Structure

Physi-Chem Properties

Molecular Weight:  354.16
Volume:  353.03
LogP:  1.437
LogD:  1.212
LogS:  -2.309
# Rotatable Bonds:  3
TPSA:  79.2
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.82
Synthetic Accessibility Score:  5.76
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:  -4.741
MDCK Permeability:  2.2641472241957672e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.646
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.779

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.987
Plasma Protein Binding (PPB):  45.18848419189453%
Volume Distribution (VD):  3.1
Pgp-substrate:  62.58024597167969%

ADMET: Metabolism

CYP1A2-inhibitor:  0.031
CYP1A2-substrate:  0.32
CYP2C19-inhibitor:  0.038
CYP2C19-substrate:  0.934
CYP2C9-inhibitor:  0.029
CYP2C9-substrate:  0.56
CYP2D6-inhibitor:  0.03
CYP2D6-substrate:  0.802
CYP3A4-inhibitor:  0.297
CYP3A4-substrate:  0.819

ADMET: Excretion

Clearance (CL):  13.886
Half-life (T1/2):  0.605

ADMET: Toxicity

hERG Blockers:  0.059
Human Hepatotoxicity (H-HT):  0.422
Drug-inuced Liver Injury (DILI):  0.189
AMES Toxicity:  0.022
Rat Oral Acute Toxicity:  0.794
Maximum Recommended Daily Dose:  0.892
Skin Sensitization:  0.095
Carcinogencity:  0.178
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.8

Download Data

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

  Natural Product: NPC265642

Natural Product ID:  NPC265642
Common Name*:   Alpneumine B
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  LNRAHCYSFBURKI-UVHYSYGYSA-N
Standard InCHI:  InChI=1S/C20H22N2O4/c1-10(23)12-9-22-7-6-20-13-4-3-5-14(24)17(13)21-18(20)16(19(25)26-2)11(12)8-15(20)22/h3-5,11-12,15,21,24H,6-9H2,1-2H3/t11-,12-,15-,20+/m1/s1
SMILES:  COC(=O)C1=C2Nc3c([C@]42[C@H]2C[C@@H]1[C@H](CN2CC4)C(=O)C)cccc3O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1164346
PubChem CID:   46906268
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002749] Strychnos 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
NPT43 Individual Protein Tyrosinase Agaricus bisporus IC50 > 100000.0 nM PMID[469063]

☑ 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 NPC265642 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 NPC218733
1.0 High Similarity NPC132874
1.0 High Similarity NPC138615
0.9396 High Similarity NPC469732
0.9344 High Similarity NPC1464
0.8889 High Similarity NPC246140
0.8889 High Similarity NPC195787
0.8641 High Similarity NPC5630
0.8396 Intermediate Similarity NPC203628
0.8371 Intermediate Similarity NPC167724
0.8371 Intermediate Similarity NPC223595
0.8371 Intermediate Similarity NPC224970
0.822 Intermediate Similarity NPC303214
0.8103 Intermediate Similarity NPC232600
0.8087 Intermediate Similarity NPC329338
0.8087 Intermediate Similarity NPC469726
0.8066 Intermediate Similarity NPC33507
0.8034 Intermediate Similarity NPC193410
0.8034 Intermediate Similarity NPC36495
0.7989 Intermediate Similarity NPC248117
0.796 Intermediate Similarity NPC269449
0.7957 Intermediate Similarity NPC218594
0.7957 Intermediate Similarity NPC99043
0.7917 Intermediate Similarity NPC22476
0.7889 Intermediate Similarity NPC87714
0.7884 Intermediate Similarity NPC97584
0.7882 Intermediate Similarity NPC119722
0.7877 Intermediate Similarity NPC61013
0.7849 Intermediate Similarity NPC203202
0.7849 Intermediate Similarity NPC264482
0.7845 Intermediate Similarity NPC293458
0.7835 Intermediate Similarity NPC470485
0.7766 Intermediate Similarity NPC6974
0.776 Intermediate Similarity NPC14994
0.774 Intermediate Similarity NPC475609
0.7732 Intermediate Similarity NPC470483
0.7732 Intermediate Similarity NPC25401
0.7725 Intermediate Similarity NPC19175
0.7718 Intermediate Similarity NPC189661
0.7711 Intermediate Similarity NPC475147
0.768 Intermediate Similarity NPC123241
0.7667 Intermediate Similarity NPC128476
0.7664 Intermediate Similarity NPC223242
0.7661 Intermediate Similarity NPC301501
0.7644 Intermediate Similarity NPC126556
0.7644 Intermediate Similarity NPC159963
0.7636 Intermediate Similarity NPC469451
0.7626 Intermediate Similarity NPC469450
0.7619 Intermediate Similarity NPC186669
0.7593 Intermediate Similarity NPC139373
0.7588 Intermediate Similarity NPC100863
0.7568 Intermediate Similarity NPC329932
0.7561 Intermediate Similarity NPC475133
0.756 Intermediate Similarity NPC195636
0.7557 Intermediate Similarity NPC469452
0.7524 Intermediate Similarity NPC77777
0.7512 Intermediate Similarity NPC234772
0.7488 Intermediate Similarity NPC288110
0.7488 Intermediate Similarity NPC471513
0.7488 Intermediate Similarity NPC222046
0.7487 Intermediate Similarity NPC21425
0.7477 Intermediate Similarity NPC477394
0.7455 Intermediate Similarity NPC131977
0.7453 Intermediate Similarity NPC476069
0.7452 Intermediate Similarity NPC470482
0.7452 Intermediate Similarity NPC470481
0.745 Intermediate Similarity NPC161804
0.7409 Intermediate Similarity NPC291173
0.7379 Intermediate Similarity NPC478075
0.7368 Intermediate Similarity NPC127996
0.7366 Intermediate Similarity NPC99632
0.7366 Intermediate Similarity NPC282339
0.7327 Intermediate Similarity NPC473458
0.7282 Intermediate Similarity NPC470484
0.7268 Intermediate Similarity NPC166169
0.726 Intermediate Similarity NPC329567
0.726 Intermediate Similarity NPC477397
0.726 Intermediate Similarity NPC330683
0.7255 Intermediate Similarity NPC138830
0.7249 Intermediate Similarity NPC472115
0.7249 Intermediate Similarity NPC472114
0.7244 Intermediate Similarity NPC477395
0.7235 Intermediate Similarity NPC115588
0.7219 Intermediate Similarity NPC225319
0.7196 Intermediate Similarity NPC52059
0.7196 Intermediate Similarity NPC470069
0.7192 Intermediate Similarity NPC90967
0.7188 Intermediate Similarity NPC151171
0.7158 Intermediate Similarity NPC279527
0.7158 Intermediate Similarity NPC214960
0.7157 Intermediate Similarity NPC302235
0.7156 Intermediate Similarity NPC231924
0.7136 Intermediate Similarity NPC181928
0.7121 Intermediate Similarity NPC52262
0.7103 Intermediate Similarity NPC469928
0.7098 Intermediate Similarity NPC154922
0.7093 Intermediate Similarity NPC469722
0.7087 Intermediate Similarity NPC67904
0.7078 Intermediate Similarity NPC122886
0.7074 Intermediate Similarity NPC263709
0.7074 Intermediate Similarity NPC148468
0.7074 Intermediate Similarity NPC310403
0.7074 Intermediate Similarity NPC97380
0.7074 Intermediate Similarity NPC63210
0.7074 Intermediate Similarity NPC243673
0.7065 Intermediate Similarity NPC473298
0.7065 Intermediate Similarity NPC474059
0.7044 Intermediate Similarity NPC203972
0.7037 Intermediate Similarity NPC474058
0.7028 Intermediate Similarity NPC474366
0.7021 Intermediate Similarity NPC153694
0.7021 Intermediate Similarity NPC211525
0.701 Intermediate Similarity NPC298851
0.701 Intermediate Similarity NPC293255
0.701 Intermediate Similarity NPC210415
0.701 Intermediate Similarity NPC21752
0.701 Intermediate Similarity NPC181138
0.701 Intermediate Similarity NPC34717
0.701 Intermediate Similarity NPC276993
0.6976 Remote Similarity NPC170333
0.6973 Remote Similarity NPC241392
0.6967 Remote Similarity NPC212123
0.6966 Remote Similarity NPC329982
0.6963 Remote Similarity NPC313757
0.6957 Remote Similarity NPC477393
0.6952 Remote Similarity NPC133156
0.6944 Remote Similarity NPC330009
0.6943 Remote Similarity NPC113455
0.6937 Remote Similarity NPC470480
0.6935 Remote Similarity NPC314659
0.6931 Remote Similarity NPC113946
0.6927 Remote Similarity NPC221687
0.6915 Remote Similarity NPC161827
0.6912 Remote Similarity NPC204970
0.6911 Remote Similarity NPC472121
0.6907 Remote Similarity NPC472118
0.6903 Remote Similarity NPC160113
0.6903 Remote Similarity NPC476220
0.6897 Remote Similarity NPC22689
0.6897 Remote Similarity NPC105055
0.6897 Remote Similarity NPC477396
0.6895 Remote Similarity NPC318525
0.6895 Remote Similarity NPC471122
0.6895 Remote Similarity NPC10653
0.6884 Remote Similarity NPC159815
0.6884 Remote Similarity NPC197335
0.6863 Remote Similarity NPC28510
0.6859 Remote Similarity NPC309531
0.6859 Remote Similarity NPC472102
0.6857 Remote Similarity NPC474077
0.6853 Remote Similarity NPC469734
0.6853 Remote Similarity NPC120239
0.6845 Remote Similarity NPC243626
0.6842 Remote Similarity NPC127178
0.6837 Remote Similarity NPC251212
0.6837 Remote Similarity NPC139085
0.6837 Remote Similarity NPC214626
0.683 Remote Similarity NPC311906
0.6827 Remote Similarity NPC17677
0.6823 Remote Similarity NPC257763
0.6823 Remote Similarity NPC472117
0.6814 Remote Similarity NPC475720
0.6814 Remote Similarity NPC474192
0.6812 Remote Similarity NPC473375
0.6812 Remote Similarity NPC97100
0.681 Remote Similarity NPC471512
0.681 Remote Similarity NPC471489
0.6806 Remote Similarity NPC301163
0.6804 Remote Similarity NPC96321
0.68 Remote Similarity NPC270301
0.6792 Remote Similarity NPC268077
0.6784 Remote Similarity NPC321211
0.6783 Remote Similarity NPC476258
0.6783 Remote Similarity NPC475816
0.6783 Remote Similarity NPC304837
0.6782 Remote Similarity NPC322621
0.6773 Remote Similarity NPC219397
0.6772 Remote Similarity NPC478076
0.6768 Remote Similarity NPC476441
0.6763 Remote Similarity NPC230313
0.6761 Remote Similarity NPC477161
0.6755 Remote Similarity NPC243756
0.6755 Remote Similarity NPC154602
0.6754 Remote Similarity NPC469428
0.6753 Remote Similarity NPC471124
0.675 Remote Similarity NPC39822
0.6749 Remote Similarity NPC87391
0.6746 Remote Similarity NPC71124
0.6745 Remote Similarity NPC207971
0.6745 Remote Similarity NPC476098
0.6744 Remote Similarity NPC477160
0.6743 Remote Similarity NPC176113
0.6743 Remote Similarity NPC118228
0.6736 Remote Similarity NPC472120
0.6736 Remote Similarity NPC472101
0.6735 Remote Similarity NPC469915
0.6734 Remote Similarity NPC260075
0.6729 Remote Similarity NPC53344
0.6728 Remote Similarity NPC305542
0.6726 Remote Similarity NPC51388

  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 NPC265642 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
0.7707 Intermediate Similarity NPD4494 Approved
0.7707 Intermediate Similarity NPD4492 Approved
0.7635 Intermediate Similarity NPD4596 Phase 1
0.7598 Intermediate Similarity NPD4082 Approved
0.7573 Intermediate Similarity NPD4493 Discontinued
0.756 Intermediate Similarity NPD3940 Clinical (unspecified phase)
0.7537 Intermediate Similarity NPD4456 Clinical (unspecified phase)
0.7524 Intermediate Similarity NPD3893 Discontinued
0.7512 Intermediate Similarity NPD3472 Approved
0.7512 Intermediate Similarity NPD4022 Approved
0.75 Intermediate Similarity NPD4455 Discontinued
0.7452 Intermediate Similarity NPD3888 Discontinued
0.744 Intermediate Similarity NPD3372 Discontinued
0.7371 Intermediate Similarity NPD5433 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD5860 Discontinued
0.729 Intermediate Similarity NPD3783 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD2906 Approved
0.726 Intermediate Similarity NPD2907 Approved
0.7182 Intermediate Similarity NPD6199 Discontinued
0.7156 Intermediate Similarity NPD1945 Phase 1
0.698 Remote Similarity NPD5928 Phase 1
0.6961 Remote Similarity NPD5610 Approved
0.6959 Remote Similarity NPD7293 Approved
0.6934 Remote Similarity NPD4859 Phase 1
0.6919 Remote Similarity NPD6293 Clinical (unspecified phase)
0.6915 Remote Similarity NPD3684 Discontinued
0.6908 Remote Similarity NPD4668 Phase 2
0.6895 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6872 Remote Similarity NPD4465 Phase 2
0.6872 Remote Similarity NPD4467 Phase 2
0.685 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6821 Remote Similarity NPD5186 Approved
0.6821 Remote Similarity NPD5183 Approved
0.6818 Remote Similarity NPD5600 Discontinued
0.68 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6777 Remote Similarity NPD6795 Clinical (unspecified phase)
0.6769 Remote Similarity NPD2680 Approved
0.6769 Remote Similarity NPD2681 Approved
0.6746 Remote Similarity NPD5197 Approved
0.6746 Remote Similarity NPD5194 Approved
0.6746 Remote Similarity NPD5196 Approved
0.673 Remote Similarity NPD6238 Discontinued
0.6726 Remote Similarity NPD7542 Phase 3
0.6714 Remote Similarity NPD6874 Approved
0.6699 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6699 Remote Similarity NPD5195 Discontinued
0.6684 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6684 Remote Similarity NPD3983 Phase 3
0.6683 Remote Similarity NPD5603 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7186 Phase 3
0.6667 Remote Similarity NPD5445 Approved
0.6667 Remote Similarity NPD4796 Discontinued
0.6667 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5937 Approved
0.665 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6649 Remote Similarity NPD19 Approved
0.6649 Remote Similarity NPD1742 Approved
0.6649 Remote Similarity NPD1743 Approved
0.6638 Remote Similarity NPD6625 Approved
0.6636 Remote Similarity NPD1294 Discontinued
0.6635 Remote Similarity NPD5609 Approved
0.6635 Remote Similarity NPD5608 Approved
0.6634 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6633 Remote Similarity NPD7449 Clinical (unspecified phase)
0.6632 Remote Similarity NPD5294 Clinical (unspecified phase)
0.662 Remote Similarity NPD7071 Clinical (unspecified phase)
0.662 Remote Similarity NPD7300 Phase 3
0.662 Remote Similarity NPD6376 Discontinued
0.662 Remote Similarity NPD7302 Phase 3
0.6617 Remote Similarity NPD7479 Phase 2
0.6617 Remote Similarity NPD5190 Phase 2
0.6617 Remote Similarity NPD2869 Clinical (unspecified phase)
0.6615 Remote Similarity NPD2672 Discontinued
0.6614 Remote Similarity NPD2737 Clinical (unspecified phase)
0.6599 Remote Similarity NPD2455 Approved
0.6599 Remote Similarity NPD2454 Approved
0.6596 Remote Similarity NPD1802 Approved
0.6596 Remote Similarity NPD1801 Approved
0.6584 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6584 Remote Similarity NPD6297 Approved
0.6583 Remote Similarity NPD3377 Discontinued
0.658 Remote Similarity NPD3006 Discontinued
0.658 Remote Similarity NPD1769 Discontinued
0.6577 Remote Similarity NPD7292 Approved
0.6575 Remote Similarity NPD7178 Clinical (unspecified phase)
0.6575 Remote Similarity NPD7301 Phase 3
0.6573 Remote Similarity NPD3416 Discontinued
0.6573 Remote Similarity NPD6321 Discontinued
0.657 Remote Similarity NPD7630 Phase 3
0.657 Remote Similarity NPD7629 Clinical (unspecified phase)
0.657 Remote Similarity NPD7628 Phase 3
0.6567 Remote Similarity NPD4603 Phase 2
0.6567 Remote Similarity NPD5334 Clinical (unspecified phase)
0.6566 Remote Similarity NPD3376 Clinical (unspecified phase)
0.6558 Remote Similarity NPD3298 Approved
0.6552 Remote Similarity NPD3470 Approved
0.6552 Remote Similarity NPD3471 Approved
0.655 Remote Similarity NPD5466 Approved
0.6547 Remote Similarity NPD5496 Approved
0.6542 Remote Similarity NPD956 Clinical (unspecified phase)
0.654 Remote Similarity NPD3828 Approved
0.6533 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6528 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6526 Remote Similarity NPD6805 Discontinued
0.6522 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6518 Remote Similarity NPD3437 Discontinued
0.6516 Remote Similarity NPD4562 Clinical (unspecified phase)
0.6515 Remote Similarity NPD6457 Approved
0.6515 Remote Similarity NPD2037 Approved
0.6515 Remote Similarity NPD7126 Discontinued
0.6502 Remote Similarity NPD4330 Approved
0.6502 Remote Similarity NPD4329 Approved
0.6497 Remote Similarity NPD5430 Discontinued
0.6473 Remote Similarity NPD2899 Discontinued
0.6473 Remote Similarity NPD4515 Suspended
0.6468 Remote Similarity NPD3422 Phase 3
0.6468 Remote Similarity NPD3423 Phase 2
0.6465 Remote Similarity NPD5823 Approved
0.6462 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6462 Remote Similarity NPD2427 Approved
0.6459 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6456 Remote Similarity NPD8167 Discontinued
0.6456 Remote Similarity NPD6851 Approved
0.6456 Remote Similarity NPD6853 Approved
0.6452 Remote Similarity NPD6807 Phase 3
0.645 Remote Similarity NPD2431 Approved
0.645 Remote Similarity NPD2432 Approved
0.6432 Remote Similarity NPD5071 Phase 2
0.6432 Remote Similarity NPD2404 Discontinued
0.6432 Remote Similarity NPD3912 Discontinued
0.6432 Remote Similarity NPD7278 Phase 2
0.6432 Remote Similarity NPD7279 Phase 2
0.6429 Remote Similarity NPD4311 Approved
0.6429 Remote Similarity NPD2506 Approved
0.6426 Remote Similarity NPD7560 Approved
0.6419 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6415 Remote Similarity NPD5582 Discontinued
0.6411 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6411 Remote Similarity NPD5896 Clinical (unspecified phase)
0.641 Remote Similarity NPD3812 Clinical (unspecified phase)
0.6408 Remote Similarity NPD7280 Phase 3
0.6408 Remote Similarity NPD7281 Phase 3
0.6406 Remote Similarity NPD3640 Phase 3
0.6406 Remote Similarity NPD3641 Approved
0.6406 Remote Similarity NPD3639 Approved
0.6404 Remote Similarity NPD5312 Approved
0.6404 Remote Similarity NPD5313 Approved
0.6404 Remote Similarity NPD3792 Approved
0.6402 Remote Similarity NPD3297 Approved
0.6402 Remote Similarity NPD8358 Approved
0.6387 Remote Similarity NPD7528 Approved
0.6387 Remote Similarity NPD4888 Discontinued
0.6382 Remote Similarity NPD2162 Clinical (unspecified phase)
0.6381 Remote Similarity NPD5504 Discontinued
0.6378 Remote Similarity NPD6636 Phase 3
0.6378 Remote Similarity NPD2670 Approved
0.6372 Remote Similarity NPD5497 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6835 Approved
0.6364 Remote Similarity NPD6533 Clinical (unspecified phase)
0.636 Remote Similarity NPD8364 Approved
0.636 Remote Similarity NPD7820 Phase 3
0.636 Remote Similarity NPD8363 Approved
0.6359 Remote Similarity NPD7205 Discontinued
0.6359 Remote Similarity NPD6480 Clinical (unspecified phase)
0.6356 Remote Similarity NPD4429 Discontinued
0.6356 Remote Similarity NPD8016 Phase 3
0.6356 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6355 Remote Similarity NPD3978 Clinical (unspecified phase)
0.6352 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6352 Remote Similarity NPD6723 Discontinued
0.635 Remote Similarity NPD3468 Approved
0.6349 Remote Similarity NPD3986 Discontinued
0.6348 Remote Similarity NPD1755 Approved
0.6347 Remote Similarity NPD5143 Clinical (unspecified phase)
0.6339 Remote Similarity NPD7475 Clinical (unspecified phase)
0.6339 Remote Similarity NPD8149 Discontinued
0.6338 Remote Similarity NPD5548 Clinical (unspecified phase)
0.6337 Remote Similarity NPD2898 Approved
0.6337 Remote Similarity NPD6607 Clinical (unspecified phase)
0.6324 Remote Similarity NPD3050 Clinical (unspecified phase)
0.6324 Remote Similarity NPD3793 Phase 3
0.632 Remote Similarity NPD7924 Phase 2
0.632 Remote Similarity NPD7925 Phase 2
0.6318 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6318 Remote Similarity NPD2916 Discontinued
0.6316 Remote Similarity NPD6017 Discontinued
0.631 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6309 Remote Similarity NPD3746 Discontinued
0.6308 Remote Similarity NPD6161 Approved
0.6308 Remote Similarity NPD6162 Approved
0.6305 Remote Similarity NPD5033 Approved
0.6305 Remote Similarity NPD5919 Clinical (unspecified phase)
0.6304 Remote Similarity NPD7603 Discontinued
0.6303 Remote Similarity NPD3884 Discontinued
0.6303 Remote Similarity NPD2490 Approved
0.6303 Remote Similarity NPD6716 Phase 1
0.6303 Remote Similarity NPD7283 Approved
0.6303 Remote Similarity NPD6659 Phase 2
0.6303 Remote Similarity NPD2488 Approved
0.63 Remote Similarity NPD6037 Discontinued

  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