Structure

Physi-Chem Properties

Molecular Weight:  310.2
Volume:  331.932
LogP:  4.569
LogD:  4.289
LogS:  -4.285
# Rotatable Bonds:  2
TPSA:  28.26
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.91
Synthetic Accessibility Score:  4.905
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.085
MDCK Permeability:  1.298310326092178e-05
Pgp-inhibitor:  0.974
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.812
30% Bioavailability (F30%):  0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.965
Plasma Protein Binding (PPB):  88.62449645996094%
Volume Distribution (VD):  2.099
Pgp-substrate:  8.668347358703613%

ADMET: Metabolism

CYP1A2-inhibitor:  0.944
CYP1A2-substrate:  0.966
CYP2C19-inhibitor:  0.671
CYP2C19-substrate:  0.85
CYP2C9-inhibitor:  0.234
CYP2C9-substrate:  0.709
CYP2D6-inhibitor:  0.932
CYP2D6-substrate:  0.926
CYP3A4-inhibitor:  0.4
CYP3A4-substrate:  0.704

ADMET: Excretion

Clearance (CL):  5.702
Half-life (T1/2):  0.504

ADMET: Toxicity

hERG Blockers:  0.943
Human Hepatotoxicity (H-HT):  0.479
Drug-inuced Liver Injury (DILI):  0.748
AMES Toxicity:  0.629
Rat Oral Acute Toxicity:  0.894
Maximum Recommended Daily Dose:  0.936
Skin Sensitization:  0.34
Carcinogencity:  0.729
Eye Corrosion:  0.005
Eye Irritation:  0.237
Respiratory Toxicity:  0.943

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General Info & Identifiers & Properties  
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Similar NPs/Drugs  

  Natural Product: NPC329793

Natural Product ID:  NPC329793
Common Name*:   Ibogaine
IUPAC Name:   n.a.
Synonyms:   10-Methoxyibogamine; Ibogaine
Standard InCHIKey:  HSIBGVUMFOSJPD-NXWOVTFFSA-N
Standard InCHI:  InChI=1S/C20H26N2O/c1-3-13-8-12-9-17-19-15(6-7-22(11-12)20(13)17)16-10-14(23-2)4-5-18(16)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13-,17-,20-/m0/s1
SMILES:  CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL222287
PubChem CID:   442108
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002748] Ibogan-type alkaloids

*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
NPO32495 tabernaemontana calcarea Species Apocynaceae Eukaryota n.a. Madagascar rainforest n.a. PMID[12713407]

☑ 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
NPT1073 Individual Protein Dopamine transporter Rattus norvegicus IC50 = 4110.0 nM PMID[533123]
NPT1072 Individual Protein Serotonin transporter Rattus norvegicus IC50 = 590.0 nM PMID[533123]
NPT1857 Individual Protein Dopamine D1 receptor Rattus norvegicus IC50 > 10000.0 nM PMID[533123]
NPT1858 Individual Protein Dopamine D2 receptor Rattus norvegicus IC50 > 10000.0 nM PMID[533123]
NPT3056 Individual Protein Dopamine D3 receptor Rattus norvegicus IC50 > 10000.0 nM PMID[533123]
NPT1069 Individual Protein Mu opioid receptor Rattus norvegicus IC50 = 3760.0 nM PMID[533123]
NPT3601 Individual Protein Kappa opioid receptor Rattus norvegicus IC50 = 25000.0 nM PMID[533123]
NPT1070 Individual Protein Sigma-1 receptor Cavia porcellus Ki = 250.0 nM PMID[533124]
NPT1072 Individual Protein Serotonin transporter Rattus norvegicus IC50 = 6300.0 nM PMID[533125]
NPT1072 Individual Protein Serotonin transporter Rattus norvegicus IC50 = 2500.0 nM PMID[533125]
NPT1072 Individual Protein Serotonin transporter Rattus norvegicus Km = 170.0 nM PMID[533125]
NPT1072 Individual Protein Serotonin transporter Rattus norvegicus Vmax = 14.0 pmol/min/mg PMID[533125]
NPT295 Individual Protein Serotonin transporter Homo sapiens Kinact = 2.26 nM PMID[533125]
NPT179 Cell Line A2780 Homo sapiens IC50 = 10.2 ug.mL-1 PMID[533126]
NPT296 Individual Protein Sigma opioid receptor Homo sapiens Ki = 8554.0 nM PMID[533129]
NPT1496 Protein Complex Glutamate NMDA receptor Rattus norvegicus IC50 = 5200.0 nM PMID[533123]
NPT2 Others Unspecified Ki = 9310.0 nM PMID[533124]
NPT2 Others Unspecified Ratio = 95.0 % PMID[533124]
NPT2 Others Unspecified Activity = 0.98 uM PMID[533125]
NPT2 Others Unspecified Activity = 7.95 nmol PMID[533127]
NPT2 Others Unspecified Activity = 5.82 nmol PMID[533127]
NPT20913 TISSUE Whole blood Homo sapiens Retention_time = 4.94 min PMID[533128]
NPT2 Others Unspecified Ratio Ki = 43.0 n.a. PMID[533129]
NPT2 Others Unspecified Ki = 201.0 nM PMID[533129]

☑ 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 NPC329793 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
0.9309 High Similarity NPC471304
0.9239 High Similarity NPC329747
0.9101 High Similarity NPC475910
0.9062 High Similarity NPC478074
0.8974 High Similarity NPC96321
0.8939 High Similarity NPC176127
0.8806 High Similarity NPC478078
0.8762 High Similarity NPC311906
0.8703 High Similarity NPC92111
0.8649 High Similarity NPC76748
0.8595 High Similarity NPC296527
0.8571 High Similarity NPC208284
0.8534 High Similarity NPC249040
0.8534 High Similarity NPC176538
0.8511 High Similarity NPC307963
0.85 High Similarity NPC473041
0.8454 Intermediate Similarity NPC475720
0.8454 Intermediate Similarity NPC474192
0.8424 Intermediate Similarity NPC280272
0.841 Intermediate Similarity NPC472111
0.8402 Intermediate Similarity NPC223427
0.84 Intermediate Similarity NPC469928
0.8378 Intermediate Similarity NPC84478
0.8376 Intermediate Similarity NPC476116
0.8368 Intermediate Similarity NPC131017
0.8349 Intermediate Similarity NPC477066
0.8325 Intermediate Similarity NPC251090
0.831 Intermediate Similarity NPC478081
0.831 Intermediate Similarity NPC477067
0.831 Intermediate Similarity NPC478082
0.8308 Intermediate Similarity NPC162484
0.83 Intermediate Similarity NPC471080
0.83 Intermediate Similarity NPC469592
0.825 Intermediate Similarity NPC94157
0.8235 Intermediate Similarity NPC472099
0.8218 Intermediate Similarity NPC152768
0.8218 Intermediate Similarity NPC148183
0.8216 Intermediate Similarity NPC475816
0.8201 Intermediate Similarity NPC242928
0.8173 Intermediate Similarity NPC285558
0.8159 Intermediate Similarity NPC472098
0.8157 Intermediate Similarity NPC17437
0.8152 Intermediate Similarity NPC473105
0.814 Intermediate Similarity NPC473540
0.8137 Intermediate Similarity NPC469594
0.8131 Intermediate Similarity NPC474145
0.8131 Intermediate Similarity NPC475841
0.809 Intermediate Similarity NPC193777
0.8088 Intermediate Similarity NPC305984
0.8081 Intermediate Similarity NPC475070
0.8065 Intermediate Similarity NPC88363
0.806 Intermediate Similarity NPC123976
0.806 Intermediate Similarity NPC167860
0.8051 Intermediate Similarity NPC72211
0.805 Intermediate Similarity NPC476465
0.8041 Intermediate Similarity NPC70259
0.802 Intermediate Similarity NPC267423
0.802 Intermediate Similarity NPC232727
0.801 Intermediate Similarity NPC201697
0.8 Intermediate Similarity NPC189812
0.8 Intermediate Similarity NPC243834
0.8 Intermediate Similarity NPC329688
0.8 Intermediate Similarity NPC171171
0.8 Intermediate Similarity NPC70956
0.7991 Intermediate Similarity NPC295228
0.799 Intermediate Similarity NPC205934
0.799 Intermediate Similarity NPC43787
0.7979 Intermediate Similarity NPC474798
0.7971 Intermediate Similarity NPC132642
0.797 Intermediate Similarity NPC315957
0.7951 Intermediate Similarity NPC330009
0.795 Intermediate Similarity NPC300156
0.795 Intermediate Similarity NPC45190
0.7949 Intermediate Similarity NPC13880
0.7941 Intermediate Similarity NPC266931
0.794 Intermediate Similarity NPC476138
0.794 Intermediate Similarity NPC245816
0.7937 Intermediate Similarity NPC478080
0.7929 Intermediate Similarity NPC476044
0.7919 Intermediate Similarity NPC128823
0.7917 Intermediate Similarity NPC246700
0.7915 Intermediate Similarity NPC157931
0.7905 Intermediate Similarity NPC21638
0.79 Intermediate Similarity NPC165349
0.79 Intermediate Similarity NPC47059
0.79 Intermediate Similarity NPC118832
0.79 Intermediate Similarity NPC264166
0.79 Intermediate Similarity NPC329708
0.79 Intermediate Similarity NPC274291
0.79 Intermediate Similarity NPC81939
0.7895 Intermediate Similarity NPC204717
0.7892 Intermediate Similarity NPC48353
0.7889 Intermediate Similarity NPC199277
0.7889 Intermediate Similarity NPC135887
0.788 Intermediate Similarity NPC317430
0.7864 Intermediate Similarity NPC475666
0.7853 Intermediate Similarity NPC314002
0.7842 Intermediate Similarity NPC220765
0.7837 Intermediate Similarity NPC193267
0.7837 Intermediate Similarity NPC213530
0.7833 Intermediate Similarity NPC473181
0.7833 Intermediate Similarity NPC469589
0.7826 Intermediate Similarity NPC304926
0.7826 Intermediate Similarity NPC476041
0.7824 Intermediate Similarity NPC128751
0.7821 Intermediate Similarity NPC26872
0.7816 Intermediate Similarity NPC470549
0.7805 Intermediate Similarity NPC316981
0.78 Intermediate Similarity NPC475112
0.78 Intermediate Similarity NPC475085
0.78 Intermediate Similarity NPC291535
0.7797 Intermediate Similarity NPC21605
0.7795 Intermediate Similarity NPC99666
0.7794 Intermediate Similarity NPC199667
0.7793 Intermediate Similarity NPC314954
0.779 Intermediate Similarity NPC26850
0.7789 Intermediate Similarity NPC19872
0.7784 Intermediate Similarity NPC106833
0.7784 Intermediate Similarity NPC469497
0.7783 Intermediate Similarity NPC82548
0.7778 Intermediate Similarity NPC170114
0.7746 Intermediate Similarity NPC473185
0.7739 Intermediate Similarity NPC287437
0.7734 Intermediate Similarity NPC53344
0.7718 Intermediate Similarity NPC26679
0.7718 Intermediate Similarity NPC473180
0.7718 Intermediate Similarity NPC264176
0.7713 Intermediate Similarity NPC312872
0.77 Intermediate Similarity NPC227908
0.77 Intermediate Similarity NPC11017
0.77 Intermediate Similarity NPC121772
0.7692 Intermediate Similarity NPC329858
0.7685 Intermediate Similarity NPC101543
0.7685 Intermediate Similarity NPC469554
0.7685 Intermediate Similarity NPC476106
0.7684 Intermediate Similarity NPC72980
0.7682 Intermediate Similarity NPC81175
0.7678 Intermediate Similarity NPC280799
0.7678 Intermediate Similarity NPC310118
0.7673 Intermediate Similarity NPC476098
0.7665 Intermediate Similarity NPC478083
0.7664 Intermediate Similarity NPC6215
0.766 Intermediate Similarity NPC472123
0.7659 Intermediate Similarity NPC185782
0.7656 Intermediate Similarity NPC19679
0.765 Intermediate Similarity NPC476578
0.765 Intermediate Similarity NPC4071
0.765 Intermediate Similarity NPC476582
0.7641 Intermediate Similarity NPC196251
0.7641 Intermediate Similarity NPC63199
0.7641 Intermediate Similarity NPC102338
0.7641 Intermediate Similarity NPC111602
0.7639 Intermediate Similarity NPC475253
0.7638 Intermediate Similarity NPC153042
0.7638 Intermediate Similarity NPC77555
0.7635 Intermediate Similarity NPC470930
0.7632 Intermediate Similarity NPC184964
0.763 Intermediate Similarity NPC477533
0.763 Intermediate Similarity NPC86078
0.7622 Intermediate Similarity NPC118511
0.7621 Intermediate Similarity NPC11464
0.7621 Intermediate Similarity NPC5145
0.7619 Intermediate Similarity NPC303658
0.7608 Intermediate Similarity NPC183407
0.7602 Intermediate Similarity NPC314333
0.7592 Intermediate Similarity NPC232340
0.759 Intermediate Similarity NPC66083
0.7583 Intermediate Similarity NPC473179
0.7581 Intermediate Similarity NPC470126
0.7577 Intermediate Similarity NPC329982
0.7577 Intermediate Similarity NPC94943
0.7576 Intermediate Similarity NPC475190
0.7569 Intermediate Similarity NPC180504
0.7568 Intermediate Similarity NPC177404
0.7566 Intermediate Similarity NPC471294
0.7565 Intermediate Similarity NPC472108
0.7565 Intermediate Similarity NPC139291
0.7561 Intermediate Similarity NPC313189
0.7549 Intermediate Similarity NPC16452
0.7549 Intermediate Similarity NPC36229
0.7549 Intermediate Similarity NPC476581
0.7546 Intermediate Similarity NPC253580
0.7546 Intermediate Similarity NPC252251
0.7545 Intermediate Similarity NPC184680
0.7538 Intermediate Similarity NPC276517
0.7538 Intermediate Similarity NPC204385
0.7536 Intermediate Similarity NPC46561
0.7534 Intermediate Similarity NPC39370
0.7526 Intermediate Similarity NPC190007
0.7525 Intermediate Similarity NPC195268
0.7525 Intermediate Similarity NPC133140
0.7525 Intermediate Similarity NPC234197
0.7524 Intermediate Similarity NPC470931
0.7523 Intermediate Similarity NPC473186
0.7514 Intermediate Similarity NPC63157
0.7514 Intermediate Similarity NPC473868
0.7513 Intermediate Similarity NPC472112
0.7513 Intermediate Similarity NPC206201
0.7512 Intermediate Similarity NPC476287
0.7512 Intermediate Similarity NPC323345

  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 NPC329793 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
0.9831 High Similarity NPD4118 Clinical (unspecified phase)
0.861 High Similarity NPD1304 Clinical (unspecified phase)
0.8608 High Similarity NPD5658 Approved
0.8511 High Similarity NPD1038 Approved
0.8466 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.8157 Intermediate Similarity NPD8358 Approved
0.809 Intermediate Similarity NPD7452 Approved
0.809 Intermediate Similarity NPD7453 Approved
0.8081 Intermediate Similarity NPD4795 Phase 2
0.8071 Intermediate Similarity NPD5669 Clinical (unspecified phase)
0.805 Intermediate Similarity NPD2189 Approved
0.805 Intermediate Similarity NPD2187 Approved
0.8 Intermediate Similarity NPD7222 Phase 2
0.799 Intermediate Similarity NPD4418 Discontinued
0.797 Intermediate Similarity NPD1740 Approved
0.797 Intermediate Similarity NPD1739 Approved
0.795 Intermediate Similarity NPD3003 Approved
0.7938 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD3825 Phase 3
0.79 Intermediate Similarity NPD4038 Approved
0.79 Intermediate Similarity NPD4122 Approved
0.79 Intermediate Similarity NPD31 Approved
0.79 Intermediate Similarity NPD32 Approved
0.79 Intermediate Similarity NPD4035 Approved
0.79 Intermediate Similarity NPD4033 Approved
0.79 Intermediate Similarity NPD4036 Approved
0.79 Intermediate Similarity NPD4039 Approved
0.79 Intermediate Similarity NPD4034 Approved
0.79 Intermediate Similarity NPD4037 Approved
0.7892 Intermediate Similarity NPD5680 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD6242 Discontinued
0.7864 Intermediate Similarity NPD5612 Discontinued
0.785 Intermediate Similarity NPD4885 Approved
0.7835 Intermediate Similarity NPD5913 Phase 3
0.7835 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7828 Intermediate Similarity NPD1768 Approved
0.7826 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7793 Intermediate Similarity NPD5559 Phase 2
0.7789 Intermediate Similarity NPD4203 Approved
0.7789 Intermediate Similarity NPD4204 Approved
0.7767 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD3402 Phase 1
0.772 Intermediate Similarity NPD5256 Discontinued
0.7701 Intermediate Similarity NPD1078 Clinical (unspecified phase)
0.7685 Intermediate Similarity NPD5530 Phase 1
0.7684 Intermediate Similarity NPD3920 Phase 2
0.7668 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD7194 Discontinued
0.7656 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1326 Approved
0.7647 Intermediate Similarity NPD1325 Approved
0.7644 Intermediate Similarity NPD5902 Approved
0.7644 Intermediate Similarity NPD5903 Approved
0.763 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD5930 Phase 3
0.7626 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD4499 Approved
0.7598 Intermediate Similarity NPD8403 Phase 1
0.7585 Intermediate Similarity NPD4502 Phase 2
0.7574 Intermediate Similarity NPD4511 Phase 1
0.7571 Intermediate Similarity NPD3440 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD1392 Approved
0.7559 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.755 Intermediate Similarity NPD6769 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD5670 Approved
0.7536 Intermediate Similarity NPD6985 Discontinued
0.7525 Intermediate Similarity NPD3923 Approved
0.7525 Intermediate Similarity NPD3921 Approved
0.7525 Intermediate Similarity NPD3922 Approved
0.7525 Intermediate Similarity NPD3924 Approved
0.75 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3477 Phase 2
0.7488 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD7219 Approved
0.7477 Intermediate Similarity NPD7221 Approved
0.7476 Intermediate Similarity NPD5293 Phase 2
0.7464 Intermediate Similarity NPD3815 Phase 1
0.7464 Intermediate Similarity NPD3816 Phase 1
0.745 Intermediate Similarity NPD3810 Clinical (unspecified phase)
0.7441 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD5065 Approved
0.7424 Intermediate Similarity NPD2410 Phase 2
0.7416 Intermediate Similarity NPD6220 Phase 3
0.7412 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD802 Phase 2
0.7395 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7393 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD1305 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD7948 Phase 1
0.7353 Intermediate Similarity NPD4501 Approved
0.7353 Intermediate Similarity NPD484 Approved
0.7353 Intermediate Similarity NPD4500 Approved
0.7345 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5066 Phase 2
0.7333 Intermediate Similarity NPD5067 Phase 2
0.733 Intermediate Similarity NPD6991 Approved
0.7325 Intermediate Similarity NPD4558 Phase 2
0.7323 Intermediate Similarity NPD2383 Phase 1
0.7321 Intermediate Similarity NPD8017 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD8016 Phase 3
0.7306 Intermediate Similarity NPD2380 Approved
0.7306 Intermediate Similarity NPD2381 Approved
0.7306 Intermediate Similarity NPD2382 Approved
0.7304 Intermediate Similarity NPD2175 Phase 3
0.7304 Intermediate Similarity NPD2176 Approved
0.7304 Intermediate Similarity NPD5999 Phase 2
0.7304 Intermediate Similarity NPD2177 Approved
0.7304 Intermediate Similarity NPD4548 Discontinued
0.7299 Intermediate Similarity NPD3330 Phase 1
0.7296 Intermediate Similarity NPD7956 Approved
0.7296 Intermediate Similarity NPD7955 Approved
0.729 Intermediate Similarity NPD5632 Approved
0.7285 Intermediate Similarity NPD7796 Approved
0.7285 Intermediate Similarity NPD7797 Approved
0.7277 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD7112 Discontinued
0.7277 Intermediate Similarity NPD6147 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD6590 Discontinued
0.7277 Intermediate Similarity NPD6251 Discontinued
0.7273 Intermediate Similarity NPD7671 Approved
0.7273 Intermediate Similarity NPD7589 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6968 Phase 2
0.7273 Intermediate Similarity NPD5529 Phase 1
0.7273 Intermediate Similarity NPD7672 Approved
0.7273 Intermediate Similarity NPD5528 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6969 Phase 2
0.7268 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD1032 Phase 2
0.7265 Intermediate Similarity NPD7708 Approved
0.7264 Intermediate Similarity NPD6569 Phase 2
0.726 Intermediate Similarity NPD5601 Phase 2
0.7252 Intermediate Similarity NPD7558 Phase 2
0.7236 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD1034 Phase 3
0.7228 Intermediate Similarity NPD4551 Phase 2
0.7227 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.722 Intermediate Similarity NPD3814 Phase 1
0.7217 Intermediate Similarity NPD6243 Phase 3
0.7217 Intermediate Similarity NPD6244 Phase 3
0.7215 Intermediate Similarity NPD7050 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD7051 Phase 3
0.7206 Intermediate Similarity NPD5003 Discontinued
0.72 Intermediate Similarity NPD7729 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD1684 Approved
0.7196 Intermediate Similarity NPD1685 Approved
0.7193 Intermediate Similarity NPD6230 Discontinued
0.719 Intermediate Similarity NPD2916 Discontinued
0.7184 Intermediate Similarity NPD4601 Approved
0.7184 Intermediate Similarity NPD4600 Approved
0.7183 Intermediate Similarity NPD4457 Phase 2
0.7175 Intermediate Similarity NPD6494 Phase 2
0.7171 Intermediate Similarity NPD3084 Phase 3
0.7171 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD5936 Approved
0.717 Intermediate Similarity NPD5939 Approved
0.7164 Intermediate Similarity NPD6281 Approved
0.715 Intermediate Similarity NPD4897 Phase 2
0.7149 Intermediate Similarity NPD7555 Discontinued
0.7143 Intermediate Similarity NPD6634 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6633 Phase 2
0.7143 Intermediate Similarity NPD7803 Approved
0.7136 Intermediate Similarity NPD4889 Approved
0.7136 Intermediate Similarity NPD8395 Approved
0.7136 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD8396 Approved
0.713 Intermediate Similarity NPD3354 Phase 2
0.713 Intermediate Similarity NPD4429 Discontinued
0.7129 Intermediate Similarity NPD3946 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD3397 Phase 2
0.7122 Intermediate Similarity NPD2952 Discontinued
0.7122 Intermediate Similarity NPD4673 Phase 2
0.7121 Intermediate Similarity NPD5596 Phase 2
0.712 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD2917 Approved
0.7098 Intermediate Similarity NPD6741 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6158 Phase 2
0.7097 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD6150 Discontinued
0.7093 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD4072 Approved
0.7092 Intermediate Similarity NPD6159 Phase 2
0.7092 Intermediate Similarity NPD4071 Approved
0.7087 Intermediate Similarity NPD7889 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5164 Discontinued
0.7078 Intermediate Similarity NPD1954 Phase 1
0.7077 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD7592 Phase 2
0.7073 Intermediate Similarity NPD2482 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD6550 Discontinued
0.7073 Intermediate Similarity NPD5512 Phase 3
0.7071 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD3037 Phase 1
0.707 Intermediate Similarity NPD3257 Approved
0.7067 Intermediate Similarity NPD6963 Approved
0.7067 Intermediate Similarity NPD6964 Approved
0.7065 Intermediate Similarity NPD6257 Clinical (unspecified phase)

  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