Structure

Physi-Chem Properties

Molecular Weight:  370.19
Volume:  372.962
LogP:  0.823
LogD:  1.755
LogS:  -1.45
# Rotatable Bonds:  3
TPSA:  74.52
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.501
Synthetic Accessibility Score:  4.686
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.578
MDCK Permeability:  3.0289078495115973e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.845
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.518
Plasma Protein Binding (PPB):  54.77227783203125%
Volume Distribution (VD):  4.03
Pgp-substrate:  42.96984100341797%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.523
CYP2C19-inhibitor:  0.049
CYP2C19-substrate:  0.733
CYP2C9-inhibitor:  0.021
CYP2C9-substrate:  0.269
CYP2D6-inhibitor:  0.043
CYP2D6-substrate:  0.234
CYP3A4-inhibitor:  0.625
CYP3A4-substrate:  0.923

ADMET: Excretion

Clearance (CL):  12.4
Half-life (T1/2):  0.859

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.511
Drug-inuced Liver Injury (DILI):  0.045
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.995
Skin Sensitization:  0.125
Carcinogencity:  0.941
Eye Corrosion:  0.003
Eye Irritation:  0.014
Respiratory Toxicity:  0.261

Download Data

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

  Natural Product: NPC469736

Natural Product ID:  NPC469736
Common Name*:   Alpneumine G
IUPAC Name:   n.a.
Synonyms:   Alpneumine G
Standard InCHIKey:  YMNSBLFXXIFOLR-IMWDKWLZSA-N
Standard InCHI:  InChI=1S/C21H26N2O4/c1-3-20-10-6-11-23(26)12-9-15-14-7-4-5-8-16(14)22(17(15)18(20)23)21(25,13-20)19(24)27-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+,23?/m1/s1
SMILES:  COC(=O)[C@@]1(O)C[C@]2(CC)CCCN3(=O)[C@@H]2c2n1c1ccccc1c2CC3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1164480
PubChem CID:   3039951
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002671] Eburnan-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
NPO25579 Alstonia pneumatophora Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[20576577]
NPO25579 Alstonia pneumatophora 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
NPT319 Cell Line B16 Mus musculus IC50 = 58300.0 nM PMID[501365]
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 > 100000.0 nM PMID[501365]
NPT319 Cell Line B16 Mus musculus Activity < 50.0 % PMID[501365]

☑ 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 NPC469736 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
0.9011 High Similarity NPC289299
0.9011 High Similarity NPC57994
0.8352 Intermediate Similarity NPC469541
0.8261 Intermediate Similarity NPC143533
0.7895 Intermediate Similarity NPC472323
0.7887 Intermediate Similarity NPC472116
0.7842 Intermediate Similarity NPC478077
0.7766 Intermediate Similarity NPC15840
0.7737 Intermediate Similarity NPC472119
0.7713 Intermediate Similarity NPC133261
0.7672 Intermediate Similarity NPC469896
0.7668 Intermediate Similarity NPC175474
0.7644 Intermediate Similarity NPC258480
0.7626 Intermediate Similarity NPC52557
0.7619 Intermediate Similarity NPC219336
0.7566 Intermediate Similarity NPC15573
0.7566 Intermediate Similarity NPC183662
0.7566 Intermediate Similarity NPC217372
0.7565 Intermediate Similarity NPC66210
0.7513 Intermediate Similarity NPC472107
0.7513 Intermediate Similarity NPC79062
0.7488 Intermediate Similarity NPC185742
0.7488 Intermediate Similarity NPC475847
0.7463 Intermediate Similarity NPC195461
0.7463 Intermediate Similarity NPC79129
0.7463 Intermediate Similarity NPC81654
0.7463 Intermediate Similarity NPC313985
0.7463 Intermediate Similarity NPC49196
0.7463 Intermediate Similarity NPC249150
0.7446 Intermediate Similarity NPC81229
0.7446 Intermediate Similarity NPC255229
0.7416 Intermediate Similarity NPC469525
0.7411 Intermediate Similarity NPC472097
0.7398 Intermediate Similarity NPC63199
0.7398 Intermediate Similarity NPC102338
0.7398 Intermediate Similarity NPC196251
0.7398 Intermediate Similarity NPC111602
0.7387 Intermediate Similarity NPC474121
0.7363 Intermediate Similarity NPC50503
0.736 Intermediate Similarity NPC472112
0.7358 Intermediate Similarity NPC113626
0.735 Intermediate Similarity NPC245916
0.7323 Intermediate Similarity NPC117244
0.7323 Intermediate Similarity NPC473763
0.732 Intermediate Similarity NPC159125
0.7312 Intermediate Similarity NPC194881
0.7302 Intermediate Similarity NPC475271
0.7292 Intermediate Similarity NPC326575
0.7292 Intermediate Similarity NPC234987
0.7291 Intermediate Similarity NPC294909
0.7291 Intermediate Similarity NPC254240
0.7291 Intermediate Similarity NPC128265
0.7291 Intermediate Similarity NPC312870
0.7291 Intermediate Similarity NPC199851
0.7286 Intermediate Similarity NPC472113
0.7277 Intermediate Similarity NPC149708
0.724 Intermediate Similarity NPC24594
0.724 Intermediate Similarity NPC472122
0.7231 Intermediate Similarity NPC472104
0.7216 Intermediate Similarity NPC91179
0.7214 Intermediate Similarity NPC220151
0.7214 Intermediate Similarity NPC19692
0.7196 Intermediate Similarity NPC52254
0.7186 Intermediate Similarity NPC314333
0.7165 Intermediate Similarity NPC248462
0.7157 Intermediate Similarity NPC472209
0.715 Intermediate Similarity NPC129909
0.715 Intermediate Similarity NPC82070
0.7136 Intermediate Similarity NPC476114
0.7135 Intermediate Similarity NPC477976
0.7128 Intermediate Similarity NPC187827
0.7128 Intermediate Similarity NPC472105
0.7115 Intermediate Similarity NPC238457
0.7107 Intermediate Similarity NPC470003
0.7098 Intermediate Similarity NPC469938
0.7073 Intermediate Similarity NPC123395
0.7071 Intermediate Similarity NPC469460
0.707 Intermediate Similarity NPC281049
0.707 Intermediate Similarity NPC174788
0.7056 Intermediate Similarity NPC472110
0.7056 Intermediate Similarity NPC472109
0.7035 Intermediate Similarity NPC235684
0.7024 Intermediate Similarity NPC470499
0.7022 Intermediate Similarity NPC184680
0.7019 Intermediate Similarity NPC476098
0.7016 Intermediate Similarity NPC472115
0.7016 Intermediate Similarity NPC472114
0.7015 Intermediate Similarity NPC329858
0.7005 Intermediate Similarity NPC476428
0.7 Intermediate Similarity NPC21174
0.7 Intermediate Similarity NPC271797
0.6995 Remote Similarity NPC472295
0.6995 Remote Similarity NPC269886
0.6995 Remote Similarity NPC81802
0.6995 Remote Similarity NPC472210
0.6995 Remote Similarity NPC247735
0.6991 Remote Similarity NPC470785
0.699 Remote Similarity NPC248041
0.699 Remote Similarity NPC283219
0.699 Remote Similarity NPC126709
0.6981 Remote Similarity NPC234999
0.6979 Remote Similarity NPC317430
0.6976 Remote Similarity NPC232130
0.6971 Remote Similarity NPC57398
0.697 Remote Similarity NPC472108
0.697 Remote Similarity NPC139291
0.6968 Remote Similarity NPC469720
0.6965 Remote Similarity NPC61435
0.6963 Remote Similarity NPC317752
0.6959 Remote Similarity NPC161861
0.6959 Remote Similarity NPC472123
0.6952 Remote Similarity NPC473297
0.695 Remote Similarity NPC311858
0.695 Remote Similarity NPC62749
0.6944 Remote Similarity NPC312645
0.6939 Remote Similarity NPC145885
0.6939 Remote Similarity NPC84827
0.6939 Remote Similarity NPC14113
0.6937 Remote Similarity NPC33949
0.6934 Remote Similarity NPC478158
0.6923 Remote Similarity NPC20144
0.6916 Remote Similarity NPC318299
0.6916 Remote Similarity NPC474183
0.6916 Remote Similarity NPC475778
0.6916 Remote Similarity NPC472098
0.6915 Remote Similarity NPC285469
0.6908 Remote Similarity NPC192674
0.689 Remote Similarity NPC162730
0.6888 Remote Similarity NPC134586
0.6888 Remote Similarity NPC267885
0.6884 Remote Similarity NPC221100
0.6884 Remote Similarity NPC472291
0.6884 Remote Similarity NPC234078
0.6884 Remote Similarity NPC472444
0.6884 Remote Similarity NPC89508
0.6875 Remote Similarity NPC470497
0.6875 Remote Similarity NPC214428
0.6872 Remote Similarity NPC277350
0.6872 Remote Similarity NPC317373
0.6866 Remote Similarity NPC315555
0.6863 Remote Similarity NPC472292
0.6853 Remote Similarity NPC476326
0.6853 Remote Similarity NPC211997
0.6852 Remote Similarity NPC478157
0.685 Remote Similarity NPC228835
0.6845 Remote Similarity NPC472293
0.6842 Remote Similarity NPC470784
0.684 Remote Similarity NPC244741
0.684 Remote Similarity NPC53344
0.6837 Remote Similarity NPC472586
0.6837 Remote Similarity NPC110500
0.6837 Remote Similarity NPC149155
0.6837 Remote Similarity NPC203468
0.6832 Remote Similarity NPC17059
0.6825 Remote Similarity NPC327592
0.6821 Remote Similarity NPC158129
0.682 Remote Similarity NPC148183
0.682 Remote Similarity NPC152768
0.6818 Remote Similarity NPC472443
0.6816 Remote Similarity NPC62510
0.681 Remote Similarity NPC476874
0.681 Remote Similarity NPC328596
0.681 Remote Similarity NPC328318
0.681 Remote Similarity NPC474116
0.681 Remote Similarity NPC137589
0.6806 Remote Similarity NPC74562
0.6806 Remote Similarity NPC316181
0.6806 Remote Similarity NPC151781
0.6789 Remote Similarity NPC129721
0.678 Remote Similarity NPC55493
0.6776 Remote Similarity NPC472070
0.6776 Remote Similarity NPC469743
0.6773 Remote Similarity NPC128115
0.6773 Remote Similarity NPC472099
0.6772 Remote Similarity NPC207726
0.6771 Remote Similarity NPC16667
0.677 Remote Similarity NPC89987
0.6768 Remote Similarity NPC64436
0.6766 Remote Similarity NPC472294
0.6765 Remote Similarity NPC469470
0.6765 Remote Similarity NPC469501
0.6759 Remote Similarity NPC264176
0.6758 Remote Similarity NPC473310
0.6754 Remote Similarity NPC469461
0.6746 Remote Similarity NPC81535
0.6746 Remote Similarity NPC472297
0.6746 Remote Similarity NPC241024
0.6746 Remote Similarity NPC472296
0.6743 Remote Similarity NPC469928
0.6741 Remote Similarity NPC476491
0.6734 Remote Similarity NPC11126
0.6734 Remote Similarity NPC55772
0.6731 Remote Similarity NPC141454
0.6728 Remote Similarity NPC54744
0.6726 Remote Similarity NPC475859
0.6726 Remote Similarity NPC475969
0.672 Remote Similarity NPC478076
0.6717 Remote Similarity NPC84347
0.6716 Remote Similarity NPC469358
0.6716 Remote Similarity NPC321708

  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 NPC469736 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
0.9011 High Similarity NPD4602 Approved
0.841 Intermediate Similarity NPD4520 Approved
0.7696 Intermediate Similarity NPD5075 Discontinued
0.7513 Intermediate Similarity NPD5104 Approved
0.7476 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.7463 Intermediate Similarity NPD4600 Approved
0.7463 Intermediate Similarity NPD4601 Approved
0.7326 Intermediate Similarity NPD2915 Discontinued
0.7304 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7291 Intermediate Similarity NPD4500 Approved
0.7291 Intermediate Similarity NPD4501 Approved
0.7282 Intermediate Similarity NPD7482 Phase 2
0.7282 Intermediate Similarity NPD7483 Phase 2
0.7282 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD4397 Phase 1
0.7255 Intermediate Similarity NPD7903 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD6206 Phase 1
0.7186 Intermediate Similarity NPD4499 Approved
0.7157 Intermediate Similarity NPD6227 Discontinued
0.715 Intermediate Similarity NPD3785 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD750 Phase 2
0.7129 Intermediate Similarity NPD4427 Phase 2
0.7101 Intermediate Similarity NPD5487 Phase 1
0.7073 Intermediate Similarity NPD6248 Phase 2
0.7073 Intermediate Similarity NPD6249 Phase 2
0.7048 Intermediate Similarity NPD7666 Phase 3
0.7048 Intermediate Similarity NPD7665 Phase 2
0.7024 Intermediate Similarity NPD6261 Phase 3
0.7019 Intermediate Similarity NPD3777 Phase 3
0.701 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.699 Remote Similarity NPD6661 Clinical (unspecified phase)
0.697 Remote Similarity NPD2095 Phase 2
0.697 Remote Similarity NPD2092 Phase 2
0.697 Remote Similarity NPD2094 Phase 2
0.6968 Remote Similarity NPD4326 Phase 2
0.6961 Remote Similarity NPD7944 Discontinued
0.695 Remote Similarity NPD5444 Phase 1
0.6942 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6935 Remote Similarity NPD2096 Phase 2
0.6935 Remote Similarity NPD2091 Phase 2
0.6927 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6908 Remote Similarity NPD3800 Clinical (unspecified phase)
0.6905 Remote Similarity NPD6987 Phase 1
0.6897 Remote Similarity NPD6630 Clinical (unspecified phase)
0.6884 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6881 Remote Similarity NPD4334 Discontinued
0.6875 Remote Similarity NPD5427 Suspended
0.6872 Remote Similarity NPD7001 Phase 3
0.6872 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6869 Remote Similarity NPD6452 Discontinued
0.6866 Remote Similarity NPD8326 Phase 3
0.6866 Remote Similarity NPD8327 Clinical (unspecified phase)
0.6866 Remote Similarity NPD8325 Phase 3
0.6852 Remote Similarity NPD4897 Phase 2
0.6837 Remote Similarity NPD482 Approved
0.6834 Remote Similarity NPD4383 Clinical (unspecified phase)
0.683 Remote Similarity NPD7824 Approved
0.6827 Remote Similarity NPD6999 Discontinued
0.6827 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6825 Remote Similarity NPD8114 Approved
0.6825 Remote Similarity NPD8115 Approved
0.6814 Remote Similarity NPD2336 Approved
0.6804 Remote Similarity NPD2844 Phase 3
0.6802 Remote Similarity NPD749 Clinical (unspecified phase)
0.6784 Remote Similarity NPD5897 Approved
0.6784 Remote Similarity NPD5899 Approved
0.6784 Remote Similarity NPD5898 Approved
0.6774 Remote Similarity NPD4682 Phase 2
0.6772 Remote Similarity NPD5257 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6178 Phase 3
0.6759 Remote Similarity NPD7594 Clinical (unspecified phase)
0.6753 Remote Similarity NPD4554 Clinical (unspecified phase)
0.6751 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6741 Remote Similarity NPD7730 Approved
0.6741 Remote Similarity NPD7731 Approved
0.674 Remote Similarity NPD7950 Approved
0.674 Remote Similarity NPD7791 Approved
0.674 Remote Similarity NPD7952 Approved
0.674 Remote Similarity NPD7953 Approved
0.674 Remote Similarity NPD7789 Approved
0.674 Remote Similarity NPD7951 Approved
0.674 Remote Similarity NPD7790 Approved
0.6731 Remote Similarity NPD5003 Discontinued
0.6726 Remote Similarity NPD7271 Approved
0.6716 Remote Similarity NPD6965 Clinical (unspecified phase)
0.6714 Remote Similarity NPD5043 Discontinued
0.6714 Remote Similarity NPD7568 Phase 1
0.67 Remote Similarity NPD5809 Phase 3
0.6699 Remote Similarity NPD4315 Phase 2
0.6683 Remote Similarity NPD2307 Discontinued
0.6683 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6682 Remote Similarity NPD7727 Phase 2
0.6667 Remote Similarity NPD7599 Phase 2
0.6667 Remote Similarity NPD5507 Approved
0.6667 Remote Similarity NPD5506 Approved
0.6667 Remote Similarity NPD7882 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7103 Approved
0.665 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6649 Remote Similarity NPD5088 Discontinued
0.6637 Remote Similarity NPD7780 Approved
0.6637 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7781 Approved
0.6634 Remote Similarity NPD7233 Approved
0.6634 Remote Similarity NPD7234 Approved
0.6634 Remote Similarity NPD4345 Clinical (unspecified phase)
0.6633 Remote Similarity NPD7866 Approved
0.6623 Remote Similarity NPD4885 Approved
0.6623 Remote Similarity NPD7797 Approved
0.6623 Remote Similarity NPD7796 Approved
0.6619 Remote Similarity NPD7777 Approved
0.6619 Remote Similarity NPD53 Approved
0.6619 Remote Similarity NPD7778 Approved
0.6607 Remote Similarity NPD7717 Approved
0.6607 Remote Similarity NPD7716 Approved
0.6606 Remote Similarity NPD4852 Phase 2
0.6606 Remote Similarity NPD7573 Discontinued
0.6606 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6604 Remote Similarity NPD7817 Phase 1
0.6602 Remote Similarity NPD2565 Phase 2
0.6602 Remote Similarity NPD2564 Approved
0.659 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6589 Remote Similarity NPD5426 Phase 3
0.6588 Remote Similarity NPD7621 Clinical (unspecified phase)
0.6579 Remote Similarity NPD2882 Phase 1
0.6579 Remote Similarity NPD6158 Phase 2
0.6579 Remote Similarity NPD6476 Clinical (unspecified phase)
0.6577 Remote Similarity NPD6770 Approved
0.6575 Remote Similarity NPD7557 Clinical (unspecified phase)
0.6564 Remote Similarity NPD1631 Approved
0.656 Remote Similarity NPD7470 Discontinued
0.6555 Remote Similarity NPD7618 Phase 3
0.6555 Remote Similarity NPD7619 Phase 3
0.655 Remote Similarity NPD6375 Clinical (unspecified phase)
0.6548 Remote Similarity NPD5862 Discovery
0.6546 Remote Similarity NPD7600 Phase 2
0.6544 Remote Similarity NPD5835 Phase 3
0.6544 Remote Similarity NPD5834 Phase 3
0.6544 Remote Similarity NPD4506 Discontinued
0.6538 Remote Similarity NPD6665 Discontinued
0.6535 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6533 Remote Similarity NPD6182 Approved
0.6533 Remote Similarity NPD6183 Clinical (unspecified phase)
0.6533 Remote Similarity NPD43 Approved
0.6531 Remote Similarity NPD4550 Clinical (unspecified phase)
0.6526 Remote Similarity NPD5017 Discontinued
0.6517 Remote Similarity NPD8122 Approved
0.6517 Remote Similarity NPD8123 Approved
0.6515 Remote Similarity NPD1575 Approved
0.6515 Remote Similarity NPD1573 Approved
0.6512 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6512 Remote Similarity NPD5901 Discontinued
0.6505 Remote Similarity NPD4805 Approved
0.6502 Remote Similarity NPD7168 Phase 3
0.65 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6498 Remote Similarity NPD2916 Discontinued
0.6497 Remote Similarity NPD7864 Approved
0.6495 Remote Similarity NPD5255 Approved
0.6489 Remote Similarity NPD8356 Approved
0.6485 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6485 Remote Similarity NPD8037 Clinical (unspecified phase)
0.6485 Remote Similarity NPD8036 Clinical (unspecified phase)
0.6484 Remote Similarity NPD8013 Clinical (unspecified phase)
0.6482 Remote Similarity NPD5934 Clinical (unspecified phase)
0.6481 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6481 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6481 Remote Similarity NPD7957 Phase 1
0.6468 Remote Similarity NPD2382 Approved
0.6468 Remote Similarity NPD6716 Phase 1
0.6468 Remote Similarity NPD6529 Discontinued
0.6468 Remote Similarity NPD2381 Approved
0.6468 Remote Similarity NPD2380 Approved
0.6462 Remote Similarity NPD7889 Clinical (unspecified phase)
0.6459 Remote Similarity NPD5505 Discontinued
0.6457 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6453 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6452 Remote Similarity NPD6838 Clinical (unspecified phase)
0.645 Remote Similarity NPD4373 Phase 2
0.6447 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6447 Remote Similarity NPD8430 Approved
0.6447 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6445 Remote Similarity NPD5512 Phase 3
0.6443 Remote Similarity NPD4669 Clinical (unspecified phase)
0.6443 Remote Similarity NPD4671 Clinical (unspecified phase)
0.6443 Remote Similarity NPD4670 Clinical (unspecified phase)
0.6439 Remote Similarity NPD721 Approved
0.6438 Remote Similarity NPD7825 Clinical (unspecified phase)
0.6436 Remote Similarity NPD7869 Discontinued
0.6436 Remote Similarity NPD751 Clinical (unspecified phase)
0.6436 Remote Similarity NPD7865 Approved
0.6435 Remote Similarity NPD8372 Clinical (unspecified phase)
0.6435 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6432 Remote Similarity NPD2896 Discontinued
0.6432 Remote Similarity NPD4184 Clinical (unspecified phase)
0.6432 Remote Similarity NPD8463 Approved
0.6425 Remote Similarity NPD4948 Discontinued
0.6425 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6425 Remote Similarity NPD2383 Phase 1
0.6425 Remote Similarity NPD6285 Phase 2
0.6422 Remote Similarity NPD8423 Phase 2
0.6422 Remote Similarity NPD8399 Phase 1

  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