Structure

Physi-Chem Properties

Molecular Weight:  488.35
Volume:  523.332
LogP:  2.894
LogD:  3.132
LogS:  -3.361
# Rotatable Bonds:  5
TPSA:  97.99
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.4
Synthetic Accessibility Score:  6.046
Fsp3:  0.9
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.75
MDCK Permeability:  1.592884109413717e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.358
Human Intestinal Absorption (HIA):  0.01
20% Bioavailability (F20%):  0.923
30% Bioavailability (F30%):  0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.823
Plasma Protein Binding (PPB):  93.36511993408203%
Volume Distribution (VD):  0.571
Pgp-substrate:  4.999350547790527%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.331
CYP2C19-inhibitor:  0.008
CYP2C19-substrate:  0.734
CYP2C9-inhibitor:  0.071
CYP2C9-substrate:  0.382
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.13
CYP3A4-inhibitor:  0.699
CYP3A4-substrate:  0.273

ADMET: Excretion

Clearance (CL):  3.285
Half-life (T1/2):  0.726

ADMET: Toxicity

hERG Blockers:  0.051
Human Hepatotoxicity (H-HT):  0.625
Drug-inuced Liver Injury (DILI):  0.011
AMES Toxicity:  0.004
Rat Oral Acute Toxicity:  0.294
Maximum Recommended Daily Dose:  0.835
Skin Sensitization:  0.861
Carcinogencity:  0.728
Eye Corrosion:  0.035
Eye Irritation:  0.023
Respiratory Toxicity:  0.984

Download Data

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

  Natural Product: NPC201763

Natural Product ID:  NPC201763
Common Name*:   Quadrangularic Acid K
IUPAC Name:   n.a.
Synonyms:   Quadrangularic Acid K
Standard InCHIKey:  FHXLGIIQMAKDCP-CHXITZBTSA-N
Standard InCHI:  InChI=1S/C30H48O5/c1-18(8-7-12-25(2,3)35)19-11-13-27(5)20-9-10-21-28(6,24(33)34)22(31)16-23(32)30(21)17-29(20,30)15-14-26(19,27)4/h7,12,18-23,31-32,35H,8-11,13-17H2,1-6H3,(H,33,34)/b12-7-/t18-,19-,20+,21+,22+,23+,26-,27+,28+,29+,30-/m1/s1
SMILES:  C[C@H](C/C=CC(C)(C)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4[C@@](C)([C@H](C[C@@H]([C@]54C[C@@]35CC[C@]12C)O)O)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL473038
PubChem CID:   10814872
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO30384 Combretum quadrangulare Species Combretaceae Eukaryota n.a. n.a. n.a. PMID[10650080]
NPO30384 Combretum quadrangulare Species Combretaceae Eukaryota seeds n.a. n.a. PMID[10785422]
NPO30384 Combretum quadrangulare Species Combretaceae Eukaryota Seeds n.a. n.a. PMID[11277757]
NPO30384 Combretum quadrangulare Species Combretaceae Eukaryota n.a. leaf n.a. PMID[21265555]
NPO30384 Combretum quadrangulare Species Combretaceae Eukaryota leaves Khon Kaen, Thailand 2006-AUG PMID[21265555]
NPO30384 Combretum quadrangulare Species Combretaceae Eukaryota n.a. n.a. n.a. PMID[9934464]

☑ 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. ED50 = 82.6 ug ml-1 PMID[504451]

☑ 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 NPC201763 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
0.96 High Similarity NPC257082
0.9596 High Similarity NPC263729
0.95 High Similarity NPC163216
0.9406 High Similarity NPC285298
0.9192 High Similarity NPC193934
0.9192 High Similarity NPC271980
0.91 High Similarity NPC312900
0.899 High Similarity NPC37047
0.899 High Similarity NPC41971
0.899 High Similarity NPC180733
0.8969 High Similarity NPC288906
0.8969 High Similarity NPC263135
0.8725 High Similarity NPC222153
0.8713 High Similarity NPC75941
0.8687 High Similarity NPC234564
0.8614 High Similarity NPC94906
0.8586 High Similarity NPC84383
0.8586 High Similarity NPC266899
0.8571 High Similarity NPC477855
0.8529 High Similarity NPC477052
0.8529 High Similarity NPC477051
0.8529 High Similarity NPC477053
0.8529 High Similarity NPC71706
0.8515 High Similarity NPC119036
0.8515 High Similarity NPC477854
0.8515 High Similarity NPC472028
0.85 High Similarity NPC477853
0.85 High Similarity NPC195366
0.85 High Similarity NPC114743
0.85 High Similarity NPC160056
0.85 High Similarity NPC327788
0.8447 Intermediate Similarity NPC124544
0.8447 Intermediate Similarity NPC477054
0.8431 Intermediate Similarity NPC477521
0.8431 Intermediate Similarity NPC470074
0.8416 Intermediate Similarity NPC156546
0.84 Intermediate Similarity NPC279974
0.84 Intermediate Similarity NPC266431
0.8396 Intermediate Similarity NPC472218
0.8396 Intermediate Similarity NPC472217
0.8396 Intermediate Similarity NPC472219
0.8364 Intermediate Similarity NPC469794
0.8364 Intermediate Similarity NPC72772
0.8351 Intermediate Similarity NPC146937
0.835 Intermediate Similarity NPC472924
0.835 Intermediate Similarity NPC282524
0.8333 Intermediate Similarity NPC302111
0.8317 Intermediate Similarity NPC29152
0.8302 Intermediate Similarity NPC472925
0.8286 Intermediate Similarity NPC474281
0.8286 Intermediate Similarity NPC72255
0.8283 Intermediate Similarity NPC275671
0.8265 Intermediate Similarity NPC128496
0.8265 Intermediate Similarity NPC56962
0.8265 Intermediate Similarity NPC474704
0.8265 Intermediate Similarity NPC475921
0.8265 Intermediate Similarity NPC24705
0.8235 Intermediate Similarity NPC472851
0.823 Intermediate Similarity NPC184555
0.8218 Intermediate Similarity NPC476174
0.82 Intermediate Similarity NPC477520
0.82 Intermediate Similarity NPC476304
0.8198 Intermediate Similarity NPC270929
0.819 Intermediate Similarity NPC249187
0.819 Intermediate Similarity NPC247957
0.819 Intermediate Similarity NPC475050
0.8182 Intermediate Similarity NPC469400
0.8163 Intermediate Similarity NPC193360
0.8155 Intermediate Similarity NPC191565
0.8155 Intermediate Similarity NPC114274
0.8148 Intermediate Similarity NPC173905
0.8148 Intermediate Similarity NPC5475
0.8148 Intermediate Similarity NPC284828
0.8148 Intermediate Similarity NPC472216
0.8137 Intermediate Similarity NPC173272
0.8137 Intermediate Similarity NPC249954
0.8131 Intermediate Similarity NPC64844
0.8131 Intermediate Similarity NPC42847
0.8131 Intermediate Similarity NPC477916
0.8119 Intermediate Similarity NPC470958
0.8119 Intermediate Similarity NPC469406
0.8119 Intermediate Similarity NPC209662
0.8119 Intermediate Similarity NPC470957
0.8119 Intermediate Similarity NPC476186
0.8113 Intermediate Similarity NPC471293
0.8113 Intermediate Similarity NPC29705
0.8113 Intermediate Similarity NPC160843
0.81 Intermediate Similarity NPC198242
0.81 Intermediate Similarity NPC110923
0.81 Intermediate Similarity NPC211403
0.81 Intermediate Similarity NPC74296
0.8091 Intermediate Similarity NPC90952
0.8081 Intermediate Similarity NPC57954
0.8081 Intermediate Similarity NPC213832
0.8077 Intermediate Similarity NPC471041
0.807 Intermediate Similarity NPC476962
0.8061 Intermediate Similarity NPC474684
0.8061 Intermediate Similarity NPC142361
0.8058 Intermediate Similarity NPC170978
0.8058 Intermediate Similarity NPC320306
0.8058 Intermediate Similarity NPC108078
0.8058 Intermediate Similarity NPC469810
0.8058 Intermediate Similarity NPC253586
0.8058 Intermediate Similarity NPC189880
0.8053 Intermediate Similarity NPC329736
0.8041 Intermediate Similarity NPC470360
0.8039 Intermediate Similarity NPC290481
0.8039 Intermediate Similarity NPC272617
0.8039 Intermediate Similarity NPC271195
0.8039 Intermediate Similarity NPC48330
0.8039 Intermediate Similarity NPC259286
0.8039 Intermediate Similarity NPC88310
0.8039 Intermediate Similarity NPC83693
0.8037 Intermediate Similarity NPC37600
0.8037 Intermediate Similarity NPC323834
0.8037 Intermediate Similarity NPC257353
0.8037 Intermediate Similarity NPC166607
0.8034 Intermediate Similarity NPC293112
0.8021 Intermediate Similarity NPC82623
0.802 Intermediate Similarity NPC244356
0.802 Intermediate Similarity NPC224060
0.8019 Intermediate Similarity NPC72151
0.8019 Intermediate Similarity NPC90177
0.8019 Intermediate Similarity NPC112009
0.8018 Intermediate Similarity NPC122056
0.8017 Intermediate Similarity NPC55602
0.8017 Intermediate Similarity NPC11895
0.8017 Intermediate Similarity NPC469789
0.8 Intermediate Similarity NPC270586
0.8 Intermediate Similarity NPC46848
0.8 Intermediate Similarity NPC472928
0.8 Intermediate Similarity NPC289670
0.8 Intermediate Similarity NPC121218
0.8 Intermediate Similarity NPC253886
0.8 Intermediate Similarity NPC476897
0.7982 Intermediate Similarity NPC474901
0.7982 Intermediate Similarity NPC475941
0.7982 Intermediate Similarity NPC61520
0.7982 Intermediate Similarity NPC476960
0.7981 Intermediate Similarity NPC174663
0.798 Intermediate Similarity NPC16377
0.798 Intermediate Similarity NPC471900
0.7965 Intermediate Similarity NPC55296
0.7965 Intermediate Similarity NPC476959
0.7963 Intermediate Similarity NPC83744
0.7963 Intermediate Similarity NPC473284
0.7963 Intermediate Similarity NPC59530
0.7961 Intermediate Similarity NPC54248
0.7961 Intermediate Similarity NPC471153
0.7961 Intermediate Similarity NPC471903
0.7961 Intermediate Similarity NPC276103
0.7961 Intermediate Similarity NPC301534
0.7961 Intermediate Similarity NPC250757
0.7961 Intermediate Similarity NPC476327
0.7961 Intermediate Similarity NPC476318
0.7961 Intermediate Similarity NPC235053
0.7961 Intermediate Similarity NPC329910
0.7959 Intermediate Similarity NPC299068
0.7959 Intermediate Similarity NPC70661
0.7949 Intermediate Similarity NPC81736
0.7949 Intermediate Similarity NPC172154
0.7949 Intermediate Similarity NPC8369
0.7946 Intermediate Similarity NPC470953
0.7944 Intermediate Similarity NPC475036
0.7944 Intermediate Similarity NPC209502
0.7944 Intermediate Similarity NPC204833
0.7941 Intermediate Similarity NPC279410
0.7941 Intermediate Similarity NPC470385
0.7941 Intermediate Similarity NPC292793
0.7941 Intermediate Similarity NPC470386
0.7941 Intermediate Similarity NPC469982
0.7941 Intermediate Similarity NPC119562
0.7941 Intermediate Similarity NPC60692
0.7941 Intermediate Similarity NPC159365
0.7941 Intermediate Similarity NPC8993
0.7941 Intermediate Similarity NPC474529
0.7938 Intermediate Similarity NPC476038
0.7938 Intermediate Similarity NPC194937
0.7931 Intermediate Similarity NPC170538
0.7928 Intermediate Similarity NPC4573
0.7928 Intermediate Similarity NPC475970
0.7928 Intermediate Similarity NPC277769
0.7925 Intermediate Similarity NPC475558
0.7925 Intermediate Similarity NPC304832
0.7925 Intermediate Similarity NPC473788
0.7925 Intermediate Similarity NPC136289
0.7925 Intermediate Similarity NPC88203
0.7925 Intermediate Similarity NPC76866
0.7925 Intermediate Similarity NPC148628
0.7925 Intermediate Similarity NPC246736
0.7925 Intermediate Similarity NPC275990
0.7925 Intermediate Similarity NPC286519
0.7925 Intermediate Similarity NPC214946
0.7925 Intermediate Similarity NPC320447
0.7925 Intermediate Similarity NPC293753
0.7925 Intermediate Similarity NPC234892
0.7921 Intermediate Similarity NPC288833
0.7921 Intermediate Similarity NPC23217
0.7921 Intermediate Similarity NPC189520
0.7921 Intermediate Similarity NPC475708

  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 NPC201763 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
0.7905 Intermediate Similarity NPD7640 Approved
0.7905 Intermediate Similarity NPD7639 Approved
0.781 Intermediate Similarity NPD7638 Approved
0.7807 Intermediate Similarity NPD7115 Discovery
0.7757 Intermediate Similarity NPD5211 Phase 2
0.7745 Intermediate Similarity NPD6079 Approved
0.7745 Intermediate Similarity NPD7637 Suspended
0.7727 Intermediate Similarity NPD6899 Approved
0.7727 Intermediate Similarity NPD6881 Approved
0.7723 Intermediate Similarity NPD5328 Approved
0.7706 Intermediate Similarity NPD6402 Approved
0.7706 Intermediate Similarity NPD5739 Approved
0.7706 Intermediate Similarity NPD7128 Approved
0.7706 Intermediate Similarity NPD6675 Approved
0.7677 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD5697 Approved
0.7615 Intermediate Similarity NPD5141 Approved
0.7589 Intermediate Similarity NPD7290 Approved
0.7589 Intermediate Similarity NPD4634 Approved
0.7589 Intermediate Similarity NPD6883 Approved
0.7589 Intermediate Similarity NPD7102 Approved
0.757 Intermediate Similarity NPD5286 Approved
0.757 Intermediate Similarity NPD4696 Approved
0.757 Intermediate Similarity NPD5285 Approved
0.7568 Intermediate Similarity NPD7320 Approved
0.7547 Intermediate Similarity NPD4755 Approved
0.7541 Intermediate Similarity NPD7319 Approved
0.7522 Intermediate Similarity NPD8130 Phase 1
0.7522 Intermediate Similarity NPD6617 Approved
0.7522 Intermediate Similarity NPD6869 Approved
0.7522 Intermediate Similarity NPD6650 Approved
0.7522 Intermediate Similarity NPD6649 Approved
0.7522 Intermediate Similarity NPD6847 Approved
0.75 Intermediate Similarity NPD5779 Approved
0.75 Intermediate Similarity NPD5778 Approved
0.75 Intermediate Similarity NPD6114 Approved
0.75 Intermediate Similarity NPD6013 Approved
0.75 Intermediate Similarity NPD6373 Approved
0.75 Intermediate Similarity NPD6118 Approved
0.75 Intermediate Similarity NPD6012 Approved
0.75 Intermediate Similarity NPD6697 Approved
0.75 Intermediate Similarity NPD6372 Approved
0.75 Intermediate Similarity NPD6014 Approved
0.75 Intermediate Similarity NPD6115 Approved
0.7477 Intermediate Similarity NPD5701 Approved
0.7458 Intermediate Similarity NPD6319 Approved
0.7456 Intermediate Similarity NPD8297 Approved
0.7456 Intermediate Similarity NPD6882 Approved
0.7453 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD5222 Approved
0.7453 Intermediate Similarity NPD5221 Approved
0.7431 Intermediate Similarity NPD5224 Approved
0.7431 Intermediate Similarity NPD5226 Approved
0.7431 Intermediate Similarity NPD5225 Approved
0.7431 Intermediate Similarity NPD4633 Approved
0.7411 Intermediate Similarity NPD6011 Approved
0.7411 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4700 Approved
0.7404 Intermediate Similarity NPD7515 Phase 2
0.74 Intermediate Similarity NPD4786 Approved
0.7391 Intermediate Similarity NPD4632 Approved
0.7383 Intermediate Similarity NPD5173 Approved
0.7364 Intermediate Similarity NPD5175 Approved
0.7364 Intermediate Similarity NPD5174 Approved
0.7355 Intermediate Similarity NPD7492 Approved
0.7347 Intermediate Similarity NPD7525 Registered
0.7339 Intermediate Similarity NPD5223 Approved
0.7333 Intermediate Similarity NPD6399 Phase 3
0.732 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD7736 Approved
0.7311 Intermediate Similarity NPD6054 Approved
0.7295 Intermediate Similarity NPD7507 Approved
0.7295 Intermediate Similarity NPD6616 Approved
0.7292 Intermediate Similarity NPD6117 Approved
0.729 Intermediate Similarity NPD4697 Phase 3
0.7273 Intermediate Similarity NPD7632 Discontinued
0.7273 Intermediate Similarity NPD7604 Phase 2
0.7255 Intermediate Similarity NPD3618 Phase 1
0.7238 Intermediate Similarity NPD8035 Phase 2
0.7238 Intermediate Similarity NPD6411 Approved
0.7238 Intermediate Similarity NPD8034 Phase 2
0.7236 Intermediate Similarity NPD7078 Approved
0.7232 Intermediate Similarity NPD6008 Approved
0.7222 Intermediate Similarity NPD6083 Phase 2
0.7222 Intermediate Similarity NPD6084 Phase 2
0.7217 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD6116 Phase 1
0.7203 Intermediate Similarity NPD6009 Approved
0.72 Intermediate Similarity NPD3667 Approved
0.719 Intermediate Similarity NPD6370 Approved
0.717 Intermediate Similarity NPD4202 Approved
0.7167 Intermediate Similarity NPD6059 Approved
0.7107 Intermediate Similarity NPD6015 Approved
0.7107 Intermediate Similarity NPD6016 Approved
0.7105 Intermediate Similarity NPD4730 Approved
0.7105 Intermediate Similarity NPD4729 Approved
0.7103 Intermediate Similarity NPD7748 Approved
0.71 Intermediate Similarity NPD6902 Approved
0.7097 Intermediate Similarity NPD8293 Discontinued
0.7087 Intermediate Similarity NPD5786 Approved
0.7083 Intermediate Similarity NPD7100 Approved
0.7083 Intermediate Similarity NPD7101 Approved
0.7083 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD4768 Approved
0.708 Intermediate Similarity NPD4767 Approved
0.7054 Intermediate Similarity NPD4754 Approved
0.7049 Intermediate Similarity NPD5988 Approved
0.7048 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD4753 Phase 2
0.7048 Intermediate Similarity NPD6101 Approved
0.7043 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4269 Approved
0.703 Intermediate Similarity NPD4270 Approved
0.701 Intermediate Similarity NPD3703 Phase 2
0.7 Intermediate Similarity NPD6931 Approved
0.7 Intermediate Similarity NPD4225 Approved
0.7 Intermediate Similarity NPD6335 Approved
0.7 Intermediate Similarity NPD6930 Phase 2
0.7 Intermediate Similarity NPD7514 Phase 3
0.6983 Remote Similarity NPD5248 Approved
0.6983 Remote Similarity NPD5250 Approved
0.6983 Remote Similarity NPD5247 Approved
0.6983 Remote Similarity NPD5251 Approved
0.6983 Remote Similarity NPD5249 Phase 3
0.6975 Remote Similarity NPD6274 Approved
0.6975 Remote Similarity NPD6868 Approved
0.6967 Remote Similarity NPD5983 Phase 2
0.6961 Remote Similarity NPD6695 Phase 3
0.6957 Remote Similarity NPD5128 Approved
0.6923 Remote Similarity NPD5215 Approved
0.6923 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5217 Approved
0.6923 Remote Similarity NPD5216 Approved
0.6917 Remote Similarity NPD6317 Approved
0.6909 Remote Similarity NPD7902 Approved
0.69 Remote Similarity NPD6929 Approved
0.6893 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6893 Remote Similarity NPD3665 Phase 1
0.6893 Remote Similarity NPD3133 Approved
0.6893 Remote Similarity NPD3666 Approved
0.6881 Remote Similarity NPD5695 Phase 3
0.6881 Remote Similarity NPD4629 Approved
0.6881 Remote Similarity NPD5210 Approved
0.688 Remote Similarity NPD6336 Discontinued
0.6864 Remote Similarity NPD6053 Discontinued
0.686 Remote Similarity NPD6313 Approved
0.686 Remote Similarity NPD7328 Approved
0.686 Remote Similarity NPD6314 Approved
0.686 Remote Similarity NPD7327 Approved
0.6857 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6847 Remote Similarity NPD5696 Approved
0.6838 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6838 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6838 Remote Similarity NPD5169 Approved
0.6838 Remote Similarity NPD5135 Approved
0.6832 Remote Similarity NPD4252 Approved
0.6832 Remote Similarity NPD7332 Phase 2
0.6832 Remote Similarity NPD4819 Approved
0.6832 Remote Similarity NPD5368 Approved
0.6832 Remote Similarity NPD4821 Approved
0.6832 Remote Similarity NPD4822 Approved
0.6832 Remote Similarity NPD4820 Approved
0.6829 Remote Similarity NPD6909 Approved
0.6829 Remote Similarity NPD6908 Approved
0.6827 Remote Similarity NPD5363 Approved
0.6822 Remote Similarity NPD5785 Approved
0.681 Remote Similarity NPD5168 Approved
0.6803 Remote Similarity NPD7516 Approved
0.68 Remote Similarity NPD7145 Approved
0.6796 Remote Similarity NPD4788 Approved
0.6796 Remote Similarity NPD5362 Discontinued
0.6792 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6792 Remote Similarity NPD6672 Approved
0.6792 Remote Similarity NPD5737 Approved
0.678 Remote Similarity NPD5127 Approved
0.6765 Remote Similarity NPD5369 Approved
0.6762 Remote Similarity NPD6684 Approved
0.6762 Remote Similarity NPD7334 Approved
0.6762 Remote Similarity NPD7146 Approved
0.6762 Remote Similarity NPD6409 Approved
0.6762 Remote Similarity NPD5330 Approved
0.6762 Remote Similarity NPD7521 Approved
0.6759 Remote Similarity NPD5281 Approved
0.6759 Remote Similarity NPD5284 Approved
0.6731 Remote Similarity NPD3668 Phase 3
0.672 Remote Similarity NPD8328 Phase 3
0.6701 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6701 Remote Similarity NPD4809 Clinical (unspecified phase)
0.67 Remote Similarity NPD6925 Approved
0.67 Remote Similarity NPD6932 Approved
0.67 Remote Similarity NPD5776 Phase 2
0.6699 Remote Similarity NPD4223 Phase 3
0.6699 Remote Similarity NPD6435 Approved
0.6699 Remote Similarity NPD4221 Approved
0.6698 Remote Similarity NPD7524 Approved
0.6698 Remote Similarity NPD7750 Discontinued
0.6698 Remote Similarity NPD3573 Approved
0.6694 Remote Similarity NPD8335 Approved
0.6694 Remote Similarity NPD6291 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