Structure

Physi-Chem Properties

Molecular Weight:  318.22
Volume:  347.268
LogP:  3.764
LogD:  3.767
LogS:  -4.09
# Rotatable Bonds:  4
TPSA:  53.6
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.792
Synthetic Accessibility Score:  4.358
Fsp3:  0.7
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.848
MDCK Permeability:  1.5501216694246978e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.263
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.197
Plasma Protein Binding (PPB):  93.2941665649414%
Volume Distribution (VD):  1.389
Pgp-substrate:  4.064950942993164%

ADMET: Metabolism

CYP1A2-inhibitor:  0.153
CYP1A2-substrate:  0.23
CYP2C19-inhibitor:  0.046
CYP2C19-substrate:  0.383
CYP2C9-inhibitor:  0.296
CYP2C9-substrate:  0.161
CYP2D6-inhibitor:  0.06
CYP2D6-substrate:  0.412
CYP3A4-inhibitor:  0.644
CYP3A4-substrate:  0.233

ADMET: Excretion

Clearance (CL):  12.288
Half-life (T1/2):  0.394

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.167
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.468
Maximum Recommended Daily Dose:  0.793
Skin Sensitization:  0.173
Carcinogencity:  0.294
Eye Corrosion:  0.007
Eye Irritation:  0.086
Respiratory Toxicity:  0.943

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

  Natural Product: NPC106416

Natural Product ID:  NPC106416
Common Name*:   19-Hydroxylabda-8(17),13-Dien-16,15-Olide
IUPAC Name:   4-[2-[(1S,4aR,5S,8aR)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one
Synonyms:  
Standard InCHIKey:  WKKBRRFSRMDTJB-RAUXBKROSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-14-5-8-17-19(2,13-21)10-4-11-20(17,3)16(14)7-6-15-9-12-23-18(15)22/h9,16-17,21H,1,4-8,10-13H2,2-3H3/t16-,17-,19+,20+/m0/s1
SMILES:  C=C1CC[C@H]2[C@](C)(CCC[C@]2(C)[C@H]1CCC1=CCOC1=O)CO
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL497243
PubChem CID:   23238929
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001538] Diterpene lactones

*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
NPO30573 Antrodia camphorata Species Fomitopsidaceae Eukaryota n.a. n.a. n.a. PMID[14738384]
NPO30573 Antrodia camphorata Species Fomitopsidaceae Eukaryota fruiting bodies n.a. n.a. PMID[16643055]
NPO30573 Antrodia camphorata Species Fomitopsidaceae Eukaryota n.a. n.a. n.a. PMID[17559265]
NPO30573 Antrodia camphorata Species Fomitopsidaceae Eukaryota n.a. n.a. n.a. PMID[24387703]
NPO30573 Antrodia camphorata Species Fomitopsidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]

☑ 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 41.2 % PMID[453378]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 34.8 % PMID[453378]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 28.9 % PMID[453378]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 32.6 % PMID[453378]

☑ 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 NPC106416 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC86316
0.975 High Similarity NPC65661
0.9518 High Similarity NPC174342
0.9405 High Similarity NPC51486
0.9375 High Similarity NPC200513
0.9294 High Similarity NPC477783
0.9294 High Similarity NPC472814
0.9294 High Similarity NPC177037
0.9286 High Similarity NPC5509
0.9286 High Similarity NPC251528
0.9186 High Similarity NPC139692
0.9176 High Similarity NPC477782
0.9012 High Similarity NPC14203
0.9012 High Similarity NPC229584
0.9012 High Similarity NPC40228
0.8977 High Similarity NPC209355
0.8966 High Similarity NPC115021
0.8876 High Similarity NPC234993
0.8876 High Similarity NPC242848
0.8876 High Similarity NPC134072
0.8837 High Similarity NPC168131
0.8824 High Similarity NPC312561
0.881 High Similarity NPC30984
0.881 High Similarity NPC189311
0.8795 High Similarity NPC311070
0.8778 High Similarity NPC475709
0.8667 High Similarity NPC29952
0.8642 High Similarity NPC198240
0.8642 High Similarity NPC239098
0.8642 High Similarity NPC59436
0.8621 High Similarity NPC50488
0.8621 High Similarity NPC474396
0.8587 High Similarity NPC201406
0.8571 High Similarity NPC474343
0.8571 High Similarity NPC22611
0.8556 High Similarity NPC293052
0.8539 High Similarity NPC472303
0.8539 High Similarity NPC166346
0.8523 High Similarity NPC232426
0.8523 High Similarity NPC182136
0.8523 High Similarity NPC281942
0.8523 High Similarity NPC310479
0.8519 High Similarity NPC316500
0.8519 High Similarity NPC61952
0.8506 High Similarity NPC226863
0.8495 Intermediate Similarity NPC471412
0.8488 Intermediate Similarity NPC474062
0.8488 Intermediate Similarity NPC131813
0.8471 Intermediate Similarity NPC149869
0.8471 Intermediate Similarity NPC475100
0.8444 Intermediate Similarity NPC476415
0.8427 Intermediate Similarity NPC72845
0.8427 Intermediate Similarity NPC289479
0.8427 Intermediate Similarity NPC141831
0.8427 Intermediate Similarity NPC470113
0.8427 Intermediate Similarity NPC303697
0.8387 Intermediate Similarity NPC117685
0.8387 Intermediate Similarity NPC474012
0.8387 Intermediate Similarity NPC476767
0.8387 Intermediate Similarity NPC471413
0.8387 Intermediate Similarity NPC476299
0.8387 Intermediate Similarity NPC477720
0.8372 Intermediate Similarity NPC42586
0.8372 Intermediate Similarity NPC473251
0.837 Intermediate Similarity NPC208094
0.837 Intermediate Similarity NPC253826
0.8353 Intermediate Similarity NPC215893
0.8353 Intermediate Similarity NPC193198
0.8352 Intermediate Similarity NPC183012
0.8352 Intermediate Similarity NPC295347
0.8333 Intermediate Similarity NPC90055
0.8333 Intermediate Similarity NPC152778
0.8333 Intermediate Similarity NPC162615
0.8333 Intermediate Similarity NPC472871
0.8333 Intermediate Similarity NPC205034
0.8316 Intermediate Similarity NPC112009
0.8315 Intermediate Similarity NPC8062
0.8315 Intermediate Similarity NPC476369
0.8315 Intermediate Similarity NPC221111
0.8315 Intermediate Similarity NPC280149
0.8315 Intermediate Similarity NPC476437
0.8298 Intermediate Similarity NPC303559
0.8298 Intermediate Similarity NPC63249
0.8295 Intermediate Similarity NPC472870
0.8295 Intermediate Similarity NPC104560
0.8295 Intermediate Similarity NPC472302
0.8295 Intermediate Similarity NPC472810
0.8295 Intermediate Similarity NPC472809
0.828 Intermediate Similarity NPC108368
0.828 Intermediate Similarity NPC316598
0.828 Intermediate Similarity NPC57079
0.828 Intermediate Similarity NPC98868
0.8276 Intermediate Similarity NPC329692
0.8261 Intermediate Similarity NPC470801
0.8256 Intermediate Similarity NPC248758
0.8256 Intermediate Similarity NPC19849
0.8256 Intermediate Similarity NPC472864
0.8256 Intermediate Similarity NPC30486
0.8242 Intermediate Similarity NPC57117
0.8235 Intermediate Similarity NPC186276
0.8235 Intermediate Similarity NPC94200
0.8222 Intermediate Similarity NPC233345
0.8222 Intermediate Similarity NPC476187
0.8222 Intermediate Similarity NPC186363
0.8214 Intermediate Similarity NPC195424
0.8211 Intermediate Similarity NPC162973
0.8211 Intermediate Similarity NPC476081
0.8211 Intermediate Similarity NPC134077
0.8202 Intermediate Similarity NPC66344
0.8193 Intermediate Similarity NPC471220
0.8182 Intermediate Similarity NPC475678
0.8171 Intermediate Similarity NPC476601
0.8161 Intermediate Similarity NPC283733
0.8161 Intermediate Similarity NPC52628
0.8161 Intermediate Similarity NPC217394
0.8161 Intermediate Similarity NPC471795
0.8148 Intermediate Similarity NPC20025
0.814 Intermediate Similarity NPC42476
0.814 Intermediate Similarity NPC97913
0.8132 Intermediate Similarity NPC151722
0.8132 Intermediate Similarity NPC476416
0.8132 Intermediate Similarity NPC475657
0.8125 Intermediate Similarity NPC180204
0.8125 Intermediate Similarity NPC120321
0.8118 Intermediate Similarity NPC325031
0.8118 Intermediate Similarity NPC282293
0.8111 Intermediate Similarity NPC159748
0.8111 Intermediate Similarity NPC472866
0.8111 Intermediate Similarity NPC158488
0.8111 Intermediate Similarity NPC78973
0.8111 Intermediate Similarity NPC101651
0.8095 Intermediate Similarity NPC263951
0.8095 Intermediate Similarity NPC327674
0.8095 Intermediate Similarity NPC150646
0.809 Intermediate Similarity NPC24816
0.8085 Intermediate Similarity NPC23364
0.8072 Intermediate Similarity NPC97377
0.8072 Intermediate Similarity NPC165711
0.8072 Intermediate Similarity NPC189206
0.8068 Intermediate Similarity NPC186975
0.8068 Intermediate Similarity NPC471219
0.8068 Intermediate Similarity NPC185638
0.8068 Intermediate Similarity NPC85698
0.8068 Intermediate Similarity NPC472869
0.8065 Intermediate Similarity NPC472363
0.8065 Intermediate Similarity NPC319692
0.8065 Intermediate Similarity NPC473153
0.8065 Intermediate Similarity NPC154526
0.8065 Intermediate Similarity NPC325960
0.8065 Intermediate Similarity NPC16967
0.8065 Intermediate Similarity NPC202833
0.8065 Intermediate Similarity NPC472362
0.8049 Intermediate Similarity NPC476795
0.8046 Intermediate Similarity NPC71626
0.8046 Intermediate Similarity NPC164577
0.8046 Intermediate Similarity NPC194937
0.8046 Intermediate Similarity NPC476412
0.8046 Intermediate Similarity NPC476038
0.8046 Intermediate Similarity NPC82297
0.8046 Intermediate Similarity NPC472865
0.8043 Intermediate Similarity NPC53685
0.8043 Intermediate Similarity NPC191521
0.8043 Intermediate Similarity NPC84893
0.8043 Intermediate Similarity NPC474554
0.8023 Intermediate Similarity NPC471159
0.8023 Intermediate Similarity NPC178676
0.8023 Intermediate Similarity NPC142683
0.8023 Intermediate Similarity NPC123880
0.8022 Intermediate Similarity NPC65513
0.8022 Intermediate Similarity NPC473986
0.8022 Intermediate Similarity NPC472811
0.8022 Intermediate Similarity NPC472975
0.8022 Intermediate Similarity NPC474018
0.8022 Intermediate Similarity NPC179517
0.8022 Intermediate Similarity NPC165904
0.8021 Intermediate Similarity NPC114540
0.8021 Intermediate Similarity NPC155332
0.8021 Intermediate Similarity NPC476769
0.8021 Intermediate Similarity NPC32577
0.8 Intermediate Similarity NPC271104
0.8 Intermediate Similarity NPC10636
0.8 Intermediate Similarity NPC54705
0.8 Intermediate Similarity NPC91369
0.8 Intermediate Similarity NPC67183
0.8 Intermediate Similarity NPC472644
0.8 Intermediate Similarity NPC470734
0.8 Intermediate Similarity NPC47024
0.798 Intermediate Similarity NPC177524
0.798 Intermediate Similarity NPC219900
0.798 Intermediate Similarity NPC392
0.7979 Intermediate Similarity NPC121402
0.7979 Intermediate Similarity NPC476253
0.7979 Intermediate Similarity NPC132753
0.7979 Intermediate Similarity NPC73911
0.7979 Intermediate Similarity NPC224356
0.7979 Intermediate Similarity NPC53844
0.7979 Intermediate Similarity NPC151681
0.7979 Intermediate Similarity NPC175351
0.7978 Intermediate Similarity NPC236618
0.7978 Intermediate Similarity NPC181103

  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 NPC106416 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
0.9375 High Similarity NPD4752 Clinical (unspecified phase)
0.798 Intermediate Similarity NPD6686 Approved
0.7895 Intermediate Similarity NPD7638 Approved
0.7895 Intermediate Similarity NPD4225 Approved
0.7812 Intermediate Similarity NPD7640 Approved
0.7812 Intermediate Similarity NPD7639 Approved
0.7753 Intermediate Similarity NPD1694 Approved
0.7667 Intermediate Similarity NPD7521 Approved
0.7667 Intermediate Similarity NPD7334 Approved
0.7667 Intermediate Similarity NPD7146 Approved
0.7667 Intermediate Similarity NPD6409 Approved
0.7667 Intermediate Similarity NPD6684 Approved
0.7667 Intermediate Similarity NPD5330 Approved
0.764 Intermediate Similarity NPD3133 Approved
0.764 Intermediate Similarity NPD3665 Phase 1
0.764 Intermediate Similarity NPD3666 Approved
0.7604 Intermediate Similarity NPD6083 Phase 2
0.7604 Intermediate Similarity NPD6084 Phase 2
0.75 Intermediate Similarity NPD6903 Approved
0.75 Intermediate Similarity NPD6672 Approved
0.75 Intermediate Similarity NPD5737 Approved
0.75 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7748 Approved
0.7473 Intermediate Similarity NPD3618 Phase 1
0.7447 Intermediate Similarity NPD7515 Phase 2
0.7447 Intermediate Similarity NPD5693 Phase 1
0.7416 Intermediate Similarity NPD3667 Approved
0.7412 Intermediate Similarity NPD8039 Approved
0.7396 Intermediate Similarity NPD5695 Phase 3
0.7386 Intermediate Similarity NPD4695 Discontinued
0.7368 Intermediate Similarity NPD6399 Phase 3
0.7347 Intermediate Similarity NPD5696 Approved
0.734 Intermediate Similarity NPD5785 Approved
0.7283 Intermediate Similarity NPD4623 Approved
0.7283 Intermediate Similarity NPD4519 Discontinued
0.7283 Intermediate Similarity NPD5279 Phase 3
0.7263 Intermediate Similarity NPD6079 Approved
0.7253 Intermediate Similarity NPD4786 Approved
0.7245 Intermediate Similarity NPD7902 Approved
0.7234 Intermediate Similarity NPD5328 Approved
0.7234 Intermediate Similarity NPD4753 Phase 2
0.7222 Intermediate Similarity NPD4223 Phase 3
0.7222 Intermediate Similarity NPD7115 Discovery
0.7222 Intermediate Similarity NPD4221 Approved
0.7216 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD3573 Approved
0.7184 Intermediate Similarity NPD5697 Approved
0.7129 Intermediate Similarity NPD7632 Discontinued
0.7128 Intermediate Similarity NPD5208 Approved
0.7115 Intermediate Similarity NPD6899 Approved
0.7115 Intermediate Similarity NPD6881 Approved
0.7115 Intermediate Similarity NPD6011 Approved
0.7087 Intermediate Similarity NPD6402 Approved
0.7087 Intermediate Similarity NPD6675 Approved
0.7087 Intermediate Similarity NPD7128 Approved
0.7087 Intermediate Similarity NPD5739 Approved
0.7065 Intermediate Similarity NPD4197 Approved
0.7065 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD6904 Approved
0.7053 Intermediate Similarity NPD6673 Approved
0.7053 Intermediate Similarity NPD6080 Approved
0.7048 Intermediate Similarity NPD6014 Approved
0.7048 Intermediate Similarity NPD6012 Approved
0.7048 Intermediate Similarity NPD6013 Approved
0.7041 Intermediate Similarity NPD4629 Approved
0.7041 Intermediate Similarity NPD5210 Approved
0.7019 Intermediate Similarity NPD5701 Approved
0.701 Intermediate Similarity NPD4202 Approved
0.6989 Remote Similarity NPD5329 Approved
0.6989 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7290 Approved
0.6981 Remote Similarity NPD6883 Approved
0.6981 Remote Similarity NPD7102 Approved
0.6979 Remote Similarity NPD46 Approved
0.6979 Remote Similarity NPD6698 Approved
0.697 Remote Similarity NPD5220 Clinical (unspecified phase)
0.697 Remote Similarity NPD5221 Approved
0.697 Remote Similarity NPD5222 Approved
0.6966 Remote Similarity NPD3617 Approved
0.6966 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6957 Remote Similarity NPD4788 Approved
0.6952 Remote Similarity NPD7320 Approved
0.6939 Remote Similarity NPD7900 Approved
0.6939 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6931 Remote Similarity NPD6404 Discontinued
0.6916 Remote Similarity NPD6650 Approved
0.6916 Remote Similarity NPD6869 Approved
0.6916 Remote Similarity NPD8130 Phase 1
0.6916 Remote Similarity NPD6617 Approved
0.6916 Remote Similarity NPD6649 Approved
0.6916 Remote Similarity NPD6847 Approved
0.6915 Remote Similarity NPD4690 Approved
0.6915 Remote Similarity NPD4689 Approved
0.6915 Remote Similarity NPD4693 Phase 3
0.6915 Remote Similarity NPD4138 Approved
0.6915 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6915 Remote Similarity NPD5205 Approved
0.6915 Remote Similarity NPD6098 Approved
0.6915 Remote Similarity NPD4688 Approved
0.6915 Remote Similarity NPD5690 Phase 2
0.6907 Remote Similarity NPD7637 Suspended
0.6907 Remote Similarity NPD5284 Approved
0.6907 Remote Similarity NPD5281 Approved
0.6907 Remote Similarity NPD6411 Approved
0.69 Remote Similarity NPD5173 Approved
0.6887 Remote Similarity NPD6372 Approved
0.6887 Remote Similarity NPD6373 Approved
0.6875 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6051 Approved
0.6869 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6852 Remote Similarity NPD6882 Approved
0.6852 Remote Similarity NPD8297 Approved
0.6848 Remote Similarity NPD5209 Approved
0.6837 Remote Similarity NPD5779 Approved
0.6837 Remote Similarity NPD5778 Approved
0.6809 Remote Similarity NPD5363 Approved
0.6804 Remote Similarity NPD5207 Approved
0.6804 Remote Similarity NPD5692 Phase 3
0.68 Remote Similarity NPD4697 Phase 3
0.6796 Remote Similarity NPD5211 Phase 2
0.6774 Remote Similarity NPD7154 Phase 3
0.6774 Remote Similarity NPD5362 Discontinued
0.6768 Remote Similarity NPD6001 Approved
0.6765 Remote Similarity NPD5285 Approved
0.6765 Remote Similarity NPD5286 Approved
0.6765 Remote Similarity NPD4696 Approved
0.6759 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6744 Remote Similarity NPD4691 Approved
0.6737 Remote Similarity NPD4694 Approved
0.6737 Remote Similarity NPD5280 Approved
0.6735 Remote Similarity NPD5694 Approved
0.6735 Remote Similarity NPD6050 Approved
0.6735 Remote Similarity NPD8035 Phase 2
0.6735 Remote Similarity NPD8034 Phase 2
0.6733 Remote Similarity NPD4755 Approved
0.6724 Remote Similarity NPD7507 Approved
0.6703 Remote Similarity NPD4195 Approved
0.6702 Remote Similarity NPD3668 Phase 3
0.6701 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6701 Remote Similarity NPD6101 Approved
0.6699 Remote Similarity NPD5223 Approved
0.6698 Remote Similarity NPD6412 Phase 2
0.6698 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6697 Remote Similarity NPD6053 Discontinued
0.6667 Remote Similarity NPD6868 Approved
0.6667 Remote Similarity NPD5141 Approved
0.6667 Remote Similarity NPD6274 Approved
0.6667 Remote Similarity NPD6371 Approved
0.6636 Remote Similarity NPD4632 Approved
0.6635 Remote Similarity NPD4633 Approved
0.6635 Remote Similarity NPD5224 Approved
0.6635 Remote Similarity NPD5226 Approved
0.6635 Remote Similarity NPD5225 Approved
0.6634 Remote Similarity NPD7614 Phase 1
0.6632 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6628 Remote Similarity NPD4137 Phase 3
0.6607 Remote Similarity NPD6317 Approved
0.6602 Remote Similarity NPD4700 Approved
0.6571 Remote Similarity NPD5174 Approved
0.6571 Remote Similarity NPD5175 Approved
0.6556 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6555 Remote Similarity NPD7319 Approved
0.6552 Remote Similarity NPD4747 Approved
0.6549 Remote Similarity NPD6335 Approved
0.6549 Remote Similarity NPD6313 Approved
0.6549 Remote Similarity NPD6314 Approved
0.6548 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6517 Remote Similarity NPD6926 Approved
0.6517 Remote Similarity NPD6924 Approved
0.6517 Remote Similarity NPD4058 Approved
0.6491 Remote Similarity NPD7101 Approved
0.6491 Remote Similarity NPD7100 Approved
0.6489 Remote Similarity NPD4270 Approved
0.6489 Remote Similarity NPD4269 Approved
0.6489 Remote Similarity NPD6435 Approved
0.6471 Remote Similarity NPD7732 Phase 3
0.6465 Remote Similarity NPD7838 Discovery
0.6465 Remote Similarity NPD4096 Approved
0.646 Remote Similarity NPD6009 Approved
0.6458 Remote Similarity NPD1696 Phase 3
0.6452 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6008 Approved
0.6444 Remote Similarity NPD3702 Approved
0.6444 Remote Similarity NPD7339 Approved
0.6444 Remote Similarity NPD6942 Approved
0.6435 Remote Similarity NPD6319 Approved
0.6429 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6421 Remote Similarity NPD6695 Phase 3
0.6415 Remote Similarity NPD4754 Approved
0.6404 Remote Similarity NPD7328 Approved
0.6404 Remote Similarity NPD7327 Approved
0.6392 Remote Similarity NPD5786 Approved
0.6389 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6383 Remote Similarity NPD5369 Approved
0.6381 Remote Similarity NPD5344 Discontinued
0.6379 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6379 Remote Similarity NPD5983 Phase 2
0.6374 Remote Similarity NPD6933 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