Structure

Physi-Chem Properties

Molecular Weight:  248.14
Volume:  266.708
LogP:  1.779
LogD:  1.607
LogS:  -3.272
# Rotatable Bonds:  1
TPSA:  51.21
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.529
Synthetic Accessibility Score:  4.366
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.559
MDCK Permeability:  2.9345674192882143e-05
Pgp-inhibitor:  0.402
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.035
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.861
Plasma Protein Binding (PPB):  70.53260803222656%
Volume Distribution (VD):  0.385
Pgp-substrate:  25.605419158935547%

ADMET: Metabolism

CYP1A2-inhibitor:  0.044
CYP1A2-substrate:  0.352
CYP2C19-inhibitor:  0.315
CYP2C19-substrate:  0.786
CYP2C9-inhibitor:  0.049
CYP2C9-substrate:  0.258
CYP2D6-inhibitor:  0.013
CYP2D6-substrate:  0.518
CYP3A4-inhibitor:  0.111
CYP3A4-substrate:  0.253

ADMET: Excretion

Clearance (CL):  6.197
Half-life (T1/2):  0.86

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.154
Drug-inuced Liver Injury (DILI):  0.07
AMES Toxicity:  0.212
Rat Oral Acute Toxicity:  0.254
Maximum Recommended Daily Dose:  0.862
Skin Sensitization:  0.618
Carcinogencity:  0.872
Eye Corrosion:  0.693
Eye Irritation:  0.556
Respiratory Toxicity:  0.934

Download Data

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

  Natural Product: NPC471514

Natural Product ID:  NPC471514
Common Name*:   1Beta-Hydroxy-11(R,S)-8-Oxoeremophil-6,9-Dien-12-Al
IUPAC Name:   2-[(5R,8S,8aS)-5-hydroxy-8,8a-dimethyl-3-oxo-5,6,7,8-tetrahydronaphthalen-2-yl]propanal
Synonyms:  
Standard InCHIKey:  VPFADTWMSCOYGD-HIQSBDGRSA-N
Standard InCHI:  InChI=1S/C15H20O3/c1-9(8-16)11-7-15(3)10(2)4-5-13(17)12(15)6-14(11)18/h6-10,13,17H,4-5H2,1-3H3/t9?,10-,13+,15+/m0/s1
SMILES:  O=CC(C1=C[C@]2(C)[C@@H](C)CC[C@H](C2=CC1=O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL253776
PubChem CID:   23627126
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids
          • [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane 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
NPO1183 Ligularia macrophylla Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[17672504]
NPO1183 Ligularia macrophylla Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[18044832]
NPO1183 Ligularia macrophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell Line A549 Homo sapiens EC50 = 18.4 ug.mL-1 PMID[509868]
NPT83 Cell Line MCF7 Homo sapiens EC50 > 20.0 ug.mL-1 PMID[509868]

☑ 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 NPC471514 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
0.9333 High Similarity NPC203403
0.8846 High Similarity NPC308038
0.8846 High Similarity NPC152061
0.875 High Similarity NPC93590
0.869 High Similarity NPC472983
0.85 High Similarity NPC172013
0.8481 Intermediate Similarity NPC62336
0.8462 Intermediate Similarity NPC250621
0.8462 Intermediate Similarity NPC263582
0.8415 Intermediate Similarity NPC105173
0.8375 Intermediate Similarity NPC281138
0.8354 Intermediate Similarity NPC197659
0.8354 Intermediate Similarity NPC470428
0.8354 Intermediate Similarity NPC74995
0.8333 Intermediate Similarity NPC472974
0.8333 Intermediate Similarity NPC472985
0.8333 Intermediate Similarity NPC472986
0.8313 Intermediate Similarity NPC470812
0.8272 Intermediate Similarity NPC148685
0.8272 Intermediate Similarity NPC157895
0.8272 Intermediate Similarity NPC104120
0.8272 Intermediate Similarity NPC472301
0.8256 Intermediate Similarity NPC472973
0.825 Intermediate Similarity NPC476949
0.825 Intermediate Similarity NPC475994
0.8171 Intermediate Similarity NPC6663
0.8148 Intermediate Similarity NPC170394
0.8148 Intermediate Similarity NPC470429
0.8148 Intermediate Similarity NPC19900
0.8125 Intermediate Similarity NPC266193
0.8125 Intermediate Similarity NPC257666
0.8118 Intermediate Similarity NPC194417
0.8095 Intermediate Similarity NPC476412
0.8077 Intermediate Similarity NPC186042
0.8068 Intermediate Similarity NPC472978
0.8046 Intermediate Similarity NPC473100
0.8046 Intermediate Similarity NPC473999
0.8046 Intermediate Similarity NPC309603
0.8026 Intermediate Similarity NPC117804
0.8026 Intermediate Similarity NPC96484
0.8025 Intermediate Similarity NPC253561
0.8025 Intermediate Similarity NPC178852
0.8025 Intermediate Similarity NPC80088
0.8 Intermediate Similarity NPC476426
0.8 Intermediate Similarity NPC472305
0.8 Intermediate Similarity NPC70685
0.8 Intermediate Similarity NPC470525
0.7978 Intermediate Similarity NPC109305
0.7976 Intermediate Similarity NPC297398
0.7976 Intermediate Similarity NPC169941
0.7976 Intermediate Similarity NPC64600
0.7976 Intermediate Similarity NPC251475
0.7955 Intermediate Similarity NPC191684
0.7955 Intermediate Similarity NPC473099
0.7955 Intermediate Similarity NPC134321
0.7931 Intermediate Similarity NPC206060
0.7931 Intermediate Similarity NPC104560
0.7931 Intermediate Similarity NPC473229
0.7907 Intermediate Similarity NPC198761
0.7901 Intermediate Similarity NPC85105
0.7901 Intermediate Similarity NPC149550
0.7901 Intermediate Similarity NPC97377
0.7889 Intermediate Similarity NPC472976
0.7889 Intermediate Similarity NPC472977
0.7882 Intermediate Similarity NPC40687
0.7875 Intermediate Similarity NPC114236
0.7865 Intermediate Similarity NPC172101
0.7865 Intermediate Similarity NPC473998
0.7865 Intermediate Similarity NPC475806
0.7865 Intermediate Similarity NPC116726
0.7865 Intermediate Similarity NPC472975
0.7857 Intermediate Similarity NPC158411
0.7857 Intermediate Similarity NPC38796
0.7848 Intermediate Similarity NPC247586
0.7841 Intermediate Similarity NPC123912
0.7831 Intermediate Similarity NPC281880
0.7831 Intermediate Similarity NPC271104
0.7831 Intermediate Similarity NPC45495
0.7802 Intermediate Similarity NPC476245
0.7791 Intermediate Similarity NPC470574
0.7791 Intermediate Similarity NPC15807
0.7791 Intermediate Similarity NPC109528
0.7778 Intermediate Similarity NPC69454
0.7765 Intermediate Similarity NPC79945
0.7765 Intermediate Similarity NPC307258
0.7753 Intermediate Similarity NPC48010
0.7753 Intermediate Similarity NPC230332
0.7753 Intermediate Similarity NPC128672
0.775 Intermediate Similarity NPC215050
0.775 Intermediate Similarity NPC78527
0.7738 Intermediate Similarity NPC90055
0.7738 Intermediate Similarity NPC119229
0.7738 Intermediate Similarity NPC159148
0.7727 Intermediate Similarity NPC158778
0.7727 Intermediate Similarity NPC474925
0.7722 Intermediate Similarity NPC95863
0.7717 Intermediate Similarity NPC202833
0.7717 Intermediate Similarity NPC117133
0.7717 Intermediate Similarity NPC5532
0.7717 Intermediate Similarity NPC61369
0.7717 Intermediate Similarity NPC469545
0.7711 Intermediate Similarity NPC7232
0.7701 Intermediate Similarity NPC473226
0.7701 Intermediate Similarity NPC179591
0.7692 Intermediate Similarity NPC196227
0.7692 Intermediate Similarity NPC8993
0.7692 Intermediate Similarity NPC299100
0.7683 Intermediate Similarity NPC34110
0.7674 Intermediate Similarity NPC472326
0.7674 Intermediate Similarity NPC472265
0.7667 Intermediate Similarity NPC233116
0.7667 Intermediate Similarity NPC99380
0.7667 Intermediate Similarity NPC63748
0.7662 Intermediate Similarity NPC106613
0.7662 Intermediate Similarity NPC96962
0.7647 Intermediate Similarity NPC103486
0.7647 Intermediate Similarity NPC92226
0.7647 Intermediate Similarity NPC48362
0.7647 Intermediate Similarity NPC279186
0.7647 Intermediate Similarity NPC470813
0.764 Intermediate Similarity NPC472240
0.764 Intermediate Similarity NPC50488
0.764 Intermediate Similarity NPC474396
0.764 Intermediate Similarity NPC119416
0.764 Intermediate Similarity NPC184663
0.764 Intermediate Similarity NPC472970
0.764 Intermediate Similarity NPC262858
0.764 Intermediate Similarity NPC472971
0.764 Intermediate Similarity NPC314727
0.7634 Intermediate Similarity NPC253826
0.7625 Intermediate Similarity NPC29542
0.7625 Intermediate Similarity NPC201562
0.7625 Intermediate Similarity NPC323437
0.7619 Intermediate Similarity NPC2482
0.7619 Intermediate Similarity NPC476809
0.7614 Intermediate Similarity NPC109900
0.7614 Intermediate Similarity NPC287079
0.7614 Intermediate Similarity NPC475772
0.7609 Intermediate Similarity NPC183012
0.7609 Intermediate Similarity NPC259286
0.7609 Intermediate Similarity NPC180950
0.7609 Intermediate Similarity NPC271195
0.7595 Intermediate Similarity NPC34834
0.759 Intermediate Similarity NPC471409
0.759 Intermediate Similarity NPC297996
0.759 Intermediate Similarity NPC275494
0.759 Intermediate Similarity NPC59436
0.7586 Intermediate Similarity NPC474853
0.7586 Intermediate Similarity NPC471224
0.7586 Intermediate Similarity NPC274724
0.7586 Intermediate Similarity NPC474083
0.7586 Intermediate Similarity NPC52628
0.7586 Intermediate Similarity NPC179006
0.7582 Intermediate Similarity NPC474736
0.7564 Intermediate Similarity NPC471238
0.7564 Intermediate Similarity NPC155198
0.7561 Intermediate Similarity NPC253190
0.7561 Intermediate Similarity NPC186554
0.7561 Intermediate Similarity NPC151622
0.7561 Intermediate Similarity NPC76966
0.7561 Intermediate Similarity NPC1973
0.7561 Intermediate Similarity NPC167873
0.7561 Intermediate Similarity NPC19907
0.7561 Intermediate Similarity NPC7629
0.7558 Intermediate Similarity NPC57370
0.7558 Intermediate Similarity NPC470165
0.7556 Intermediate Similarity NPC85173
0.7556 Intermediate Similarity NPC183283
0.7553 Intermediate Similarity NPC103051
0.7553 Intermediate Similarity NPC478056
0.7531 Intermediate Similarity NPC306727
0.7531 Intermediate Similarity NPC470299
0.7529 Intermediate Similarity NPC226068
0.7529 Intermediate Similarity NPC121984
0.7529 Intermediate Similarity NPC136150
0.7529 Intermediate Similarity NPC14151
0.7529 Intermediate Similarity NPC470298
0.7529 Intermediate Similarity NPC473420
0.7529 Intermediate Similarity NPC116797
0.7528 Intermediate Similarity NPC471793
0.7528 Intermediate Similarity NPC48107
0.7528 Intermediate Similarity NPC328539
0.7528 Intermediate Similarity NPC471791
0.7528 Intermediate Similarity NPC472802
0.7528 Intermediate Similarity NPC471722
0.7528 Intermediate Similarity NPC291665
0.7527 Intermediate Similarity NPC301534
0.7527 Intermediate Similarity NPC250757
0.7527 Intermediate Similarity NPC471463
0.7527 Intermediate Similarity NPC249954
0.7527 Intermediate Similarity NPC192428
0.75 Intermediate Similarity NPC474884
0.75 Intermediate Similarity NPC283789
0.75 Intermediate Similarity NPC72133
0.75 Intermediate Similarity NPC158393
0.75 Intermediate Similarity NPC94755
0.75 Intermediate Similarity NPC23954
0.75 Intermediate Similarity NPC94666
0.75 Intermediate Similarity NPC84790
0.75 Intermediate Similarity NPC474562

  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 NPC471514 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
0.7701 Intermediate Similarity NPD3618 Phase 1
0.7527 Intermediate Similarity NPD4697 Phase 3
0.7473 Intermediate Similarity NPD6079 Approved
0.7471 Intermediate Similarity NPD3665 Phase 1
0.7471 Intermediate Similarity NPD3666 Approved
0.7471 Intermediate Similarity NPD3133 Approved
0.7444 Intermediate Similarity NPD5328 Approved
0.7442 Intermediate Similarity NPD3667 Approved
0.7386 Intermediate Similarity NPD1696 Phase 3
0.7303 Intermediate Similarity NPD5279 Phase 3
0.7283 Intermediate Similarity NPD7515 Phase 2
0.7273 Intermediate Similarity NPD4786 Approved
0.7229 Intermediate Similarity NPD8264 Approved
0.7209 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD4695 Discontinued
0.7204 Intermediate Similarity NPD4202 Approved
0.7158 Intermediate Similarity NPD5221 Approved
0.7158 Intermediate Similarity NPD5222 Approved
0.7158 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5211 Phase 2
0.7111 Intermediate Similarity NPD4519 Discontinued
0.7111 Intermediate Similarity NPD4623 Approved
0.7083 Intermediate Similarity NPD5173 Approved
0.701 Intermediate Similarity NPD4225 Approved
0.7 Intermediate Similarity NPD1694 Approved
0.7 Intermediate Similarity NPD5141 Approved
0.6947 Remote Similarity NPD7748 Approved
0.6939 Remote Similarity NPD5286 Approved
0.6939 Remote Similarity NPD4696 Approved
0.6939 Remote Similarity NPD7640 Approved
0.6939 Remote Similarity NPD5285 Approved
0.6939 Remote Similarity NPD7639 Approved
0.6907 Remote Similarity NPD4755 Approved
0.6907 Remote Similarity NPD7902 Approved
0.6882 Remote Similarity NPD4753 Phase 2
0.6869 Remote Similarity NPD5223 Approved
0.6854 Remote Similarity NPD4223 Phase 3
0.6854 Remote Similarity NPD4221 Approved
0.6837 Remote Similarity NPD7638 Approved
0.68 Remote Similarity NPD5225 Approved
0.68 Remote Similarity NPD5226 Approved
0.68 Remote Similarity NPD5224 Approved
0.68 Remote Similarity NPD4633 Approved
0.6795 Remote Similarity NPD368 Approved
0.6782 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6768 Remote Similarity NPD4700 Approved
0.6744 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6739 Remote Similarity NPD5690 Phase 2
0.6739 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5174 Approved
0.6733 Remote Similarity NPD5175 Approved
0.6705 Remote Similarity NPD7645 Phase 2
0.6705 Remote Similarity NPD4195 Approved
0.6703 Remote Similarity NPD3668 Phase 3
0.6703 Remote Similarity NPD4197 Approved
0.6701 Remote Similarity NPD4629 Approved
0.6701 Remote Similarity NPD5210 Approved
0.6667 Remote Similarity NPD6399 Phase 3
0.6667 Remote Similarity NPD4752 Clinical (unspecified phase)
0.663 Remote Similarity NPD5329 Approved
0.6628 Remote Similarity NPD6942 Approved
0.6628 Remote Similarity NPD7339 Approved
0.6598 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6598 Remote Similarity NPD7900 Approved
0.6591 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6591 Remote Similarity NPD3617 Approved
0.6569 Remote Similarity NPD4754 Approved
0.6559 Remote Similarity NPD4138 Approved
0.6559 Remote Similarity NPD4693 Phase 3
0.6559 Remote Similarity NPD4689 Approved
0.6559 Remote Similarity NPD7334 Approved
0.6559 Remote Similarity NPD4690 Approved
0.6559 Remote Similarity NPD7521 Approved
0.6559 Remote Similarity NPD5330 Approved
0.6559 Remote Similarity NPD6684 Approved
0.6559 Remote Similarity NPD4688 Approved
0.6559 Remote Similarity NPD5280 Approved
0.6559 Remote Similarity NPD6409 Approved
0.6559 Remote Similarity NPD7146 Approved
0.6559 Remote Similarity NPD4694 Approved
0.6559 Remote Similarity NPD5205 Approved
0.6548 Remote Similarity NPD4691 Approved
0.6538 Remote Similarity NPD5697 Approved
0.6517 Remote Similarity NPD6929 Approved
0.6512 Remote Similarity NPD6926 Approved
0.6512 Remote Similarity NPD6924 Approved
0.65 Remote Similarity NPD5290 Discontinued
0.6495 Remote Similarity NPD5778 Approved
0.6495 Remote Similarity NPD5779 Approved
0.6489 Remote Similarity NPD3573 Approved
0.6489 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6477 Remote Similarity NPD5776 Phase 2
0.6477 Remote Similarity NPD6925 Approved
0.6476 Remote Similarity NPD5128 Approved
0.6476 Remote Similarity NPD4730 Approved
0.6476 Remote Similarity NPD6899 Approved
0.6476 Remote Similarity NPD6011 Approved
0.6476 Remote Similarity NPD5168 Approved
0.6476 Remote Similarity NPD4729 Approved
0.6476 Remote Similarity NPD6881 Approved
0.6471 Remote Similarity NPD7150 Approved
0.6471 Remote Similarity NPD7151 Approved
0.6471 Remote Similarity NPD7152 Approved
0.6463 Remote Similarity NPD7331 Phase 2
0.6458 Remote Similarity NPD5785 Approved
0.6455 Remote Similarity NPD7115 Discovery
0.6452 Remote Similarity NPD5363 Approved
0.6449 Remote Similarity NPD6649 Approved
0.6449 Remote Similarity NPD6650 Approved
0.6447 Remote Similarity NPD342 Phase 1
0.6444 Remote Similarity NPD7514 Phase 3
0.6444 Remote Similarity NPD6931 Approved
0.6444 Remote Similarity NPD6930 Phase 2
0.6444 Remote Similarity NPD7525 Registered
0.6444 Remote Similarity NPD7332 Phase 2
0.6442 Remote Similarity NPD4768 Approved
0.6442 Remote Similarity NPD6402 Approved
0.6442 Remote Similarity NPD7128 Approved
0.6442 Remote Similarity NPD4767 Approved
0.6442 Remote Similarity NPD5739 Approved
0.6442 Remote Similarity NPD6675 Approved
0.6429 Remote Similarity NPD6922 Approved
0.6429 Remote Similarity NPD6923 Approved
0.6429 Remote Similarity NPD4137 Phase 3
0.6421 Remote Similarity NPD6903 Approved
0.6421 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6415 Remote Similarity NPD6372 Approved
0.6415 Remote Similarity NPD6373 Approved
0.6415 Remote Similarity NPD6012 Approved
0.6415 Remote Similarity NPD6014 Approved
0.6415 Remote Similarity NPD6013 Approved
0.6413 Remote Similarity NPD4788 Approved
0.6413 Remote Similarity NPD6110 Phase 1
0.6404 Remote Similarity NPD7145 Approved
0.64 Remote Similarity NPD6083 Phase 2
0.64 Remote Similarity NPD6084 Phase 2
0.6392 Remote Similarity NPD7637 Suspended
0.6392 Remote Similarity NPD6411 Approved
0.6381 Remote Similarity NPD5701 Approved
0.6374 Remote Similarity NPD6902 Approved
0.6364 Remote Similarity NPD6933 Approved
0.6364 Remote Similarity NPD5695 Phase 3
0.6355 Remote Similarity NPD5248 Approved
0.6355 Remote Similarity NPD5169 Approved
0.6355 Remote Similarity NPD7102 Approved
0.6355 Remote Similarity NPD6883 Approved
0.6355 Remote Similarity NPD5135 Approved
0.6355 Remote Similarity NPD5249 Phase 3
0.6355 Remote Similarity NPD5247 Approved
0.6355 Remote Similarity NPD7290 Approved
0.6355 Remote Similarity NPD5251 Approved
0.6355 Remote Similarity NPD5250 Approved
0.6355 Remote Similarity NPD4634 Approved
0.6355 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6353 Remote Similarity NPD4747 Approved
0.6353 Remote Similarity NPD7143 Approved
0.6353 Remote Similarity NPD7144 Approved
0.6344 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6341 Remote Similarity NPD7341 Phase 2
0.6322 Remote Similarity NPD4058 Approved
0.6321 Remote Similarity NPD7320 Approved
0.6311 Remote Similarity NPD7632 Discontinued
0.6296 Remote Similarity NPD6847 Approved
0.6296 Remote Similarity NPD6869 Approved
0.6296 Remote Similarity NPD5127 Approved
0.6296 Remote Similarity NPD5217 Approved
0.6296 Remote Similarity NPD6617 Approved
0.6296 Remote Similarity NPD5215 Approved
0.6296 Remote Similarity NPD8130 Phase 1
0.6296 Remote Similarity NPD5216 Approved
0.6289 Remote Similarity NPD4096 Approved
0.6279 Remote Similarity NPD5276 Approved
0.6277 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6264 Remote Similarity NPD7509 Discontinued
0.625 Remote Similarity NPD6672 Approved
0.625 Remote Similarity NPD5737 Approved
0.625 Remote Similarity NPD4518 Approved
0.6239 Remote Similarity NPD8297 Approved
0.6239 Remote Similarity NPD6882 Approved
0.6237 Remote Similarity NPD6695 Phase 3
0.6224 Remote Similarity NPD5284 Approved
0.6224 Remote Similarity NPD5281 Approved
0.6203 Remote Similarity NPD287 Approved
0.62 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6196 Remote Similarity NPD6898 Phase 1
0.6186 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6186 Remote Similarity NPD6101 Approved
0.6186 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6182 Remote Similarity NPD4632 Approved
0.6176 Remote Similarity NPD5696 Approved
0.6173 Remote Similarity NPD4192 Approved
0.6173 Remote Similarity NPD4191 Approved
0.6173 Remote Similarity NPD4193 Approved
0.6173 Remote Similarity NPD4194 Approved
0.617 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6168 Remote Similarity NPD6686 Approved
0.6154 Remote Similarity NPD4219 Approved
0.6147 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6136 Remote Similarity NPD4687 Approved
0.6136 Remote Similarity NPD5733 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