Structure

Physi-Chem Properties

Molecular Weight:  468.36
Volume:  520.411
LogP:  6.69
LogD:  5.24
LogS:  -6.032
# Rotatable Bonds:  2
TPSA:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.295
Synthetic Accessibility Score:  4.572
Fsp3:  0.871
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.152
MDCK Permeability:  1.180910476250574e-05
Pgp-inhibitor:  0.264
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.031
20% Bioavailability (F20%):  0.94
30% Bioavailability (F30%):  0.974

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.138
Plasma Protein Binding (PPB):  93.69300079345703%
Volume Distribution (VD):  1.148
Pgp-substrate:  3.3250880241394043%

ADMET: Metabolism

CYP1A2-inhibitor:  0.049
CYP1A2-substrate:  0.622
CYP2C19-inhibitor:  0.186
CYP2C19-substrate:  0.953
CYP2C9-inhibitor:  0.267
CYP2C9-substrate:  0.703
CYP2D6-inhibitor:  0.101
CYP2D6-substrate:  0.492
CYP3A4-inhibitor:  0.828
CYP3A4-substrate:  0.676

ADMET: Excretion

Clearance (CL):  6.935
Half-life (T1/2):  0.098

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.496
Drug-inuced Liver Injury (DILI):  0.037
AMES Toxicity:  0.008
Rat Oral Acute Toxicity:  0.417
Maximum Recommended Daily Dose:  0.847
Skin Sensitization:  0.04
Carcinogencity:  0.233
Eye Corrosion:  0.036
Eye Irritation:  0.097
Respiratory Toxicity:  0.977

Download Data

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

  Natural Product: NPC267517

Natural Product ID:  NPC267517
Common Name*:   Methyl 3-Oxo-Olean-12-En-28-Oate
IUPAC Name:   methyl (4aS,6aR,6aS,6bR,8aR,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylate
Synonyms:  
Standard InCHIKey:  PPMUFCXCVKVCSV-VNNAKPRGSA-N
Standard InCHI:  InChI=1S/C31H48O3/c1-26(2)15-17-31(25(33)34-8)18-16-29(6)20(21(31)19-26)9-10-23-28(5)13-12-24(32)27(3,4)22(28)11-14-30(23,29)7/h9,21-23H,10-19H2,1-8H3/t21-,22-,23+,28-,29+,30+,31-/m0/s1
SMILES:  COC(=O)[C@@]12CCC(C[C@H]2C2=CC[C@H]3[C@@]([C@@]2(CC1)C)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1631518
PubChem CID:   10695622
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO3125 Scaphechinus mirabilis Species Scutellidae Eukaryota n.a. n.a. n.a. PMID[16180820]
NPO18521 Capparis flavicans Species Capparaceae Eukaryota aerial parts Khon Kaen Province, Thailand 2006-Aug PMID[19943620]
NPO17392 Ipomoea hederacea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO829 Vaccaria hispanica Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17392 Ipomoea hederacea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16834 Baccharis sarothroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17392 Ipomoea hederacea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO829 Vaccaria hispanica Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15360 Stephania hispidula Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13976 Sonchus gummifer Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19129 Oxytropis pseudoglandulosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1604 Micranthes stellaris Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3125 Scaphechinus mirabilis Species Scutellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13598 Pedicularis plicata Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18307 Peltigera venosa Species Peltigeraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17604 Lasioderma serricorne Species Anobiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3113 Xyris semifuscata Species Xyridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17720 Andropogon laniger Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18712 Malus sieboldii Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18521 Capparis flavicans Species Capparaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17392 Ipomoea hederacea Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12652 Xylosalsola richteri Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15625 Umbilicaria spodochroa Species Umbilicariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO829 Vaccaria hispanica Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16834 Baccharis sarothroides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16655 Rabdosia flexicaulis Species Lamiaceae 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
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 1.56 % PMID[453313]
NPT396 Cell Line T47D Homo sapiens Activity = 75.65 % PMID[453314]
NPT306 Cell Line PC-3 Homo sapiens Activity = 85.25 % PMID[453314]
NPT385 Cell Line SR Homo sapiens Activity = 63.87 % PMID[453314]
NPT139 Cell Line HT-29 Homo sapiens IC50 > 100000.0 nM PMID[453315]
NPT306 Cell Line PC-3 Homo sapiens IC50 > 100000.0 nM PMID[453315]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 100000.0 nM PMID[453315]
NPT2488 Cell Line MDA-MB-453 Homo sapiens IC50 > 100000.0 nM PMID[453315]
NPT165 Cell Line HeLa Homo sapiens IC50 > 100000.0 nM PMID[453315]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 78700.0 nM PMID[453315]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 31700.0 nM PMID[453316]
NPT1182 Cell Line J774.A1 Mus musculus IC50 = 33500.0 nM PMID[453316]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 79300.0 nM PMID[453316]
NPT139 Cell Line HT-29 Homo sapiens EC50 = 4470.0 nM PMID[453317]
NPT83 Cell Line MCF7 Homo sapiens EC50 = 5440.0 nM PMID[453317]
NPT38 Individual Protein Signal transducer and activator of transcription 3 Homo sapiens IC50 > 25000.0 nM PMID[453318]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens EC50 > 25000.0 nM PMID[453318]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[453315]
NPT27 Others Unspecified IC50 = 82470.0 nM PMID[453316]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 4110.0 nM PMID[453317]
NPT2 Others Unspecified IC50 > 25000.0 nM PMID[453318]

☑ 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 NPC267517 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
0.9487 High Similarity NPC312660
0.9351 High Similarity NPC267691
0.9351 High Similarity NPC274050
0.9351 High Similarity NPC263272
0.9351 High Similarity NPC162632
0.9231 High Similarity NPC251779
0.9231 High Similarity NPC69101
0.9114 High Similarity NPC70834
0.9114 High Similarity NPC200752
0.9091 High Similarity NPC16394
0.9079 High Similarity NPC472300
0.9024 High Similarity NPC474845
0.9012 High Similarity NPC10005
0.9012 High Similarity NPC9892
0.9012 High Similarity NPC329943
0.9012 High Similarity NPC91525
0.9 High Similarity NPC96095
0.8987 High Similarity NPC163236
0.8974 High Similarity NPC104545
0.8933 High Similarity NPC166797
0.8916 High Similarity NPC474700
0.8902 High Similarity NPC173089
0.8902 High Similarity NPC158141
0.8902 High Similarity NPC162107
0.8902 High Similarity NPC46912
0.8861 High Similarity NPC471898
0.8861 High Similarity NPC3915
0.8846 High Similarity NPC231431
0.8831 High Similarity NPC107039
0.8831 High Similarity NPC471897
0.8831 High Similarity NPC471899
0.881 High Similarity NPC198818
0.8795 High Similarity NPC474511
0.8795 High Similarity NPC224145
0.8795 High Similarity NPC40552
0.8795 High Similarity NPC474474
0.8795 High Similarity NPC246708
0.8795 High Similarity NPC1753
0.875 High Similarity NPC310989
0.8734 High Similarity NPC37038
0.8734 High Similarity NPC477057
0.8718 High Similarity NPC280654
0.8718 High Similarity NPC110094
0.8718 High Similarity NPC260385
0.8718 High Similarity NPC63020
0.8701 High Similarity NPC89294
0.8701 High Similarity NPC899
0.869 High Similarity NPC470588
0.869 High Similarity NPC475049
0.869 High Similarity NPC281524
0.8675 High Similarity NPC130577
0.8675 High Similarity NPC18064
0.8675 High Similarity NPC102683
0.8675 High Similarity NPC88716
0.8675 High Similarity NPC98442
0.8675 High Similarity NPC51700
0.8675 High Similarity NPC171203
0.8675 High Similarity NPC142415
0.8675 High Similarity NPC293564
0.8675 High Similarity NPC68160
0.8675 High Similarity NPC242468
0.8675 High Similarity NPC307426
0.8659 High Similarity NPC474537
0.8649 High Similarity NPC286814
0.8625 High Similarity NPC474955
0.8625 High Similarity NPC142244
0.8608 High Similarity NPC199595
0.8605 High Similarity NPC214756
0.8605 High Similarity NPC272075
0.8605 High Similarity NPC169343
0.8605 High Similarity NPC295643
0.8588 High Similarity NPC474728
0.8588 High Similarity NPC291028
0.8588 High Similarity NPC113989
0.8588 High Similarity NPC120840
0.8588 High Similarity NPC46441
0.8588 High Similarity NPC193750
0.8571 High Similarity NPC52169
0.8571 High Similarity NPC181225
0.8571 High Similarity NPC290690
0.8571 High Similarity NPC470629
0.8571 High Similarity NPC473242
0.8571 High Similarity NPC182797
0.8571 High Similarity NPC17733
0.8571 High Similarity NPC474512
0.8554 High Similarity NPC72638
0.8554 High Similarity NPC324063
0.8537 High Similarity NPC156981
0.8537 High Similarity NPC180834
0.8514 High Similarity NPC296697
0.8514 High Similarity NPC82477
0.8514 High Similarity NPC39157
0.8514 High Similarity NPC142754
0.8506 High Similarity NPC74751
0.8488 Intermediate Similarity NPC105189
0.8488 Intermediate Similarity NPC233455
0.8488 Intermediate Similarity NPC158030
0.8488 Intermediate Similarity NPC471588
0.8488 Intermediate Similarity NPC145067
0.8488 Intermediate Similarity NPC77099
0.8488 Intermediate Similarity NPC60755
0.8488 Intermediate Similarity NPC65120
0.8488 Intermediate Similarity NPC4036
0.8488 Intermediate Similarity NPC285184
0.8488 Intermediate Similarity NPC474525
0.8488 Intermediate Similarity NPC470590
0.8488 Intermediate Similarity NPC38754
0.8488 Intermediate Similarity NPC6255
0.8481 Intermediate Similarity NPC321514
0.8481 Intermediate Similarity NPC4827
0.8471 Intermediate Similarity NPC290972
0.8471 Intermediate Similarity NPC274330
0.8471 Intermediate Similarity NPC121798
0.8471 Intermediate Similarity NPC263393
0.8471 Intermediate Similarity NPC161751
0.8471 Intermediate Similarity NPC130520
0.8471 Intermediate Similarity NPC469546
0.8471 Intermediate Similarity NPC64872
0.8471 Intermediate Similarity NPC127689
0.8471 Intermediate Similarity NPC95246
0.8471 Intermediate Similarity NPC474972
0.8471 Intermediate Similarity NPC30522
0.8471 Intermediate Similarity NPC61543
0.8471 Intermediate Similarity NPC293048
0.8471 Intermediate Similarity NPC234346
0.8471 Intermediate Similarity NPC59263
0.8471 Intermediate Similarity NPC25906
0.8471 Intermediate Similarity NPC225585
0.8471 Intermediate Similarity NPC143232
0.8471 Intermediate Similarity NPC270768
0.8471 Intermediate Similarity NPC198664
0.8452 Intermediate Similarity NPC71507
0.8452 Intermediate Similarity NPC477228
0.8442 Intermediate Similarity NPC306928
0.8434 Intermediate Similarity NPC133954
0.8434 Intermediate Similarity NPC470223
0.8434 Intermediate Similarity NPC274724
0.8421 Intermediate Similarity NPC190035
0.8395 Intermediate Similarity NPC147066
0.8395 Intermediate Similarity NPC278459
0.8395 Intermediate Similarity NPC108476
0.8395 Intermediate Similarity NPC221647
0.8395 Intermediate Similarity NPC195334
0.8395 Intermediate Similarity NPC290495
0.8391 Intermediate Similarity NPC263780
0.8391 Intermediate Similarity NPC307335
0.8391 Intermediate Similarity NPC136313
0.8391 Intermediate Similarity NPC49776
0.8391 Intermediate Similarity NPC86368
0.8391 Intermediate Similarity NPC63118
0.8391 Intermediate Similarity NPC118490
0.8391 Intermediate Similarity NPC74855
0.8391 Intermediate Similarity NPC474436
0.8378 Intermediate Similarity NPC220210
0.8378 Intermediate Similarity NPC20181
0.8372 Intermediate Similarity NPC76286
0.8372 Intermediate Similarity NPC126369
0.8372 Intermediate Similarity NPC210037
0.8372 Intermediate Similarity NPC111110
0.8372 Intermediate Similarity NPC477872
0.8372 Intermediate Similarity NPC7260
0.8372 Intermediate Similarity NPC86372
0.8372 Intermediate Similarity NPC273621
0.8372 Intermediate Similarity NPC120968
0.8372 Intermediate Similarity NPC172361
0.8372 Intermediate Similarity NPC227467
0.8372 Intermediate Similarity NPC290614
0.8372 Intermediate Similarity NPC18872
0.8372 Intermediate Similarity NPC130278
0.8372 Intermediate Similarity NPC470589
0.8354 Intermediate Similarity NPC165711
0.8333 Intermediate Similarity NPC475862
0.8333 Intermediate Similarity NPC279666
0.8333 Intermediate Similarity NPC213412
0.8333 Intermediate Similarity NPC192540
0.8333 Intermediate Similarity NPC74363
0.8333 Intermediate Similarity NPC195640
0.8315 Intermediate Similarity NPC98874
0.8312 Intermediate Similarity NPC279241
0.8312 Intermediate Similarity NPC474488
0.8312 Intermediate Similarity NPC36310
0.8295 Intermediate Similarity NPC474529
0.8295 Intermediate Similarity NPC148964
0.8295 Intermediate Similarity NPC296164
0.8295 Intermediate Similarity NPC184006
0.8295 Intermediate Similarity NPC78580
0.8295 Intermediate Similarity NPC23621
0.8295 Intermediate Similarity NPC91010
0.8293 Intermediate Similarity NPC286786
0.8293 Intermediate Similarity NPC100297
0.8293 Intermediate Similarity NPC240302
0.8276 Intermediate Similarity NPC71074
0.8276 Intermediate Similarity NPC25299
0.8276 Intermediate Similarity NPC228784
0.8276 Intermediate Similarity NPC174167
0.8276 Intermediate Similarity NPC300351
0.8276 Intermediate Similarity NPC84319
0.8276 Intermediate Similarity NPC472149
0.8276 Intermediate Similarity NPC288833
0.8276 Intermediate Similarity NPC324341

  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 NPC267517 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
0.8571 High Similarity NPD7513 Clinical (unspecified phase)
0.8506 High Similarity NPD7748 Approved
0.8506 High Similarity NPD7900 Approved
0.8506 High Similarity NPD7901 Clinical (unspecified phase)
0.8488 Intermediate Similarity NPD7515 Phase 2
0.8333 Intermediate Similarity NPD7146 Approved
0.8333 Intermediate Similarity NPD7334 Approved
0.8333 Intermediate Similarity NPD6684 Approved
0.8333 Intermediate Similarity NPD6409 Approved
0.8333 Intermediate Similarity NPD5330 Approved
0.8333 Intermediate Similarity NPD7521 Approved
0.8222 Intermediate Similarity NPD7902 Approved
0.814 Intermediate Similarity NPD6672 Approved
0.814 Intermediate Similarity NPD6903 Approved
0.814 Intermediate Similarity NPD5737 Approved
0.8118 Intermediate Similarity NPD6098 Approved
0.8046 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.8023 Intermediate Similarity NPD3573 Approved
0.7912 Intermediate Similarity NPD7732 Phase 3
0.7841 Intermediate Similarity NPD6080 Approved
0.7841 Intermediate Similarity NPD6673 Approved
0.7841 Intermediate Similarity NPD6904 Approved
0.7778 Intermediate Similarity NPD6399 Phase 3
0.7727 Intermediate Similarity NPD5208 Approved
0.7674 Intermediate Similarity NPD4786 Approved
0.7647 Intermediate Similarity NPD3667 Approved
0.7609 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD7614 Phase 1
0.75 Intermediate Similarity NPD7645 Phase 2
0.7473 Intermediate Similarity NPD6050 Approved
0.7473 Intermediate Similarity NPD5693 Phase 1
0.7471 Intermediate Similarity NPD3665 Phase 1
0.7471 Intermediate Similarity NPD3668 Phase 3
0.7471 Intermediate Similarity NPD3666 Approved
0.7471 Intermediate Similarity NPD3133 Approved
0.7468 Intermediate Similarity NPD4137 Phase 3
0.7447 Intermediate Similarity NPD6084 Phase 2
0.7447 Intermediate Similarity NPD6083 Phase 2
0.7442 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD4221 Approved
0.7442 Intermediate Similarity NPD4223 Phase 3
0.7412 Intermediate Similarity NPD4695 Discontinued
0.7386 Intermediate Similarity NPD5329 Approved
0.7375 Intermediate Similarity NPD4747 Approved
0.7375 Intermediate Similarity NPD4691 Approved
0.7363 Intermediate Similarity NPD5692 Phase 3
0.7363 Intermediate Similarity NPD5207 Approved
0.7342 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD6001 Approved
0.7303 Intermediate Similarity NPD3618 Phase 1
0.7283 Intermediate Similarity NPD8035 Phase 2
0.7283 Intermediate Similarity NPD5694 Approved
0.7283 Intermediate Similarity NPD8034 Phase 2
0.7273 Intermediate Similarity NPD4197 Approved
0.7253 Intermediate Similarity NPD5328 Approved
0.7234 Intermediate Similarity NPD5695 Phase 3
0.7188 Intermediate Similarity NPD5696 Approved
0.7176 Intermediate Similarity NPD3617 Approved
0.7126 Intermediate Similarity NPD8028 Phase 2
0.7111 Intermediate Similarity NPD4690 Approved
0.7111 Intermediate Similarity NPD5205 Approved
0.7111 Intermediate Similarity NPD4138 Approved
0.7111 Intermediate Similarity NPD4623 Approved
0.7111 Intermediate Similarity NPD4689 Approved
0.7111 Intermediate Similarity NPD4688 Approved
0.7111 Intermediate Similarity NPD4693 Phase 3
0.7111 Intermediate Similarity NPD4519 Discontinued
0.7108 Intermediate Similarity NPD4058 Approved
0.7108 Intermediate Similarity NPD5733 Approved
0.7097 Intermediate Similarity NPD5281 Approved
0.7097 Intermediate Similarity NPD5284 Approved
0.7097 Intermediate Similarity NPD6079 Approved
0.7073 Intermediate Similarity NPD5777 Approved
0.7065 Intermediate Similarity NPD4753 Phase 2
0.7024 Intermediate Similarity NPD8039 Approved
0.7 Intermediate Similarity NPD1694 Approved
0.6966 Remote Similarity NPD4788 Approved
0.6931 Remote Similarity NPD6675 Approved
0.6931 Remote Similarity NPD6402 Approved
0.6931 Remote Similarity NPD7128 Approved
0.6931 Remote Similarity NPD5739 Approved
0.6923 Remote Similarity NPD4694 Approved
0.6923 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5690 Phase 2
0.6923 Remote Similarity NPD5279 Phase 3
0.6923 Remote Similarity NPD5280 Approved
0.6915 Remote Similarity NPD6411 Approved
0.6905 Remote Similarity NPD4687 Approved
0.69 Remote Similarity NPD6052 Approved
0.6882 Remote Similarity NPD6051 Approved
0.6875 Remote Similarity NPD4224 Phase 2
0.6875 Remote Similarity NPD5654 Approved
0.6867 Remote Similarity NPD5276 Approved
0.6842 Remote Similarity NPD4202 Approved
0.6837 Remote Similarity NPD7638 Approved
0.6796 Remote Similarity NPD6899 Approved
0.6796 Remote Similarity NPD6881 Approved
0.6796 Remote Similarity NPD7320 Approved
0.6792 Remote Similarity NPD6858 Approved
0.6792 Remote Similarity NPD7094 Approved
0.6768 Remote Similarity NPD7640 Approved
0.6768 Remote Similarity NPD7639 Approved
0.6765 Remote Similarity NPD6008 Approved
0.6742 Remote Similarity NPD4139 Approved
0.6742 Remote Similarity NPD4692 Approved
0.6735 Remote Similarity NPD5959 Approved
0.6731 Remote Similarity NPD6372 Approved
0.6731 Remote Similarity NPD6373 Approved
0.6705 Remote Similarity NPD4195 Approved
0.6702 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6702 Remote Similarity NPD6101 Approved
0.6701 Remote Similarity NPD4629 Approved
0.6701 Remote Similarity NPD5210 Approved
0.6699 Remote Similarity NPD6412 Phase 2
0.6699 Remote Similarity NPD5697 Approved
0.6699 Remote Similarity NPD6614 Approved
0.6699 Remote Similarity NPD5701 Approved
0.6667 Remote Similarity NPD6081 Approved
0.6667 Remote Similarity NPD4243 Approved
0.6667 Remote Similarity NPD7290 Approved
0.6667 Remote Similarity NPD7102 Approved
0.6667 Remote Similarity NPD6883 Approved
0.6635 Remote Similarity NPD6011 Approved
0.6633 Remote Similarity NPD5221 Approved
0.6633 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6633 Remote Similarity NPD5222 Approved
0.6633 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6633 Remote Similarity NPD4697 Phase 3
0.6628 Remote Similarity NPD6942 Approved
0.6628 Remote Similarity NPD7339 Approved
0.6604 Remote Similarity NPD6847 Approved
0.6604 Remote Similarity NPD6617 Approved
0.6604 Remote Similarity NPD6650 Approved
0.6604 Remote Similarity NPD6869 Approved
0.6604 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6604 Remote Similarity NPD8130 Phase 1
0.6604 Remote Similarity NPD6649 Approved
0.6571 Remote Similarity NPD6013 Approved
0.6571 Remote Similarity NPD6012 Approved
0.6571 Remote Similarity NPD6014 Approved
0.6571 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6566 Remote Similarity NPD5173 Approved
0.6566 Remote Similarity NPD4755 Approved
0.6552 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6549 Remote Similarity NPD8328 Phase 3
0.6542 Remote Similarity NPD8297 Approved
0.6542 Remote Similarity NPD6882 Approved
0.6512 Remote Similarity NPD4784 Approved
0.6512 Remote Similarity NPD4785 Approved
0.6512 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6463 Remote Similarity NPD7331 Phase 2
0.6458 Remote Similarity NPD4096 Approved
0.6455 Remote Similarity NPD7115 Discovery
0.6444 Remote Similarity NPD7525 Registered
0.6436 Remote Similarity NPD4696 Approved
0.6436 Remote Similarity NPD6404 Discontinued
0.6436 Remote Similarity NPD4700 Approved
0.6436 Remote Similarity NPD5286 Approved
0.6436 Remote Similarity NPD5285 Approved
0.641 Remote Similarity NPD287 Approved
0.6404 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6373 Remote Similarity NPD5223 Approved
0.6364 Remote Similarity NPD6117 Approved
0.6364 Remote Similarity NPD6868 Approved
0.6353 Remote Similarity NPD4244 Approved
0.6353 Remote Similarity NPD4789 Approved
0.6353 Remote Similarity NPD4245 Approved
0.6341 Remote Similarity NPD7341 Phase 2
0.633 Remote Similarity NPD4632 Approved
0.6327 Remote Similarity NPD5133 Approved
0.6327 Remote Similarity NPD5778 Approved
0.6327 Remote Similarity NPD5779 Approved
0.6321 Remote Similarity NPD6686 Approved
0.6311 Remote Similarity NPD5226 Approved
0.6311 Remote Similarity NPD5225 Approved
0.6311 Remote Similarity NPD5224 Approved
0.6311 Remote Similarity NPD4633 Approved
0.6311 Remote Similarity NPD5211 Phase 2
0.631 Remote Similarity NPD5360 Phase 3
0.631 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6306 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6292 Remote Similarity NPD6116 Phase 1
0.6279 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6279 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6263 Remote Similarity NPD5707 Approved
0.625 Remote Similarity NPD4190 Phase 3
0.625 Remote Similarity NPD3702 Approved
0.625 Remote Similarity NPD5174 Approved
0.625 Remote Similarity NPD6335 Approved
0.625 Remote Similarity NPD5275 Approved
0.625 Remote Similarity NPD4754 Approved
0.625 Remote Similarity NPD4518 Approved
0.625 Remote Similarity NPD5175 Approved
0.6237 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6235 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6235 Remote Similarity NPD3698 Phase 2
0.6235 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6222 Remote Similarity NPD6114 Approved
0.6222 Remote Similarity NPD6115 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