Structure

Physi-Chem Properties

Molecular Weight:  260.21
Volume:  303.652
LogP:  4.939
LogD:  3.777
LogS:  -4.857
# Rotatable Bonds:  2
TPSA:  17.07
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.633
Synthetic Accessibility Score:  3.704
Fsp3:  0.722
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:  -4.68
MDCK Permeability:  1.8990287571796216e-05
Pgp-inhibitor:  0.985
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.694
30% Bioavailability (F30%):  0.391

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.046
Plasma Protein Binding (PPB):  94.70188903808594%
Volume Distribution (VD):  1.928
Pgp-substrate:  3.680657148361206%

ADMET: Metabolism

CYP1A2-inhibitor:  0.208
CYP1A2-substrate:  0.61
CYP2C19-inhibitor:  0.47
CYP2C19-substrate:  0.932
CYP2C9-inhibitor:  0.279
CYP2C9-substrate:  0.282
CYP2D6-inhibitor:  0.361
CYP2D6-substrate:  0.348
CYP3A4-inhibitor:  0.398
CYP3A4-substrate:  0.754

ADMET: Excretion

Clearance (CL):  5.588
Half-life (T1/2):  0.248

ADMET: Toxicity

hERG Blockers:  0.048
Human Hepatotoxicity (H-HT):  0.533
Drug-inuced Liver Injury (DILI):  0.134
AMES Toxicity:  0.027
Rat Oral Acute Toxicity:  0.436
Maximum Recommended Daily Dose:  0.778
Skin Sensitization:  0.868
Carcinogencity:  0.89
Eye Corrosion:  0.799
Eye Irritation:  0.684
Respiratory Toxicity:  0.976

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

  Natural Product: NPC60772

Natural Product ID:  NPC60772
Common Name*:   (E)-15,16-Bisnorlabda-8(17),11-Dien-13-One
IUPAC Name:   (E)-4-[(1S,4aS,8aS)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]but-3-en-2-one
Synonyms:  
Standard InCHIKey:  GWLGWWOKIBLQJF-YGUYEABBSA-N
Standard InCHI:  InChI=1S/C18H28O/c1-13-7-10-16-17(3,4)11-6-12-18(16,5)15(13)9-8-14(2)19/h8-9,15-16H,1,6-7,10-12H2,2-5H3/b9-8+/t15-,16-,18+/m0/s1
SMILES:  CC(=O)/C=C/[C@H]1C(=C)CC[C@@H]2[C@]1(C)CCCC2(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2332436
PubChem CID:   13994560
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO17780 Curcuma heyneana Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23387824]
NPO17780 Curcuma heyneana Species Zingiberaceae 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
NPT1210 Individual Protein T-cell protein-tyrosine phosphatase Homo sapiens IC50 = 9300.0 nM PMID[500711]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 14700.0 nM PMID[500711]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 88.8 % PMID[500711]

☑ 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 NPC60772 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
0.8852 High Similarity NPC92327
0.8727 High Similarity NPC14002
0.871 High Similarity NPC176107
0.8571 High Similarity NPC5626
0.8548 High Similarity NPC176171
0.8393 Intermediate Similarity NPC23117
0.8361 Intermediate Similarity NPC197238
0.8361 Intermediate Similarity NPC202118
0.8333 Intermediate Similarity NPC127582
0.8281 Intermediate Similarity NPC188292
0.8281 Intermediate Similarity NPC260474
0.8226 Intermediate Similarity NPC469662
0.8226 Intermediate Similarity NPC169275
0.8226 Intermediate Similarity NPC52449
0.8182 Intermediate Similarity NPC54123
0.8095 Intermediate Similarity NPC251118
0.807 Intermediate Similarity NPC295777
0.807 Intermediate Similarity NPC69898
0.8065 Intermediate Similarity NPC288253
0.806 Intermediate Similarity NPC251705
0.803 Intermediate Similarity NPC251929
0.803 Intermediate Similarity NPC265782
0.803 Intermediate Similarity NPC2634
0.8 Intermediate Similarity NPC311852
0.8 Intermediate Similarity NPC155198
0.8 Intermediate Similarity NPC310992
0.8 Intermediate Similarity NPC87141
0.7941 Intermediate Similarity NPC329866
0.7941 Intermediate Similarity NPC474797
0.7941 Intermediate Similarity NPC309852
0.7941 Intermediate Similarity NPC474796
0.7937 Intermediate Similarity NPC285371
0.7937 Intermediate Similarity NPC475124
0.791 Intermediate Similarity NPC234707
0.791 Intermediate Similarity NPC225467
0.791 Intermediate Similarity NPC115023
0.7879 Intermediate Similarity NPC139397
0.7879 Intermediate Similarity NPC256846
0.7869 Intermediate Similarity NPC276764
0.7869 Intermediate Similarity NPC472304
0.7833 Intermediate Similarity NPC115385
0.7826 Intermediate Similarity NPC293803
0.7812 Intermediate Similarity NPC107258
0.7794 Intermediate Similarity NPC470044
0.7794 Intermediate Similarity NPC303613
0.7794 Intermediate Similarity NPC470045
0.7794 Intermediate Similarity NPC474228
0.7761 Intermediate Similarity NPC159577
0.7761 Intermediate Similarity NPC260040
0.7761 Intermediate Similarity NPC307176
0.7761 Intermediate Similarity NPC282593
0.7761 Intermediate Similarity NPC35734
0.7714 Intermediate Similarity NPC469796
0.7714 Intermediate Similarity NPC474463
0.7714 Intermediate Similarity NPC469793
0.7714 Intermediate Similarity NPC69408
0.7705 Intermediate Similarity NPC27610
0.7705 Intermediate Similarity NPC56905
0.7692 Intermediate Similarity NPC185587
0.7692 Intermediate Similarity NPC323005
0.7681 Intermediate Similarity NPC22134
0.7681 Intermediate Similarity NPC20025
0.7679 Intermediate Similarity NPC22765
0.7656 Intermediate Similarity NPC212210
0.7647 Intermediate Similarity NPC190035
0.7647 Intermediate Similarity NPC305501
0.7647 Intermediate Similarity NPC133253
0.7647 Intermediate Similarity NPC21944
0.7619 Intermediate Similarity NPC60565
0.7619 Intermediate Similarity NPC213152
0.7612 Intermediate Similarity NPC182815
0.7571 Intermediate Similarity NPC476346
0.7571 Intermediate Similarity NPC255650
0.7571 Intermediate Similarity NPC473171
0.7541 Intermediate Similarity NPC208749
0.7541 Intermediate Similarity NPC22019
0.7541 Intermediate Similarity NPC281986
0.7541 Intermediate Similarity NPC321568
0.7538 Intermediate Similarity NPC268039
0.75 Intermediate Similarity NPC105197
0.75 Intermediate Similarity NPC124851
0.75 Intermediate Similarity NPC200258
0.7465 Intermediate Similarity NPC1254
0.7463 Intermediate Similarity NPC20610
0.7463 Intermediate Similarity NPC142754
0.7463 Intermediate Similarity NPC296697
0.7463 Intermediate Similarity NPC39157
0.7463 Intermediate Similarity NPC82477
0.746 Intermediate Similarity NPC25853
0.7455 Intermediate Similarity NPC86683
0.7429 Intermediate Similarity NPC255021
0.7424 Intermediate Similarity NPC242945
0.7424 Intermediate Similarity NPC259156
0.7419 Intermediate Similarity NPC94991
0.7419 Intermediate Similarity NPC170799
0.7419 Intermediate Similarity NPC308108
0.7419 Intermediate Similarity NPC266295
0.7419 Intermediate Similarity NPC30215
0.7397 Intermediate Similarity NPC190211
0.7391 Intermediate Similarity NPC470078
0.7391 Intermediate Similarity NPC5701
0.7391 Intermediate Similarity NPC474562
0.7385 Intermediate Similarity NPC6697
0.7385 Intermediate Similarity NPC4638
0.7368 Intermediate Similarity NPC17518
0.7353 Intermediate Similarity NPC286814
0.7344 Intermediate Similarity NPC469728
0.7313 Intermediate Similarity NPC4370
0.7313 Intermediate Similarity NPC475523
0.7313 Intermediate Similarity NPC290350
0.7313 Intermediate Similarity NPC20181
0.7313 Intermediate Similarity NPC220210
0.7302 Intermediate Similarity NPC285594
0.7302 Intermediate Similarity NPC259261
0.7302 Intermediate Similarity NPC96551
0.7297 Intermediate Similarity NPC474509
0.7297 Intermediate Similarity NPC476809
0.7286 Intermediate Similarity NPC130016
0.7286 Intermediate Similarity NPC109576
0.7286 Intermediate Similarity NPC180015
0.7286 Intermediate Similarity NPC144947
0.7286 Intermediate Similarity NPC56747
0.726 Intermediate Similarity NPC115515
0.7258 Intermediate Similarity NPC192427
0.7246 Intermediate Similarity NPC214770
0.7246 Intermediate Similarity NPC477856
0.7246 Intermediate Similarity NPC40574
0.7241 Intermediate Similarity NPC228776
0.7241 Intermediate Similarity NPC118788
0.7231 Intermediate Similarity NPC165695
0.7222 Intermediate Similarity NPC4509
0.7222 Intermediate Similarity NPC292589
0.7222 Intermediate Similarity NPC112680
0.72 Intermediate Similarity NPC6434
0.7188 Intermediate Similarity NPC176621
0.7183 Intermediate Similarity NPC128346
0.7183 Intermediate Similarity NPC211641
0.7183 Intermediate Similarity NPC168975
0.7183 Intermediate Similarity NPC75485
0.7183 Intermediate Similarity NPC219232
0.7183 Intermediate Similarity NPC238146
0.7167 Intermediate Similarity NPC37644
0.7167 Intermediate Similarity NPC296311
0.7167 Intermediate Similarity NPC268564
0.7164 Intermediate Similarity NPC255781
0.7162 Intermediate Similarity NPC476177
0.7162 Intermediate Similarity NPC170394
0.7143 Intermediate Similarity NPC181204
0.7143 Intermediate Similarity NPC474539
0.7123 Intermediate Similarity NPC470428
0.7123 Intermediate Similarity NPC165711
0.7123 Intermediate Similarity NPC472300
0.7119 Intermediate Similarity NPC236623
0.7119 Intermediate Similarity NPC64866
0.7105 Intermediate Similarity NPC469804
0.7105 Intermediate Similarity NPC469806
0.7105 Intermediate Similarity NPC238991
0.7105 Intermediate Similarity NPC469805
0.7105 Intermediate Similarity NPC302661
0.7105 Intermediate Similarity NPC469799
0.7105 Intermediate Similarity NPC94200
0.7097 Intermediate Similarity NPC473733
0.7091 Intermediate Similarity NPC216921
0.7083 Intermediate Similarity NPC65650
0.7077 Intermediate Similarity NPC475795
0.7077 Intermediate Similarity NPC97322
0.7067 Intermediate Similarity NPC469797
0.7067 Intermediate Similarity NPC469798
0.7042 Intermediate Similarity NPC474488
0.7037 Intermediate Similarity NPC103290
0.7027 Intermediate Similarity NPC476949
0.7027 Intermediate Similarity NPC471409
0.7027 Intermediate Similarity NPC275494
0.7027 Intermediate Similarity NPC189485
0.7018 Intermediate Similarity NPC262558
0.7018 Intermediate Similarity NPC8610
0.7015 Intermediate Similarity NPC470329
0.7013 Intermediate Similarity NPC279639
0.7013 Intermediate Similarity NPC474790
0.7013 Intermediate Similarity NPC474976
0.7013 Intermediate Similarity NPC3856
0.6986 Remote Similarity NPC180886
0.6986 Remote Similarity NPC26504
0.6984 Remote Similarity NPC49575
0.6984 Remote Similarity NPC230823
0.6984 Remote Similarity NPC11130
0.6984 Remote Similarity NPC55004
0.6984 Remote Similarity NPC267626
0.6974 Remote Similarity NPC90055
0.6974 Remote Similarity NPC475833
0.6974 Remote Similarity NPC473217
0.6974 Remote Similarity NPC278459
0.697 Remote Similarity NPC472306
0.697 Remote Similarity NPC32285
0.697 Remote Similarity NPC283247
0.6957 Remote Similarity NPC117804
0.6949 Remote Similarity NPC176819
0.6949 Remote Similarity NPC32351
0.6949 Remote Similarity NPC163984
0.6949 Remote Similarity NPC58970

  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 NPC60772 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
0.803 Intermediate Similarity NPD4691 Approved
0.7941 Intermediate Similarity NPD4058 Approved
0.7879 Intermediate Similarity NPD4137 Phase 3
0.7761 Intermediate Similarity NPD4747 Approved
0.7463 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD4687 Approved
0.7419 Intermediate Similarity NPD287 Approved
0.7397 Intermediate Similarity NPD4195 Approved
0.7391 Intermediate Similarity NPD5276 Approved
0.7183 Intermediate Similarity NPD5733 Approved
0.7067 Intermediate Similarity NPD4695 Discontinued
0.6909 Remote Similarity NPD1799 Clinical (unspecified phase)
0.6818 Remote Similarity NPD4194 Approved
0.6818 Remote Similarity NPD4193 Approved
0.6818 Remote Similarity NPD4192 Approved
0.6818 Remote Similarity NPD4191 Approved
0.6795 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6753 Remote Similarity NPD8028 Phase 2
0.6667 Remote Similarity NPD4223 Phase 3
0.6667 Remote Similarity NPD4221 Approved
0.6667 Remote Similarity NPD3573 Approved
0.6543 Remote Similarity NPD5690 Phase 2
0.6543 Remote Similarity NPD4519 Discontinued
0.6543 Remote Similarity NPD4623 Approved
0.6528 Remote Similarity NPD7143 Approved
0.6528 Remote Similarity NPD7144 Approved
0.65 Remote Similarity NPD3666 Approved
0.65 Remote Similarity NPD8262 Approved
0.65 Remote Similarity NPD3665 Phase 1
0.65 Remote Similarity NPD4197 Approved
0.65 Remote Similarity NPD3133 Approved
0.6486 Remote Similarity NPD4785 Approved
0.6486 Remote Similarity NPD4784 Approved
0.6456 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6438 Remote Similarity NPD7150 Approved
0.6438 Remote Similarity NPD7152 Approved
0.6438 Remote Similarity NPD4243 Approved
0.6438 Remote Similarity NPD7151 Approved
0.642 Remote Similarity NPD5329 Approved
0.6389 Remote Similarity NPD6923 Approved
0.6389 Remote Similarity NPD6922 Approved
0.6364 Remote Similarity NPD3617 Approved
0.6353 Remote Similarity NPD6079 Approved
0.6341 Remote Similarity NPD3618 Phase 1
0.6341 Remote Similarity NPD4690 Approved
0.6341 Remote Similarity NPD5205 Approved
0.6341 Remote Similarity NPD7334 Approved
0.6341 Remote Similarity NPD4138 Approved
0.6341 Remote Similarity NPD7146 Approved
0.6341 Remote Similarity NPD6684 Approved
0.6341 Remote Similarity NPD4689 Approved
0.6341 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6341 Remote Similarity NPD5330 Approved
0.6341 Remote Similarity NPD7521 Approved
0.6341 Remote Similarity NPD6409 Approved
0.6341 Remote Similarity NPD4688 Approved
0.6341 Remote Similarity NPD4693 Phase 3
0.6308 Remote Similarity NPD4219 Approved
0.625 Remote Similarity NPD3667 Approved
0.619 Remote Similarity NPD7513 Clinical (unspecified phase)
0.619 Remote Similarity NPD5208 Approved
0.619 Remote Similarity NPD6903 Approved
0.619 Remote Similarity NPD6672 Approved
0.619 Remote Similarity NPD5737 Approved
0.6184 Remote Similarity NPD4190 Phase 3
0.6184 Remote Similarity NPD7339 Approved
0.6184 Remote Similarity NPD6942 Approved
0.6184 Remote Similarity NPD5275 Approved
0.6145 Remote Similarity NPD4694 Approved
0.6145 Remote Similarity NPD5280 Approved
0.6145 Remote Similarity NPD5279 Phase 3
0.6143 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6136 Remote Similarity NPD5210 Approved
0.6136 Remote Similarity NPD4629 Approved
0.6118 Remote Similarity NPD6673 Approved
0.6118 Remote Similarity NPD5328 Approved
0.6118 Remote Similarity NPD4753 Phase 2
0.6118 Remote Similarity NPD6080 Approved
0.6118 Remote Similarity NPD6904 Approved
0.6104 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6098 Remote Similarity NPD4786 Approved
0.6098 Remote Similarity NPD3668 Phase 3
0.6067 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6067 Remote Similarity NPD5222 Approved
0.6067 Remote Similarity NPD5221 Approved
0.6053 Remote Similarity NPD6926 Approved
0.6053 Remote Similarity NPD6924 Approved
0.6047 Remote Similarity NPD5207 Approved
0.6026 Remote Similarity NPD6932 Approved
0.6 Remote Similarity NPD3495 Discontinued
0.6 Remote Similarity NPD5173 Approved
0.6 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5977 Remote Similarity NPD5281 Approved
0.5977 Remote Similarity NPD5284 Approved
0.5977 Remote Similarity NPD5694 Approved
0.5977 Remote Similarity NPD5693 Phase 1
0.5977 Remote Similarity NPD7515 Phase 2
0.5974 Remote Similarity NPD8264 Approved
0.5972 Remote Similarity NPD7331 Phase 2
0.5952 Remote Similarity NPD6098 Approved
0.5949 Remote Similarity NPD7145 Approved
0.5949 Remote Similarity NPD7322 Clinical (unspecified phase)
0.5934 Remote Similarity NPD5290 Discontinued
0.593 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5909 Remote Similarity NPD4202 Approved
0.5897 Remote Similarity NPD6933 Approved
0.5875 Remote Similarity NPD7645 Phase 2
0.587 Remote Similarity NPD4696 Approved
0.587 Remote Similarity NPD5285 Approved
0.587 Remote Similarity NPD5286 Approved
0.5867 Remote Similarity NPD6938 Clinical (unspecified phase)
0.5867 Remote Similarity NPD6939 Phase 2
0.5862 Remote Similarity NPD4096 Approved
0.5862 Remote Similarity NPD5692 Phase 3
0.5843 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5843 Remote Similarity NPD7900 Approved
0.5843 Remote Similarity NPD6001 Approved
0.5843 Remote Similarity NPD7748 Approved
0.5833 Remote Similarity NPD1694 Approved
0.5823 Remote Similarity NPD6925 Approved
0.5823 Remote Similarity NPD5776 Phase 2
0.5814 Remote Similarity NPD4518 Approved
0.5806 Remote Similarity NPD5223 Approved
0.5802 Remote Similarity NPD7332 Phase 2
0.5802 Remote Similarity NPD7514 Phase 3
0.5802 Remote Similarity NPD7525 Registered
0.5795 Remote Similarity NPD6050 Approved
0.5789 Remote Similarity NPD5783 Phase 3
0.5783 Remote Similarity NPD4788 Approved
0.5778 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5745 Remote Similarity NPD4633 Approved
0.5745 Remote Similarity NPD5091 Approved
0.5745 Remote Similarity NPD5224 Approved
0.5745 Remote Similarity NPD5226 Approved
0.5745 Remote Similarity NPD5211 Phase 2
0.5745 Remote Similarity NPD5225 Approved
0.5732 Remote Similarity NPD6902 Approved
0.573 Remote Similarity NPD7631 Approved
0.5714 Remote Similarity NPD7732 Phase 3
0.5714 Remote Similarity NPD319 Phase 1
0.5714 Remote Similarity NPD7614 Phase 1
0.5714 Remote Similarity NPD4697 Phase 3
0.5684 Remote Similarity NPD5174 Approved
0.5684 Remote Similarity NPD5175 Approved
0.5679 Remote Similarity NPD6929 Approved
0.5679 Remote Similarity NPD6683 Phase 2
0.5663 Remote Similarity NPD5209 Approved
0.5652 Remote Similarity NPD6083 Phase 2
0.5652 Remote Similarity NPD6084 Phase 2
0.5652 Remote Similarity NPD4755 Approved
0.5652 Remote Similarity NPD7902 Approved
0.5625 Remote Similarity NPD5141 Approved
0.5618 Remote Similarity NPD7609 Phase 3
0.5616 Remote Similarity NPD7341 Phase 2
0.5616 Remote Similarity NPD2685 Clinical (unspecified phase)
0.561 Remote Similarity NPD6931 Approved
0.561 Remote Similarity NPD6930 Phase 2
0.561 Remote Similarity NPD7509 Discontinued
0.5604 Remote Similarity NPD5695 Phase 3
0.5604 Remote Similarity NPD6049 Phase 2
0.5604 Remote Similarity NPD6048 Clinical (unspecified phase)

  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