16-17H,7-9H2,1-3H3/t13-,14-,16+,17+/m1/s1
SMILES:  CN1C2CC3C(C1CC4=C2N(C5=C4C=C(C=C5)OC)C)COC3=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3338221
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0001213] Pyridoindoles
          • [CHEMONTID:0001914] Beta carbolines

*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
NPO28762 Alstonia angustifolia Species Apocynaceae Eukaryota bark and leaf Pahang, Malaysia n.a. PMID[25211145]
NPO28762 Alstonia angustifolia Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28762 Alstonia angustifolia Species Apocynaceae 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 IC50 > 25.0 ug.mL-1 PMID[551381]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 25.0 ug.mL-1 PMID[551381]

☑ 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 NPC472098 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
0.9246 High Similarity NPC472099
0.88 High Similarity NPC264176
0.8687 High Similarity NPC472111
0.867 High Similarity NPC472119
0.867 High Similarity NPC152768
0.867 High Similarity NPC148183
0.8495 Intermediate Similarity NPC96321
0.8396 Intermediate Similarity NPC311906
0.8366 Intermediate Similarity NPC53344
0.8357 Intermediate Similarity NPC305984
0.8341 Intermediate Similarity NPC21638
0.8333 Intermediate Similarity NPC471304
0.8195 Intermediate Similarity NPC469589
0.8178 Intermediate Similarity NPC478078
0.8159 Intermediate Similarity NPC329793
0.8141 Intermediate Similarity NPC245916
0.8137 Intermediate Similarity NPC474145
0.8137 Intermediate Similarity NPC475841
0.8122 Intermediate Similarity NPC472097
0.8111 Intermediate Similarity NPC475720
0.8111 Intermediate Similarity NPC474192
0.8103 Intermediate Similarity NPC66210
0.81 Intermediate Similarity NPC477066
0.8093 Intermediate Similarity NPC258480
0.8063 Intermediate Similarity NPC478081
0.8063 Intermediate Similarity NPC477067
0.8063 Intermediate Similarity NPC478082
0.8061 Intermediate Similarity NPC472323
0.8057 Intermediate Similarity NPC473041
0.802 Intermediate Similarity NPC196251
0.802 Intermediate Similarity NPC102338
0.802 Intermediate Similarity NPC111602
0.802 Intermediate Similarity NPC63199
0.8009 Intermediate Similarity NPC474183
0.7973 Intermediate Similarity NPC475816
0.7971 Intermediate Similarity NPC82548
0.797 Intermediate Similarity NPC21425
0.7962 Intermediate Similarity NPC469928
0.7959 Intermediate Similarity NPC79062
0.7959 Intermediate Similarity NPC472107
0.7951 Intermediate Similarity NPC476098
0.7944 Intermediate Similarity NPC60621
0.7938 Intermediate Similarity NPC15840
0.792 Intermediate Similarity NPC17437
0.7909 Intermediate Similarity NPC329631
0.7904 Intermediate Similarity NPC329982
0.7902 Intermediate Similarity NPC473540
0.7892 Intermediate Similarity NPC249040
0.7887 Intermediate Similarity NPC303658
0.7883 Intermediate Similarity NPC184680
0.7874 Intermediate Similarity NPC300156
0.7867 Intermediate Similarity NPC471080
0.7867 Intermediate Similarity NPC469592
0.7857 Intermediate Similarity NPC143533
0.7848 Intermediate Similarity NPC470785
0.7848 Intermediate Similarity NPC470784
0.7835 Intermediate Similarity NPC478083
0.7828 Intermediate Similarity NPC473105
0.7805 Intermediate Similarity NPC128265
0.7805 Intermediate Similarity NPC312870
0.7805 Intermediate Similarity NPC254240
0.7805 Intermediate Similarity NPC199851
0.7805 Intermediate Similarity NPC294909
0.7792 Intermediate Similarity NPC478080
0.7768 Intermediate Similarity NPC284685
0.7766 Intermediate Similarity NPC176127
0.7751 Intermediate Similarity NPC193238
0.774 Intermediate Similarity NPC165349
0.774 Intermediate Similarity NPC274291
0.774 Intermediate Similarity NPC264166
0.774 Intermediate Similarity NPC118832
0.774 Intermediate Similarity NPC47059
0.774 Intermediate Similarity NPC329708
0.7729 Intermediate Similarity NPC295898
0.7723 Intermediate Similarity NPC472113
0.7721 Intermediate Similarity NPC469594
0.7718 Intermediate Similarity NPC176538
0.7714 Intermediate Similarity NPC475910
0.7713 Intermediate Similarity NPC39370
0.7711 Intermediate Similarity NPC472112
0.7703 Intermediate Similarity NPC238457
0.7703 Intermediate Similarity NPC45190
0.77 Intermediate Similarity NPC151781
0.77 Intermediate Similarity NPC478074
0.77 Intermediate Similarity NPC74562
0.77 Intermediate Similarity NPC316181
0.7696 Intermediate Similarity NPC280799
0.7682 Intermediate Similarity NPC157931
0.7677 Intermediate Similarity NPC472104
0.7675 Intermediate Similarity NPC81939
0.7673 Intermediate Similarity NPC92111
0.7664 Intermediate Similarity NPC16066
0.7661 Intermediate Similarity NPC280272
0.766 Intermediate Similarity NPC191489
0.765 Intermediate Similarity NPC128115
0.7642 Intermediate Similarity NPC475666
0.7634 Intermediate Similarity NPC253675
0.7633 Intermediate Similarity NPC329747
0.7624 Intermediate Similarity NPC76748
0.7623 Intermediate Similarity NPC473186
0.761 Intermediate Similarity NPC472116
0.7608 Intermediate Similarity NPC223427
0.7605 Intermediate Similarity NPC100734
0.7605 Intermediate Similarity NPC315634
0.7605 Intermediate Similarity NPC88923
0.7598 Intermediate Similarity NPC307963
0.7594 Intermediate Similarity NPC174672
0.7594 Intermediate Similarity NPC174758
0.7585 Intermediate Similarity NPC280714
0.7583 Intermediate Similarity NPC321428
0.7574 Intermediate Similarity NPC296527
0.7574 Intermediate Similarity NPC175474
0.7568 Intermediate Similarity NPC194740
0.7563 Intermediate Similarity NPC234987
0.7562 Intermediate Similarity NPC194040
0.7561 Intermediate Similarity NPC276517
0.7559 Intermediate Similarity NPC470020
0.7549 Intermediate Similarity NPC55493
0.7548 Intermediate Similarity NPC315957
0.7548 Intermediate Similarity NPC214428
0.7548 Intermediate Similarity NPC213308
0.7546 Intermediate Similarity NPC330009
0.7524 Intermediate Similarity NPC251090
0.7524 Intermediate Similarity NPC475774
0.7513 Intermediate Similarity NPC84347
0.75 Intermediate Similarity NPC476578
0.75 Intermediate Similarity NPC4071
0.75 Intermediate Similarity NPC476582
0.75 Intermediate Similarity NPC4687
0.75 Intermediate Similarity NPC135549
0.75 Intermediate Similarity NPC313189
0.7489 Intermediate Similarity NPC469734
0.7488 Intermediate Similarity NPC53069
0.7488 Intermediate Similarity NPC96405
0.7488 Intermediate Similarity NPC296482
0.7488 Intermediate Similarity NPC476581
0.7488 Intermediate Similarity NPC16452
0.7488 Intermediate Similarity NPC36229
0.7488 Intermediate Similarity NPC171409
0.7488 Intermediate Similarity NPC94157
0.7488 Intermediate Similarity NPC202768
0.7477 Intermediate Similarity NPC269367
0.7476 Intermediate Similarity NPC19692
0.7476 Intermediate Similarity NPC57994
0.7476 Intermediate Similarity NPC220151
0.7476 Intermediate Similarity NPC289299
0.7475 Intermediate Similarity NPC478077
0.7466 Intermediate Similarity NPC322482
0.7464 Intermediate Similarity NPC45459
0.7464 Intermediate Similarity NPC195461
0.7464 Intermediate Similarity NPC79129
0.7464 Intermediate Similarity NPC81654
0.7464 Intermediate Similarity NPC249150
0.7464 Intermediate Similarity NPC138830
0.7464 Intermediate Similarity NPC315491
0.7464 Intermediate Similarity NPC313985
0.7464 Intermediate Similarity NPC49196
0.746 Intermediate Similarity NPC26872
0.7454 Intermediate Similarity NPC39500
0.7454 Intermediate Similarity NPC476287
0.7454 Intermediate Similarity NPC221100
0.7454 Intermediate Similarity NPC234078
0.7453 Intermediate Similarity NPC277350
0.7452 Intermediate Similarity NPC52557
0.7442 Intermediate Similarity NPC208284
0.7438 Intermediate Similarity NPC66083
0.7435 Intermediate Similarity NPC26850
0.743 Intermediate Similarity NPC476116
0.7427 Intermediate Similarity NPC203972
0.7424 Intermediate Similarity NPC472122
0.7424 Intermediate Similarity NPC24594
0.7422 Intermediate Similarity NPC474688
0.7418 Intermediate Similarity NPC270918
0.7411 Intermediate Similarity NPC33949
0.7411 Intermediate Similarity NPC314954
0.7399 Intermediate Similarity NPC470018
0.7397 Intermediate Similarity NPC46561
0.7395 Intermediate Similarity NPC167860
0.7395 Intermediate Similarity NPC123976
0.7389 Intermediate Similarity NPC204385
0.7389 Intermediate Similarity NPC469554
0.7385 Intermediate Similarity NPC274982
0.7384 Intermediate Similarity NPC53534
0.7383 Intermediate Similarity NPC287208
0.7381 Intermediate Similarity NPC234197
0.7381 Intermediate Similarity NPC477019
0.7381 Intermediate Similarity NPC11017
0.738 Intermediate Similarity NPC101350
0.7376 Intermediate Similarity NPC84478
0.7374 Intermediate Similarity NPC312872
0.7368 Intermediate Similarity NPC295228
0.7368 Intermediate Similarity NPC306376
0.7368 Intermediate Similarity NPC50503
0.7363 Intermediate Similarity NPC113626
0.7361 Intermediate Similarity NPC87413
0.7361 Intermediate Similarity NPC146418
0.7358 Intermediate Similarity NPC81229
0.7358 Intermediate Similarity NPC255229
0.7358 Intermediate Similarity NPC162484
0.7346 Intermediate Similarity NPC31930

  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 NPC472098 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
0.8367 Intermediate Similarity NPD4418 Discontinued
0.8111 Intermediate Similarity NPD4885 Approved
0.8029 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.802 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.801 Intermediate Similarity NPD7222 Phase 2
0.7991 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.797 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7926 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.792 Intermediate Similarity NPD8358 Approved
0.7915 Intermediate Similarity NPD3257 Approved
0.7909 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7904 Intermediate Similarity NPD8463 Approved
0.7885 Intermediate Similarity NPD5658 Approved
0.7876 Intermediate Similarity NPD8100 Phase 3
0.7864 Intermediate Similarity NPD7796 Approved
0.7864 Intermediate Similarity NPD7797 Approved
0.7854 Intermediate Similarity NPD4952 Phase 3
0.785 Intermediate Similarity NPD3258 Approved
0.7837 Intermediate Similarity NPD7453 Approved
0.7837 Intermediate Similarity NPD7452 Approved
0.783 Intermediate Similarity NPD5293 Phase 2
0.7807 Intermediate Similarity NPD8102 Discontinued
0.7806 Intermediate Similarity NPD4203 Approved
0.7806 Intermediate Similarity NPD4204 Approved
0.7805 Intermediate Similarity NPD4501 Approved
0.7805 Intermediate Similarity NPD4500 Approved
0.7804 Intermediate Similarity NPD3354 Phase 2
0.7783 Intermediate Similarity NPD5512 Phase 3
0.7773 Intermediate Similarity NPD8101 Phase 3
0.7768 Intermediate Similarity NPD7955 Approved
0.7768 Intermediate Similarity NPD7956 Approved
0.7763 Intermediate Similarity NPD4328 Approved
0.7748 Intermediate Similarity NPD4373 Phase 2
0.7746 Intermediate Similarity NPD4897 Phase 2
0.774 Intermediate Similarity NPD4038 Approved
0.774 Intermediate Similarity NPD32 Approved
0.774 Intermediate Similarity NPD4033 Approved
0.774 Intermediate Similarity NPD4122 Approved
0.774 Intermediate Similarity NPD3946 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD4039 Approved
0.774 Intermediate Similarity NPD4037 Approved
0.774 Intermediate Similarity NPD4036 Approved
0.774 Intermediate Similarity NPD4035 Approved
0.774 Intermediate Similarity NPD4034 Approved
0.774 Intermediate Similarity NPD31 Approved
0.7734 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD8017 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD8016 Phase 3
0.7731 Intermediate Similarity NPD6242 Discontinued
0.7692 Intermediate Similarity NPD7589 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7686 Intermediate Similarity NPD6276 Discontinued
0.766 Intermediate Similarity NPD7708 Approved
0.7656 Intermediate Similarity NPD4795 Phase 2
0.7655 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7617 Intermediate Similarity NPD7571 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD7868 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD7803 Approved
0.76 Intermediate Similarity NPD3006 Discontinued
0.7598 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD1038 Approved
0.7585 Intermediate Similarity NPD6228 Discontinued
0.7583 Intermediate Similarity NPD5429 Discontinued
0.758 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.757 Intermediate Similarity NPD7069 Discontinued
0.7565 Intermediate Similarity NPD5488 Discontinued
0.7561 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD7426 Phase 1
0.7548 Intermediate Similarity NPD1740 Approved
0.7548 Intermediate Similarity NPD1739 Approved
0.7543 Intermediate Similarity NPD5482 Discontinued
0.7537 Intermediate Similarity NPD4081 Clinical (unspecified phase)
0.7536 Intermediate Similarity NPD5530 Phase 1
0.7534 Intermediate Similarity NPD5506 Approved
0.7534 Intermediate Similarity NPD5507 Approved
0.7511 Intermediate Similarity NPD6716 Phase 1
0.75 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.7488 Intermediate Similarity NPD3816 Phase 1
0.7488 Intermediate Similarity NPD3815 Phase 1
0.7477 Intermediate Similarity NPD5632 Approved
0.7477 Intermediate Similarity NPD6568 Discontinued
0.7476 Intermediate Similarity NPD4602 Approved
0.7465 Intermediate Similarity NPD2510 Approved
0.7465 Intermediate Similarity NPD2916 Discontinued
0.7465 Intermediate Similarity NPD2509 Approved
0.7464 Intermediate Similarity NPD484 Approved
0.7464 Intermediate Similarity NPD4601 Approved
0.7464 Intermediate Similarity NPD4600 Approved
0.7455 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD5601 Phase 2
0.7447 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD3259 Approved
0.744 Intermediate Similarity NPD6550 Discontinued
0.7438 Intermediate Similarity NPD6393 Clinical (unspecified phase)
0.7426 Intermediate Similarity NPD4889 Approved
0.7425 Intermediate Similarity NPD4558 Phase 2
0.7422 Intermediate Similarity NPD7284 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD5559 Phase 2
0.7404 Intermediate Similarity NPD5003 Discontinued
0.7404 Intermediate Similarity NPD6769 Clinical (unspecified phase)
0.7395 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD6790 Phase 1
0.7391 Intermediate Similarity NPD7417 Discontinued
0.7385 Intermediate Similarity NPD3389 Approved
0.7385 Intermediate Similarity NPD3393 Approved
0.7385 Intermediate Similarity NPD3394 Approved
0.7361 Intermediate Similarity NPD5416 Discontinued
0.7356 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD3477 Phase 2
0.7352 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.735 Intermediate Similarity NPD3920 Phase 2
0.7333 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD5930 Phase 3
0.7327 Intermediate Similarity NPD5866 Approved
0.7318 Intermediate Similarity NPD7395 Discontinued
0.7311 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD5256 Discontinued
0.7301 Intermediate Similarity NPD5479 Discontinued
0.7301 Intermediate Similarity NPD8052 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD6569 Phase 2
0.7295 Intermediate Similarity NPD3923 Approved
0.7295 Intermediate Similarity NPD3924 Approved
0.7295 Intermediate Similarity NPD3922 Approved
0.7295 Intermediate Similarity NPD3921 Approved
0.7291 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD3003 Approved
0.729 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7994 Phase 2
0.7286 Intermediate Similarity NPD4397 Phase 1
0.7282 Intermediate Similarity NPD4499 Approved
0.7269 Intermediate Similarity NPD6962 Phase 2
0.726 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD4429 Discontinued
0.723 Intermediate Similarity NPD5669 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD5612 Discontinued
0.7224 Intermediate Similarity NPD8363 Approved
0.7224 Intermediate Similarity NPD8364 Approved
0.7222 Intermediate Similarity NPD7666 Phase 3
0.7222 Intermediate Similarity NPD7665 Phase 2
0.721 Intermediate Similarity NPD6517 Phase 3
0.7209 Intermediate Similarity NPD3507 Phase 2
0.7207 Intermediate Similarity NPD7194 Discontinued
0.7204 Intermediate Similarity NPD53 Approved
0.7204 Intermediate Similarity NPD7778 Approved
0.7204 Intermediate Similarity NPD7777 Approved
0.7202 Intermediate Similarity NPD7470 Discontinued
0.7198 Intermediate Similarity NPD2564 Approved
0.7198 Intermediate Similarity NPD2565 Phase 2
0.7196 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD3440 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD8465 Approved
0.7189 Intermediate Similarity NPD8466 Approved
0.7189 Intermediate Similarity NPD8467 Approved
0.7188 Intermediate Similarity NPD7219 Approved
0.7188 Intermediate Similarity NPD7221 Approved
0.7186 Intermediate Similarity NPD1078 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD1034 Phase 3
0.7184 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD5014 Discontinued
0.7172 Intermediate Similarity NPD5450 Discontinued
0.717 Intermediate Similarity NPD6999 Discontinued
0.717 Intermediate Similarity NPD1768 Approved
0.717 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD3825 Phase 3
0.7166 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD5104 Approved
0.7149 Intermediate Similarity NPD7112 Discontinued
0.7143 Intermediate Similarity NPD2189 Approved
0.7143 Intermediate Similarity NPD5147 Discontinued
0.7143 Intermediate Similarity NPD4154 Approved
0.7143 Intermediate Similarity NPD5891 Approved
0.7143 Intermediate Similarity NPD2187 Approved
0.713 Intermediate Similarity NPD3875 Discontinued
0.713 Intermediate Similarity NPD3763 Approved
0.713 Intermediate Similarity NPD7001 Phase 3
0.713 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD7719 Discontinued
0.7119 Intermediate Similarity NPD8359 Phase 2
0.7118 Intermediate Similarity NPD7688 Phase 1
0.7116 Intermediate Similarity NPD6991 Approved
0.7111 Intermediate Similarity NPD6995 Phase 1
0.7101 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD2383 Phase 1
0.7098 Intermediate Similarity NPD8479 Phase 2
0.7098 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD8255 Phase 2
0.7093 Intermediate Similarity NPD7675 Phase 3
0.7093 Intermediate Similarity NPD7674 Phase 3
0.7093 Intermediate Similarity NPD7676 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD3947 Discontinued
0.7083 Intermediate Similarity NPD3397 Phase 2
0.7082 Intermediate Similarity NPD7729 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6531 Approved
0.7078 Intermediate Similarity NPD6530 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