Structure

Physi-Chem Properties

Molecular Weight:  356.17
Volume:  355.666
LogP:  0.164
LogD:  1.13
LogS:  -1.159
# Rotatable Bonds:  2
TPSA:  74.38
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.484
Synthetic Accessibility Score:  5.675
Fsp3:  0.55
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:  -5.576
MDCK Permeability:  1.105119736166671e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.92
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.518
Plasma Protein Binding (PPB):  16.839519500732422%
Volume Distribution (VD):  1.813
Pgp-substrate:  77.39994049072266%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.94
CYP2C19-inhibitor:  0.048
CYP2C19-substrate:  0.811
CYP2C9-inhibitor:  0.02
CYP2C9-substrate:  0.39
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.494
CYP3A4-inhibitor:  0.164
CYP3A4-substrate:  0.91

ADMET: Excretion

Clearance (CL):  8.339
Half-life (T1/2):  0.94

ADMET: Toxicity

hERG Blockers:  0.017
Human Hepatotoxicity (H-HT):  0.196
Drug-inuced Liver Injury (DILI):  0.027
AMES Toxicity:  0.268
Rat Oral Acute Toxicity:  0.973
Maximum Recommended Daily Dose:  0.904
Skin Sensitization:  0.055
Carcinogencity:  0.702
Eye Corrosion:  0.004
Eye Irritation:  0.102
Respiratory Toxicity:  0.6

Download Data

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

  Natural Product: NPC185742

Natural Product ID:  NPC185742
Common Name*:   Alpneumine H
IUPAC Name:   n.a.
Synonyms:   Alpneumine H
Standard InCHIKey:  OSMMAUUKWDERDD-ZRWJFXDNSA-N
Standard InCHI:  InChI=1S/C20H24N2O4/c1-22(24)9-7-14-12-8-10-26-11-20(14,19(23)25-2)18-16(17(12)22)13-5-3-4-6-15(13)21-18/h3-6,12,14,17,21H,7-11H2,1-2H3/t12-,14-,17+,20-,22-/m0/s1
SMILES:  COC(=O)[C@@]12COCC[C@H]3[C@@H]1CCN(=O)([C@H]3c1c2[nH]c2c1cccc2)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1165844
PubChem CID:   46906334
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000210] Carbazoles

*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
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 > 100000.0 nM PMID[466530]

☑ 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 NPC185742 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 NPC475847
0.9149 High Similarity NPC162730
0.9048 High Similarity NPC474116
0.8978 High Similarity NPC474121
0.8466 Intermediate Similarity NPC329858
0.8368 Intermediate Similarity NPC314333
0.8358 Intermediate Similarity NPC475778
0.8281 Intermediate Similarity NPC55493
0.8182 Intermediate Similarity NPC137589
0.8168 Intermediate Similarity NPC234999
0.803 Intermediate Similarity NPC241024
0.803 Intermediate Similarity NPC469743
0.798 Intermediate Similarity NPC52557
0.79 Intermediate Similarity NPC214428
0.7882 Intermediate Similarity NPC277350
0.785 Intermediate Similarity NPC469720
0.7846 Intermediate Similarity NPC175474
0.7723 Intermediate Similarity NPC79129
0.7723 Intermediate Similarity NPC81654
0.7723 Intermediate Similarity NPC249150
0.7723 Intermediate Similarity NPC49196
0.7723 Intermediate Similarity NPC195461
0.7723 Intermediate Similarity NPC313985
0.7714 Intermediate Similarity NPC469928
0.7642 Intermediate Similarity NPC96321
0.763 Intermediate Similarity NPC330009
0.7624 Intermediate Similarity NPC50503
0.7585 Intermediate Similarity NPC477065
0.7576 Intermediate Similarity NPC111602
0.7576 Intermediate Similarity NPC102338
0.7576 Intermediate Similarity NPC196251
0.7576 Intermediate Similarity NPC63199
0.7559 Intermediate Similarity NPC473041
0.7512 Intermediate Similarity NPC472210
0.7512 Intermediate Similarity NPC269886
0.7512 Intermediate Similarity NPC247735
0.7512 Intermediate Similarity NPC472295
0.7512 Intermediate Similarity NPC81802
0.75 Intermediate Similarity NPC19679
0.7489 Intermediate Similarity NPC311906
0.7488 Intermediate Similarity NPC469736
0.7487 Intermediate Similarity NPC469896
0.7463 Intermediate Similarity NPC472113
0.7462 Intermediate Similarity NPC472119
0.745 Intermediate Similarity NPC472112
0.7389 Intermediate Similarity NPC220151
0.7389 Intermediate Similarity NPC19692
0.7387 Intermediate Similarity NPC475720
0.7387 Intermediate Similarity NPC474192
0.7368 Intermediate Similarity NPC469541
0.7353 Intermediate Similarity NPC245916
0.7295 Intermediate Similarity NPC294909
0.7295 Intermediate Similarity NPC254240
0.7295 Intermediate Similarity NPC128265
0.7295 Intermediate Similarity NPC312870
0.7295 Intermediate Similarity NPC199851
0.729 Intermediate Similarity NPC472291
0.7282 Intermediate Similarity NPC329688
0.7282 Intermediate Similarity NPC189812
0.7277 Intermediate Similarity NPC473105
0.7269 Intermediate Similarity NPC475816
0.7259 Intermediate Similarity NPC219336
0.725 Intermediate Similarity NPC472209
0.725 Intermediate Similarity NPC472107
0.725 Intermediate Similarity NPC79062
0.7234 Intermediate Similarity NPC473297
0.723 Intermediate Similarity NPC471304
0.7208 Intermediate Similarity NPC217372
0.7208 Intermediate Similarity NPC15573
0.7208 Intermediate Similarity NPC183662
0.7206 Intermediate Similarity NPC472292
0.7184 Intermediate Similarity NPC472293
0.7178 Intermediate Similarity NPC472323
0.7163 Intermediate Similarity NPC472296
0.7163 Intermediate Similarity NPC472297
0.7143 Intermediate Similarity NPC148183
0.7143 Intermediate Similarity NPC152768
0.7136 Intermediate Similarity NPC2395
0.7136 Intermediate Similarity NPC181502
0.7136 Intermediate Similarity NPC85066
0.7135 Intermediate Similarity NPC282339
0.7135 Intermediate Similarity NPC99632
0.713 Intermediate Similarity NPC475602
0.713 Intermediate Similarity NPC473540
0.7121 Intermediate Similarity NPC234987
0.7119 Intermediate Similarity NPC478080
0.7108 Intermediate Similarity NPC95783
0.7107 Intermediate Similarity NPC13367
0.7103 Intermediate Similarity NPC271862
0.7101 Intermediate Similarity NPC11445
0.7087 Intermediate Similarity NPC45850
0.7085 Intermediate Similarity NPC213468
0.7082 Intermediate Similarity NPC17437
0.7077 Intermediate Similarity NPC317430
0.7065 Intermediate Similarity NPC139291
0.7065 Intermediate Similarity NPC143533
0.7065 Intermediate Similarity NPC472108
0.7056 Intermediate Similarity NPC258062
0.7056 Intermediate Similarity NPC127677
0.7053 Intermediate Similarity NPC157828
0.7053 Intermediate Similarity NPC195239
0.705 Intermediate Similarity NPC15840
0.7044 Intermediate Similarity NPC66210
0.7044 Intermediate Similarity NPC160381
0.704 Intermediate Similarity NPC235885
0.7035 Intermediate Similarity NPC84827
0.7035 Intermediate Similarity NPC14113
0.7035 Intermediate Similarity NPC476326
0.7035 Intermediate Similarity NPC145885
0.7035 Intermediate Similarity NPC111275
0.703 Intermediate Similarity NPC258480
0.7028 Intermediate Similarity NPC98715
0.702 Intermediate Similarity NPC329338
0.702 Intermediate Similarity NPC469726
0.7018 Intermediate Similarity NPC474412
0.701 Intermediate Similarity NPC271797
0.701 Intermediate Similarity NPC21174
0.7009 Intermediate Similarity NPC46225
0.7009 Intermediate Similarity NPC225821
0.7005 Intermediate Similarity NPC151976
0.7005 Intermediate Similarity NPC87856
0.6996 Remote Similarity NPC81939
0.6995 Remote Similarity NPC143457
0.699 Remote Similarity NPC472097
0.6986 Remote Similarity NPC232130
0.6986 Remote Similarity NPC132211
0.6981 Remote Similarity NPC476874
0.6981 Remote Similarity NPC260900
0.6978 Remote Similarity NPC478078
0.6976 Remote Similarity NPC183805
0.6974 Remote Similarity NPC70155
0.6972 Remote Similarity NPC267965
0.697 Remote Similarity NPC472123
0.6968 Remote Similarity NPC52254
0.6966 Remote Similarity NPC475666
0.6963 Remote Similarity NPC18661
0.6961 Remote Similarity NPC235684
0.6952 Remote Similarity NPC67288
0.694 Remote Similarity NPC477066
0.6934 Remote Similarity NPC300183
0.6931 Remote Similarity NPC113626
0.6931 Remote Similarity NPC71037
0.6923 Remote Similarity NPC281049
0.6923 Remote Similarity NPC82070
0.6916 Remote Similarity NPC314648
0.6912 Remote Similarity NPC469460
0.6912 Remote Similarity NPC126066
0.6912 Remote Similarity NPC52262
0.691 Remote Similarity NPC477067
0.691 Remote Similarity NPC478082
0.691 Remote Similarity NPC478081
0.6909 Remote Similarity NPC203614
0.6909 Remote Similarity NPC476114
0.6909 Remote Similarity NPC204491
0.6907 Remote Similarity NPC225319
0.6904 Remote Similarity NPC154293
0.6901 Remote Similarity NPC193761
0.6901 Remote Similarity NPC476073
0.69 Remote Similarity NPC267885
0.6897 Remote Similarity NPC472104
0.6895 Remote Similarity NPC33421
0.6895 Remote Similarity NPC229348
0.689 Remote Similarity NPC289299
0.689 Remote Similarity NPC57994
0.6889 Remote Similarity NPC21638
0.6878 Remote Similarity NPC282092
0.6878 Remote Similarity NPC315555
0.6878 Remote Similarity NPC62749
0.6872 Remote Similarity NPC176983
0.6872 Remote Similarity NPC16667
0.6872 Remote Similarity NPC33949
0.6869 Remote Similarity NPC280548
0.6866 Remote Similarity NPC260075
0.6864 Remote Similarity NPC478157
0.6863 Remote Similarity NPC472294
0.6862 Remote Similarity NPC329982
0.6861 Remote Similarity NPC472099
0.686 Remote Similarity NPC469501
0.686 Remote Similarity NPC469470
0.6858 Remote Similarity NPC472762
0.6857 Remote Similarity NPC472116
0.6852 Remote Similarity NPC315545
0.6852 Remote Similarity NPC314297
0.685 Remote Similarity NPC149155
0.685 Remote Similarity NPC203468
0.685 Remote Similarity NPC110500
0.6847 Remote Similarity NPC476428
0.6844 Remote Similarity NPC266192
0.6844 Remote Similarity NPC475271
0.6842 Remote Similarity NPC88315
0.684 Remote Similarity NPC74413
0.6839 Remote Similarity NPC29285
0.6839 Remote Similarity NPC285469
0.6832 Remote Similarity NPC248041
0.6832 Remote Similarity NPC283219
0.6832 Remote Similarity NPC126709
0.6821 Remote Similarity NPC248117
0.6818 Remote Similarity NPC478074
0.6818 Remote Similarity NPC221100
0.6818 Remote Similarity NPC78020

  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 NPC185742 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
0.8368 Intermediate Similarity NPD4499 Approved
0.7723 Intermediate Similarity NPD4601 Approved
0.7723 Intermediate Similarity NPD4600 Approved
0.7415 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD4500 Approved
0.7295 Intermediate Similarity NPD4501 Approved
0.7281 Intermediate Similarity NPD6770 Approved
0.7264 Intermediate Similarity NPD4506 Discontinued
0.7233 Intermediate Similarity NPD5003 Discontinued
0.7165 Intermediate Similarity NPD2844 Phase 3
0.7115 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD6176 Phase 1
0.7082 Intermediate Similarity NPD8358 Approved
0.7075 Intermediate Similarity NPD5426 Phase 3
0.7024 Intermediate Similarity NPD2565 Phase 2
0.7024 Intermediate Similarity NPD2564 Approved
0.698 Remote Similarity NPD5728 Clinical (unspecified phase)
0.698 Remote Similarity NPD2092 Phase 2
0.698 Remote Similarity NPD2095 Phase 2
0.698 Remote Similarity NPD2094 Phase 2
0.6977 Remote Similarity NPD2509 Approved
0.6977 Remote Similarity NPD2510 Approved
0.6963 Remote Similarity NPD5257 Clinical (unspecified phase)
0.6948 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6948 Remote Similarity NPD2920 Discontinued
0.6946 Remote Similarity NPD2091 Phase 2
0.6946 Remote Similarity NPD2096 Phase 2
0.6916 Remote Similarity NPD5901 Discontinued
0.6909 Remote Similarity NPD3389 Approved
0.6909 Remote Similarity NPD3393 Approved
0.6909 Remote Similarity NPD3394 Approved
0.689 Remote Similarity NPD4602 Approved
0.6888 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6884 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6853 Remote Similarity NPD7864 Approved
0.6853 Remote Similarity NPD7863 Approved
0.685 Remote Similarity NPD482 Approved
0.6849 Remote Similarity NPD7454 Approved
0.6849 Remote Similarity NPD7455 Approved
0.684 Remote Similarity NPD4118 Clinical (unspecified phase)
0.6837 Remote Similarity NPD8098 Approved
0.6828 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6825 Remote Similarity NPD6664 Approved
0.682 Remote Similarity NPD8423 Phase 2
0.682 Remote Similarity NPD8399 Phase 1
0.6818 Remote Similarity NPD7866 Approved
0.6816 Remote Similarity NPD749 Clinical (unspecified phase)
0.6812 Remote Similarity NPD1534 Approved
0.6812 Remote Similarity NPD7233 Approved
0.6812 Remote Similarity NPD7234 Approved
0.6806 Remote Similarity NPD7010 Phase 3
0.6804 Remote Similarity NPD7470 Discontinued
0.68 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6798 Remote Similarity NPD5473 Discontinued
0.6792 Remote Similarity NPD4397 Phase 1
0.6759 Remote Similarity NPD8283 Approved
0.6759 Remote Similarity NPD8282 Approved
0.6759 Remote Similarity NPD56 Approved
0.6743 Remote Similarity NPD2916 Discontinued
0.6731 Remote Similarity NPD4334 Discontinued
0.673 Remote Similarity NPD4427 Phase 2
0.6716 Remote Similarity NPD750 Phase 2
0.6714 Remote Similarity NPD7777 Approved
0.6714 Remote Similarity NPD53 Approved
0.6714 Remote Similarity NPD7778 Approved
0.6712 Remote Similarity NPD8112 Clinical (unspecified phase)
0.67 Remote Similarity NPD1325 Approved
0.67 Remote Similarity NPD1326 Approved
0.6698 Remote Similarity NPD6226 Phase 3
0.6698 Remote Similarity NPD7818 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7878 Phase 2
0.6683 Remote Similarity NPD4948 Discontinued
0.6682 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6682 Remote Similarity NPD3947 Discontinued
0.6682 Remote Similarity NPD6987 Phase 1
0.6667 Remote Similarity NPD5913 Phase 3
0.6667 Remote Similarity NPD7688 Phase 1
0.6667 Remote Similarity NPD5912 Clinical (unspecified phase)
0.6652 Remote Similarity NPD5475 Discontinued
0.6652 Remote Similarity NPD8013 Clinical (unspecified phase)
0.6651 Remote Similarity NPD6479 Discontinued
0.665 Remote Similarity NPD5596 Phase 2
0.664 Remote Similarity NPD8467 Approved
0.664 Remote Similarity NPD8466 Approved
0.664 Remote Similarity NPD8465 Approved
0.6637 Remote Similarity NPD5293 Phase 2
0.6636 Remote Similarity NPD7946 Pre-registration
0.6636 Remote Similarity NPD6529 Discontinued
0.6636 Remote Similarity NPD8072 Approved
0.6623 Remote Similarity NPD7824 Approved
0.6622 Remote Similarity NPD8097 Phase 3
0.6622 Remote Similarity NPD8096 Phase 3
0.6621 Remote Similarity NPD6838 Clinical (unspecified phase)
0.6618 Remote Similarity NPD7865 Approved
0.6618 Remote Similarity NPD3607 Clinical (unspecified phase)
0.6618 Remote Similarity NPD2144 Approved
0.6617 Remote Similarity NPD4184 Clinical (unspecified phase)
0.6612 Remote Similarity NPD7955 Approved
0.6612 Remote Similarity NPD7956 Approved
0.6605 Remote Similarity NPD6999 Discontinued
0.6605 Remote Similarity NPD6248 Phase 2
0.6605 Remote Similarity NPD6249 Phase 2
0.6605 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6605 Remote Similarity NPD7621 Clinical (unspecified phase)
0.6602 Remote Similarity NPD3038 Discontinued
0.6588 Remote Similarity NPD2336 Approved
0.6588 Remote Similarity NPD5592 Clinical (unspecified phase)
0.6585 Remote Similarity NPD7708 Approved
0.6585 Remote Similarity NPD4076 Approved
0.6585 Remote Similarity NPD4079 Approved
0.6579 Remote Similarity NPD6995 Phase 1
0.6579 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6575 Remote Similarity NPD7958 Clinical (unspecified phase)
0.6575 Remote Similarity NPD7957 Phase 1
0.6575 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6573 Remote Similarity NPD5975 Clinical (unspecified phase)
0.657 Remote Similarity NPD3319 Phase 1
0.657 Remote Similarity NPD3320 Approved
0.657 Remote Similarity NPD3318 Approved
0.6569 Remote Similarity NPD4075 Phase 2
0.6569 Remote Similarity NPD6375 Clinical (unspecified phase)
0.6557 Remote Similarity NPD4315 Phase 2
0.6552 Remote Similarity NPD4112 Clinical (unspecified phase)
0.6547 Remote Similarity NPD7594 Clinical (unspecified phase)
0.6547 Remote Similarity NPD4852 Phase 2
0.6546 Remote Similarity NPD7803 Approved
0.6538 Remote Similarity NPD7950 Approved
0.6538 Remote Similarity NPD7951 Approved
0.6538 Remote Similarity NPD7791 Approved
0.6538 Remote Similarity NPD7952 Approved
0.6538 Remote Similarity NPD7953 Approved
0.6538 Remote Similarity NPD7790 Approved
0.6538 Remote Similarity NPD7789 Approved
0.6537 Remote Similarity NPD8459 Approved
0.6537 Remote Similarity NPD8426 Approved
0.6537 Remote Similarity NPD3505 Approved
0.6537 Remote Similarity NPD8425 Approved
0.6537 Remote Similarity NPD7730 Approved
0.6537 Remote Similarity NPD7731 Approved
0.6537 Remote Similarity NPD8460 Approved
0.6537 Remote Similarity NPD3506 Approved
0.6537 Remote Similarity NPD7869 Discontinued
0.6534 Remote Similarity NPD8364 Approved
0.6534 Remote Similarity NPD8363 Approved
0.6533 Remote Similarity NPD8160 Phase 2
0.6524 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7271 Approved
0.652 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6518 Remote Similarity NPD3794 Approved
0.6518 Remote Similarity NPD3795 Approved
0.6516 Remote Similarity NPD6376 Discontinued
0.6515 Remote Similarity NPD2214 Approved
0.6515 Remote Similarity NPD2213 Approved
0.6513 Remote Similarity NPD7882 Clinical (unspecified phase)
0.651 Remote Similarity NPD8428 Approved
0.651 Remote Similarity NPD8429 Approved
0.651 Remote Similarity NPD8427 Approved
0.6507 Remote Similarity NPD6227 Discontinued
0.6507 Remote Similarity NPD6610 Clinical (unspecified phase)
0.65 Remote Similarity NPD6732 Clinical (unspecified phase)
0.65 Remote Similarity NPD7001 Phase 3
0.65 Remote Similarity NPD6635 Approved
0.6498 Remote Similarity NPD5497 Clinical (unspecified phase)
0.6498 Remote Similarity NPD5427 Suspended
0.6495 Remote Similarity NPD7618 Phase 3
0.6495 Remote Similarity NPD7619 Phase 3
0.6486 Remote Similarity NPD2125 Clinical (unspecified phase)
0.6486 Remote Similarity NPD7941 Phase 3
0.6486 Remote Similarity NPD4520 Approved
0.6485 Remote Similarity NPD7770 Phase 3
0.6484 Remote Similarity NPD5487 Phase 1
0.6483 Remote Similarity NPD5891 Approved
0.6482 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6476 Remote Similarity NPD5444 Phase 1
0.6473 Remote Similarity NPD5899 Approved
0.6473 Remote Similarity NPD5897 Approved
0.6473 Remote Similarity NPD5898 Approved
0.6468 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6466 Remote Similarity NPD6977 Clinical (unspecified phase)
0.6466 Remote Similarity NPD6978 Phase 2
0.6466 Remote Similarity NPD6164 Phase 2
0.6466 Remote Similarity NPD6165 Phase 2
0.6465 Remote Similarity NPD2307 Discontinued
0.6462 Remote Similarity NPD6281 Approved
0.6457 Remote Similarity NPD7825 Clinical (unspecified phase)
0.6455 Remote Similarity NPD8115 Approved
0.6455 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6455 Remote Similarity NPD8114 Approved
0.6452 Remote Similarity NPD3800 Clinical (unspecified phase)
0.645 Remote Similarity NPD6976 Clinical (unspecified phase)
0.6444 Remote Similarity NPD8094 Discontinued
0.6441 Remote Similarity NPD7666 Phase 3
0.6441 Remote Similarity NPD7665 Phase 2
0.6439 Remote Similarity NPD5065 Approved
0.6438 Remote Similarity NPD8073 Approved
0.6435 Remote Similarity NPD6206 Phase 1
0.6432 Remote Similarity NPD5483 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