Structure

Physi-Chem Properties

Molecular Weight:  276.17
Volume:  295.38
LogP:  2.133
LogD:  1.497
LogS:  -3.336
# Rotatable Bonds:  1
TPSA:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.796
Synthetic Accessibility Score:  3.939
Fsp3:  0.765
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:  -5.137
MDCK Permeability:  3.086960350628942e-05
Pgp-inhibitor:  0.543
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.18

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.065
Plasma Protein Binding (PPB):  93.19136810302734%
Volume Distribution (VD):  0.364
Pgp-substrate:  4.682225704193115%

ADMET: Metabolism

CYP1A2-inhibitor:  0.025
CYP1A2-substrate:  0.737
CYP2C19-inhibitor:  0.038
CYP2C19-substrate:  0.745
CYP2C9-inhibitor:  0.183
CYP2C9-substrate:  0.715
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.284
CYP3A4-inhibitor:  0.051
CYP3A4-substrate:  0.147

ADMET: Excretion

Clearance (CL):  0.843
Half-life (T1/2):  0.78

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.212
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.062
Maximum Recommended Daily Dose:  0.759
Skin Sensitization:  0.898
Carcinogencity:  0.2
Eye Corrosion:  0.171
Eye Irritation:  0.936
Respiratory Toxicity:  0.641

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

  Natural Product: NPC165711

Natural Product ID:  NPC165711
Common Name*:   8(14)-Podocarpen-13-On-18-Oic Acid
IUPAC Name:   (1R,4aR,4bS,10aR)-1,4a-dimethyl-7-oxo-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
Synonyms:  
Standard InCHIKey:  DXXGHDAWCPTRPU-XOSAIJSUSA-N
Standard InCHI:  InChI=1S/C17H24O3/c1-16-8-3-9-17(2,15(19)20)14(16)7-4-11-10-12(18)5-6-13(11)16/h10,13-14H,3-9H2,1-2H3,(H,19,20)/t13-,14+,16+,17+/m0/s1
SMILES:  O=C1CC[C@H]2C(=C1)CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2048510
PubChem CID:   26183540
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000025] Phenanthrenes and derivatives
        • [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[2089121]
NPO29383 Abies holophylla Species Pinaceae Eukaryota trunk n.a. n.a. PMID[24224862]
NPO29383 Abies holophylla Species Pinaceae Eukaryota Trunk n.a. n.a. PMID[26812172]
NPO29383 Abies holophylla Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[30063340]
NPO12422 Pinus massoniana Species Pinaceae Eukaryota n.a. n.a. n.a. PMID[32100544]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3379416]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3443857]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3760882]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[3841557]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[7288443]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[8133299]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. xylem n.a. PMID[8133299]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. PMID[8691212]
NPO22470 Corynebacterium glutamicum Species Corynebacteriaceae Bacteria n.a. n.a. n.a. Database[Article]
NPO12422 Pinus massoniana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12422 Pinus massoniana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12422 Pinus massoniana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12422 Pinus massoniana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12422 Pinus massoniana Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17292 Asparagus racemosus Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21165 Phagnalon atlanticum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20619 Ougeinia dalbergioides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO19502 Squamopappus skutchii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21014 Brucea antidysenterica Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22470 Corynebacterium glutamicum Species Corynebacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29383 Abies holophylla Species Pinaceae 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
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens IC50 = 33260.0 nM PMID[515736]
NPT568 Individual Protein Matrix metalloproteinase-2 Homo sapiens Inhibition > 30.0 % PMID[515736]
NPT34 Cell Line BV-2 Mus musculus IC50 = 18100.0 nM PMID[515737]
NPT34 Cell Line BV-2 Mus musculus Activity = 123.8 % PMID[515737]

☑ 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 NPC165711 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
0.9467 High Similarity NPC278459
0.9467 High Similarity NPC471898
0.9342 High Similarity NPC238991
0.9342 High Similarity NPC302661
0.9315 High Similarity NPC180886
0.9306 High Similarity NPC103958
0.9306 High Similarity NPC161923
0.9306 High Similarity NPC183503
0.9306 High Similarity NPC283908
0.9221 High Similarity NPC102197
0.9189 High Similarity NPC472300
0.9189 High Similarity NPC97377
0.9178 High Similarity NPC192540
0.9178 High Similarity NPC279666
0.9103 High Similarity NPC96095
0.9091 High Similarity NPC320514
0.9067 High Similarity NPC74410
0.9054 High Similarity NPC69143
0.9041 High Similarity NPC241854
0.9041 High Similarity NPC476046
0.9041 High Similarity NPC251970
0.8987 High Similarity NPC29447
0.8987 High Similarity NPC474537
0.8974 High Similarity NPC105803
0.8961 High Similarity NPC267691
0.8961 High Similarity NPC274050
0.8961 High Similarity NPC147066
0.8961 High Similarity NPC477372
0.8961 High Similarity NPC263272
0.8961 High Similarity NPC90055
0.8961 High Similarity NPC162632
0.8947 High Similarity NPC192329
0.8947 High Similarity NPC231431
0.8933 High Similarity NPC471897
0.8933 High Similarity NPC61952
0.8933 High Similarity NPC471899
0.8933 High Similarity NPC107039
0.8846 High Similarity NPC251779
0.8846 High Similarity NPC69101
0.8831 High Similarity NPC2482
0.8831 High Similarity NPC37038
0.8831 High Similarity NPC476809
0.8831 High Similarity NPC26139
0.8816 High Similarity NPC110094
0.8816 High Similarity NPC198240
0.8816 High Similarity NPC59436
0.8816 High Similarity NPC260385
0.8816 High Similarity NPC280654
0.88 High Similarity NPC89294
0.88 High Similarity NPC309399
0.8784 High Similarity NPC237591
0.8784 High Similarity NPC3753
0.8767 High Similarity NPC160817
0.8765 High Similarity NPC476409
0.8765 High Similarity NPC136948
0.875 High Similarity NPC474680
0.8734 High Similarity NPC49019
0.8734 High Similarity NPC70834
0.8718 High Similarity NPC201912
0.8718 High Similarity NPC142244
0.8718 High Similarity NPC121984
0.8718 High Similarity NPC38350
0.8701 High Similarity NPC477371
0.8701 High Similarity NPC16394
0.8701 High Similarity NPC199595
0.8667 High Similarity NPC476844
0.8667 High Similarity NPC476795
0.8659 High Similarity NPC48107
0.8608 High Similarity NPC260956
0.8608 High Similarity NPC193347
0.859 High Similarity NPC104545
0.859 High Similarity NPC108955
0.8571 High Similarity NPC189485
0.8571 High Similarity NPC471409
0.8571 High Similarity NPC321514
0.8571 High Similarity NPC275494
0.8571 High Similarity NPC179028
0.8554 High Similarity NPC477973
0.8554 High Similarity NPC262043
0.8553 High Similarity NPC263582
0.8533 High Similarity NPC301065
0.8533 High Similarity NPC166797
0.8514 High Similarity NPC133253
0.85 High Similarity NPC168188
0.85 High Similarity NPC53733
0.85 High Similarity NPC470015
0.85 High Similarity NPC83569
0.85 High Similarity NPC69279
0.8481 Intermediate Similarity NPC55869
0.8481 Intermediate Similarity NPC225515
0.8481 Intermediate Similarity NPC40228
0.8481 Intermediate Similarity NPC473217
0.8481 Intermediate Similarity NPC221647
0.8452 Intermediate Similarity NPC476437
0.8452 Intermediate Similarity NPC476369
0.8442 Intermediate Similarity NPC266193
0.8442 Intermediate Similarity NPC471035
0.8442 Intermediate Similarity NPC257666
0.8442 Intermediate Similarity NPC212661
0.8434 Intermediate Similarity NPC72397
0.8421 Intermediate Similarity NPC201027
0.84 Intermediate Similarity NPC35656
0.84 Intermediate Similarity NPC130016
0.84 Intermediate Similarity NPC56747
0.84 Intermediate Similarity NPC472813
0.84 Intermediate Similarity NPC180015
0.84 Intermediate Similarity NPC109576
0.8395 Intermediate Similarity NPC329043
0.8395 Intermediate Similarity NPC214043
0.8395 Intermediate Similarity NPC237712
0.8395 Intermediate Similarity NPC248758
0.8395 Intermediate Similarity NPC476412
0.8395 Intermediate Similarity NPC321187
0.8395 Intermediate Similarity NPC144258
0.8395 Intermediate Similarity NPC161423
0.8395 Intermediate Similarity NPC58841
0.8395 Intermediate Similarity NPC227064
0.8395 Intermediate Similarity NPC85774
0.8395 Intermediate Similarity NPC156981
0.8375 Intermediate Similarity NPC103486
0.8375 Intermediate Similarity NPC133391
0.8356 Intermediate Similarity NPC290445
0.8356 Intermediate Similarity NPC36616
0.8354 Intermediate Similarity NPC267517
0.8354 Intermediate Similarity NPC472478
0.8354 Intermediate Similarity NPC477057
0.8354 Intermediate Similarity NPC469637
0.8353 Intermediate Similarity NPC158030
0.8353 Intermediate Similarity NPC65120
0.8353 Intermediate Similarity NPC230064
0.8353 Intermediate Similarity NPC145067
0.8353 Intermediate Similarity NPC233455
0.8353 Intermediate Similarity NPC4036
0.8333 Intermediate Similarity NPC62336
0.8333 Intermediate Similarity NPC476808
0.8333 Intermediate Similarity NPC112454
0.8333 Intermediate Similarity NPC239098
0.8313 Intermediate Similarity NPC158141
0.8313 Intermediate Similarity NPC96496
0.8313 Intermediate Similarity NPC173089
0.8312 Intermediate Similarity NPC92080
0.8312 Intermediate Similarity NPC470525
0.8293 Intermediate Similarity NPC469948
0.8293 Intermediate Similarity NPC323765
0.8293 Intermediate Similarity NPC94531
0.8293 Intermediate Similarity NPC123319
0.8293 Intermediate Similarity NPC6185
0.8293 Intermediate Similarity NPC311702
0.8293 Intermediate Similarity NPC241512
0.8293 Intermediate Similarity NPC470574
0.8289 Intermediate Similarity NPC46610
0.8289 Intermediate Similarity NPC18819
0.8272 Intermediate Similarity NPC477373
0.8272 Intermediate Similarity NPC200752
0.8272 Intermediate Similarity NPC97913
0.8272 Intermediate Similarity NPC477852
0.8267 Intermediate Similarity NPC21944
0.8256 Intermediate Similarity NPC214756
0.8256 Intermediate Similarity NPC272075
0.8256 Intermediate Similarity NPC295643
0.8256 Intermediate Similarity NPC263780
0.8256 Intermediate Similarity NPC476416
0.825 Intermediate Similarity NPC3915
0.825 Intermediate Similarity NPC327002
0.825 Intermediate Similarity NPC116797
0.825 Intermediate Similarity NPC44963
0.825 Intermediate Similarity NPC473420
0.825 Intermediate Similarity NPC472684
0.825 Intermediate Similarity NPC14151
0.8228 Intermediate Similarity NPC474113
0.8228 Intermediate Similarity NPC308038
0.8228 Intermediate Similarity NPC158846
0.8228 Intermediate Similarity NPC170394
0.8228 Intermediate Similarity NPC327674
0.8228 Intermediate Similarity NPC215843
0.8228 Intermediate Similarity NPC476177
0.8214 Intermediate Similarity NPC474511
0.8214 Intermediate Similarity NPC1753
0.8214 Intermediate Similarity NPC474474
0.8205 Intermediate Similarity NPC197659
0.8193 Intermediate Similarity NPC155011
0.8193 Intermediate Similarity NPC322159
0.8193 Intermediate Similarity NPC474778
0.8193 Intermediate Similarity NPC472986
0.8193 Intermediate Similarity NPC472985
0.8193 Intermediate Similarity NPC73038
0.8193 Intermediate Similarity NPC325594
0.8193 Intermediate Similarity NPC472869
0.8193 Intermediate Similarity NPC195640
0.8193 Intermediate Similarity NPC327115
0.8193 Intermediate Similarity NPC474732
0.8193 Intermediate Similarity NPC94666
0.8193 Intermediate Similarity NPC145879
0.8193 Intermediate Similarity NPC324063
0.8193 Intermediate Similarity NPC31564
0.8193 Intermediate Similarity NPC474733
0.8193 Intermediate Similarity NPC82979
0.8182 Intermediate Similarity NPC476346
0.8182 Intermediate Similarity NPC114236
0.8171 Intermediate Similarity NPC19849

  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 NPC165711 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
0.8831 High Similarity NPD4695 Discontinued
0.8608 High Similarity NPD4223 Phase 3
0.8608 High Similarity NPD4221 Approved
0.8395 Intermediate Similarity NPD3133 Approved
0.8395 Intermediate Similarity NPD3665 Phase 1
0.8395 Intermediate Similarity NPD4197 Approved
0.8395 Intermediate Similarity NPD3666 Approved
0.8353 Intermediate Similarity NPD7515 Phase 2
0.8333 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD3617 Approved
0.8293 Intermediate Similarity NPD5329 Approved
0.8193 Intermediate Similarity NPD5330 Approved
0.8193 Intermediate Similarity NPD3618 Phase 1
0.8193 Intermediate Similarity NPD5205 Approved
0.8193 Intermediate Similarity NPD4623 Approved
0.8193 Intermediate Similarity NPD4689 Approved
0.8193 Intermediate Similarity NPD7334 Approved
0.8193 Intermediate Similarity NPD4690 Approved
0.8193 Intermediate Similarity NPD4688 Approved
0.8193 Intermediate Similarity NPD6409 Approved
0.8193 Intermediate Similarity NPD4138 Approved
0.8193 Intermediate Similarity NPD4519 Discontinued
0.8193 Intermediate Similarity NPD6684 Approved
0.8193 Intermediate Similarity NPD7521 Approved
0.8193 Intermediate Similarity NPD7146 Approved
0.8193 Intermediate Similarity NPD4693 Phase 3
0.8161 Intermediate Similarity NPD7748 Approved
0.8148 Intermediate Similarity NPD3667 Approved
0.814 Intermediate Similarity NPD5284 Approved
0.814 Intermediate Similarity NPD5281 Approved
0.8095 Intermediate Similarity NPD3573 Approved
0.8 Intermediate Similarity NPD4137 Phase 3
0.8 Intermediate Similarity NPD6903 Approved
0.8 Intermediate Similarity NPD5737 Approved
0.8 Intermediate Similarity NPD6672 Approved
0.8 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5208 Approved
0.7976 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD5280 Approved
0.7976 Intermediate Similarity NPD5690 Phase 2
0.7976 Intermediate Similarity NPD5279 Phase 3
0.7976 Intermediate Similarity NPD4694 Approved
0.7952 Intermediate Similarity NPD4786 Approved
0.7907 Intermediate Similarity NPD6673 Approved
0.7907 Intermediate Similarity NPD6904 Approved
0.7907 Intermediate Similarity NPD5328 Approved
0.7907 Intermediate Similarity NPD6080 Approved
0.7907 Intermediate Similarity NPD4753 Phase 2
0.7895 Intermediate Similarity NPD4691 Approved
0.7895 Intermediate Similarity NPD4747 Approved
0.7889 Intermediate Similarity NPD6084 Phase 2
0.7889 Intermediate Similarity NPD6083 Phase 2
0.7889 Intermediate Similarity NPD7902 Approved
0.7865 Intermediate Similarity NPD5695 Phase 3
0.7841 Intermediate Similarity NPD6399 Phase 3
0.7802 Intermediate Similarity NPD5696 Approved
0.7778 Intermediate Similarity NPD7614 Phase 1
0.7778 Intermediate Similarity NPD4195 Approved
0.7765 Intermediate Similarity NPD6098 Approved
0.7727 Intermediate Similarity NPD5693 Phase 1
0.7727 Intermediate Similarity NPD6079 Approved
0.7711 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD4202 Approved
0.7614 Intermediate Similarity NPD5207 Approved
0.7614 Intermediate Similarity NPD4096 Approved
0.7614 Intermediate Similarity NPD5692 Phase 3
0.76 Intermediate Similarity NPD7331 Phase 2
0.7595 Intermediate Similarity NPD4058 Approved
0.7564 Intermediate Similarity NPD5276 Approved
0.7556 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD7900 Approved
0.7556 Intermediate Similarity NPD6001 Approved
0.7529 Intermediate Similarity NPD3668 Phase 3
0.7528 Intermediate Similarity NPD6050 Approved
0.7528 Intermediate Similarity NPD5694 Approved
0.7473 Intermediate Similarity NPD4629 Approved
0.7473 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD5210 Approved
0.7467 Intermediate Similarity NPD7341 Phase 2
0.7403 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD5222 Approved
0.7391 Intermediate Similarity NPD5221 Approved
0.7391 Intermediate Similarity NPD4697 Phase 3
0.7391 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4518 Approved
0.7381 Intermediate Similarity NPD4692 Approved
0.7381 Intermediate Similarity NPD4139 Approved
0.7375 Intermediate Similarity NPD5733 Approved
0.7375 Intermediate Similarity NPD4687 Approved
0.7368 Intermediate Similarity NPD4224 Phase 2
0.732 Intermediate Similarity NPD5739 Approved
0.732 Intermediate Similarity NPD6675 Approved
0.732 Intermediate Similarity NPD7128 Approved
0.732 Intermediate Similarity NPD6402 Approved
0.7312 Intermediate Similarity NPD4755 Approved
0.7312 Intermediate Similarity NPD5173 Approved
0.7253 Intermediate Similarity NPD5133 Approved
0.7245 Intermediate Similarity NPD5697 Approved
0.7245 Intermediate Similarity NPD5701 Approved
0.7241 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD4788 Approved
0.7204 Intermediate Similarity NPD7732 Phase 3
0.7172 Intermediate Similarity NPD7320 Approved
0.7172 Intermediate Similarity NPD6011 Approved
0.7172 Intermediate Similarity NPD6881 Approved
0.7172 Intermediate Similarity NPD6899 Approved
0.7158 Intermediate Similarity NPD5285 Approved
0.7158 Intermediate Similarity NPD6404 Discontinued
0.7158 Intermediate Similarity NPD4700 Approved
0.7158 Intermediate Similarity NPD5286 Approved
0.7158 Intermediate Similarity NPD4696 Approved
0.7143 Intermediate Similarity NPD6411 Approved
0.7125 Intermediate Similarity NPD4243 Approved
0.71 Intermediate Similarity NPD6013 Approved
0.71 Intermediate Similarity NPD6373 Approved
0.71 Intermediate Similarity NPD6372 Approved
0.71 Intermediate Similarity NPD6012 Approved
0.71 Intermediate Similarity NPD6014 Approved
0.7097 Intermediate Similarity NPD5654 Approved
0.7083 Intermediate Similarity NPD5223 Approved
0.7053 Intermediate Similarity NPD7638 Approved
0.7045 Intermediate Similarity NPD1694 Approved
0.703 Intermediate Similarity NPD7102 Approved
0.703 Intermediate Similarity NPD7290 Approved
0.703 Intermediate Similarity NPD6883 Approved
0.701 Intermediate Similarity NPD5226 Approved
0.701 Intermediate Similarity NPD5224 Approved
0.701 Intermediate Similarity NPD5091 Approved
0.701 Intermediate Similarity NPD5211 Phase 2
0.701 Intermediate Similarity NPD5225 Approved
0.701 Intermediate Similarity NPD4633 Approved
0.6988 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6979 Remote Similarity NPD7639 Approved
0.6979 Remote Similarity NPD7640 Approved
0.6961 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6961 Remote Similarity NPD6869 Approved
0.6961 Remote Similarity NPD6649 Approved
0.6961 Remote Similarity NPD6847 Approved
0.6961 Remote Similarity NPD8130 Phase 1
0.6961 Remote Similarity NPD6617 Approved
0.6961 Remote Similarity NPD6650 Approved
0.6951 Remote Similarity NPD4785 Approved
0.6951 Remote Similarity NPD4784 Approved
0.6947 Remote Similarity NPD5959 Approved
0.6939 Remote Similarity NPD4754 Approved
0.6939 Remote Similarity NPD5174 Approved
0.6939 Remote Similarity NPD6052 Approved
0.6939 Remote Similarity NPD5175 Approved
0.6923 Remote Similarity NPD6101 Approved
0.6923 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6914 Remote Similarity NPD6081 Approved
0.69 Remote Similarity NPD6412 Phase 2
0.6893 Remote Similarity NPD8297 Approved
0.6893 Remote Similarity NPD6882 Approved
0.6892 Remote Similarity NPD287 Approved
0.6869 Remote Similarity NPD5141 Approved
0.6867 Remote Similarity NPD4190 Phase 3
0.6867 Remote Similarity NPD5275 Approved
0.6867 Remote Similarity NPD6942 Approved
0.6867 Remote Similarity NPD7339 Approved
0.6832 Remote Similarity NPD6686 Approved
0.6827 Remote Similarity NPD4632 Approved
0.6824 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6809 Remote Similarity NPD5122 Clinical (unspecified phase)
0.68 Remote Similarity NPD4767 Approved
0.68 Remote Similarity NPD4768 Approved
0.68 Remote Similarity NPD6008 Approved
0.6782 Remote Similarity NPD8028 Phase 2
0.6774 Remote Similarity NPD8035 Phase 2
0.6774 Remote Similarity NPD8034 Phase 2
0.6753 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6744 Remote Similarity NPD7645 Phase 2
0.6733 Remote Similarity NPD6614 Approved
0.6701 Remote Similarity NPD4225 Approved
0.6698 Remote Similarity NPD6274 Approved
0.6698 Remote Similarity NPD6868 Approved
0.6667 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4729 Approved
0.6667 Remote Similarity NPD4730 Approved
0.6667 Remote Similarity NPD8039 Approved
0.6667 Remote Similarity NPD5128 Approved
0.6667 Remote Similarity NPD3172 Approved
0.6667 Remote Similarity NPD5168 Approved
0.6636 Remote Similarity NPD7115 Discovery
0.6636 Remote Similarity NPD6317 Approved
0.6636 Remote Similarity NPD6009 Approved
0.6629 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6623 Remote Similarity NPD4191 Approved
0.6623 Remote Similarity NPD4194 Approved
0.6623 Remote Similarity NPD4193 Approved
0.6623 Remote Similarity NPD4192 Approved
0.6591 Remote Similarity NPD857 Phase 3
0.6582 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6575 Remote Similarity NPD4266 Approved
0.6575 Remote Similarity NPD3196 Approved
0.6575 Remote Similarity NPD3195 Phase 2
0.6575 Remote Similarity NPD3194 Approved
0.6574 Remote Similarity NPD6335 Approved
0.6574 Remote Similarity NPD6313 Approved
0.6574 Remote Similarity NPD6314 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