Structure

Physi-Chem Properties

Molecular Weight:  526.13
Volume:  518.299
LogP:  5.935
LogD:  3.417
LogS:  -5.119
# Rotatable Bonds:  4
TPSA:  160.82
# H-Bond Aceptor:  9
# H-Bond Donor:  6
# Rings:  6
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.163
Synthetic Accessibility Score:  3.57
Fsp3:  0.1
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.37
MDCK Permeability:  8.302192327391822e-06
Pgp-inhibitor:  0.046
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.024
20% Bioavailability (F20%):  0.983
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  100.32669830322266%
Volume Distribution (VD):  0.395
Pgp-substrate:  1.2019540071487427%

ADMET: Metabolism

CYP1A2-inhibitor:  0.856
CYP1A2-substrate:  0.122
CYP2C19-inhibitor:  0.865
CYP2C19-substrate:  0.039
CYP2C9-inhibitor:  0.662
CYP2C9-substrate:  0.962
CYP2D6-inhibitor:  0.1
CYP2D6-substrate:  0.606
CYP3A4-inhibitor:  0.415
CYP3A4-substrate:  0.103

ADMET: Excretion

Clearance (CL):  12.057
Half-life (T1/2):  0.66

ADMET: Toxicity

hERG Blockers:  0.085
Human Hepatotoxicity (H-HT):  0.238
Drug-inuced Liver Injury (DILI):  0.985
AMES Toxicity:  0.751
Rat Oral Acute Toxicity:  0.545
Maximum Recommended Daily Dose:  0.794
Skin Sensitization:  0.93
Carcinogencity:  0.275
Eye Corrosion:  0.003
Eye Irritation:  0.913
Respiratory Toxicity:  0.038

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

  Natural Product: NPC38591

Natural Product ID:  NPC38591
Common Name*:   Daphnodorin A
IUPAC Name:   [(2S)-5-hydroxy-2,8-bis(4-hydroxyphenyl)-3,4-dihydro-2H-furo[2,3-h]chromen-9-yl]-(2,4,6-trihydroxyphenyl)methanone
Synonyms:  
Standard InCHIKey:  SFIBBWQCUADULX-QHCPKHFHSA-N
Standard InCHI:  InChI=1S/C30H22O9/c31-16-5-1-14(2-6-16)23-10-9-19-20(34)13-24-26(30(19)38-23)27(29(39-24)15-3-7-17(32)8-4-15)28(37)25-21(35)11-18(33)12-22(25)36/h1-8,11-13,23,31-36H,9-10H2/t23-/m0/s1
SMILES:  Oc1ccc(cc1)[C@@H]1CCc2c(O1)c1c(cc2O)oc(c1C(=O)c1c(O)cc(cc1O)O)c1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2273051
PubChem CID:   72426
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO12339 Daphne feddei Species Thymelaeaceae Eukaryota stem bark Kunming, Yunnan Province, China n.a. PMID[18986199]
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22494026]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[24156713]
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]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO12444 Astragalus sinicus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19303 Auricularia auricula-judae Species Auriculariaceae 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]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23754 Solanum aculeatissimum Species Solanaceae 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]
NPO12444 Astragalus sinicus Species Fabaceae 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]
NPO17135 Mikania goyazensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18816 Lindera glauca Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10211 Pajanelia multijuga n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO14508 Aconitum heterophyllum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16416 Serratula strangulata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19406 Chrysanthemum leptophyllum 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]
NPO4035 Daphne odora Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21329 Ilyonectria destructans Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13505 Grateloupia livida Species Halymeniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12339 Daphne feddei Species Thymelaeaceae 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]
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]
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]
NPO23754 Solanum aculeatissimum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7037 Rumohra adiantiformis Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19803 Oxytropis ochrocephala Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18393 Eugenia sandwicensis Species Myrtaceae 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
NPT350 Organism Tetranychus urticae Tetranychus urticae mortality = 30.0 % PMID[520488]
NPT2720 Organism Nilaparvata lugens Nilaparvata lugens mortality = 10.0 % PMID[520488]
NPT2721 Organism Callosobruchus chinensis Callosobruchus chinensis mortality = 0.0 % PMID[520488]
NPT1175 Organism Spodoptera litura Spodoptera litura mortality = 20.0 % PMID[520488]
NPT826 Organism Magnaporthe oryzae Magnaporthe oryzae Activity = 48.0 % PMID[520488]
NPT826 Organism Magnaporthe oryzae Magnaporthe oryzae Activity = 58.0 % PMID[520488]
NPT826 Organism Magnaporthe oryzae Magnaporthe oryzae Activity = 83.0 % PMID[520488]
NPT826 Organism Magnaporthe oryzae Magnaporthe oryzae Activity = 93.0 % PMID[520488]
NPT2564 Organism Blumeria graminis Blumeria graminis Activity = 0.0 % PMID[520488]
NPT829 Organism Puccinia recondita Puccinia recondita Activity = 0.0 % PMID[520488]
NPT635 Organism Botryotinia fuckeliana Botryotinia fuckeliana Activity = 0.0 % PMID[520488]
NPT825 Organism Phytophthora infestans Phytophthora infestans Activity = 0.0 % PMID[520488]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani Activity = 0.0 % PMID[520488]
NPT826 Organism Magnaporthe oryzae Magnaporthe oryzae Activity = 95.0 % PMID[520488]

☑ 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 NPC38591 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
0.9747 High Similarity NPC53252
0.9419 High Similarity NPC134171
0.9419 High Similarity NPC300668
0.9419 High Similarity NPC182555
0.9419 High Similarity NPC66441
0.9359 High Similarity NPC32867
0.9359 High Similarity NPC309648
0.9359 High Similarity NPC69531
0.9355 High Similarity NPC1477
0.9355 High Similarity NPC213608
0.9299 High Similarity NPC65504
0.9295 High Similarity NPC258474
0.9295 High Similarity NPC201227
0.929 High Similarity NPC5871
0.929 High Similarity NPC174086
0.9245 High Similarity NPC301256
0.9245 High Similarity NPC312273
0.9241 High Similarity NPC40583
0.9241 High Similarity NPC476349
0.9241 High Similarity NPC51760
0.9241 High Similarity NPC295090
0.9241 High Similarity NPC476350
0.9236 High Similarity NPC247677
0.9236 High Similarity NPC61112
0.9236 High Similarity NPC198489
0.9236 High Similarity NPC160015
0.9187 High Similarity NPC473012
0.9187 High Similarity NPC473011
0.9182 High Similarity NPC260296
0.9182 High Similarity NPC115432
0.9177 High Similarity NPC271741
0.9177 High Similarity NPC287789
0.9177 High Similarity NPC296957
0.9177 High Similarity NPC260902
0.9177 High Similarity NPC475184
0.9156 High Similarity NPC122894
0.9152 High Similarity NPC300657
0.9136 High Similarity NPC82330
0.913 High Similarity NPC155640
0.913 High Similarity NPC473009
0.9119 High Similarity NPC244750
0.9119 High Similarity NPC15815
0.9119 High Similarity NPC105584
0.9114 High Similarity NPC137100
0.9108 High Similarity NPC71061
0.9108 High Similarity NPC303485
0.9108 High Similarity NPC122365
0.9108 High Similarity NPC194593
0.9108 High Similarity NPC121568
0.9108 High Similarity NPC290830
0.9108 High Similarity NPC72425
0.9103 High Similarity NPC111112
0.9103 High Similarity NPC138299
0.9103 High Similarity NPC222713
0.9103 High Similarity NPC67322
0.9097 High Similarity NPC3642
0.9097 High Similarity NPC226644
0.9097 High Similarity NPC37226
0.908 High Similarity NPC253730
0.908 High Similarity NPC286230
0.9074 High Similarity NPC169471
0.9074 High Similarity NPC473010
0.9074 High Similarity NPC474591
0.9062 High Similarity NPC98023
0.9062 High Similarity NPC226462
0.9062 High Similarity NPC195136
0.9059 High Similarity NPC139683
0.9059 High Similarity NPC73929
0.9059 High Similarity NPC47905
0.9057 High Similarity NPC257166
0.9057 High Similarity NPC1796
0.9051 High Similarity NPC205026
0.9051 High Similarity NPC121649
0.9051 High Similarity NPC248739
0.9051 High Similarity NPC215203
0.9051 High Similarity NPC52611
0.9051 High Similarity NPC150908
0.9051 High Similarity NPC159707
0.9051 High Similarity NPC100049
0.9051 High Similarity NPC14606
0.9051 High Similarity NPC158027
0.9051 High Similarity NPC79375
0.9051 High Similarity NPC37253
0.9051 High Similarity NPC265624
0.9051 High Similarity NPC186227
0.9045 High Similarity NPC208011
0.9045 High Similarity NPC39154
0.9045 High Similarity NPC67654
0.9045 High Similarity NPC78324
0.9045 High Similarity NPC115601
0.9032 High Similarity NPC135325
0.9012 High Similarity NPC63438
0.9012 High Similarity NPC159508
0.9 High Similarity NPC123544
0.9 High Similarity NPC304322
0.9 High Similarity NPC51247
0.9 High Similarity NPC472877
0.8981 High Similarity NPC156244
0.8981 High Similarity NPC170169
0.8974 High Similarity NPC291746
0.8974 High Similarity NPC288840
0.8974 High Similarity NPC317492
0.8974 High Similarity NPC39929
0.8974 High Similarity NPC296030
0.897 High Similarity NPC287884
0.897 High Similarity NPC120220
0.897 High Similarity NPC8704
0.8968 High Similarity NPC130581
0.8968 High Similarity NPC12148
0.8963 High Similarity NPC320789
0.8961 High Similarity NPC39045
0.8961 High Similarity NPC470135
0.8961 High Similarity NPC470136
0.8944 High Similarity NPC42965
0.8944 High Similarity NPC121647
0.8944 High Similarity NPC184326
0.8944 High Similarity NPC292863
0.8938 High Similarity NPC322459
0.8938 High Similarity NPC318527
0.8938 High Similarity NPC323627
0.8938 High Similarity NPC324358
0.8938 High Similarity NPC208258
0.8931 High Similarity NPC148938
0.8931 High Similarity NPC198490
0.8924 High Similarity NPC41326
0.8917 High Similarity NPC78335
0.8917 High Similarity NPC230713
0.8916 High Similarity NPC477529
0.8916 High Similarity NPC248593
0.8916 High Similarity NPC472584
0.8916 High Similarity NPC28589
0.891 High Similarity NPC168085
0.891 High Similarity NPC39195
0.8903 High Similarity NPC470134
0.8903 High Similarity NPC51641
0.8903 High Similarity NPC470131
0.8903 High Similarity NPC470132
0.8903 High Similarity NPC228779
0.8903 High Similarity NPC473078
0.8903 High Similarity NPC470133
0.8903 High Similarity NPC109183
0.8903 High Similarity NPC300267
0.8903 High Similarity NPC210826
0.8902 High Similarity NPC320741
0.8902 High Similarity NPC224851
0.8902 High Similarity NPC171985
0.8902 High Similarity NPC251336
0.8896 High Similarity NPC472581
0.8896 High Similarity NPC109180
0.8889 High Similarity NPC137232
0.8889 High Similarity NPC30655
0.8889 High Similarity NPC74854
0.8889 High Similarity NPC18380
0.8889 High Similarity NPC45124
0.8882 High Similarity NPC195167
0.8869 High Similarity NPC101991
0.8868 High Similarity NPC183874
0.8868 High Similarity NPC472462
0.8868 High Similarity NPC235333
0.8862 High Similarity NPC24748
0.8862 High Similarity NPC59491
0.8861 High Similarity NPC316960
0.8861 High Similarity NPC148945
0.8861 High Similarity NPC204561
0.8861 High Similarity NPC317715
0.8861 High Similarity NPC78835
0.8861 High Similarity NPC116604
0.8861 High Similarity NPC309512
0.8861 High Similarity NPC178484
0.8854 High Similarity NPC132345
0.8854 High Similarity NPC178202
0.8854 High Similarity NPC221868
0.8854 High Similarity NPC37208
0.8848 High Similarity NPC50394
0.8848 High Similarity NPC476459
0.8846 High Similarity NPC308200
0.8841 High Similarity NPC136641
0.8839 High Similarity NPC230943
0.8834 High Similarity NPC15374
0.8834 High Similarity NPC477239
0.8834 High Similarity NPC3448
0.882 High Similarity NPC246647
0.882 High Similarity NPC268360
0.882 High Similarity NPC212967
0.882 High Similarity NPC164110
0.882 High Similarity NPC96342
0.8812 High Similarity NPC254351
0.8812 High Similarity NPC213936
0.8812 High Similarity NPC297531
0.8805 High Similarity NPC43345
0.8805 High Similarity NPC263676
0.8805 High Similarity NPC473996
0.8805 High Similarity NPC207624
0.8797 High Similarity NPC29777
0.8797 High Similarity NPC321896
0.8797 High Similarity NPC476185
0.8797 High Similarity NPC471115
0.8795 High Similarity NPC107627
0.879 High Similarity NPC145467
0.879 High Similarity NPC272194

  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 NPC38591 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
0.8889 High Similarity NPD6959 Discontinued
0.8841 High Similarity NPD7852 Clinical (unspecified phase)
0.882 High Similarity NPD3749 Approved
0.8812 High Similarity NPD8443 Clinical (unspecified phase)
0.8679 High Similarity NPD4380 Phase 2
0.8625 High Similarity NPD7411 Suspended
0.8599 High Similarity NPD7410 Clinical (unspecified phase)
0.8571 High Similarity NPD1549 Phase 2
0.8528 High Similarity NPD7768 Phase 2
0.8506 High Similarity NPD1552 Clinical (unspecified phase)
0.8506 High Similarity NPD1550 Clinical (unspecified phase)
0.8481 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8405 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8387 Intermediate Similarity NPD2344 Approved
0.8364 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8364 Intermediate Similarity NPD7075 Discontinued
0.8314 Intermediate Similarity NPD6559 Discontinued
0.8293 Intermediate Similarity NPD7819 Suspended
0.8284 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD6166 Phase 2
0.8263 Intermediate Similarity NPD5494 Approved
0.8258 Intermediate Similarity NPD1510 Phase 2
0.8205 Intermediate Similarity NPD2796 Approved
0.8193 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD2309 Approved
0.8165 Intermediate Similarity NPD2800 Approved
0.8148 Intermediate Similarity NPD920 Approved
0.814 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD1934 Approved
0.8081 Intermediate Similarity NPD3818 Discontinued
0.8059 Intermediate Similarity NPD6232 Discontinued
0.8046 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD7473 Discontinued
0.8012 Intermediate Similarity NPD6801 Discontinued
0.8012 Intermediate Similarity NPD3926 Phase 2
0.8012 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1240 Approved
0.7976 Intermediate Similarity NPD3882 Suspended
0.7963 Intermediate Similarity NPD7390 Discontinued
0.7937 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7937 Intermediate Similarity NPD1243 Approved
0.7931 Intermediate Similarity NPD5844 Phase 1
0.7898 Intermediate Similarity NPD1607 Approved
0.7888 Intermediate Similarity NPD3750 Approved
0.7886 Intermediate Similarity NPD7074 Phase 3
0.7857 Intermediate Similarity NPD2801 Approved
0.7853 Intermediate Similarity NPD1511 Approved
0.7829 Intermediate Similarity NPD7054 Approved
0.7809 Intermediate Similarity NPD8312 Approved
0.7809 Intermediate Similarity NPD8313 Approved
0.7805 Intermediate Similarity NPD2533 Approved
0.7805 Intermediate Similarity NPD2532 Approved
0.7805 Intermediate Similarity NPD2534 Approved
0.779 Intermediate Similarity NPD4287 Approved
0.7784 Intermediate Similarity NPD7472 Approved
0.7758 Intermediate Similarity NPD1512 Approved
0.7756 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD6799 Approved
0.774 Intermediate Similarity NPD5953 Discontinued
0.774 Intermediate Similarity NPD6797 Phase 2
0.7725 Intermediate Similarity NPD3226 Approved
0.7711 Intermediate Similarity NPD5403 Approved
0.7706 Intermediate Similarity NPD5402 Approved
0.7705 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD7251 Discontinued
0.7688 Intermediate Similarity NPD1247 Approved
0.7679 Intermediate Similarity NPD6599 Discontinued
0.767 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD7808 Phase 3
0.7654 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD8455 Phase 2
0.764 Intermediate Similarity NPD1551 Phase 2
0.7628 Intermediate Similarity NPD4908 Phase 1
0.7602 Intermediate Similarity NPD2296 Approved
0.7602 Intermediate Similarity NPD3817 Phase 2
0.7596 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD5401 Approved
0.7578 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD2799 Discontinued
0.7578 Intermediate Similarity NPD3748 Approved
0.7572 Intermediate Similarity NPD919 Approved
0.7571 Intermediate Similarity NPD3751 Discontinued
0.7562 Intermediate Similarity NPD6651 Approved
0.7544 Intermediate Similarity NPD1465 Phase 2
0.7532 Intermediate Similarity NPD2313 Discontinued
0.7531 Intermediate Similarity NPD2935 Discontinued
0.7528 Intermediate Similarity NPD7286 Phase 2
0.7515 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD6279 Approved
0.7485 Intermediate Similarity NPD6280 Approved
0.7474 Intermediate Similarity NPD8151 Discontinued
0.7455 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD7229 Phase 3
0.7443 Intermediate Similarity NPD6808 Phase 2
0.7443 Intermediate Similarity NPD3787 Discontinued
0.7439 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7433 Intermediate Similarity NPD4363 Phase 3
0.7433 Intermediate Similarity NPD4360 Phase 2
0.7423 Intermediate Similarity NPD5404 Approved
0.7423 Intermediate Similarity NPD5406 Approved
0.7423 Intermediate Similarity NPD5408 Approved
0.7423 Intermediate Similarity NPD5405 Approved
0.7421 Intermediate Similarity NPD6781 Approved
0.7421 Intermediate Similarity NPD6777 Approved
0.7421 Intermediate Similarity NPD6779 Approved
0.7421 Intermediate Similarity NPD6776 Approved
0.7421 Intermediate Similarity NPD6780 Approved
0.7421 Intermediate Similarity NPD6778 Approved
0.7421 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD6782 Approved
0.7403 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD8434 Phase 2
0.7378 Intermediate Similarity NPD1471 Phase 3
0.7378 Intermediate Similarity NPD2346 Discontinued
0.7358 Intermediate Similarity NPD7870 Phase 2
0.7358 Intermediate Similarity NPD7871 Phase 2
0.7354 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD4628 Phase 3
0.7349 Intermediate Similarity NPD7003 Approved
0.7345 Intermediate Similarity NPD5711 Approved
0.7345 Intermediate Similarity NPD5710 Approved
0.7341 Intermediate Similarity NPD5761 Phase 2
0.7341 Intermediate Similarity NPD5760 Phase 2
0.7312 Intermediate Similarity NPD3764 Approved
0.731 Intermediate Similarity NPD7458 Discontinued
0.7306 Intermediate Similarity NPD7435 Discontinued
0.7306 Intermediate Similarity NPD7697 Approved
0.7306 Intermediate Similarity NPD7696 Phase 3
0.7306 Intermediate Similarity NPD7698 Approved
0.7294 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD1610 Phase 2
0.7225 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD943 Approved
0.7215 Intermediate Similarity NPD1203 Approved
0.7212 Intermediate Similarity NPD6099 Approved
0.7212 Intermediate Similarity NPD6100 Approved
0.7211 Intermediate Similarity NPD4361 Phase 2
0.7211 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD1729 Discontinued
0.7188 Intermediate Similarity NPD6832 Phase 2
0.7182 Intermediate Similarity NPD7177 Discontinued
0.7176 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD6534 Approved
0.7158 Intermediate Similarity NPD6535 Approved
0.7157 Intermediate Similarity NPD7701 Phase 2
0.7152 Intermediate Similarity NPD7033 Discontinued
0.7151 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD7783 Phase 2
0.7112 Intermediate Similarity NPD8150 Discontinued
0.7107 Intermediate Similarity NPD1470 Approved
0.7107 Intermediate Similarity NPD7584 Approved
0.7095 Intermediate Similarity NPD7199 Phase 2
0.7088 Intermediate Similarity NPD7228 Approved
0.7086 Intermediate Similarity NPD37 Approved
0.7085 Intermediate Similarity NPD7874 Approved
0.7085 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD6234 Discontinued
0.7077 Intermediate Similarity NPD6823 Phase 2
0.7073 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD5124 Phase 1
0.7063 Intermediate Similarity NPD2798 Approved
0.7062 Intermediate Similarity NPD4965 Approved
0.7062 Intermediate Similarity NPD4966 Approved
0.7062 Intermediate Similarity NPD4967 Phase 2
0.705 Intermediate Similarity NPD7801 Approved
0.7047 Intermediate Similarity NPD7699 Phase 2
0.7047 Intermediate Similarity NPD7700 Phase 2
0.7037 Intermediate Similarity NPD4625 Phase 3
0.7035 Intermediate Similarity NPD6273 Approved
0.7032 Intermediate Similarity NPD1548 Phase 1
0.7019 Intermediate Similarity NPD2861 Phase 2
0.7017 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD1613 Approved
0.7006 Intermediate Similarity NPD4288 Approved
0.6994 Remote Similarity NPD3268 Approved
0.6989 Remote Similarity NPD6844 Discontinued
0.6988 Remote Similarity NPD7097 Phase 1
0.6982 Remote Similarity NPD2654 Approved
0.6978 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6927 Remote Similarity NPD6212 Phase 3
0.6927 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6927 Remote Similarity NPD6213 Phase 3
0.6923 Remote Similarity NPD2424 Discontinued
0.6919 Remote Similarity NPD7212 Phase 2
0.6919 Remote Similarity NPD8320 Phase 1
0.6919 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6919 Remote Similarity NPD8319 Approved
0.6919 Remote Similarity NPD7213 Phase 3
0.6918 Remote Similarity NPD3972 Approved

  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