Structure

Physi-Chem Properties

Molecular Weight:  666.3
Volume:  676.054
LogP:  4.529
LogD:  2.321
LogS:  -4.003
# Rotatable Bonds:  13
TPSA:  183.35
# H-Bond Aceptor:  11
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.058
Synthetic Accessibility Score:  5.585
Fsp3:  0.541
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.131
MDCK Permeability:  1.7812692021834664e-05
Pgp-inhibitor:  0.993
Pgp-substrate:  0.026
Human Intestinal Absorption (HIA):  0.762
20% Bioavailability (F20%):  0.68
30% Bioavailability (F30%):  0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.196
Plasma Protein Binding (PPB):  92.99195098876953%
Volume Distribution (VD):  2.012
Pgp-substrate:  4.555408954620361%

ADMET: Metabolism

CYP1A2-inhibitor:  0.065
CYP1A2-substrate:  0.126
CYP2C19-inhibitor:  0.054
CYP2C19-substrate:  0.183
CYP2C9-inhibitor:  0.626
CYP2C9-substrate:  0.038
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.082
CYP3A4-inhibitor:  0.652
CYP3A4-substrate:  0.166

ADMET: Excretion

Clearance (CL):  2.617
Half-life (T1/2):  0.164

ADMET: Toxicity

hERG Blockers:  0.691
Human Hepatotoxicity (H-HT):  0.95
Drug-inuced Liver Injury (DILI):  0.118
AMES Toxicity:  0.058
Rat Oral Acute Toxicity:  0.834
Maximum Recommended Daily Dose:  0.982
Skin Sensitization:  0.875
Carcinogencity:  0.05
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.975

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

  Natural Product: NPC251139

Natural Product ID:  NPC251139
Common Name*:   Yuanhuaoate E
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  CVBJNFGURGOCOF-INWCUTKTSA-N
Standard InCHI:  InChI=1S/C37H46O11/c1-6-7-8-9-10-11-15-18-26(39)46-31-27-30-34(20-38,48-30)33(42)37(45)25(19-22(4)28(37)40)36(27,44)23(5)29(35(31,43)21(2)3)47-32(41)24-16-13-12-14-17-24/h10-19,23,25,27,29-31,33,38,42-45H,2,6-9,20H2,1,3-5H3/b11-10+,18-15+/t23-,25+,27+,29-,30+,31-,33-,34+,35+,36+,37-/m1/s1
SMILES:  CCCCC/C=C/C=C/C(=O)O[C@@H]1[C@@H]2[C@H]3[C@@](CO)([C@H]([C@]4([C@@H](C=C(C)C4=O)[C@]2([C@H](C)[C@H]([C@]1(C(=C)C)O)OC(=O)c1ccccc1)O)O)O)O3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2376825
PubChem CID:   73348817
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

*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
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. flower n.a. PMID[21916433]
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22494026]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota flower buds n.a. n.a. PMID[23558238]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[24156713]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[27228307]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota Roots n.a. n.a. PMID[31150241]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[31860304]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[32223193]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. PMID[32997496]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18393 Eugenia sandwicensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10705 Marshallia graminifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17558 Cynoglossum formosanum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12376 Baccharis macraei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7037 Rumohra adiantiformis Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18393 Eugenia sandwicensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17135 Mikania goyazensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9756 Daphne genkwa Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19406 Chrysanthemum leptophyllum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18247 Globicephala melas Species Delphinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19303 Auricularia auricula-judae Species Auriculariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19479 Trametes feei Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15287 Vernonia megapotamica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13505 Grateloupia livida Species Halymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10882 Acer caudatifolium Species Aceraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14015 Salacia cordata Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12444 Astragalus sinicus Species Fabaceae 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
NPT111 Cell Line K562 Homo sapiens IC50 = 29030.0 nM PMID[521361]
NPT466 Cell Line U-937 Homo sapiens IC50 = 11620.0 nM PMID[521361]
NPT116 Cell Line HL-60 Homo sapiens IC50 = 18510.0 nM PMID[521361]
NPT453 Cell Line HT-1080 Homo sapiens IC50 = 18400.0 nM PMID[521361]
NPT81 Cell Line A549 Homo sapiens IC50 = 13340.0 nM PMID[521361]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 16440.0 nM PMID[521361]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 11050.0 nM PMID[521361]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 50000.0 nM PMID[521361]
NPT165 Cell Line HeLa Homo sapiens IC50 = 16670.0 nM PMID[521361]
NPT323 Cell Line SW-620 Homo sapiens IC50 > 10000.0 nM PMID[521362]
NPT2170 Cell Line RKO Homo sapiens IC50 > 10000.0 nM PMID[521362]
NPT114 Cell Line LoVo Homo sapiens IC50 > 10000.0 nM PMID[521362]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 26510.0 nM PMID[521361]

☑ 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 NPC251139 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
0.9527 High Similarity NPC11410
0.947 High Similarity NPC477188
0.947 High Similarity NPC477190
0.947 High Similarity NPC43304
0.9324 High Similarity NPC283875
0.9324 High Similarity NPC469647
0.9324 High Similarity NPC138641
0.9324 High Similarity NPC469648
0.9324 High Similarity NPC22571
0.9286 High Similarity NPC61891
0.9272 High Similarity NPC49297
0.9205 High Similarity NPC181924
0.9195 High Similarity NPC145649
0.9195 High Similarity NPC233581
0.9156 High Similarity NPC66193
0.9156 High Similarity NPC322420
0.9128 High Similarity NPC472398
0.9091 High Similarity NPC275477
0.9054 High Similarity NPC132652
0.9045 High Similarity NPC40138
0.9007 High Similarity NPC146310
0.9 High Similarity NPC51602
0.9 High Similarity NPC471103
0.8986 High Similarity NPC312393
0.8974 High Similarity NPC471134
0.8947 High Similarity NPC473670
0.8947 High Similarity NPC21410
0.8933 High Similarity NPC7095
0.8919 High Similarity NPC127857
0.8917 High Similarity NPC324769
0.8917 High Similarity NPC325732
0.8912 High Similarity NPC95449
0.8889 High Similarity NPC106895
0.8882 High Similarity NPC134685
0.8882 High Similarity NPC229545
0.8882 High Similarity NPC11588
0.8882 High Similarity NPC248265
0.8867 High Similarity NPC250046
0.8867 High Similarity NPC81698
0.8867 High Similarity NPC60509
0.8851 High Similarity NPC34943
0.8824 High Similarity NPC155329
0.8824 High Similarity NPC228204
0.8824 High Similarity NPC282239
0.8824 High Similarity NPC26033
0.8824 High Similarity NPC114357
0.8824 High Similarity NPC259144
0.8808 High Similarity NPC165260
0.8808 High Similarity NPC161239
0.8808 High Similarity NPC198455
0.8808 High Similarity NPC112216
0.8784 High Similarity NPC477894
0.8766 High Similarity NPC154675
0.8758 High Similarity NPC473414
0.8758 High Similarity NPC472005
0.8758 High Similarity NPC304876
0.8758 High Similarity NPC158333
0.8758 High Similarity NPC472030
0.8758 High Similarity NPC1173
0.8758 High Similarity NPC472022
0.8758 High Similarity NPC242262
0.8758 High Similarity NPC219419
0.8758 High Similarity NPC237549
0.8758 High Similarity NPC257213
0.8758 High Similarity NPC256142
0.8758 High Similarity NPC265395
0.8758 High Similarity NPC249471
0.875 High Similarity NPC470153
0.875 High Similarity NPC197037
0.8733 High Similarity NPC20255
0.8733 High Similarity NPC240115
0.8716 High Similarity NPC140021
0.8716 High Similarity NPC192658
0.8716 High Similarity NPC183540
0.871 High Similarity NPC472393
0.8701 High Similarity NPC472549
0.8701 High Similarity NPC114410
0.8701 High Similarity NPC132599
0.8701 High Similarity NPC112523
0.8701 High Similarity NPC473611
0.8701 High Similarity NPC469730
0.8701 High Similarity NPC473632
0.8684 High Similarity NPC125033
0.8684 High Similarity NPC91730
0.8675 High Similarity NPC327031
0.8667 High Similarity NPC471107
0.8667 High Similarity NPC471100
0.8667 High Similarity NPC311825
0.8667 High Similarity NPC92867
0.8667 High Similarity NPC125882
0.8654 High Similarity NPC471102
0.8645 High Similarity NPC70344
0.8645 High Similarity NPC290683
0.8645 High Similarity NPC475548
0.8645 High Similarity NPC217091
0.8645 High Similarity NPC475638
0.8636 High Similarity NPC77719
0.8627 High Similarity NPC306799
0.8627 High Similarity NPC101043
0.8614 High Similarity NPC254588
0.8609 High Similarity NPC477737
0.8608 High Similarity NPC55744
0.8591 High Similarity NPC182869
0.859 High Similarity NPC469771
0.8581 High Similarity NPC87934
0.8581 High Similarity NPC162613
0.8571 High Similarity NPC477905
0.8571 High Similarity NPC472548
0.8562 High Similarity NPC473214
0.8562 High Similarity NPC470245
0.8562 High Similarity NPC254558
0.8562 High Similarity NPC232583
0.8562 High Similarity NPC25484
0.8553 High Similarity NPC217918
0.8553 High Similarity NPC478073
0.8543 High Similarity NPC134131
0.8543 High Similarity NPC25043
0.8523 High Similarity NPC118080
0.8523 High Similarity NPC87448
0.8523 High Similarity NPC16912
0.8523 High Similarity NPC97947
0.8523 High Similarity NPC27377
0.8523 High Similarity NPC41481
0.8523 High Similarity NPC291599
0.8523 High Similarity NPC472576
0.8516 High Similarity NPC477098
0.8516 High Similarity NPC471135
0.8516 High Similarity NPC477100
0.8514 High Similarity NPC9905
0.85 High Similarity NPC471493
0.8497 Intermediate Similarity NPC473215
0.8497 Intermediate Similarity NPC476975
0.8487 Intermediate Similarity NPC473602
0.8481 Intermediate Similarity NPC326328
0.8481 Intermediate Similarity NPC323356
0.8481 Intermediate Similarity NPC309991
0.8481 Intermediate Similarity NPC471138
0.8467 Intermediate Similarity NPC34012
0.8467 Intermediate Similarity NPC472546
0.8456 Intermediate Similarity NPC90614
0.8456 Intermediate Similarity NPC100913
0.8456 Intermediate Similarity NPC171207
0.8456 Intermediate Similarity NPC472547
0.8456 Intermediate Similarity NPC97667
0.8456 Intermediate Similarity NPC275592
0.8447 Intermediate Similarity NPC477491
0.8442 Intermediate Similarity NPC477099
0.8442 Intermediate Similarity NPC477097
0.8442 Intermediate Similarity NPC477101
0.8431 Intermediate Similarity NPC205389
0.8431 Intermediate Similarity NPC473760
0.8428 Intermediate Similarity NPC476077
0.8421 Intermediate Similarity NPC70403
0.8421 Intermediate Similarity NPC472568
0.8421 Intermediate Similarity NPC472556
0.8421 Intermediate Similarity NPC469349
0.8421 Intermediate Similarity NPC471104
0.8421 Intermediate Similarity NPC473088
0.8421 Intermediate Similarity NPC301946
0.8421 Intermediate Similarity NPC472575
0.8421 Intermediate Similarity NPC200471
0.8421 Intermediate Similarity NPC472571
0.8421 Intermediate Similarity NPC472572
0.8421 Intermediate Similarity NPC158663
0.8421 Intermediate Similarity NPC470157
0.8421 Intermediate Similarity NPC277053
0.8421 Intermediate Similarity NPC184817
0.8421 Intermediate Similarity NPC470159
0.8421 Intermediate Similarity NPC96903
0.8421 Intermediate Similarity NPC174982
0.8421 Intermediate Similarity NPC29704
0.8421 Intermediate Similarity NPC171525
0.8421 Intermediate Similarity NPC177940
0.8421 Intermediate Similarity NPC476973
0.8418 Intermediate Similarity NPC319404
0.8402 Intermediate Similarity NPC186746
0.8397 Intermediate Similarity NPC133430
0.8397 Intermediate Similarity NPC469477
0.8377 Intermediate Similarity NPC76103
0.8375 Intermediate Similarity NPC478124
0.8366 Intermediate Similarity NPC478263
0.8366 Intermediate Similarity NPC48599
0.8366 Intermediate Similarity NPC475552
0.8366 Intermediate Similarity NPC209592
0.8355 Intermediate Similarity NPC471912
0.8355 Intermediate Similarity NPC188865
0.8355 Intermediate Similarity NPC38696
0.8355 Intermediate Similarity NPC470152
0.8355 Intermediate Similarity NPC25768
0.8355 Intermediate Similarity NPC475122
0.8355 Intermediate Similarity NPC472569
0.8355 Intermediate Similarity NPC472573
0.8355 Intermediate Similarity NPC11685
0.8355 Intermediate Similarity NPC95810
0.8355 Intermediate Similarity NPC95265
0.8355 Intermediate Similarity NPC80895
0.8355 Intermediate Similarity NPC125106
0.8355 Intermediate Similarity NPC57628
0.8355 Intermediate Similarity NPC241951
0.8355 Intermediate Similarity NPC70716

  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 NPC251139 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
0.7949 Intermediate Similarity NPD7236 Approved
0.7941 Intermediate Similarity NPD8368 Discontinued
0.7919 Intermediate Similarity NPD8434 Phase 2
0.7917 Intermediate Similarity NPD7799 Discontinued
0.7907 Intermediate Similarity NPD8407 Phase 2
0.7861 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD7239 Suspended
0.7727 Intermediate Similarity NPD8361 Approved
0.7727 Intermediate Similarity NPD8360 Approved
0.7697 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD8435 Approved
0.7614 Intermediate Similarity NPD8150 Discontinued
0.7473 Intermediate Similarity NPD8485 Approved
0.7457 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD7057 Phase 3
0.7381 Intermediate Similarity NPD7058 Phase 2
0.7351 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7075 Discontinued
0.7329 Intermediate Similarity NPD6190 Approved
0.7262 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD7685 Pre-registration
0.7202 Intermediate Similarity NPD6801 Discontinued
0.719 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7819 Suspended
0.716 Intermediate Similarity NPD4628 Phase 3
0.7143 Intermediate Similarity NPD7473 Discontinued
0.7123 Intermediate Similarity NPD2629 Approved
0.7118 Intermediate Similarity NPD5402 Approved
0.7083 Intermediate Similarity NPD4380 Phase 2
0.7083 Intermediate Similarity NPD6599 Discontinued
0.7059 Intermediate Similarity NPD7700 Phase 2
0.7059 Intermediate Similarity NPD7699 Phase 2
0.7051 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD6799 Approved
0.7018 Intermediate Similarity NPD3817 Phase 2
0.7016 Intermediate Similarity NPD8320 Phase 1
0.7016 Intermediate Similarity NPD8319 Approved
0.7006 Intermediate Similarity NPD3751 Discontinued
0.6989 Remote Similarity NPD6534 Approved
0.6989 Remote Similarity NPD6535 Approved
0.6988 Remote Similarity NPD2532 Approved
0.6988 Remote Similarity NPD2533 Approved
0.6988 Remote Similarity NPD2534 Approved
0.6983 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6977 Remote Similarity NPD3882 Suspended
0.6971 Remote Similarity NPD6232 Discontinued
0.6966 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6966 Remote Similarity NPD5844 Phase 1
0.6963 Remote Similarity NPD7435 Discontinued
0.6962 Remote Similarity NPD7961 Discontinued
0.6961 Remote Similarity NPD8312 Approved
0.6961 Remote Similarity NPD8313 Approved
0.6959 Remote Similarity NPD5761 Phase 2
0.6959 Remote Similarity NPD5760 Phase 2
0.6957 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6939 Remote Similarity NPD8462 Phase 1
0.691 Remote Similarity NPD3818 Discontinued
0.6906 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6905 Remote Similarity NPD5403 Approved
0.6893 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6893 Remote Similarity NPD6166 Phase 2
0.6893 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6892 Remote Similarity NPD690 Clinical (unspecified phase)
0.6884 Remote Similarity NPD8404 Phase 2
0.6879 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6875 Remote Similarity NPD230 Phase 1
0.6875 Remote Similarity NPD3787 Discontinued
0.686 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5494 Approved
0.6851 Remote Similarity NPD6764 Approved
0.6851 Remote Similarity NPD6765 Approved
0.6849 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7874 Approved
0.6824 Remote Similarity NPD3226 Approved
0.6821 Remote Similarity NPD7741 Discontinued
0.6821 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6818 Remote Similarity NPD8127 Discontinued
0.6813 Remote Similarity NPD7808 Phase 3
0.6807 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6806 Remote Similarity NPD6779 Approved
0.6806 Remote Similarity NPD6777 Approved
0.6806 Remote Similarity NPD6776 Approved
0.6806 Remote Similarity NPD6782 Approved
0.6806 Remote Similarity NPD6781 Approved
0.6806 Remote Similarity NPD6780 Approved
0.6806 Remote Similarity NPD6778 Approved
0.6802 Remote Similarity NPD37 Approved
0.6802 Remote Similarity NPD1934 Approved
0.6792 Remote Similarity NPD3764 Approved
0.6788 Remote Similarity NPD7696 Phase 3
0.6788 Remote Similarity NPD7698 Approved
0.6788 Remote Similarity NPD7697 Approved
0.6786 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6786 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6786 Remote Similarity NPD5401 Approved
0.6782 Remote Similarity NPD4967 Phase 2
0.6782 Remote Similarity NPD4965 Approved
0.6782 Remote Similarity NPD4966 Approved
0.6768 Remote Similarity NPD5762 Approved
0.6768 Remote Similarity NPD5763 Approved
0.6763 Remote Similarity NPD2801 Approved
0.6758 Remote Similarity NPD7251 Discontinued
0.6758 Remote Similarity NPD6559 Discontinued
0.6753 Remote Similarity NPD7871 Phase 2
0.6753 Remote Similarity NPD7870 Phase 2
0.6752 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6752 Remote Similarity NPD6085 Phase 2
0.6748 Remote Similarity NPD2799 Discontinued
0.6747 Remote Similarity NPD2575 Approved
0.6747 Remote Similarity NPD8166 Discontinued
0.6744 Remote Similarity NPD7411 Suspended
0.674 Remote Similarity NPD7074 Phase 3
0.6735 Remote Similarity NPD7701 Phase 2
0.6733 Remote Similarity NPD4198 Discontinued
0.6727 Remote Similarity NPD970 Clinical (unspecified phase)
0.6717 Remote Similarity NPD7801 Approved
0.6712 Remote Similarity NPD2182 Approved
0.6707 Remote Similarity NPD2935 Discontinued
0.6705 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6705 Remote Similarity NPD6234 Discontinued
0.6703 Remote Similarity NPD6784 Approved
0.6703 Remote Similarity NPD6797 Phase 2
0.6703 Remote Similarity NPD6785 Approved
0.6687 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6685 Remote Similarity NPD7054 Approved
0.6667 Remote Similarity NPD6355 Discontinued
0.6667 Remote Similarity NPD2346 Discontinued
0.6648 Remote Similarity NPD7472 Approved
0.6647 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6646 Remote Similarity NPD651 Clinical (unspecified phase)
0.6633 Remote Similarity NPD7211 Clinical (unspecified phase)
0.663 Remote Similarity NPD7228 Approved
0.6628 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6628 Remote Similarity NPD7458 Discontinued
0.6625 Remote Similarity NPD7008 Discontinued
0.6623 Remote Similarity NPD5125 Phase 3
0.6623 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6623 Remote Similarity NPD5126 Approved
0.6622 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6621 Remote Similarity NPD5048 Discontinued
0.6615 Remote Similarity NPD7497 Discontinued
0.6611 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6601 Remote Similarity NPD9545 Approved
0.6597 Remote Similarity NPD6647 Phase 2
0.6591 Remote Similarity NPD7768 Phase 2
0.6588 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6568 Remote Similarity NPD3300 Phase 2
0.6556 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6554 Remote Similarity NPD2067 Discontinued
0.6554 Remote Similarity NPD3749 Approved
0.6552 Remote Similarity NPD1237 Approved
0.655 Remote Similarity NPD6273 Approved
0.655 Remote Similarity NPD7314 Clinical (unspecified phase)
0.655 Remote Similarity NPD1512 Approved
0.6545 Remote Similarity NPD7033 Discontinued
0.6545 Remote Similarity NPD1510 Phase 2
0.6545 Remote Similarity NPD7305 Phase 1
0.6538 Remote Similarity NPD4807 Approved
0.6538 Remote Similarity NPD4806 Approved
0.6536 Remote Similarity NPD7199 Phase 2
0.6536 Remote Similarity NPD6959 Discontinued
0.6535 Remote Similarity NPD7930 Approved
0.6533 Remote Similarity NPD8151 Discontinued
0.6527 Remote Similarity NPD1549 Phase 2
0.6524 Remote Similarity NPD1607 Approved
0.6517 Remote Similarity NPD919 Approved
0.6516 Remote Similarity NPD5306 Approved
0.6516 Remote Similarity NPD5305 Approved
0.6513 Remote Similarity NPD7115 Discovery
0.6512 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6506 Remote Similarity NPD2796 Approved
0.6505 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6503 Remote Similarity NPD943 Approved
0.6503 Remote Similarity NPD1240 Approved
0.65 Remote Similarity NPD5711 Approved
0.65 Remote Similarity NPD5710 Approved
0.6492 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6492 Remote Similarity NPD6212 Phase 3
0.6492 Remote Similarity NPD6213 Phase 3
0.6491 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6491 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6486 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6481 Remote Similarity NPD2313 Discontinued
0.648 Remote Similarity NPD6823 Phase 2
0.6477 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6477 Remote Similarity NPD1465 Phase 2
0.6474 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6467 Remote Similarity NPD7266 Discontinued
0.6467 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6467 Remote Similarity NPD6004 Phase 3
0.6467 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6467 Remote Similarity NPD1471 Phase 3
0.6467 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6467 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6467 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6467 Remote Similarity NPD1550 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