Structure

Physi-Chem Properties

Molecular Weight:  342.22
Volume:  382.507
LogP:  5.268
LogD:  4.292
LogS:  -4.754
# Rotatable Bonds:  7
TPSA:  49.69
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.66
Synthetic Accessibility Score:  4.08
Fsp3:  0.455
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.697
MDCK Permeability:  2.6930383683065884e-05
Pgp-inhibitor:  0.996
Pgp-substrate:  0.022
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.953
30% Bioavailability (F30%):  0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.287
Plasma Protein Binding (PPB):  99.04371643066406%
Volume Distribution (VD):  1.456
Pgp-substrate:  1.6263233423233032%

ADMET: Metabolism

CYP1A2-inhibitor:  0.81
CYP1A2-substrate:  0.597
CYP2C19-inhibitor:  0.282
CYP2C19-substrate:  0.761
CYP2C9-inhibitor:  0.363
CYP2C9-substrate:  0.902
CYP2D6-inhibitor:  0.93
CYP2D6-substrate:  0.541
CYP3A4-inhibitor:  0.884
CYP3A4-substrate:  0.367

ADMET: Excretion

Clearance (CL):  12.462
Half-life (T1/2):  0.238

ADMET: Toxicity

hERG Blockers:  0.24
Human Hepatotoxicity (H-HT):  0.94
Drug-inuced Liver Injury (DILI):  0.052
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.053
Maximum Recommended Daily Dose:  0.822
Skin Sensitization:  0.792
Carcinogencity:  0.561
Eye Corrosion:  0.003
Eye Irritation:  0.294
Respiratory Toxicity:  0.773

Download Data

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

  Natural Product: NPC131397

Natural Product ID:  NPC131397
Common Name*:   Daurichromene B
IUPAC Name:   (2R)-2-(3-hydroxy-8-methyl-4-methylidenenon-7-enyl)-2,7-dimethylchromen-5-ol
Synonyms:   Daurichromene B
Standard InCHIKey:  RXKAJVPBSTXEAH-BPARTEKVSA-N
Standard InCHI:  InChI=1S/C22H30O3/c1-15(2)7-6-8-17(4)19(23)10-12-22(5)11-9-18-20(24)13-16(3)14-21(18)25-22/h7,9,11,13-14,19,23-24H,4,6,8,10,12H2,1-3,5H3/t19?,22-/m0/s1
SMILES:  CC(=CCCC(=C)C(CC[C@]1(C)C=Cc2c(cc(C)cc2O1)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL487801
PubChem CID:   10043034
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001549] Monoterpenoids
          • [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. whole plant n.a. DOI[10.1007/BF02329610]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. PMID[15270561]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21072 Rhododendron dauricum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21072 Rhododendron dauricum Species Ericaceae 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
NPT2 Others Unspecified IC50 = 4.4 uL PMID[476570]

☑ 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 NPC131397 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 NPC476254
0.9746 High Similarity NPC120638
0.9661 High Similarity NPC212965
0.9576 High Similarity NPC218753
0.9431 High Similarity NPC38604
0.9431 High Similarity NPC211179
0.9407 High Similarity NPC85895
0.9407 High Similarity NPC137294
0.9355 High Similarity NPC472795
0.9355 High Similarity NPC472797
0.9355 High Similarity NPC472796
0.9256 High Similarity NPC18128
0.9256 High Similarity NPC77789
0.9106 High Similarity NPC270030
0.9083 High Similarity NPC184302
0.9055 High Similarity NPC472590
0.904 High Similarity NPC46978
0.9024 High Similarity NPC96940
0.9 High Similarity NPC190514
0.8984 High Similarity NPC472798
0.8943 High Similarity NPC74137
0.8917 High Similarity NPC69261
0.8917 High Similarity NPC33270
0.8871 High Similarity NPC261992
0.8855 High Similarity NPC327735
0.8855 High Similarity NPC126101
0.8855 High Similarity NPC476698
0.8855 High Similarity NPC472800
0.8843 High Similarity NPC283616
0.8833 High Similarity NPC150624
0.8819 High Similarity NPC274717
0.879 High Similarity NPC36016
0.879 High Similarity NPC188997
0.879 High Similarity NPC100099
0.8788 High Similarity NPC134260
0.876 High Similarity NPC82503
0.875 High Similarity NPC222108
0.875 High Similarity NPC16577
0.875 High Similarity NPC53906
0.875 High Similarity NPC134360
0.875 High Similarity NPC96719
0.875 High Similarity NPC808
0.874 High Similarity NPC149796
0.873 High Similarity NPC293801
0.872 High Similarity NPC76465
0.872 High Similarity NPC38761
0.872 High Similarity NPC474160
0.8672 High Similarity NPC87224
0.8672 High Similarity NPC222572
0.8667 High Similarity NPC276737
0.8667 High Similarity NPC22610
0.8661 High Similarity NPC276212
0.8661 High Similarity NPC476006
0.8661 High Similarity NPC50315
0.8661 High Similarity NPC283049
0.8661 High Similarity NPC230479
0.8661 High Similarity NPC26879
0.8651 High Similarity NPC134195
0.8651 High Similarity NPC197351
0.8651 High Similarity NPC86502
0.8651 High Similarity NPC246648
0.8651 High Similarity NPC106914
0.8644 High Similarity NPC168657
0.8636 High Similarity NPC164787
0.8636 High Similarity NPC61946
0.8636 High Similarity NPC151224
0.8629 High Similarity NPC96423
0.8629 High Similarity NPC473875
0.8626 High Similarity NPC269528
0.8626 High Similarity NPC11060
0.8626 High Similarity NPC475840
0.8626 High Similarity NPC469610
0.8618 High Similarity NPC295259
0.8618 High Similarity NPC471449
0.8615 High Similarity NPC68205
0.8615 High Similarity NPC211413
0.8615 High Similarity NPC244888
0.8615 High Similarity NPC118683
0.8615 High Similarity NPC162801
0.8615 High Similarity NPC164804
0.8615 High Similarity NPC293203
0.8615 High Similarity NPC160623
0.8615 High Similarity NPC103799
0.8607 High Similarity NPC15860
0.8607 High Similarity NPC50521
0.8607 High Similarity NPC244816
0.8607 High Similarity NPC127894
0.8607 High Similarity NPC219070
0.8607 High Similarity NPC221549
0.8607 High Similarity NPC474933
0.8607 High Similarity NPC470759
0.8594 High Similarity NPC473221
0.8593 High Similarity NPC210192
0.8583 High Similarity NPC103420
0.8583 High Similarity NPC17809
0.8583 High Similarity NPC285040
0.8583 High Similarity NPC188022
0.8583 High Similarity NPC105031
0.8583 High Similarity NPC102540
0.8571 High Similarity NPC230734
0.8571 High Similarity NPC306441
0.8571 High Similarity NPC474639
0.8571 High Similarity NPC141717
0.8571 High Similarity NPC472336
0.8571 High Similarity NPC227503
0.8571 High Similarity NPC472334
0.8571 High Similarity NPC302701
0.8571 High Similarity NPC269091
0.8571 High Similarity NPC16435
0.8561 High Similarity NPC115335
0.8561 High Similarity NPC97834
0.8561 High Similarity NPC296915
0.8561 High Similarity NPC223008
0.8561 High Similarity NPC225696
0.8561 High Similarity NPC198154
0.856 High Similarity NPC54972
0.856 High Similarity NPC476633
0.855 High Similarity NPC469611
0.855 High Similarity NPC13005
0.8548 High Similarity NPC232295
0.8548 High Similarity NPC258979
0.8548 High Similarity NPC93398
0.8548 High Similarity NPC8283
0.8538 High Similarity NPC474481
0.8538 High Similarity NPC220935
0.8538 High Similarity NPC262606
0.8537 High Similarity NPC74821
0.8527 High Similarity NPC38664
0.8527 High Similarity NPC39064
0.8527 High Similarity NPC53986
0.8527 High Similarity NPC47283
0.8525 High Similarity NPC114064
0.8525 High Similarity NPC85292
0.8525 High Similarity NPC229147
0.8525 High Similarity NPC54507
0.8525 High Similarity NPC141090
0.8516 High Similarity NPC82299
0.8507 High Similarity NPC476171
0.85 High Similarity NPC228452
0.85 High Similarity NPC474920
0.8496 Intermediate Similarity NPC112246
0.8496 Intermediate Similarity NPC281521
0.8496 Intermediate Similarity NPC472337
0.8496 Intermediate Similarity NPC473413
0.8496 Intermediate Similarity NPC47398
0.8496 Intermediate Similarity NPC470356
0.8496 Intermediate Similarity NPC255147
0.8496 Intermediate Similarity NPC201357
0.8496 Intermediate Similarity NPC121812
0.8496 Intermediate Similarity NPC134968
0.8496 Intermediate Similarity NPC112939
0.8496 Intermediate Similarity NPC234333
0.8496 Intermediate Similarity NPC94750
0.8496 Intermediate Similarity NPC260898
0.8496 Intermediate Similarity NPC327382
0.8496 Intermediate Similarity NPC474206
0.8492 Intermediate Similarity NPC57199
0.8485 Intermediate Similarity NPC36661
0.8485 Intermediate Similarity NPC263064
0.8485 Intermediate Similarity NPC85435
0.8485 Intermediate Similarity NPC168059
0.8485 Intermediate Similarity NPC92805
0.8485 Intermediate Similarity NPC229442
0.8485 Intermediate Similarity NPC31849
0.8485 Intermediate Similarity NPC77196
0.848 Intermediate Similarity NPC102639
0.848 Intermediate Similarity NPC475529
0.8478 Intermediate Similarity NPC469557
0.8473 Intermediate Similarity NPC129106
0.8473 Intermediate Similarity NPC268917
0.8473 Intermediate Similarity NPC118114
0.8473 Intermediate Similarity NPC129784
0.8473 Intermediate Similarity NPC196765
0.8473 Intermediate Similarity NPC206224
0.8473 Intermediate Similarity NPC12875
0.8473 Intermediate Similarity NPC228369
0.8473 Intermediate Similarity NPC300875
0.8473 Intermediate Similarity NPC476166
0.8473 Intermediate Similarity NPC236014
0.8473 Intermediate Similarity NPC17343
0.8473 Intermediate Similarity NPC472597
0.8473 Intermediate Similarity NPC207892
0.8473 Intermediate Similarity NPC8899
0.8473 Intermediate Similarity NPC150011
0.8473 Intermediate Similarity NPC164574
0.8473 Intermediate Similarity NPC280653
0.8468 Intermediate Similarity NPC32152
0.8467 Intermediate Similarity NPC477616
0.8462 Intermediate Similarity NPC202582
0.8462 Intermediate Similarity NPC470258
0.8462 Intermediate Similarity NPC158477
0.8462 Intermediate Similarity NPC273295
0.8462 Intermediate Similarity NPC218856
0.8462 Intermediate Similarity NPC226788
0.8462 Intermediate Similarity NPC285339
0.8462 Intermediate Similarity NPC190629
0.8462 Intermediate Similarity NPC469963
0.8462 Intermediate Similarity NPC222004
0.8462 Intermediate Similarity NPC93962
0.8462 Intermediate Similarity NPC469951

  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 NPC131397 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
0.9024 High Similarity NPD4749 Approved
0.8976 High Similarity NPD6410 Clinical (unspecified phase)
0.875 High Similarity NPD4625 Phase 3
0.8537 High Similarity NPD1548 Phase 1
0.8516 High Similarity NPD6917 Clinical (unspecified phase)
0.8443 Intermediate Similarity NPD6671 Approved
0.8413 Intermediate Similarity NPD1610 Phase 2
0.8409 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8409 Intermediate Similarity NPD1613 Approved
0.8385 Intermediate Similarity NPD4908 Phase 1
0.8321 Intermediate Similarity NPD3027 Phase 3
0.8258 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8168 Intermediate Similarity NPD2861 Phase 2
0.8125 Intermediate Similarity NPD422 Phase 1
0.8106 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8102 Intermediate Similarity NPD6099 Approved
0.8102 Intermediate Similarity NPD6100 Approved
0.8099 Intermediate Similarity NPD4750 Phase 3
0.8077 Intermediate Similarity NPD6696 Suspended
0.803 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7984 Intermediate Similarity NPD1091 Approved
0.7941 Intermediate Similarity NPD5124 Phase 1
0.7941 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7934 Intermediate Similarity NPD290 Approved
0.7872 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD1778 Approved
0.7801 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7737 Intermediate Similarity NPD2238 Phase 2
0.7724 Intermediate Similarity NPD2684 Approved
0.7721 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7705 Intermediate Similarity NPD968 Approved
0.7698 Intermediate Similarity NPD1398 Phase 1
0.7667 Intermediate Similarity NPD940 Approved
0.7667 Intermediate Similarity NPD846 Approved
0.7656 Intermediate Similarity NPD7340 Approved
0.7652 Intermediate Similarity NPD2235 Phase 2
0.7652 Intermediate Similarity NPD2231 Phase 2
0.7643 Intermediate Similarity NPD7033 Discontinued
0.7634 Intermediate Similarity NPD3496 Discontinued
0.7622 Intermediate Similarity NPD3892 Phase 2
0.7586 Intermediate Similarity NPD7212 Phase 2
0.7586 Intermediate Similarity NPD7213 Phase 3
0.7552 Intermediate Similarity NPD1652 Phase 2
0.7542 Intermediate Similarity NPD844 Approved
0.7534 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7534 Intermediate Similarity NPD7447 Phase 1
0.75 Intermediate Similarity NPD1653 Approved
0.7483 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD7843 Approved
0.7465 Intermediate Similarity NPD2796 Approved
0.7465 Intermediate Similarity NPD1551 Phase 2
0.7442 Intermediate Similarity NPD7157 Approved
0.7426 Intermediate Similarity NPD6584 Phase 3
0.7424 Intermediate Similarity NPD4626 Approved
0.7417 Intermediate Similarity NPD1934 Approved
0.7413 Intermediate Similarity NPD5763 Approved
0.7413 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7413 Intermediate Similarity NPD5762 Approved
0.7407 Intermediate Similarity NPD8651 Approved
0.7388 Intermediate Similarity NPD2233 Approved
0.7388 Intermediate Similarity NPD2232 Approved
0.7388 Intermediate Similarity NPD2230 Approved
0.7376 Intermediate Similarity NPD1607 Approved
0.7372 Intermediate Similarity NPD3018 Phase 2
0.7361 Intermediate Similarity NPD1549 Phase 2
0.7357 Intermediate Similarity NPD4060 Phase 1
0.7353 Intermediate Similarity NPD2797 Approved
0.7348 Intermediate Similarity NPD5691 Approved
0.7333 Intermediate Similarity NPD288 Approved
0.7333 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD600 Approved
0.7319 Intermediate Similarity NPD596 Approved
0.7305 Intermediate Similarity NPD5735 Approved
0.7299 Intermediate Similarity NPD3691 Phase 2
0.7299 Intermediate Similarity NPD3690 Phase 2
0.7295 Intermediate Similarity NPD1242 Phase 1
0.7292 Intermediate Similarity NPD6004 Phase 3
0.7292 Intermediate Similarity NPD6002 Phase 3
0.7292 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD6005 Phase 3
0.7292 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD4380 Phase 2
0.7273 Intermediate Similarity NPD1510 Phase 2
0.7266 Intermediate Similarity NPD228 Approved
0.726 Intermediate Similarity NPD3750 Approved
0.726 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7259 Intermediate Similarity NPD1608 Approved
0.7255 Intermediate Similarity NPD2801 Approved
0.7241 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD2424 Discontinued
0.7234 Intermediate Similarity NPD1240 Approved
0.7234 Intermediate Similarity NPD4140 Approved
0.723 Intermediate Similarity NPD7837 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD1511 Approved
0.7226 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD2677 Approved
0.7209 Intermediate Similarity NPD821 Approved
0.7208 Intermediate Similarity NPD5402 Approved
0.7206 Intermediate Similarity NPD6582 Phase 2
0.7206 Intermediate Similarity NPD5327 Phase 3
0.7206 Intermediate Similarity NPD2982 Phase 2
0.7206 Intermediate Similarity NPD2983 Phase 2
0.7206 Intermediate Similarity NPD6583 Phase 3
0.7203 Intermediate Similarity NPD4536 Approved
0.7203 Intermediate Similarity NPD4538 Approved
0.7203 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD2200 Suspended
0.7197 Intermediate Similarity NPD6959 Discontinued
0.7192 Intermediate Similarity NPD6674 Discontinued
0.7185 Intermediate Similarity NPD1611 Approved
0.7181 Intermediate Similarity NPD2533 Approved
0.7181 Intermediate Similarity NPD2534 Approved
0.7181 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD2532 Approved
0.7176 Intermediate Similarity NPD2557 Approved
0.7174 Intermediate Similarity NPD558 Phase 2
0.717 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD6166 Phase 2
0.717 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD839 Approved
0.7163 Intermediate Similarity NPD840 Approved
0.7161 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7153 Intermediate Similarity NPD4308 Phase 3
0.7153 Intermediate Similarity NPD3225 Approved
0.7143 Intermediate Similarity NPD7466 Approved
0.7143 Intermediate Similarity NPD4628 Phase 3
0.7143 Intermediate Similarity NPD5844 Phase 1
0.7133 Intermediate Similarity NPD4097 Suspended
0.7133 Intermediate Similarity NPD6653 Approved
0.7133 Intermediate Similarity NPD6353 Approved
0.7133 Intermediate Similarity NPD1512 Approved
0.7132 Intermediate Similarity NPD2981 Phase 2
0.7124 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD1712 Approved
0.7122 Intermediate Similarity NPD2237 Approved
0.7117 Intermediate Similarity NPD6559 Discontinued
0.7103 Intermediate Similarity NPD6032 Approved
0.7097 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD3268 Approved
0.709 Intermediate Similarity NPD3445 Approved
0.709 Intermediate Similarity NPD3444 Approved
0.709 Intermediate Similarity NPD5585 Approved
0.709 Intermediate Similarity NPD3443 Approved
0.7086 Intermediate Similarity NPD5403 Approved
0.7081 Intermediate Similarity NPD3818 Discontinued
0.708 Intermediate Similarity NPD3685 Discontinued
0.7078 Intermediate Similarity NPD37 Approved
0.7077 Intermediate Similarity NPD7635 Approved
0.7075 Intermediate Similarity NPD5177 Phase 3
0.7071 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD4965 Approved
0.7051 Intermediate Similarity NPD3882 Suspended
0.7051 Intermediate Similarity NPD4966 Approved
0.7051 Intermediate Similarity NPD4967 Phase 2
0.7047 Intermediate Similarity NPD5058 Phase 3
0.7037 Intermediate Similarity NPD17 Approved
0.7037 Intermediate Similarity NPD6516 Phase 2
0.7037 Intermediate Similarity NPD7054 Approved
0.7037 Intermediate Similarity NPD5846 Approved
0.7034 Intermediate Similarity NPD5588 Approved
0.7034 Intermediate Similarity NPD5960 Phase 3
0.7032 Intermediate Similarity NPD7819 Suspended
0.7025 Intermediate Similarity NPD6746 Phase 2
0.7023 Intermediate Similarity NPD5283 Phase 1
0.7014 Intermediate Similarity NPD3054 Approved
0.7014 Intermediate Similarity NPD3052 Approved
0.7006 Intermediate Similarity NPD7075 Discontinued
0.7006 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7074 Phase 3
0.6994 Remote Similarity NPD7472 Approved
0.6993 Remote Similarity NPD3620 Phase 2
0.6993 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6993 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6987 Remote Similarity NPD3817 Phase 2
0.6986 Remote Similarity NPD2935 Discontinued
0.6972 Remote Similarity NPD1296 Phase 2
0.6972 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6798 Discontinued
0.6968 Remote Similarity NPD6801 Discontinued
0.6967 Remote Similarity NPD2860 Approved
0.6967 Remote Similarity NPD2859 Approved
0.6963 Remote Similarity NPD1357 Approved
0.6963 Remote Similarity NPD3049 Approved
0.6962 Remote Similarity NPD6234 Discontinued
0.6954 Remote Similarity NPD3158 Phase 1
0.6954 Remote Similarity NPD5401 Approved
0.6954 Remote Similarity NPD3157 Approved
0.6951 Remote Similarity NPD6797 Phase 2
0.6948 Remote Similarity NPD4675 Approved
0.6948 Remote Similarity NPD6599 Discontinued
0.6948 Remote Similarity NPD4678 Approved
0.6947 Remote Similarity NPD5535 Approved
0.6944 Remote Similarity NPD6355 Discontinued
0.6943 Remote Similarity NPD7768 Phase 2
0.694 Remote Similarity NPD7644 Approved
0.6935 Remote Similarity NPD3020 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