Structure

Physi-Chem Properties

Molecular Weight:  326.2
Volume:  340.722
LogP:  3.11
LogD:  2.959
LogS:  -3.379
# Rotatable Bonds:  1
TPSA:  48.49
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.847
Synthetic Accessibility Score:  5.046
Fsp3:  0.6
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:  -5.427
MDCK Permeability:  5.445445822260808e-06
Pgp-inhibitor:  0.976
Pgp-substrate:  0.966
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.303
Plasma Protein Binding (PPB):  60.23486328125%
Volume Distribution (VD):  5.157
Pgp-substrate:  31.726043701171875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.17
CYP1A2-substrate:  0.667
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.849
CYP2C9-inhibitor:  0.016
CYP2C9-substrate:  0.114
CYP2D6-inhibitor:  0.465
CYP2D6-substrate:  0.897
CYP3A4-inhibitor:  0.097
CYP3A4-substrate:  0.868

ADMET: Excretion

Clearance (CL):  8.561
Half-life (T1/2):  0.583

ADMET: Toxicity

hERG Blockers:  0.221
Human Hepatotoxicity (H-HT):  0.406
Drug-inuced Liver Injury (DILI):  0.904
AMES Toxicity:  0.036
Rat Oral Acute Toxicity:  0.882
Maximum Recommended Daily Dose:  0.981
Skin Sensitization:  0.172
Carcinogencity:  0.533
Eye Corrosion:  0.053
Eye Irritation:  0.104
Respiratory Toxicity:  0.983

Download Data

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

  Natural Product: NPC472108

Natural Product ID:  NPC472108
Common Name*:   VTKMAZPMLOELMZ-ZLHXMRDPSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  VTKMAZPMLOELMZ-ZLHXMRDPSA-N
Standard InCHI:  InChI=1S/C20H26N2O2/c1-11-15(9-23)13-7-19-20-14(12-5-3-4-6-17(12)21-20)8-18(22(19)2)16(13)10-24-11/h3-6,11,13,15-16,18-19,21,23H,7-10H2,1-2H3/t11-,13-,15+,16+,18-,19-/m0/s1
SMILES:  CC1C(C2CC3C4=C(CC(C2CO1)N3C)C5=CC=CC=C5N4)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3338231
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0003759] Macroline 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
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[464202]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 25.0 ug.mL-1 PMID[464202]

☑ 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 NPC472108 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
1.0 High Similarity NPC139291
0.9636 High Similarity NPC472109
0.9636 High Similarity NPC472110
0.9451 High Similarity NPC24594
0.9451 High Similarity NPC472122
0.9448 High Similarity NPC472123
0.9298 High Similarity NPC469470
0.9298 High Similarity NPC469501
0.9281 High Similarity NPC187827
0.9281 High Similarity NPC472105
0.903 High Similarity NPC317430
0.8824 High Similarity NPC326575
0.8817 High Similarity NPC189812
0.8817 High Similarity NPC329688
0.8728 High Similarity NPC472104
0.8722 High Similarity NPC52557
0.8693 High Similarity NPC175474
0.8663 High Similarity NPC133261
0.8626 High Similarity NPC79129
0.8626 High Similarity NPC195461
0.8626 High Similarity NPC49196
0.8626 High Similarity NPC81654
0.8626 High Similarity NPC313985
0.8626 High Similarity NPC249150
0.8621 High Similarity NPC19679
0.8547 High Similarity NPC472113
0.8539 High Similarity NPC472112
0.8525 High Similarity NPC249040
0.8516 High Similarity NPC50503
0.84 Intermediate Similarity NPC15840
0.8393 Intermediate Similarity NPC81229
0.8393 Intermediate Similarity NPC255229
0.8333 Intermediate Similarity NPC95783
0.8324 Intermediate Similarity NPC254240
0.8324 Intermediate Similarity NPC312870
0.8324 Intermediate Similarity NPC294909
0.8324 Intermediate Similarity NPC199851
0.8324 Intermediate Similarity NPC128265
0.8323 Intermediate Similarity NPC285469
0.8315 Intermediate Similarity NPC79062
0.8315 Intermediate Similarity NPC472107
0.8258 Intermediate Similarity NPC472294
0.822 Intermediate Similarity NPC475422
0.8211 Intermediate Similarity NPC87755
0.8201 Intermediate Similarity NPC472111
0.8187 Intermediate Similarity NPC472097
0.8177 Intermediate Similarity NPC102338
0.8177 Intermediate Similarity NPC196251
0.8177 Intermediate Similarity NPC111602
0.8177 Intermediate Similarity NPC63199
0.8163 Intermediate Similarity NPC52254
0.814 Intermediate Similarity NPC470508
0.8129 Intermediate Similarity NPC16667
0.8122 Intermediate Similarity NPC472323
0.8112 Intermediate Similarity NPC174788
0.8108 Intermediate Similarity NPC245916
0.8092 Intermediate Similarity NPC54988
0.8092 Intermediate Similarity NPC474561
0.8092 Intermediate Similarity NPC49954
0.8086 Intermediate Similarity NPC88097
0.8081 Intermediate Similarity NPC311276
0.8066 Intermediate Similarity NPC66210
0.8056 Intermediate Similarity NPC258480
0.8047 Intermediate Similarity NPC207726
0.8011 Intermediate Similarity NPC34508
0.7989 Intermediate Similarity NPC243716
0.7989 Intermediate Similarity NPC160105
0.7977 Intermediate Similarity NPC271797
0.7977 Intermediate Similarity NPC21174
0.7966 Intermediate Similarity NPC472586
0.7956 Intermediate Similarity NPC472119
0.7953 Intermediate Similarity NPC469762
0.7944 Intermediate Similarity NPC314394
0.7944 Intermediate Similarity NPC233936
0.7943 Intermediate Similarity NPC154293
0.7943 Intermediate Similarity NPC63751
0.7941 Intermediate Similarity NPC470507
0.7938 Intermediate Similarity NPC126066
0.7933 Intermediate Similarity NPC472443
0.7933 Intermediate Similarity NPC219336
0.7929 Intermediate Similarity NPC82070
0.7927 Intermediate Similarity NPC475910
0.7919 Intermediate Similarity NPC476114
0.7919 Intermediate Similarity NPC282231
0.7914 Intermediate Similarity NPC231342
0.791 Intermediate Similarity NPC314603
0.7908 Intermediate Similarity NPC471080
0.7908 Intermediate Similarity NPC469592
0.7907 Intermediate Similarity NPC474880
0.7907 Intermediate Similarity NPC67056
0.7907 Intermediate Similarity NPC221786
0.7901 Intermediate Similarity NPC472444
0.7898 Intermediate Similarity NPC280548
0.7895 Intermediate Similarity NPC469785
0.7889 Intermediate Similarity NPC469896
0.7887 Intermediate Similarity NPC477548
0.7882 Intermediate Similarity NPC476492
0.7877 Intermediate Similarity NPC151939
0.7877 Intermediate Similarity NPC15573
0.7877 Intermediate Similarity NPC217372
0.7877 Intermediate Similarity NPC183662
0.7874 Intermediate Similarity NPC40779
0.7869 Intermediate Similarity NPC478077
0.7861 Intermediate Similarity NPC229173
0.7861 Intermediate Similarity NPC279918
0.7857 Intermediate Similarity NPC21605
0.7841 Intermediate Similarity NPC201700
0.784 Intermediate Similarity NPC198988
0.7839 Intermediate Similarity NPC469594
0.7833 Intermediate Similarity NPC270009
0.7826 Intermediate Similarity NPC119700
0.7822 Intermediate Similarity NPC475271
0.7814 Intermediate Similarity NPC62510
0.7811 Intermediate Similarity NPC471506
0.7803 Intermediate Similarity NPC475990
0.7803 Intermediate Similarity NPC230869
0.7802 Intermediate Similarity NPC163055
0.7802 Intermediate Similarity NPC143533
0.7791 Intermediate Similarity NPC325252
0.779 Intermediate Similarity NPC300688
0.7778 Intermediate Similarity NPC469786
0.7778 Intermediate Similarity NPC25008
0.7778 Intermediate Similarity NPC469763
0.7778 Intermediate Similarity NPC469760
0.7778 Intermediate Similarity NPC259644
0.7778 Intermediate Similarity NPC469765
0.7778 Intermediate Similarity NPC73952
0.7771 Intermediate Similarity NPC194640
0.7771 Intermediate Similarity NPC473868
0.7771 Intermediate Similarity NPC63157
0.7766 Intermediate Similarity NPC19692
0.7766 Intermediate Similarity NPC220151
0.776 Intermediate Similarity NPC165201
0.776 Intermediate Similarity NPC476874
0.7756 Intermediate Similarity NPC33949
0.7754 Intermediate Similarity NPC55493
0.775 Intermediate Similarity NPC281049
0.7747 Intermediate Similarity NPC71037
0.7747 Intermediate Similarity NPC192270
0.7747 Intermediate Similarity NPC113626
0.7747 Intermediate Similarity NPC302191
0.7742 Intermediate Similarity NPC329858
0.7742 Intermediate Similarity NPC314333
0.7738 Intermediate Similarity NPC470440
0.7733 Intermediate Similarity NPC70922
0.7733 Intermediate Similarity NPC80597
0.7733 Intermediate Similarity NPC212376
0.7733 Intermediate Similarity NPC75540
0.7733 Intermediate Similarity NPC211572
0.7727 Intermediate Similarity NPC234078
0.7727 Intermediate Similarity NPC221100
0.7722 Intermediate Similarity NPC121903
0.7722 Intermediate Similarity NPC203754
0.7722 Intermediate Similarity NPC150048
0.7717 Intermediate Similarity NPC188387
0.7717 Intermediate Similarity NPC163421
0.7711 Intermediate Similarity NPC59084
0.7709 Intermediate Similarity NPC97525
0.7708 Intermediate Similarity NPC475506
0.7706 Intermediate Similarity NPC37548
0.7696 Intermediate Similarity NPC241024
0.768 Intermediate Similarity NPC68354
0.768 Intermediate Similarity NPC293472
0.768 Intermediate Similarity NPC59269
0.7676 Intermediate Similarity NPC474707
0.7672 Intermediate Similarity NPC289299
0.7672 Intermediate Similarity NPC57994
0.767 Intermediate Similarity NPC469541
0.7668 Intermediate Similarity NPC162730
0.7668 Intermediate Similarity NPC193761
0.7668 Intermediate Similarity NPC155143
0.7667 Intermediate Similarity NPC275305
0.7667 Intermediate Similarity NPC37423
0.7654 Intermediate Similarity NPC158129
0.7644 Intermediate Similarity NPC473640
0.7638 Intermediate Similarity NPC475602
0.7634 Intermediate Similarity NPC204565
0.7634 Intermediate Similarity NPC317030
0.7629 Intermediate Similarity NPC477135
0.7619 Intermediate Similarity NPC474177
0.7619 Intermediate Similarity NPC247735
0.7619 Intermediate Similarity NPC269886
0.7619 Intermediate Similarity NPC472210
0.7619 Intermediate Similarity NPC472295
0.7619 Intermediate Similarity NPC81802
0.7614 Intermediate Similarity NPC476116
0.7611 Intermediate Similarity NPC161861
0.7609 Intermediate Similarity NPC48938
0.7609 Intermediate Similarity NPC469358
0.7605 Intermediate Similarity NPC2949
0.7604 Intermediate Similarity NPC100321
0.7598 Intermediate Similarity NPC474897
0.7596 Intermediate Similarity NPC198339
0.7596 Intermediate Similarity NPC91179
0.7594 Intermediate Similarity NPC65215
0.7594 Intermediate Similarity NPC46413
0.7594 Intermediate Similarity NPC173028
0.7594 Intermediate Similarity NPC213629
0.7592 Intermediate Similarity NPC232130
0.7586 Intermediate Similarity NPC141353

  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 NPC472108 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
0.8626 High Similarity NPD4601 Approved
0.8626 High Similarity NPD4600 Approved
0.8324 Intermediate Similarity NPD4500 Approved
0.8324 Intermediate Similarity NPD4501 Approved
0.8035 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7802 Intermediate Similarity NPD5596 Phase 2
0.7797 Intermediate Similarity NPD1325 Approved
0.7797 Intermediate Similarity NPD1326 Approved
0.779 Intermediate Similarity NPD6595 Phase 3
0.7742 Intermediate Similarity NPD4499 Approved
0.7735 Intermediate Similarity NPD4079 Approved
0.7735 Intermediate Similarity NPD4076 Approved
0.7722 Intermediate Similarity NPD2381 Approved
0.7722 Intermediate Similarity NPD2380 Approved
0.7722 Intermediate Similarity NPD2382 Approved
0.7722 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7717 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7709 Intermediate Similarity NPD4112 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD3505 Approved
0.768 Intermediate Similarity NPD3506 Approved
0.7672 Intermediate Similarity NPD4602 Approved
0.7667 Intermediate Similarity NPD5065 Approved
0.7619 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD5913 Phase 3
0.7594 Intermediate Similarity NPD8110 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD2144 Approved
0.7571 Intermediate Similarity NPD5138 Approved
0.7571 Intermediate Similarity NPD5140 Approved
0.7558 Intermediate Similarity NPD4463 Approved
0.7558 Intermediate Similarity NPD4462 Approved
0.7554 Intermediate Similarity NPD3038 Discontinued
0.7551 Intermediate Similarity NPD7957 Phase 1
0.7551 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7541 Intermediate Similarity NPD8386 Phase 2
0.754 Intermediate Similarity NPD8431 Approved
0.7527 Intermediate Similarity NPD6227 Discontinued
0.7514 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD2882 Phase 1
0.75 Intermediate Similarity NPD5003 Discontinued
0.75 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD2383 Phase 1
0.7444 Intermediate Similarity NPD5021 Discontinued
0.7443 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD7271 Approved
0.7423 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD2094 Phase 2
0.7419 Intermediate Similarity NPD2092 Phase 2
0.7419 Intermediate Similarity NPD2095 Phase 2
0.7414 Intermediate Similarity NPD6158 Phase 2
0.7414 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD8115 Approved
0.7411 Intermediate Similarity NPD8272 Phase 2
0.7411 Intermediate Similarity NPD8114 Approved
0.7396 Intermediate Similarity NPD3943 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7944 Discontinued
0.7391 Intermediate Similarity NPD4181 Approved
0.7391 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD1683 Approved
0.738 Intermediate Similarity NPD2096 Phase 2
0.738 Intermediate Similarity NPD2091 Phase 2
0.7377 Intermediate Similarity NPD482 Approved
0.7377 Intermediate Similarity NPD6492 Phase 2
0.7374 Intermediate Similarity NPD3003 Approved
0.7371 Intermediate Similarity NPD2837 Discontinued
0.7368 Intermediate Similarity NPD7730 Approved
0.7368 Intermediate Similarity NPD7731 Approved
0.7366 Intermediate Similarity NPD7194 Discontinued
0.7366 Intermediate Similarity NPD8408 Discontinued
0.7363 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD1722 Approved
0.7348 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD4640 Approved
0.7348 Intermediate Similarity NPD5862 Discovery
0.7348 Intermediate Similarity NPD4639 Approved
0.7348 Intermediate Similarity NPD4638 Approved
0.7337 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD8322 Phase 2
0.7337 Intermediate Similarity NPD5104 Approved
0.7333 Intermediate Similarity NPD6249 Phase 2
0.7333 Intermediate Similarity NPD6248 Phase 2
0.7333 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4550 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD972 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD3394 Approved
0.7304 Intermediate Similarity NPD3393 Approved
0.7304 Intermediate Similarity NPD3389 Approved
0.73 Intermediate Similarity NPD5658 Approved
0.7299 Intermediate Similarity NPD7824 Approved
0.7278 Intermediate Similarity NPD3323 Discontinued
0.7273 Intermediate Similarity NPD4204 Approved
0.7273 Intermediate Similarity NPD8072 Approved
0.7273 Intermediate Similarity NPD4120 Approved
0.7273 Intermediate Similarity NPD4121 Phase 3
0.7273 Intermediate Similarity NPD4203 Approved
0.7267 Intermediate Similarity NPD5254 Discontinued
0.7263 Intermediate Similarity NPD8021 Approved
0.7263 Intermediate Similarity NPD8020 Approved
0.7255 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD1592 Phase 3
0.725 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD3385 Approved
0.7245 Intermediate Similarity NPD1768 Approved
0.7241 Intermediate Similarity NPD4703 Approved
0.7241 Intermediate Similarity NPD4702 Approved
0.7236 Intermediate Similarity NPD4035 Approved
0.7236 Intermediate Similarity NPD4122 Approved
0.7236 Intermediate Similarity NPD32 Approved
0.7236 Intermediate Similarity NPD4033 Approved
0.7236 Intermediate Similarity NPD31 Approved
0.7236 Intermediate Similarity NPD4034 Approved
0.7236 Intermediate Similarity NPD4038 Approved
0.7236 Intermediate Similarity NPD4036 Approved
0.7236 Intermediate Similarity NPD4039 Approved
0.7236 Intermediate Similarity NPD4037 Approved
0.7235 Intermediate Similarity NPD786 Approved
0.7232 Intermediate Similarity NPD5742 Approved
0.7232 Intermediate Similarity NPD5741 Approved
0.7232 Intermediate Similarity NPD5743 Approved
0.7228 Intermediate Similarity NPD750 Phase 2
0.7225 Intermediate Similarity NPD4334 Discontinued
0.7219 Intermediate Similarity NPD5897 Approved
0.7219 Intermediate Similarity NPD5899 Approved
0.7219 Intermediate Similarity NPD5898 Approved
0.7219 Intermediate Similarity NPD6277 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD7952 Approved
0.7196 Intermediate Similarity NPD7791 Approved
0.7196 Intermediate Similarity NPD7953 Approved
0.7196 Intermediate Similarity NPD7950 Approved
0.7196 Intermediate Similarity NPD7951 Approved
0.7196 Intermediate Similarity NPD7789 Approved
0.7196 Intermediate Similarity NPD7790 Approved
0.7194 Intermediate Similarity NPD3230 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD7889 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD4128 Approved
0.7188 Intermediate Similarity NPD2564 Approved
0.7188 Intermediate Similarity NPD2565 Phase 2
0.7184 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7178 Intermediate Similarity NPD4520 Approved
0.7178 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD6739 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD3961 Discontinued
0.7166 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD8410 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD2844 Phase 3
0.7157 Intermediate Similarity NPD2177 Approved
0.7157 Intermediate Similarity NPD2175 Phase 3
0.7157 Intermediate Similarity NPD2176 Approved
0.7157 Intermediate Similarity NPD3330 Phase 1
0.7151 Intermediate Similarity NPD6301 Phase 2
0.715 Intermediate Similarity NPD5426 Phase 3
0.7143 Intermediate Similarity NPD7948 Phase 1
0.7143 Intermediate Similarity NPD2915 Discontinued
0.7136 Intermediate Similarity NPD8073 Approved
0.7135 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD6615 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD5473 Discontinued
0.7128 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD6977 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD6978 Phase 2
0.7109 Intermediate Similarity NPD6976 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD53 Approved
0.7107 Intermediate Similarity NPD7777 Approved
0.7107 Intermediate Similarity NPD7778 Approved
0.7105 Intermediate Similarity NPD6178 Phase 3
0.7102 Intermediate Similarity NPD3100 Discontinued
0.7098 Intermediate Similarity NPD6281 Approved
0.7098 Intermediate Similarity NPD8063 Discontinued
0.7092 Intermediate Similarity NPD7935 Phase 2
0.7092 Intermediate Similarity NPD6449 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD7867 Phase 1
0.7087 Intermediate Similarity NPD5903 Approved
0.7087 Intermediate Similarity NPD5902 Approved
0.7085 Intermediate Similarity NPD7817 Phase 1
0.7083 Intermediate Similarity NPD3486 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5590 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD1038 Approved
0.7071 Intermediate Similarity NPD3800 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD3082 Discontinued
0.7068 Intermediate Similarity NPD5075 Discontinued
0.7068 Intermediate Similarity NPD5555 Phase 1
0.7067 Intermediate Similarity NPD6985 Discontinued
0.7065 Intermediate Similarity NPD4779 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD2641 Approved
0.7065 Intermediate Similarity NPD2640 Approved
0.7062 Intermediate Similarity NPD3785 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD198 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