Structure

Physi-Chem Properties

Molecular Weight:  252.17
Volume:  271.981
LogP:  2.259
LogD:  1.778
LogS:  -2.477
# Rotatable Bonds:  2
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.74
Synthetic Accessibility Score:  4.607
Fsp3:  0.8
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:  -4.531
MDCK Permeability:  1.3491217032424174e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.526
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.193
30% Bioavailability (F30%):  0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.978
Plasma Protein Binding (PPB):  65.70214080810547%
Volume Distribution (VD):  1.711
Pgp-substrate:  20.352115631103516%

ADMET: Metabolism

CYP1A2-inhibitor:  0.037
CYP1A2-substrate:  0.164
CYP2C19-inhibitor:  0.023
CYP2C19-substrate:  0.887
CYP2C9-inhibitor:  0.038
CYP2C9-substrate:  0.279
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.288
CYP3A4-inhibitor:  0.037
CYP3A4-substrate:  0.433

ADMET: Excretion

Clearance (CL):  7.969
Half-life (T1/2):  0.275

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.148
Drug-inuced Liver Injury (DILI):  0.751
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.557
Maximum Recommended Daily Dose:  0.017
Skin Sensitization:  0.254
Carcinogencity:  0.097
Eye Corrosion:  0.066
Eye Irritation:  0.269
Respiratory Toxicity:  0.956

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

  Natural Product: NPC476043

Natural Product ID:  NPC476043
Common Name*:   (+)-(1S,2R,6S,9R)-1-Hydroxy-2-(1-Hydroxyethyl)-6-Isopropyl-9-Methylbicyclo[4.3.0]Non-4-En-3-One
IUPAC Name:   (1R,4S,7R,7aS)-7a-hydroxy-1-(1-hydroxyethyl)-7-methyl-4-propan-2-yl-4,5,6,7-tetrahydro-1H-inden-2-one
Synonyms:  
Standard InCHIKey:  GLGXNNXIVCZYRB-KLNRUYBLSA-N
Standard InCHI:  InChI=1S/C15H24O3/c1-8(2)11-6-5-9(3)15(18)12(11)7-13(17)14(15)10(4)16/h7-11,14,16,18H,5-6H2,1-4H3/t9-,10?,11+,14+,15-/m1/s1
SMILES:  CC([C@@H]1CC[C@H]([C@]2(C1=CC(=O)[C@@H]2C(O)C)O)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL523252
PubChem CID:   16086514
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
NPO29315 Dictyopteris divaricata Species Dictyotaceae Eukaryota n.a. n.a. n.a. PMID[15497933]
NPO29315 Dictyopteris divaricata Species Dictyotaceae Eukaryota n.a. n.a. n.a. PMID[16180804]
NPO29315 Dictyopteris divaricata Species Dictyotaceae Eukaryota n.a. n.a. n.a. PMID[16989516]
NPO29315 Dictyopteris divaricata Species Dictyotaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[573614]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[573614]
NPT547 Cell Line BGC-823 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[573614]
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[573614]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[573614]

☑ 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 NPC476043 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
0.925 High Similarity NPC233352
0.925 High Similarity NPC138492
0.925 High Similarity NPC824
0.8706 High Similarity NPC179006
0.8706 High Similarity NPC474853
0.8554 High Similarity NPC287817
0.8554 High Similarity NPC74445
0.8409 Intermediate Similarity NPC474854
0.8391 Intermediate Similarity NPC194417
0.8333 Intermediate Similarity NPC104120
0.8333 Intermediate Similarity NPC157895
0.8333 Intermediate Similarity NPC148685
0.8315 Intermediate Similarity NPC472971
0.8315 Intermediate Similarity NPC472970
0.8222 Intermediate Similarity NPC230332
0.8214 Intermediate Similarity NPC308038
0.8193 Intermediate Similarity NPC34110
0.8132 Intermediate Similarity NPC475806
0.8118 Intermediate Similarity NPC45495
0.8118 Intermediate Similarity NPC172013
0.8118 Intermediate Similarity NPC472301
0.8111 Intermediate Similarity NPC309603
0.8111 Intermediate Similarity NPC473999
0.8095 Intermediate Similarity NPC19443
0.8072 Intermediate Similarity NPC472305
0.8065 Intermediate Similarity NPC271195
0.8065 Intermediate Similarity NPC259286
0.8065 Intermediate Similarity NPC180950
0.8049 Intermediate Similarity NPC7382
0.8046 Intermediate Similarity NPC64600
0.8043 Intermediate Similarity NPC477520
0.8043 Intermediate Similarity NPC69454
0.8043 Intermediate Similarity NPC472930
0.8041 Intermediate Similarity NPC168575
0.8022 Intermediate Similarity NPC48010
0.8022 Intermediate Similarity NPC134321
0.8021 Intermediate Similarity NPC282524
0.8 Intermediate Similarity NPC471941
0.8 Intermediate Similarity NPC281138
0.8 Intermediate Similarity NPC7232
0.7979 Intermediate Similarity NPC249954
0.7979 Intermediate Similarity NPC117133
0.7976 Intermediate Similarity NPC197659
0.7959 Intermediate Similarity NPC294259
0.7957 Intermediate Similarity NPC8993
0.7957 Intermediate Similarity NPC53685
0.7957 Intermediate Similarity NPC474690
0.7957 Intermediate Similarity NPC299100
0.7935 Intermediate Similarity NPC233116
0.7935 Intermediate Similarity NPC63748
0.7935 Intermediate Similarity NPC473998
0.7931 Intermediate Similarity NPC93590
0.7917 Intermediate Similarity NPC154072
0.7912 Intermediate Similarity NPC170775
0.7912 Intermediate Similarity NPC119416
0.7912 Intermediate Similarity NPC2983
0.7895 Intermediate Similarity NPC474785
0.7895 Intermediate Similarity NPC474938
0.7882 Intermediate Similarity NPC207772
0.7872 Intermediate Similarity NPC472932
0.7865 Intermediate Similarity NPC79573
0.7865 Intermediate Similarity NPC471224
0.7865 Intermediate Similarity NPC474083
0.7857 Intermediate Similarity NPC151622
0.7857 Intermediate Similarity NPC263582
0.7857 Intermediate Similarity NPC7629
0.7857 Intermediate Similarity NPC475050
0.7826 Intermediate Similarity NPC128672
0.7826 Intermediate Similarity NPC126993
0.7826 Intermediate Similarity NPC85173
0.7802 Intermediate Similarity NPC474677
0.7802 Intermediate Similarity NPC471722
0.7802 Intermediate Similarity NPC292491
0.7802 Intermediate Similarity NPC471791
0.7802 Intermediate Similarity NPC310752
0.7802 Intermediate Similarity NPC328539
0.7802 Intermediate Similarity NPC471724
0.7802 Intermediate Similarity NPC471793
0.7791 Intermediate Similarity NPC229204
0.7778 Intermediate Similarity NPC472986
0.7778 Intermediate Similarity NPC469994
0.7778 Intermediate Similarity NPC472985
0.7778 Intermediate Similarity NPC470955
0.7778 Intermediate Similarity NPC472974
0.7778 Intermediate Similarity NPC72133
0.7778 Intermediate Similarity NPC198761
0.7765 Intermediate Similarity NPC74995
0.7765 Intermediate Similarity NPC266193
0.7765 Intermediate Similarity NPC257666
0.7755 Intermediate Similarity NPC473424
0.7755 Intermediate Similarity NPC477915
0.7753 Intermediate Similarity NPC227064
0.7753 Intermediate Similarity NPC58841
0.7753 Intermediate Similarity NPC321187
0.7753 Intermediate Similarity NPC85774
0.7753 Intermediate Similarity NPC473246
0.7753 Intermediate Similarity NPC329043
0.7753 Intermediate Similarity NPC214043
0.7753 Intermediate Similarity NPC161423
0.7742 Intermediate Similarity NPC131872
0.7742 Intermediate Similarity NPC472978
0.7742 Intermediate Similarity NPC116726
0.7738 Intermediate Similarity NPC89374
0.7732 Intermediate Similarity NPC470074
0.7727 Intermediate Similarity NPC256750
0.7727 Intermediate Similarity NPC133844
0.7727 Intermediate Similarity NPC20262
0.7717 Intermediate Similarity NPC214387
0.7717 Intermediate Similarity NPC1015
0.7717 Intermediate Similarity NPC86319
0.7717 Intermediate Similarity NPC472973
0.7717 Intermediate Similarity NPC326627
0.7717 Intermediate Similarity NPC31985
0.7717 Intermediate Similarity NPC275740
0.7717 Intermediate Similarity NPC310010
0.7717 Intermediate Similarity NPC472983
0.7711 Intermediate Similarity NPC275098
0.7708 Intermediate Similarity NPC18509
0.7708 Intermediate Similarity NPC156546
0.7701 Intermediate Similarity NPC271104
0.77 Intermediate Similarity NPC257353
0.7692 Intermediate Similarity NPC141292
0.7692 Intermediate Similarity NPC475740
0.7684 Intermediate Similarity NPC316215
0.7684 Intermediate Similarity NPC473170
0.7684 Intermediate Similarity NPC476245
0.7684 Intermediate Similarity NPC88310
0.7684 Intermediate Similarity NPC280725
0.7677 Intermediate Similarity NPC311612
0.7677 Intermediate Similarity NPC247957
0.7677 Intermediate Similarity NPC249187
0.7677 Intermediate Similarity NPC72151
0.7674 Intermediate Similarity NPC80088
0.7674 Intermediate Similarity NPC478122
0.7674 Intermediate Similarity NPC297996
0.7674 Intermediate Similarity NPC62336
0.7674 Intermediate Similarity NPC253561
0.7674 Intermediate Similarity NPC475994
0.7674 Intermediate Similarity NPC172066
0.7674 Intermediate Similarity NPC178852
0.7667 Intermediate Similarity NPC70685
0.7667 Intermediate Similarity NPC470574
0.766 Intermediate Similarity NPC109305
0.766 Intermediate Similarity NPC472942
0.766 Intermediate Similarity NPC134826
0.766 Intermediate Similarity NPC472871
0.766 Intermediate Similarity NPC115021
0.766 Intermediate Similarity NPC474736
0.7653 Intermediate Similarity NPC472924
0.7647 Intermediate Similarity NPC186554
0.7647 Intermediate Similarity NPC76966
0.764 Intermediate Similarity NPC474748
0.764 Intermediate Similarity NPC251475
0.764 Intermediate Similarity NPC66764
0.764 Intermediate Similarity NPC169941
0.764 Intermediate Similarity NPC297398
0.764 Intermediate Similarity NPC110150
0.7634 Intermediate Similarity NPC473099
0.7634 Intermediate Similarity NPC69622
0.7634 Intermediate Similarity NPC477147
0.7634 Intermediate Similarity NPC191684
0.7634 Intermediate Similarity NPC320026
0.7634 Intermediate Similarity NPC477149
0.7629 Intermediate Similarity NPC471717
0.7629 Intermediate Similarity NPC316598
0.7629 Intermediate Similarity NPC103051
0.7624 Intermediate Similarity NPC83744
0.7624 Intermediate Similarity NPC477916
0.7624 Intermediate Similarity NPC473284
0.7614 Intermediate Similarity NPC226068
0.7609 Intermediate Similarity NPC104560
0.7609 Intermediate Similarity NPC472870
0.7609 Intermediate Similarity NPC328313
0.7609 Intermediate Similarity NPC193843
0.7609 Intermediate Similarity NPC143767
0.7609 Intermediate Similarity NPC249889
0.7609 Intermediate Similarity NPC193360
0.7609 Intermediate Similarity NPC131470
0.7604 Intermediate Similarity NPC456
0.7604 Intermediate Similarity NPC29152
0.7604 Intermediate Similarity NPC472941
0.7604 Intermediate Similarity NPC250757
0.7604 Intermediate Similarity NPC301534
0.7604 Intermediate Similarity NPC471153
0.7604 Intermediate Similarity NPC242848
0.76 Intermediate Similarity NPC204833
0.76 Intermediate Similarity NPC209502
0.76 Intermediate Similarity NPC72255
0.7586 Intermediate Similarity NPC472013
0.7586 Intermediate Similarity NPC476624
0.7586 Intermediate Similarity NPC152061
0.7582 Intermediate Similarity NPC31564
0.7582 Intermediate Similarity NPC472869
0.7582 Intermediate Similarity NPC474733
0.7582 Intermediate Similarity NPC145879
0.7582 Intermediate Similarity NPC179591
0.7582 Intermediate Similarity NPC474778
0.7582 Intermediate Similarity NPC474732
0.7579 Intermediate Similarity NPC111015
0.7579 Intermediate Similarity NPC196227

  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 NPC476043 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
0.7849 Intermediate Similarity NPD4202 Approved
0.7778 Intermediate Similarity NPD3618 Phase 1
0.7755 Intermediate Similarity NPD5211 Phase 2
0.7753 Intermediate Similarity NPD3666 Approved
0.7753 Intermediate Similarity NPD3133 Approved
0.7753 Intermediate Similarity NPD3665 Phase 1
0.7717 Intermediate Similarity NPD5328 Approved
0.7717 Intermediate Similarity NPD4753 Phase 2
0.7708 Intermediate Similarity NPD4755 Approved
0.76 Intermediate Similarity NPD5141 Approved
0.7582 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD6079 Approved
0.7551 Intermediate Similarity NPD5286 Approved
0.7551 Intermediate Similarity NPD4700 Approved
0.7551 Intermediate Similarity NPD5285 Approved
0.7551 Intermediate Similarity NPD4696 Approved
0.7528 Intermediate Similarity NPD4223 Phase 3
0.7528 Intermediate Similarity NPD4221 Approved
0.74 Intermediate Similarity NPD5225 Approved
0.74 Intermediate Similarity NPD4633 Approved
0.74 Intermediate Similarity NPD5226 Approved
0.74 Intermediate Similarity NPD5224 Approved
0.7391 Intermediate Similarity NPD5279 Phase 3
0.7391 Intermediate Similarity NPD4623 Approved
0.7391 Intermediate Similarity NPD4519 Discontinued
0.7363 Intermediate Similarity NPD4786 Approved
0.7363 Intermediate Similarity NPD4197 Approved
0.7333 Intermediate Similarity NPD3667 Approved
0.7327 Intermediate Similarity NPD5175 Approved
0.7327 Intermediate Similarity NPD5174 Approved
0.732 Intermediate Similarity NPD5210 Approved
0.732 Intermediate Similarity NPD4629 Approved
0.73 Intermediate Similarity NPD5223 Approved
0.7283 Intermediate Similarity NPD5329 Approved
0.7283 Intermediate Similarity NPD5363 Approved
0.7245 Intermediate Similarity NPD5222 Approved
0.7245 Intermediate Similarity NPD4697 Phase 3
0.7245 Intermediate Similarity NPD5221 Approved
0.7245 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD4634 Approved
0.7204 Intermediate Similarity NPD4694 Approved
0.7204 Intermediate Similarity NPD5280 Approved
0.7204 Intermediate Similarity NPD4690 Approved
0.7204 Intermediate Similarity NPD4693 Phase 3
0.7204 Intermediate Similarity NPD4138 Approved
0.7204 Intermediate Similarity NPD5690 Phase 2
0.7204 Intermediate Similarity NPD4689 Approved
0.7204 Intermediate Similarity NPD5205 Approved
0.7204 Intermediate Similarity NPD4688 Approved
0.7184 Intermediate Similarity NPD7128 Approved
0.7184 Intermediate Similarity NPD4767 Approved
0.7184 Intermediate Similarity NPD6675 Approved
0.7184 Intermediate Similarity NPD4768 Approved
0.7184 Intermediate Similarity NPD6402 Approved
0.7184 Intermediate Similarity NPD5739 Approved
0.7172 Intermediate Similarity NPD6084 Phase 2
0.7172 Intermediate Similarity NPD6083 Phase 2
0.7172 Intermediate Similarity NPD5173 Approved
0.7157 Intermediate Similarity NPD4754 Approved
0.7156 Intermediate Similarity NPD7115 Discovery
0.7143 Intermediate Similarity NPD4270 Approved
0.7143 Intermediate Similarity NPD5695 Phase 3
0.7143 Intermediate Similarity NPD4269 Approved
0.7115 Intermediate Similarity NPD5701 Approved
0.7115 Intermediate Similarity NPD5697 Approved
0.7097 Intermediate Similarity NPD1696 Phase 3
0.7065 Intermediate Similarity NPD4788 Approved
0.7065 Intermediate Similarity NPD5362 Discontinued
0.7048 Intermediate Similarity NPD4729 Approved
0.7048 Intermediate Similarity NPD4730 Approved
0.7048 Intermediate Similarity NPD5128 Approved
0.7048 Intermediate Similarity NPD7320 Approved
0.7048 Intermediate Similarity NPD6881 Approved
0.7048 Intermediate Similarity NPD6899 Approved
0.701 Intermediate Similarity NPD7515 Phase 2
0.6981 Remote Similarity NPD6373 Approved
0.6981 Remote Similarity NPD6012 Approved
0.6981 Remote Similarity NPD6013 Approved
0.6981 Remote Similarity NPD6372 Approved
0.6981 Remote Similarity NPD6014 Approved
0.6931 Remote Similarity NPD5696 Approved
0.6931 Remote Similarity NPD4225 Approved
0.6923 Remote Similarity NPD4252 Approved
0.6916 Remote Similarity NPD5251 Approved
0.6916 Remote Similarity NPD5247 Approved
0.6916 Remote Similarity NPD5248 Approved
0.6916 Remote Similarity NPD6883 Approved
0.6916 Remote Similarity NPD5249 Phase 3
0.6916 Remote Similarity NPD7290 Approved
0.6916 Remote Similarity NPD5250 Approved
0.6916 Remote Similarity NPD7102 Approved
0.6907 Remote Similarity NPD5785 Approved
0.6889 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6887 Remote Similarity NPD6011 Approved
0.6863 Remote Similarity NPD7640 Approved
0.6863 Remote Similarity NPD7639 Approved
0.6852 Remote Similarity NPD8130 Phase 1
0.6852 Remote Similarity NPD5215 Approved
0.6852 Remote Similarity NPD5217 Approved
0.6852 Remote Similarity NPD6650 Approved
0.6852 Remote Similarity NPD6617 Approved
0.6852 Remote Similarity NPD6869 Approved
0.6852 Remote Similarity NPD5216 Approved
0.6852 Remote Similarity NPD6649 Approved
0.6852 Remote Similarity NPD6847 Approved
0.6848 Remote Similarity NPD5369 Approved
0.6842 Remote Similarity NPD5330 Approved
0.6842 Remote Similarity NPD7521 Approved
0.6842 Remote Similarity NPD5786 Approved
0.6842 Remote Similarity NPD6684 Approved
0.6842 Remote Similarity NPD7146 Approved
0.6842 Remote Similarity NPD7334 Approved
0.6842 Remote Similarity NPD6409 Approved
0.6837 Remote Similarity NPD5281 Approved
0.6837 Remote Similarity NPD5284 Approved
0.6813 Remote Similarity NPD4195 Approved
0.6789 Remote Similarity NPD6882 Approved
0.6789 Remote Similarity NPD8297 Approved
0.6768 Remote Similarity NPD5779 Approved
0.6768 Remote Similarity NPD5778 Approved
0.6765 Remote Similarity NPD7638 Approved
0.6759 Remote Similarity NPD5169 Approved
0.6759 Remote Similarity NPD5135 Approved
0.6759 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6739 Remote Similarity NPD4819 Approved
0.6739 Remote Similarity NPD4821 Approved
0.6739 Remote Similarity NPD4820 Approved
0.6739 Remote Similarity NPD7525 Registered
0.6739 Remote Similarity NPD4822 Approved
0.6737 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6737 Remote Similarity NPD1694 Approved
0.6735 Remote Similarity NPD4096 Approved
0.6707 Remote Similarity NPD368 Approved
0.6703 Remote Similarity NPD3617 Approved
0.6702 Remote Similarity NPD7154 Phase 3
0.6701 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6701 Remote Similarity NPD6903 Approved
0.67 Remote Similarity NPD7748 Approved
0.67 Remote Similarity NPD5282 Discontinued
0.6697 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6697 Remote Similarity NPD5127 Approved
0.6667 Remote Similarity NPD6054 Approved
0.6667 Remote Similarity NPD4139 Approved
0.6667 Remote Similarity NPD6319 Approved
0.6667 Remote Similarity NPD4692 Approved
0.6667 Remote Similarity NPD6059 Approved
0.6634 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6634 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6632 Remote Similarity NPD3668 Phase 3
0.6609 Remote Similarity NPD6015 Approved
0.6609 Remote Similarity NPD6016 Approved
0.6607 Remote Similarity NPD6274 Approved
0.6606 Remote Similarity NPD6371 Approved
0.66 Remote Similarity NPD6399 Phase 3
0.66 Remote Similarity NPD5133 Approved
0.6598 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6596 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6588 Remote Similarity NPD7331 Phase 2
0.6577 Remote Similarity NPD4632 Approved
0.6574 Remote Similarity NPD5168 Approved
0.6559 Remote Similarity NPD7332 Phase 2
0.6559 Remote Similarity NPD6931 Approved
0.6559 Remote Similarity NPD4695 Discontinued
0.6559 Remote Similarity NPD5368 Approved
0.6559 Remote Similarity NPD6930 Phase 2
0.6552 Remote Similarity NPD5988 Approved
0.6552 Remote Similarity NPD6370 Approved
0.6535 Remote Similarity NPD6001 Approved
0.6531 Remote Similarity NPD5208 Approved
0.6531 Remote Similarity NPD6672 Approved
0.6531 Remote Similarity NPD5737 Approved
0.6531 Remote Similarity NPD4518 Approved
0.6526 Remote Similarity NPD5332 Approved
0.6526 Remote Similarity NPD5331 Approved
0.6522 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6522 Remote Similarity NPD4271 Approved
0.6522 Remote Similarity NPD4268 Approved
0.6518 Remote Similarity NPD5167 Approved
0.6505 Remote Similarity NPD7902 Approved
0.65 Remote Similarity NPD5693 Phase 1
0.65 Remote Similarity NPD7637 Suspended
0.6489 Remote Similarity NPD4790 Discontinued
0.6486 Remote Similarity NPD6053 Discontinued
0.6484 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6481 Remote Similarity NPD6412 Phase 2
0.6477 Remote Similarity NPD4747 Approved
0.6471 Remote Similarity NPD7341 Phase 2
0.6465 Remote Similarity NPD6904 Approved
0.6465 Remote Similarity NPD6101 Approved
0.6465 Remote Similarity NPD6673 Approved
0.6465 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6465 Remote Similarity NPD6080 Approved
0.6452 Remote Similarity NPD6929 Approved
0.6444 Remote Similarity NPD6926 Approved
0.6444 Remote Similarity NPD6924 Approved
0.6441 Remote Similarity NPD7492 Approved
0.6435 Remote Similarity NPD7100 Approved
0.6435 Remote Similarity NPD4522 Approved
0.6435 Remote Similarity NPD7101 Approved
0.6421 Remote Similarity NPD6435 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