Structure

Physi-Chem Properties

Molecular Weight:  283.19
Volume:  312.195
LogP:  3.775
LogD:  3.19
LogS:  -3.669
# Rotatable Bonds:  2
TPSA:  23.47
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.838
Synthetic Accessibility Score:  4.272
Fsp3:  0.579
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.633
MDCK Permeability:  1.80114420800237e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.977
30% Bioavailability (F30%):  0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.973
Plasma Protein Binding (PPB):  77.34988403320312%
Volume Distribution (VD):  3.188
Pgp-substrate:  22.377042770385742%

ADMET: Metabolism

CYP1A2-inhibitor:  0.126
CYP1A2-substrate:  0.79
CYP2C19-inhibitor:  0.245
CYP2C19-substrate:  0.827
CYP2C9-inhibitor:  0.054
CYP2C9-substrate:  0.36
CYP2D6-inhibitor:  0.983
CYP2D6-substrate:  0.915
CYP3A4-inhibitor:  0.105
CYP3A4-substrate:  0.54

ADMET: Excretion

Clearance (CL):  10.104
Half-life (T1/2):  0.524

ADMET: Toxicity

hERG Blockers:  0.334
Human Hepatotoxicity (H-HT):  0.135
Drug-inuced Liver Injury (DILI):  0.033
AMES Toxicity:  0.03
Rat Oral Acute Toxicity:  0.137
Maximum Recommended Daily Dose:  0.893
Skin Sensitization:  0.946
Carcinogencity:  0.127
Eye Corrosion:  0.014
Eye Irritation:  0.212
Respiratory Toxicity:  0.907

Download Data

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

  Natural Product: NPC124802

Natural Product ID:  NPC124802
Common Name*:   Levallorphan
IUPAC Name:   n.a.
Synonyms:   Levallorphan; Lorfan; Naloxiphan
Standard InCHIKey:  OZYUPQUCAUTOBP-QXAKKESOSA-N
Standard InCHI:  InChI=1S/C19H25NO/c1-2-10-20-11-9-19-8-4-3-5-16(19)18(20)12-14-6-7-15(21)13-17(14)19/h2,6-7,13,16,18,21H,1,3-5,8-12H2/t16-,18+,19+/m0/s1
SMILES:  C=CCN1CC[C@@]23[C@H]([C@H]1Cc1c3cc(cc1)O)CCCC2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1254682
PubChem CID:   5359371
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000058] Morphinans

*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
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[15019787]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. PMID[23517479]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9498 Papaver somniferum Species Papaveraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9498 Papaver somniferum Species Papaveraceae 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
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 26603.2 nM PubChem BioAssay data set
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Ki = 12000.0 nM PMID[546993]
NPT145 Individual Protein Mu opioid receptor Homo sapiens Ki = 1.29 nM PMID[546994]
NPT145 Individual Protein Mu opioid receptor Homo sapiens Ki = 1.69 nM PMID[546994]
NPT145 Individual Protein Mu opioid receptor Homo sapiens Ki = 0.48 nM PMID[546994]
NPT1069 Individual Protein Mu opioid receptor Rattus norvegicus IC50 = 0.6341 nM PMID[546995]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 4731.8 nM PMID[546996]
NPT2 Others Unspecified Potency n.a. 33491.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6007 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 26806.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 31210 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 29849.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 18833.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21131.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4216.3 nM PubChem BioAssay data set
NPT29 Organism Rattus norvegicus Rattus norvegicus IC50 = 9.0 nM PMID[546991]
NPT29 Organism Rattus norvegicus Rattus norvegicus IC50 = 34.0 nM PMID[546991]
NPT2 Others Unspecified Ratio = 3.7 n.a. PMID[546991]
NPT3590 Protein Family Opioid receptor Rattus norvegicus IC50 = 1.1 nM PMID[546992]
NPT3590 Protein Family Opioid receptor Rattus norvegicus IC50 = 0.54 nM PMID[546992]
NPT4389 Protein Family Opioid receptors; mu/kappa/delta Homo sapiens Ratio = 2.0 n.a. PMID[546992]
NPT4390 Others Opioid receptors; mu & kappa Homo sapiens IC50 = 0.67 nM PMID[546992]
NPT4390 Others Opioid receptors; mu & kappa Homo sapiens IC50 = 2.6 nM PMID[546992]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[546996]
NPT2 Others Unspecified Potency n.a. 28183.8 nM PMID[546996]
NPT2 Others Unspecified Potency n.a. 25118.9 nM PMID[546996]
NPT2 Others Unspecified Ac50 n.a. 25.12 uM PMID[546997]
NPT2 Others Unspecified AC50 n.a. 25118.9 nM PMID[546997]
NPT2 Others Unspecified IC50 n.a. 20000.0 nM PMID[546997]
NPT2 Others Unspecified IC50 n.a. 10000.0 nM PMID[546997]
NPT2 Others Unspecified Ac50 n.a. 39.81 uM PMID[546997]
NPT2 Others Unspecified AC50 n.a. 39810.7 nM PMID[546997]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.1904 n.a. PMID[546998]

☑ 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 NPC124802 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
0.9756 High Similarity NPC89769
0.9756 High Similarity NPC126859
0.9756 High Similarity NPC259665
0.9754 High Similarity NPC268763
0.9754 High Similarity NPC66177
0.9754 High Similarity NPC8305
0.9444 High Similarity NPC149379
0.8779 High Similarity NPC325568
0.8071 Intermediate Similarity NPC470925
0.7955 Intermediate Similarity NPC307020
0.792 Intermediate Similarity NPC322753
0.784 Intermediate Similarity NPC141782
0.7823 Intermediate Similarity NPC11554
0.7801 Intermediate Similarity NPC211468
0.7801 Intermediate Similarity NPC219233
0.7801 Intermediate Similarity NPC170170
0.7778 Intermediate Similarity NPC176279
0.7778 Intermediate Similarity NPC260323
0.7763 Intermediate Similarity NPC27410
0.7763 Intermediate Similarity NPC166014
0.7746 Intermediate Similarity NPC323123
0.7734 Intermediate Similarity NPC195922
0.7718 Intermediate Similarity NPC26601
0.7717 Intermediate Similarity NPC250323
0.7698 Intermediate Similarity NPC13482
0.7662 Intermediate Similarity NPC1229
0.7615 Intermediate Similarity NPC471668
0.7603 Intermediate Similarity NPC185838
0.7597 Intermediate Similarity NPC268160
0.7548 Intermediate Similarity NPC324144
0.7541 Intermediate Similarity NPC155847
0.7541 Intermediate Similarity NPC289381
0.7538 Intermediate Similarity NPC147179
0.7538 Intermediate Similarity NPC35797
0.7538 Intermediate Similarity NPC192948
0.7533 Intermediate Similarity NPC81733
0.7533 Intermediate Similarity NPC326316
0.7532 Intermediate Similarity NPC226428
0.7519 Intermediate Similarity NPC715
0.7516 Intermediate Similarity NPC306555
0.7516 Intermediate Similarity NPC158376
0.7516 Intermediate Similarity NPC117188
0.7516 Intermediate Similarity NPC145832
0.7516 Intermediate Similarity NPC205421
0.7516 Intermediate Similarity NPC474931
0.7516 Intermediate Similarity NPC298979
0.7516 Intermediate Similarity NPC81218
0.7516 Intermediate Similarity NPC12053
0.75 Intermediate Similarity NPC212794
0.75 Intermediate Similarity NPC136508
0.75 Intermediate Similarity NPC78222
0.75 Intermediate Similarity NPC13504
0.75 Intermediate Similarity NPC95716
0.75 Intermediate Similarity NPC321505
0.75 Intermediate Similarity NPC255607
0.75 Intermediate Similarity NPC477563
0.75 Intermediate Similarity NPC196447
0.75 Intermediate Similarity NPC48342
0.75 Intermediate Similarity NPC253043
0.75 Intermediate Similarity NPC77772
0.75 Intermediate Similarity NPC179825
0.75 Intermediate Similarity NPC3375
0.75 Intermediate Similarity NPC476151
0.75 Intermediate Similarity NPC164649
0.75 Intermediate Similarity NPC96603
0.75 Intermediate Similarity NPC306843
0.75 Intermediate Similarity NPC191376
0.7481 Intermediate Similarity NPC38893
0.7481 Intermediate Similarity NPC308828
0.7481 Intermediate Similarity NPC477137
0.7481 Intermediate Similarity NPC308311
0.7481 Intermediate Similarity NPC219112
0.7468 Intermediate Similarity NPC221864
0.746 Intermediate Similarity NPC151477
0.7452 Intermediate Similarity NPC81247
0.7452 Intermediate Similarity NPC35627
0.7452 Intermediate Similarity NPC124657
0.7452 Intermediate Similarity NPC476573
0.745 Intermediate Similarity NPC246587
0.745 Intermediate Similarity NPC428
0.745 Intermediate Similarity NPC24233
0.745 Intermediate Similarity NPC135538
0.745 Intermediate Similarity NPC476571
0.745 Intermediate Similarity NPC147390
0.7444 Intermediate Similarity NPC42657
0.7444 Intermediate Similarity NPC93071
0.7444 Intermediate Similarity NPC126002
0.7442 Intermediate Similarity NPC46940
0.7431 Intermediate Similarity NPC150712
0.7424 Intermediate Similarity NPC477136
0.7424 Intermediate Similarity NPC16030
0.7424 Intermediate Similarity NPC172219
0.7424 Intermediate Similarity NPC304510
0.7419 Intermediate Similarity NPC119649
0.7419 Intermediate Similarity NPC230956
0.7419 Intermediate Similarity NPC235143
0.7419 Intermediate Similarity NPC205255
0.7419 Intermediate Similarity NPC271388
0.7407 Intermediate Similarity NPC109151
0.7403 Intermediate Similarity NPC79328
0.74 Intermediate Similarity NPC103379
0.74 Intermediate Similarity NPC477565
0.7398 Intermediate Similarity NPC211885
0.7391 Intermediate Similarity NPC329969
0.7388 Intermediate Similarity NPC99734
0.7388 Intermediate Similarity NPC318552
0.7388 Intermediate Similarity NPC321133
0.7388 Intermediate Similarity NPC190501
0.7385 Intermediate Similarity NPC322239
0.7385 Intermediate Similarity NPC321589
0.7383 Intermediate Similarity NPC144863
0.7383 Intermediate Similarity NPC90844
0.7383 Intermediate Similarity NPC253883
0.7383 Intermediate Similarity NPC95075
0.7376 Intermediate Similarity NPC33338
0.7376 Intermediate Similarity NPC302171
0.7376 Intermediate Similarity NPC300020
0.7372 Intermediate Similarity NPC79402
0.7372 Intermediate Similarity NPC80759
0.7368 Intermediate Similarity NPC469609
0.7368 Intermediate Similarity NPC471671
0.7364 Intermediate Similarity NPC266937
0.7364 Intermediate Similarity NPC470770
0.7361 Intermediate Similarity NPC193528
0.7351 Intermediate Similarity NPC192768
0.7351 Intermediate Similarity NPC97221
0.7351 Intermediate Similarity NPC220858
0.7351 Intermediate Similarity NPC151895
0.7351 Intermediate Similarity NPC88249
0.7348 Intermediate Similarity NPC82963
0.7348 Intermediate Similarity NPC469663
0.7348 Intermediate Similarity NPC92
0.7348 Intermediate Similarity NPC141001
0.7344 Intermediate Similarity NPC314187
0.7344 Intermediate Similarity NPC58865
0.7338 Intermediate Similarity NPC186063
0.7333 Intermediate Similarity NPC328504
0.7328 Intermediate Similarity NPC471534
0.7324 Intermediate Similarity NPC132847
0.7313 Intermediate Similarity NPC469644
0.7312 Intermediate Similarity NPC118274
0.7312 Intermediate Similarity NPC168753
0.7308 Intermediate Similarity NPC62867
0.7308 Intermediate Similarity NPC177962
0.7308 Intermediate Similarity NPC475780
0.7305 Intermediate Similarity NPC257390
0.7303 Intermediate Similarity NPC8337
0.7303 Intermediate Similarity NPC85747
0.7302 Intermediate Similarity NPC117115
0.7293 Intermediate Similarity NPC38458
0.7293 Intermediate Similarity NPC299180
0.7293 Intermediate Similarity NPC311737
0.729 Intermediate Similarity NPC476572
0.7287 Intermediate Similarity NPC474149
0.7285 Intermediate Similarity NPC219162
0.7285 Intermediate Similarity NPC207824
0.7285 Intermediate Similarity NPC92541
0.7285 Intermediate Similarity NPC60538
0.7279 Intermediate Similarity NPC142198
0.7279 Intermediate Similarity NPC77569
0.7278 Intermediate Similarity NPC134858
0.7273 Intermediate Similarity NPC189266
0.7273 Intermediate Similarity NPC249797
0.7273 Intermediate Similarity NPC110416
0.7273 Intermediate Similarity NPC99659
0.7273 Intermediate Similarity NPC2413
0.7273 Intermediate Similarity NPC325871
0.7273 Intermediate Similarity NPC469719
0.7273 Intermediate Similarity NPC184026
0.7273 Intermediate Similarity NPC172765
0.7273 Intermediate Similarity NPC127674
0.7273 Intermediate Similarity NPC5238
0.7273 Intermediate Similarity NPC295691
0.7273 Intermediate Similarity NPC204828
0.7273 Intermediate Similarity NPC469817
0.7273 Intermediate Similarity NPC278799
0.7273 Intermediate Similarity NPC207757
0.7273 Intermediate Similarity NPC276588
0.7273 Intermediate Similarity NPC54379
0.7273 Intermediate Similarity NPC39701
0.7273 Intermediate Similarity NPC193949
0.7267 Intermediate Similarity NPC239775
0.7266 Intermediate Similarity NPC24101
0.7266 Intermediate Similarity NPC96224
0.726 Intermediate Similarity NPC314682
0.7259 Intermediate Similarity NPC135467
0.7259 Intermediate Similarity NPC260832
0.7244 Intermediate Similarity NPC271274
0.7244 Intermediate Similarity NPC21594
0.7236 Intermediate Similarity NPC32674
0.7236 Intermediate Similarity NPC225464
0.7226 Intermediate Similarity NPC180756
0.7226 Intermediate Similarity NPC170503
0.7226 Intermediate Similarity NPC323443
0.7226 Intermediate Similarity NPC147091
0.7226 Intermediate Similarity NPC29647
0.7226 Intermediate Similarity NPC203784
0.7226 Intermediate Similarity NPC126519
0.7222 Intermediate Similarity NPC477020
0.7222 Intermediate Similarity NPC192135

  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 NPC124802 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
1.0 High Similarity NPD3594 Approved
1.0 High Similarity NPD3595 Approved
0.9836 High Similarity NPD2605 Approved
0.9836 High Similarity NPD2606 Approved
0.9756 High Similarity NPD5155 Approved
0.9756 High Similarity NPD5156 Approved
0.9754 High Similarity NPD3637 Approved
0.9754 High Similarity NPD3635 Approved
0.9754 High Similarity NPD3636 Approved
0.9091 High Similarity NPD4726 Approved
0.9091 High Similarity NPD4725 Approved
0.9091 High Similarity NPD4721 Approved
0.8862 High Similarity NPD4093 Discontinued
0.8779 High Similarity NPD3109 Approved
0.8779 High Similarity NPD3110 Approved
0.864 High Similarity NPD1751 Approved
0.848 Intermediate Similarity NPD2226 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD2194 Approved
0.8462 Intermediate Similarity NPD2195 Approved
0.8429 Intermediate Similarity NPD2420 Approved
0.8429 Intermediate Similarity NPD2421 Approved
0.8357 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.8217 Intermediate Similarity NPD5350 Clinical (unspecified phase)
0.8217 Intermediate Similarity NPD5351 Clinical (unspecified phase)
0.8201 Intermediate Similarity NPD4256 Phase 2
0.8201 Intermediate Similarity NPD4257 Approved
0.8197 Intermediate Similarity NPD1792 Phase 2
0.8156 Intermediate Similarity NPD8131 Suspended
0.808 Intermediate Similarity NPD2229 Approved
0.808 Intermediate Similarity NPD2228 Approved
0.808 Intermediate Similarity NPD2234 Approved
0.8047 Intermediate Similarity NPD5303 Approved
0.8047 Intermediate Similarity NPD5304 Approved
0.8043 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD4659 Approved
0.7951 Intermediate Similarity NPD1445 Approved
0.7951 Intermediate Similarity NPD1444 Approved
0.7874 Intermediate Similarity NPD1793 Approved
0.7874 Intermediate Similarity NPD1791 Approved
0.7857 Intermediate Similarity NPD1753 Discontinued
0.7847 Intermediate Similarity NPD3845 Phase 1
0.7836 Intermediate Similarity NPD4103 Phase 2
0.7836 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD3364 Phase 3
0.7786 Intermediate Similarity NPD5238 Clinical (unspecified phase)
0.7762 Intermediate Similarity NPD3638 Discontinued
0.7755 Intermediate Similarity NPD4727 Phase 1
0.7687 Intermediate Similarity NPD6025 Phase 1
0.7655 Intermediate Similarity NPD7910 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD2489 Approved
0.758 Intermediate Similarity NPD27 Approved
0.7571 Intermediate Similarity NPD6346 Approved
0.7569 Intermediate Similarity NPD7037 Approved
0.7564 Intermediate Similarity NPD3051 Approved
0.7561 Intermediate Similarity NPD4229 Approved
0.7561 Intermediate Similarity NPD4231 Approved
0.7556 Intermediate Similarity NPD1755 Approved
0.7554 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2970 Approved
0.7516 Intermediate Similarity NPD2969 Approved
0.75 Intermediate Similarity NPD3091 Approved
0.7465 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD3053 Approved
0.7445 Intermediate Similarity NPD3055 Approved
0.7431 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD4656 Approved
0.7419 Intermediate Similarity NPD4658 Approved
0.7415 Intermediate Similarity NPD5241 Discontinued
0.7388 Intermediate Similarity NPD2668 Approved
0.7388 Intermediate Similarity NPD3019 Approved
0.7388 Intermediate Similarity NPD7725 Approved
0.7388 Intermediate Similarity NPD2667 Approved
0.7388 Intermediate Similarity NPD4059 Approved
0.7383 Intermediate Similarity NPD3645 Discontinued
0.7353 Intermediate Similarity NPD2233 Approved
0.7353 Intermediate Similarity NPD2230 Approved
0.7353 Intermediate Similarity NPD2232 Approved
0.7348 Intermediate Similarity NPD6775 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2688 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD4603 Phase 2
0.7323 Intermediate Similarity NPD4095 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD4578 Approved
0.7317 Intermediate Similarity NPD4577 Approved
0.7308 Intermediate Similarity NPD7833 Phase 2
0.7308 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD7831 Phase 2
0.7287 Intermediate Similarity NPD4253 Approved
0.7287 Intermediate Similarity NPD4254 Approved
0.7284 Intermediate Similarity NPD5190 Phase 2
0.728 Intermediate Similarity NPD3681 Approved
0.728 Intermediate Similarity NPD3683 Approved
0.7279 Intermediate Similarity NPD3092 Approved
0.7259 Intermediate Similarity NPD2286 Discontinued
0.7259 Intermediate Similarity NPD2932 Approved
0.7246 Intermediate Similarity NPD5311 Approved
0.7246 Intermediate Similarity NPD5310 Approved
0.723 Intermediate Similarity NPD5754 Discontinued
0.7226 Intermediate Similarity NPD2562 Approved
0.7226 Intermediate Similarity NPD2561 Approved
0.7222 Intermediate Similarity NPD9610 Approved
0.7222 Intermediate Similarity NPD9608 Approved
0.7212 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4818 Approved
0.72 Intermediate Similarity NPD4817 Approved
0.7188 Intermediate Similarity NPD2342 Discontinued
0.7186 Intermediate Similarity NPD4663 Approved
0.7177 Intermediate Similarity NPD3020 Approved
0.7162 Intermediate Similarity NPD3599 Approved
0.7154 Intermediate Similarity NPD4025 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD2173 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7906 Approved
0.7143 Intermediate Similarity NPD3680 Approved
0.7143 Intermediate Similarity NPD3682 Approved
0.7133 Intermediate Similarity NPD6884 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD4720 Approved
0.7132 Intermediate Similarity NPD4717 Approved
0.7132 Intermediate Similarity NPD4718 Approved
0.7132 Intermediate Similarity NPD3095 Discontinued
0.7131 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD2227 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD7310 Approved
0.7108 Intermediate Similarity NPD7313 Approved
0.7108 Intermediate Similarity NPD7311 Approved
0.7108 Intermediate Similarity NPD7312 Approved
0.7103 Intermediate Similarity NPD823 Approved
0.7103 Intermediate Similarity NPD817 Approved
0.7086 Intermediate Similarity NPD3124 Discontinued
0.7071 Intermediate Similarity NPD3094 Phase 2
0.7066 Intermediate Similarity NPD7309 Approved
0.7063 Intermediate Similarity NPD7294 Phase 1
0.7059 Intermediate Similarity NPD2488 Approved
0.7059 Intermediate Similarity NPD2490 Approved
0.7059 Intermediate Similarity NPD7427 Discontinued
0.705 Intermediate Similarity NPD1669 Approved
0.7048 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD4584 Approved
0.7037 Intermediate Similarity NPD4481 Phase 3
0.7027 Intermediate Similarity NPD6809 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD6584 Phase 3
0.7014 Intermediate Similarity NPD4474 Approved
0.7014 Intermediate Similarity NPD4475 Approved
0.7 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.6986 Remote Similarity NPD2568 Approved
0.6975 Remote Similarity NPD3975 Discontinued
0.6974 Remote Similarity NPD7598 Phase 2
0.6972 Remote Similarity NPD5736 Approved
0.6966 Remote Similarity NPD2238 Phase 2
0.6947 Remote Similarity NPD3021 Approved
0.6947 Remote Similarity NPD3022 Approved
0.6935 Remote Similarity NPD2860 Approved
0.6935 Remote Similarity NPD2859 Approved
0.6934 Remote Similarity NPD4235 Clinical (unspecified phase)
0.6934 Remote Similarity NPD1710 Approved
0.6933 Remote Similarity NPD2211 Approved
0.6933 Remote Similarity NPD2209 Approved
0.6933 Remote Similarity NPD4127 Clinical (unspecified phase)
0.6933 Remote Similarity NPD2898 Approved
0.6917 Remote Similarity NPD7635 Approved
0.6917 Remote Similarity NPD9379 Approved
0.6917 Remote Similarity NPD9377 Approved
0.6913 Remote Similarity NPD2174 Clinical (unspecified phase)
0.6912 Remote Similarity NPD318 Approved
0.6912 Remote Similarity NPD856 Approved
0.6912 Remote Similarity NPD317 Approved
0.6912 Remote Similarity NPD16 Approved
0.6901 Remote Similarity NPD7905 Discontinued
0.6901 Remote Similarity NPD7451 Discontinued
0.6899 Remote Similarity NPD6818 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6407 Approved
0.6897 Remote Similarity NPD6405 Approved
0.6892 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6892 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6887 Remote Similarity NPD6748 Discontinued
0.6887 Remote Similarity NPD5819 Phase 2
0.6887 Remote Similarity NPD7066 Clinical (unspecified phase)
0.6883 Remote Similarity NPD6090 Discontinued
0.688 Remote Similarity NPD288 Approved
0.6879 Remote Similarity NPD4772 Phase 2
0.6879 Remote Similarity NPD4773 Phase 2
0.6871 Remote Similarity NPD4097 Suspended
0.6867 Remote Similarity NPD7479 Phase 2
0.6861 Remote Similarity NPD316 Approved
0.6857 Remote Similarity NPD7249 Approved
0.6857 Remote Similarity NPD7250 Approved
0.6855 Remote Similarity NPD7737 Approved
0.6855 Remote Similarity NPD2934 Approved
0.6855 Remote Similarity NPD2933 Approved
0.6855 Remote Similarity NPD7738 Approved
0.6853 Remote Similarity NPD4208 Discontinued
0.6849 Remote Similarity NPD3059 Approved
0.6849 Remote Similarity NPD3062 Approved
0.6849 Remote Similarity NPD3061 Approved
0.6842 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6839 Remote Similarity NPD5699 Approved
0.6835 Remote Similarity NPD3026 Approved
0.6835 Remote Similarity NPD3023 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