Structure

Physi-Chem Properties

Molecular Weight:  384.2
Volume:  396.178
LogP:  2.969
LogD:  3.035
LogS:  -3.71
# Rotatable Bonds:  5
TPSA:  67.87
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.491
Synthetic Accessibility Score:  4.656
Fsp3:  0.545
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:  -4.525
MDCK Permeability:  3.7369467463577166e-05
Pgp-inhibitor:  0.049
Pgp-substrate:  0.569
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.63
30% Bioavailability (F30%):  0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.993
Plasma Protein Binding (PPB):  63.65794372558594%
Volume Distribution (VD):  1.183
Pgp-substrate:  30.88608741760254%

ADMET: Metabolism

CYP1A2-inhibitor:  0.091
CYP1A2-substrate:  0.815
CYP2C19-inhibitor:  0.617
CYP2C19-substrate:  0.954
CYP2C9-inhibitor:  0.488
CYP2C9-substrate:  0.104
CYP2D6-inhibitor:  0.911
CYP2D6-substrate:  0.723
CYP3A4-inhibitor:  0.906
CYP3A4-substrate:  0.92

ADMET: Excretion

Clearance (CL):  12.066
Half-life (T1/2):  0.209

ADMET: Toxicity

hERG Blockers:  0.827
Human Hepatotoxicity (H-HT):  0.508
Drug-inuced Liver Injury (DILI):  0.418
AMES Toxicity:  0.375
Rat Oral Acute Toxicity:  0.916
Maximum Recommended Daily Dose:  0.922
Skin Sensitization:  0.902
Carcinogencity:  0.943
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.954

Download Data

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

  Natural Product: NPC263709

Natural Product ID:  NPC263709
Common Name*:   Corynoxine
IUPAC Name:   methyl (E)-2-[(3S,6'S,7'S,8'aS)-6'-ethyl-2-oxospiro[1H-indole-3,1'-3,5,6,7,8,8a-hexahydro-2H-indolizine]-7'-yl]-3-methoxyprop-2-enoate
Synonyms:   Corynoxine
Standard InCHIKey:  DAXYUDFNWXHGBE-NRAMRBJXSA-N
Standard InCHI:  InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15+,19+,22+/m1/s1
SMILES:  CO/C=C([C@H]1C[C@@H]2N(C[C@H]1CC)CC[C@]12C(=Nc2c1cccc2)O)/C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1909424
PubChem CID:   10475115
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000251] Indolizidines

*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
NPO17943 Amburana cearensis Species Fabaceae Eukaryota n.a. trunk bark n.a. DOI[10.1016/S0031-9422(98)00497-X]
NPO19381 Maxillaria densa Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[10479332]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[10869194]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota leaves n.a. n.a. PMID[18588343]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[19331340]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. aerial part n.a. PMID[21070010]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[21070010]
NPO18193 Clivia nobilis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[21469691]
NPO19381 Maxillaria densa Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[23234371]
NPO25416 Uncaria cordata Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27128898]
NPO22126 Penicillium funiculosum Species Trichocomaceae Eukaryota n.a. n.a. n.a. PMID[27359163]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27700077]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[28225280]
NPO40904 Pausinystalia yohimbe Species n.a. n.a. Bark n.a. n.a. PMID[30059216]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[31789520]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[31804070]
NPO14616 Uncaria kunstleri Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17464 Uncaria sessilifructus Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24190 Uncaria sterrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10088 Uncaria attenuata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25416 Uncaria cordata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10088 Uncaria attenuata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14616 Uncaria kunstleri Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25416 Uncaria cordata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1603 Monostroma nitidum Species Monostromataceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17464 Uncaria sessilifructus Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24190 Uncaria sterrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11476 Lecanora broccha Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4468 Cuspidaria pterocarpa Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17943 Amburana cearensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9282 Stereocaulon colensoi Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19381 Maxillaria densa Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25416 Uncaria cordata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18193 Clivia nobilis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17464 Uncaria sessilifructus Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14616 Uncaria kunstleri Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO907 Dictyostelium purpureum Species n.a. Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18862 Aria pinnatifida Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18277 Scurrula fusca Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24190 Uncaria sterrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14694 Sickingia williamsii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO19160 Klasea quinquefolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22126 Penicillium funiculosum Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10499 Haplopappus paucidentatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6849 Lomatia arborescens Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15198 Leproloma diffusum Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10088 Uncaria attenuata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1603 Monostroma nitidum Species Monostromataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10315 Cestrum parqui Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11596 Lomatia ilicifolia Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8745 Senecio alloeophyllus Species Asteraceae 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
NPT116 Cell Line HL-60 Homo sapiens IC50 > 40000.0 nM PMID[536396]
NPT660 Cell Line SW480 Homo sapiens IC50 > 40000.0 nM PMID[536396]
NPT177 Tissue Aorta Rattus norvegicus IC50 > 30.0 ug.mL-1 PMID[536396]

☑ 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 NPC263709 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 NPC243673
1.0 High Similarity NPC310403
1.0 High Similarity NPC63210
1.0 High Similarity NPC148468
1.0 High Similarity NPC97380
0.9796 High Similarity NPC211525
0.9796 High Similarity NPC153694
0.9795 High Similarity NPC161827
0.9733 High Similarity NPC52059
0.9733 High Similarity NPC470069
0.9419 High Similarity NPC181138
0.9419 High Similarity NPC298851
0.9419 High Similarity NPC276993
0.9419 High Similarity NPC210415
0.9419 High Similarity NPC293255
0.9419 High Similarity NPC21752
0.8846 High Similarity NPC472121
0.811 Intermediate Similarity NPC278887
0.8086 Intermediate Similarity NPC474058
0.8077 Intermediate Similarity NPC472100
0.8 Intermediate Similarity NPC28510
0.7949 Intermediate Similarity NPC472103
0.7853 Intermediate Similarity NPC204970
0.7849 Intermediate Similarity NPC475962
0.784 Intermediate Similarity NPC473297
0.774 Intermediate Similarity NPC174629
0.7738 Intermediate Similarity NPC469462
0.7719 Intermediate Similarity NPC476441
0.7714 Intermediate Similarity NPC469460
0.7709 Intermediate Similarity NPC203972
0.7697 Intermediate Similarity NPC193410
0.7692 Intermediate Similarity NPC243162
0.7669 Intermediate Similarity NPC478076
0.7661 Intermediate Similarity NPC13367
0.7651 Intermediate Similarity NPC248117
0.7636 Intermediate Similarity NPC61013
0.763 Intermediate Similarity NPC218594
0.763 Intermediate Similarity NPC99043
0.7602 Intermediate Similarity NPC476425
0.759 Intermediate Similarity NPC36495
0.7584 Intermediate Similarity NPC317758
0.7574 Intermediate Similarity NPC472115
0.7574 Intermediate Similarity NPC472114
0.7571 Intermediate Similarity NPC282092
0.7545 Intermediate Similarity NPC225319
0.7545 Intermediate Similarity NPC143457
0.7514 Intermediate Similarity NPC203202
0.7514 Intermediate Similarity NPC264482
0.7473 Intermediate Similarity NPC474077
0.7471 Intermediate Similarity NPC279527
0.7471 Intermediate Similarity NPC214960
0.7458 Intermediate Similarity NPC97584
0.7443 Intermediate Similarity NPC476428
0.7429 Intermediate Similarity NPC6974
0.7427 Intermediate Similarity NPC223595
0.7427 Intermediate Similarity NPC224970
0.7427 Intermediate Similarity NPC167724
0.7425 Intermediate Similarity NPC123241
0.7416 Intermediate Similarity NPC472209
0.7396 Intermediate Similarity NPC282339
0.7396 Intermediate Similarity NPC99632
0.7386 Intermediate Similarity NPC39822
0.7381 Intermediate Similarity NPC469461
0.7371 Intermediate Similarity NPC186669
0.7365 Intermediate Similarity NPC29285
0.736 Intermediate Similarity NPC245741
0.7321 Intermediate Similarity NPC113946
0.7303 Intermediate Similarity NPC159963
0.7294 Intermediate Similarity NPC472120
0.7294 Intermediate Similarity NPC472101
0.7294 Intermediate Similarity NPC472117
0.7294 Intermediate Similarity NPC293458
0.7293 Intermediate Similarity NPC111602
0.7293 Intermediate Similarity NPC63199
0.7293 Intermediate Similarity NPC196251
0.7293 Intermediate Similarity NPC102338
0.7278 Intermediate Similarity NPC291759
0.7273 Intermediate Similarity NPC476326
0.7253 Intermediate Similarity NPC5630
0.7238 Intermediate Similarity NPC14994
0.7238 Intermediate Similarity NPC21425
0.7235 Intermediate Similarity NPC472102
0.7235 Intermediate Similarity NPC309531
0.7222 Intermediate Similarity NPC133591
0.7213 Intermediate Similarity NPC203628
0.7213 Intermediate Similarity NPC25401
0.7209 Intermediate Similarity NPC472106
0.7204 Intermediate Similarity NPC302548
0.7204 Intermediate Similarity NPC475559
0.7182 Intermediate Similarity NPC207033
0.7182 Intermediate Similarity NPC38823
0.7167 Intermediate Similarity NPC472119
0.716 Intermediate Similarity NPC477156
0.716 Intermediate Similarity NPC477157
0.7159 Intermediate Similarity NPC329338
0.7159 Intermediate Similarity NPC469726
0.7158 Intermediate Similarity NPC105055
0.7158 Intermediate Similarity NPC22689
0.7151 Intermediate Similarity NPC313757
0.7143 Intermediate Similarity NPC472323
0.7135 Intermediate Similarity NPC321211
0.7127 Intermediate Similarity NPC322621
0.712 Intermediate Similarity NPC14339
0.7105 Intermediate Similarity NPC1464
0.7102 Intermediate Similarity NPC214626
0.7102 Intermediate Similarity NPC139085
0.7102 Intermediate Similarity NPC251212
0.7097 Intermediate Similarity NPC478079
0.7093 Intermediate Similarity NPC176983
0.7093 Intermediate Similarity NPC286871
0.7093 Intermediate Similarity NPC476231
0.7083 Intermediate Similarity NPC195787
0.7083 Intermediate Similarity NPC246140
0.7081 Intermediate Similarity NPC55493
0.7074 Intermediate Similarity NPC265642
0.7074 Intermediate Similarity NPC138615
0.7074 Intermediate Similarity NPC100863
0.7074 Intermediate Similarity NPC132874
0.7074 Intermediate Similarity NPC218733
0.7072 Intermediate Similarity NPC258480
0.7059 Intermediate Similarity NPC303214
0.7059 Intermediate Similarity NPC245916
0.7053 Intermediate Similarity NPC232600
0.7037 Intermediate Similarity NPC241024
0.7035 Intermediate Similarity NPC201424
0.7033 Intermediate Similarity NPC52262
0.7033 Intermediate Similarity NPC473007
0.7031 Intermediate Similarity NPC87714
0.703 Intermediate Similarity NPC116519
0.7027 Intermediate Similarity NPC22476
0.7021 Intermediate Similarity NPC90967
0.7019 Intermediate Similarity NPC281104
0.7006 Intermediate Similarity NPC96901
0.7 Intermediate Similarity NPC15840
0.7 Intermediate Similarity NPC199851
0.7 Intermediate Similarity NPC312870
0.7 Intermediate Similarity NPC294909
0.7 Intermediate Similarity NPC254240
0.7 Intermediate Similarity NPC128265
0.6989 Remote Similarity NPC472118
0.6989 Remote Similarity NPC469915
0.6984 Remote Similarity NPC52557
0.6977 Remote Similarity NPC471122
0.6973 Remote Similarity NPC473298
0.6973 Remote Similarity NPC473008
0.6973 Remote Similarity NPC474059
0.6968 Remote Similarity NPC325013
0.6963 Remote Similarity NPC469732
0.6961 Remote Similarity NPC113626
0.6957 Remote Similarity NPC181928
0.6936 Remote Similarity NPC315368
0.6933 Remote Similarity NPC315051
0.6923 Remote Similarity NPC159125
0.6923 Remote Similarity NPC477159
0.6919 Remote Similarity NPC217294
0.6919 Remote Similarity NPC175474
0.6915 Remote Similarity NPC220151
0.6915 Remote Similarity NPC221687
0.6915 Remote Similarity NPC474121
0.6915 Remote Similarity NPC19692
0.6911 Remote Similarity NPC214428
0.691 Remote Similarity NPC285622
0.6907 Remote Similarity NPC277350
0.6902 Remote Similarity NPC66210
0.6898 Remote Similarity NPC473004
0.6889 Remote Similarity NPC234987
0.6889 Remote Similarity NPC260075
0.6886 Remote Similarity NPC264589
0.6884 Remote Similarity NPC189661
0.6883 Remote Similarity NPC213126
0.6883 Remote Similarity NPC169485
0.6883 Remote Similarity NPC84281
0.6883 Remote Similarity NPC291027
0.6883 Remote Similarity NPC317474
0.6882 Remote Similarity NPC314333
0.6882 Remote Similarity NPC472112
0.6882 Remote Similarity NPC329858
0.6871 Remote Similarity NPC319645
0.6869 Remote Similarity NPC472098
0.6865 Remote Similarity NPC473815
0.6864 Remote Similarity NPC473329
0.6857 Remote Similarity NPC189116
0.6855 Remote Similarity NPC316746
0.6854 Remote Similarity NPC355
0.6853 Remote Similarity NPC269449
0.685 Remote Similarity NPC234772
0.685 Remote Similarity NPC148183
0.685 Remote Similarity NPC152768
0.6842 Remote Similarity NPC264580
0.6839 Remote Similarity NPC477158
0.6839 Remote Similarity NPC162730
0.6831 Remote Similarity NPC98197
0.6828 Remote Similarity NPC284706
0.6825 Remote Similarity NPC289299
0.6825 Remote Similarity NPC57994
0.6825 Remote Similarity NPC34717
0.6824 Remote Similarity NPC243756
0.6823 Remote Similarity NPC138830
0.6823 Remote Similarity NPC475489
0.6818 Remote Similarity NPC70172

  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 NPC263709 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
0.7261 Intermediate Similarity NPD5184 Approved
0.7261 Intermediate Similarity NPD5185 Approved
0.7261 Intermediate Similarity NPD5182 Approved
0.7188 Intermediate Similarity NPD3170 Approved
0.7176 Intermediate Similarity NPD7599 Phase 2
0.7143 Intermediate Similarity NPD8103 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7600 Phase 2
0.7067 Intermediate Similarity NPD2994 Approved
0.7041 Intermediate Similarity NPD4121 Phase 3
0.7041 Intermediate Similarity NPD4120 Approved
0.703 Intermediate Similarity NPD5595 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD2844 Phase 3
0.702 Intermediate Similarity NPD2210 Approved
0.702 Intermediate Similarity NPD2212 Approved
0.7019 Intermediate Similarity NPD2569 Approved
0.7019 Intermediate Similarity NPD2670 Approved
0.7019 Intermediate Similarity NPD2567 Approved
0.7011 Intermediate Similarity NPD7591 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5741 Approved
0.7 Intermediate Similarity NPD4500 Approved
0.7 Intermediate Similarity NPD5743 Approved
0.7 Intermediate Similarity NPD2116 Approved
0.7 Intermediate Similarity NPD4501 Approved
0.7 Intermediate Similarity NPD2117 Pre-registration
0.7 Intermediate Similarity NPD2115 Approved
0.7 Intermediate Similarity NPD5742 Approved
0.6928 Remote Similarity NPD2946 Phase 2
0.6919 Remote Similarity NPD5715 Clinical (unspecified phase)
0.6909 Remote Similarity NPD2820 Phase 3
0.6908 Remote Similarity NPD3032 Approved
0.6908 Remote Similarity NPD3030 Approved
0.6908 Remote Similarity NPD3031 Approved
0.6905 Remote Similarity NPD4682 Phase 2
0.6898 Remote Similarity NPD7570 Approved
0.6898 Remote Similarity NPD7569 Approved
0.6886 Remote Similarity NPD6416 Phase 2
0.6883 Remote Similarity NPD4217 Approved
0.6883 Remote Similarity NPD3132 Approved
0.6883 Remote Similarity NPD3131 Approved
0.6883 Remote Similarity NPD2612 Approved
0.6883 Remote Similarity NPD4216 Approved
0.6883 Remote Similarity NPD2609 Approved
0.6883 Remote Similarity NPD2611 Approved
0.6883 Remote Similarity NPD2610 Approved
0.6883 Remote Similarity NPD2608 Approved
0.6883 Remote Similarity NPD4215 Approved
0.6883 Remote Similarity NPD4218 Approved
0.6882 Remote Similarity NPD4499 Approved
0.6871 Remote Similarity NPD1109 Approved
0.6871 Remote Similarity NPD1110 Approved
0.6848 Remote Similarity NPD2365 Approved
0.6842 Remote Similarity NPD5811 Approved
0.6831 Remote Similarity NPD7252 Clinical (unspecified phase)
0.6825 Remote Similarity NPD4602 Approved
0.6813 Remote Similarity NPD6879 Phase 2
0.6813 Remote Similarity NPD6878 Phase 2
0.6802 Remote Similarity NPD7463 Clinical (unspecified phase)
0.6798 Remote Similarity NPD7795 Phase 2
0.6796 Remote Similarity NPD8006 Clinical (unspecified phase)
0.6792 Remote Similarity NPD6359 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4041 Approved
0.6771 Remote Similarity NPD6874 Approved
0.6766 Remote Similarity NPD2435 Approved
0.6746 Remote Similarity NPD1802 Approved
0.6746 Remote Similarity NPD1801 Approved
0.6738 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6724 Remote Similarity NPD3812 Clinical (unspecified phase)
0.6719 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6706 Remote Similarity NPD7528 Approved
0.6687 Remote Similarity NPD2613 Approved
0.6686 Remote Similarity NPD2948 Discontinued
0.6686 Remote Similarity NPD7114 Clinical (unspecified phase)
0.6685 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6684 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6684 Remote Similarity NPD6999 Discontinued
0.6667 Remote Similarity NPD6655 Clinical (unspecified phase)
0.6667 Remote Similarity NPD181 Approved
0.6667 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5077 Approved
0.6667 Remote Similarity NPD5076 Approved
0.6667 Remote Similarity NPD2607 Approved
0.665 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6649 Remote Similarity NPD4601 Approved
0.6649 Remote Similarity NPD4600 Approved
0.6648 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6648 Remote Similarity NPD3983 Phase 3
0.6648 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6647 Remote Similarity NPD6414 Clinical (unspecified phase)
0.6646 Remote Similarity NPD5578 Approved
0.6646 Remote Similarity NPD5577 Clinical (unspecified phase)
0.6646 Remote Similarity NPD1036 Approved
0.6645 Remote Similarity NPD2622 Approved
0.6632 Remote Similarity NPD4397 Phase 1
0.6629 Remote Similarity NPD4796 Discontinued
0.6629 Remote Similarity NPD3589 Clinical (unspecified phase)
0.6628 Remote Similarity NPD3329 Clinical (unspecified phase)
0.6626 Remote Similarity NPD8416 Discontinued
0.6624 Remote Similarity NPD2584 Suspended
0.6623 Remote Similarity NPD3149 Approved
0.6623 Remote Similarity NPD2659 Approved
0.6623 Remote Similarity NPD3147 Approved
0.6623 Remote Similarity NPD2658 Approved
0.6623 Remote Similarity NPD3150 Approved
0.6623 Remote Similarity NPD3148 Approved
0.6612 Remote Similarity NPD3965 Phase 1
0.661 Remote Similarity NPD19 Approved
0.661 Remote Similarity NPD1743 Approved
0.661 Remote Similarity NPD1742 Approved
0.6607 Remote Similarity NPD6860 Clinical (unspecified phase)
0.66 Remote Similarity NPD4900 Clinical (unspecified phase)
0.6599 Remote Similarity NPD56 Approved
0.6599 Remote Similarity NPD8282 Approved
0.6599 Remote Similarity NPD8283 Approved
0.6592 Remote Similarity NPD8002 Clinical (unspecified phase)
0.6592 Remote Similarity NPD8003 Clinical (unspecified phase)
0.659 Remote Similarity NPD3399 Approved
0.6587 Remote Similarity NPD3625 Discontinued
0.6585 Remote Similarity NPD8643 Discontinued
0.658 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6577 Remote Similarity NPD1756 Approved
0.6577 Remote Similarity NPD1752 Approved
0.6571 Remote Similarity NPD1663 Discontinued
0.6567 Remote Similarity NPD7470 Discontinued
0.6566 Remote Similarity NPD7001 Phase 3
0.6566 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6564 Remote Similarity NPD3614 Approved
0.6564 Remote Similarity NPD3615 Approved
0.6564 Remote Similarity NPD3090 Approved
0.6564 Remote Similarity NPD4746 Phase 3
0.6564 Remote Similarity NPD2570 Approved
0.6564 Remote Similarity NPD4745 Approved
0.6564 Remote Similarity NPD3088 Approved
0.6564 Remote Similarity NPD3087 Approved
0.6564 Remote Similarity NPD2573 Approved
0.6564 Remote Similarity NPD2574 Discontinued
0.6564 Remote Similarity NPD2566 Approved
0.6564 Remote Similarity NPD2572 Clinical (unspecified phase)
0.6564 Remote Similarity NPD2571 Approved
0.6564 Remote Similarity NPD6805 Discontinued
0.6564 Remote Similarity NPD3089 Approved
0.6564 Remote Similarity NPD3616 Approved
0.6556 Remote Similarity NPD1764 Approved
0.6556 Remote Similarity NPD1762 Approved
0.6556 Remote Similarity NPD4986 Clinical (unspecified phase)
0.6548 Remote Similarity NPD7205 Discontinued
0.6545 Remote Similarity NPD6073 Approved
0.6541 Remote Similarity NPD6325 Discontinued
0.6536 Remote Similarity NPD5430 Discontinued
0.6535 Remote Similarity NPD6657 Clinical (unspecified phase)
0.6532 Remote Similarity NPD5982 Phase 2
0.6529 Remote Similarity NPD6017 Discontinued
0.6527 Remote Similarity NPD4707 Clinical (unspecified phase)
0.6527 Remote Similarity NPD989 Approved
0.6519 Remote Similarity NPD3376 Clinical (unspecified phase)
0.6519 Remote Similarity NPD3622 Clinical (unspecified phase)
0.6519 Remote Similarity NPD3623 Clinical (unspecified phase)
0.6514 Remote Similarity NPD5257 Clinical (unspecified phase)
0.6514 Remote Similarity NPD5617 Suspended
0.6513 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6512 Remote Similarity NPD979 Approved
0.6512 Remote Similarity NPD5942 Approved
0.6512 Remote Similarity NPD5941 Approved
0.6512 Remote Similarity NPD4432 Discontinued
0.6508 Remote Similarity NPD6891 Phase 2
0.6503 Remote Similarity NPD5466 Approved
0.6503 Remote Similarity NPD3423 Phase 2
0.6503 Remote Similarity NPD3422 Phase 3
0.65 Remote Similarity NPD2159 Approved
0.65 Remote Similarity NPD8423 Phase 2
0.65 Remote Similarity NPD2160 Approved
0.65 Remote Similarity NPD2626 Approved
0.65 Remote Similarity NPD8399 Phase 1
0.65 Remote Similarity NPD2627 Approved
0.65 Remote Similarity NPD552 Approved
0.65 Remote Similarity NPD553 Approved
0.65 Remote Similarity NPD2625 Approved
0.65 Remote Similarity NPD2628 Approved
0.65 Remote Similarity NPD9567 Approved
0.6497 Remote Similarity NPD4335 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5003 Discontinued
0.6485 Remote Similarity NPD4686 Approved
0.6485 Remote Similarity NPD4684 Phase 3
0.6485 Remote Similarity NPD4685 Phase 3
0.6484 Remote Similarity NPD7687 Clinical (unspecified phase)
0.6482 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6481 Remote Similarity NPD5263 Approved
0.6477 Remote Similarity NPD7105 Phase 1
0.6477 Remote Similarity NPD2672 Discontinued
0.6474 Remote Similarity NPD5981 Approved
0.6474 Remote Similarity NPD4334 Discontinued
0.6471 Remote Similarity NPD2387 Approved
0.6471 Remote Similarity NPD6506 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5631 Phase 3
0.6464 Remote Similarity NPD6457 Approved
0.6462 Remote Similarity NPD7778 Approved
0.6462 Remote Similarity NPD7777 Approved
0.6462 Remote Similarity NPD53 Approved
0.6461 Remote Similarity NPD7244 Discontinued
0.6461 Remote Similarity NPD2506 Approved
0.6458 Remote Similarity NPD6665 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