Structure

Physi-Chem Properties

Molecular Weight:  236.18
Volume:  263.191
LogP:  2.51
LogD:  2.384
LogS:  -2.458
# Rotatable Bonds:  2
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.591
Synthetic Accessibility Score:  4.988
Fsp3:  0.8
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:  -4.65
MDCK Permeability:  7.544545496784849e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.982
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.197
30% Bioavailability (F30%):  0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.867
Plasma Protein Binding (PPB):  57.023311614990234%
Volume Distribution (VD):  1.882
Pgp-substrate:  51.66667175292969%

ADMET: Metabolism

CYP1A2-inhibitor:  0.031
CYP1A2-substrate:  0.395
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.785
CYP2C9-inhibitor:  0.015
CYP2C9-substrate:  0.122
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.373
CYP3A4-inhibitor:  0.428
CYP3A4-substrate:  0.244

ADMET: Excretion

Clearance (CL):  9.736
Half-life (T1/2):  0.698

ADMET: Toxicity

hERG Blockers:  0.051
Human Hepatotoxicity (H-HT):  0.34
Drug-inuced Liver Injury (DILI):  0.037
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.021
Maximum Recommended Daily Dose:  0.93
Skin Sensitization:  0.957
Carcinogencity:  0.46
Eye Corrosion:  0.974
Eye Irritation:  0.98
Respiratory Toxicity:  0.959

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

  Natural Product: NPC199316

Natural Product ID:  NPC199316
Common Name*:   Lubimin
IUPAC Name:   (3R,5S,6R,8S,10S)-8-hydroxy-6-methyl-3-prop-1-en-2-ylspiro[4.5]decane-10-carbaldehyde
Synonyms:  
Standard InCHIKey:  CEVNHRPKRNTGKO-ZSAUSMIDSA-N
Standard InCHI:  InChI=1S/C15H24O2/c1-10(2)12-4-5-15(8-12)11(3)6-14(17)7-13(15)9-16/h9,11-14,17H,1,4-8H2,2-3H3/t11-,12-,13-,14+,15+/m1/s1
SMILES:  O=C[C@H]1C[C@@H](O)C[C@H]([C@]21CC[C@H](C2)C(=C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2270658
PubChem CID:   442383
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
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)89267-5]
NPO7732 Solanum melongena Species Solanaceae Eukaryota n.a. root n.a. DOI[10.1271/bbb1961.42.623]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[12882150]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[15666542]
NPO7732 Solanum melongena Species Solanaceae Eukaryota Roots n.a. n.a. PMID[31742403]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. trunk bark n.a. PMID[556731]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Tubers n.a. Database[FooDB]
NPO7732 Solanum melongena Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7732 Solanum melongena Species Solanaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7732 Solanum melongena Species Solanaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO7732 Solanum melongena Species Solanaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota Tuber n.a. n.a. Database[FooDB]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7732 Solanum melongena Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO7732 Solanum melongena Species Solanaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7732 Solanum melongena Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7732 Solanum melongena Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16093 Achillea atrata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25348 Metapochonia suchlasporia Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4359 Solanum tuberosum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7732 Solanum melongena Species Solanaceae 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
NPT1503 Organism Verticillium dahliae Verticillium dahliae Activity = 42.0 % PMID[494259]
NPT1200 Organism Fusarium oxysporum f. sp. melongenae Fusarium oxysporum f. sp. melongenae Activity = 5.0 % PMID[494259]

☑ 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 NPC199316 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 NPC102313
0.8481 Intermediate Similarity NPC74595
0.8481 Intermediate Similarity NPC264665
0.8442 Intermediate Similarity NPC164999
0.8333 Intermediate Similarity NPC475952
0.8333 Intermediate Similarity NPC164210
0.8293 Intermediate Similarity NPC472739
0.8272 Intermediate Similarity NPC98236
0.8272 Intermediate Similarity NPC269396
0.8272 Intermediate Similarity NPC94755
0.825 Intermediate Similarity NPC146683
0.825 Intermediate Similarity NPC475745
0.825 Intermediate Similarity NPC474482
0.8125 Intermediate Similarity NPC475726
0.8125 Intermediate Similarity NPC472743
0.8125 Intermediate Similarity NPC118800
0.8125 Intermediate Similarity NPC291320
0.8125 Intermediate Similarity NPC471036
0.8052 Intermediate Similarity NPC474433
0.8052 Intermediate Similarity NPC106078
0.8049 Intermediate Similarity NPC472738
0.8025 Intermediate Similarity NPC474233
0.8 Intermediate Similarity NPC110780
0.7952 Intermediate Similarity NPC153604
0.7952 Intermediate Similarity NPC472495
0.7952 Intermediate Similarity NPC472497
0.7952 Intermediate Similarity NPC165895
0.7952 Intermediate Similarity NPC174619
0.7927 Intermediate Similarity NPC294438
0.7927 Intermediate Similarity NPC264317
0.7927 Intermediate Similarity NPC76518
0.7927 Intermediate Similarity NPC102292
0.7927 Intermediate Similarity NPC292553
0.7927 Intermediate Similarity NPC190704
0.7927 Intermediate Similarity NPC471034
0.7907 Intermediate Similarity NPC59350
0.7901 Intermediate Similarity NPC175410
0.7901 Intermediate Similarity NPC474748
0.7901 Intermediate Similarity NPC472498
0.7887 Intermediate Similarity NPC219940
0.7882 Intermediate Similarity NPC169933
0.7882 Intermediate Similarity NPC191684
0.7882 Intermediate Similarity NPC183283
0.7875 Intermediate Similarity NPC209318
0.7875 Intermediate Similarity NPC223330
0.7867 Intermediate Similarity NPC72343
0.7857 Intermediate Similarity NPC474719
0.7848 Intermediate Similarity NPC201459
0.7848 Intermediate Similarity NPC152061
0.7848 Intermediate Similarity NPC229204
0.7831 Intermediate Similarity NPC28252
0.7831 Intermediate Similarity NPC55309
0.7831 Intermediate Similarity NPC72133
0.7831 Intermediate Similarity NPC2783
0.7831 Intermediate Similarity NPC12774
0.7808 Intermediate Similarity NPC263161
0.7805 Intermediate Similarity NPC97505
0.7805 Intermediate Similarity NPC221758
0.7805 Intermediate Similarity NPC470812
0.7805 Intermediate Similarity NPC59453
0.7778 Intermediate Similarity NPC46881
0.7778 Intermediate Similarity NPC477858
0.7778 Intermediate Similarity NPC151519
0.7778 Intermediate Similarity NPC170985
0.7778 Intermediate Similarity NPC145143
0.7778 Intermediate Similarity NPC300442
0.7738 Intermediate Similarity NPC474684
0.7738 Intermediate Similarity NPC259009
0.7738 Intermediate Similarity NPC159046
0.7738 Intermediate Similarity NPC57469
0.7738 Intermediate Similarity NPC233836
0.7738 Intermediate Similarity NPC264005
0.7738 Intermediate Similarity NPC142361
0.7738 Intermediate Similarity NPC187376
0.7738 Intermediate Similarity NPC33768
0.7738 Intermediate Similarity NPC269360
0.7738 Intermediate Similarity NPC4643
0.7733 Intermediate Similarity NPC163020
0.7733 Intermediate Similarity NPC91369
0.7727 Intermediate Similarity NPC29112
0.7711 Intermediate Similarity NPC470574
0.7711 Intermediate Similarity NPC474218
0.7701 Intermediate Similarity NPC82138
0.7692 Intermediate Similarity NPC92489
0.7692 Intermediate Similarity NPC476601
0.7683 Intermediate Similarity NPC471037
0.7683 Intermediate Similarity NPC278648
0.7683 Intermediate Similarity NPC476082
0.7683 Intermediate Similarity NPC245866
0.7683 Intermediate Similarity NPC470948
0.7683 Intermediate Similarity NPC105173
0.7683 Intermediate Similarity NPC312480
0.7674 Intermediate Similarity NPC46758
0.7674 Intermediate Similarity NPC80401
0.7674 Intermediate Similarity NPC261994
0.7674 Intermediate Similarity NPC149761
0.7674 Intermediate Similarity NPC180849
0.7674 Intermediate Similarity NPC100313
0.7674 Intermediate Similarity NPC470378
0.7671 Intermediate Similarity NPC103734
0.7654 Intermediate Similarity NPC473420
0.7654 Intermediate Similarity NPC136150
0.7654 Intermediate Similarity NPC103754
0.7654 Intermediate Similarity NPC474484
0.7654 Intermediate Similarity NPC328264
0.7647 Intermediate Similarity NPC242864
0.7647 Intermediate Similarity NPC471900
0.7647 Intermediate Similarity NPC146937
0.7647 Intermediate Similarity NPC16377
0.7647 Intermediate Similarity NPC328539
0.7647 Intermediate Similarity NPC471724
0.7647 Intermediate Similarity NPC471722
0.7647 Intermediate Similarity NPC193360
0.7647 Intermediate Similarity NPC131470
0.7647 Intermediate Similarity NPC143767
0.7647 Intermediate Similarity NPC473229
0.764 Intermediate Similarity NPC192428
0.764 Intermediate Similarity NPC135548
0.764 Intermediate Similarity NPC264979
0.7639 Intermediate Similarity NPC144650
0.7625 Intermediate Similarity NPC181195
0.7625 Intermediate Similarity NPC472490
0.7625 Intermediate Similarity NPC261125
0.7625 Intermediate Similarity NPC308038
0.7619 Intermediate Similarity NPC155011
0.7619 Intermediate Similarity NPC477579
0.7619 Intermediate Similarity NPC51014
0.7619 Intermediate Similarity NPC34190
0.7619 Intermediate Similarity NPC6979
0.7619 Intermediate Similarity NPC474732
0.7619 Intermediate Similarity NPC474733
0.7619 Intermediate Similarity NPC235341
0.7619 Intermediate Similarity NPC95594
0.7619 Intermediate Similarity NPC31564
0.7619 Intermediate Similarity NPC474778
0.7619 Intermediate Similarity NPC477920
0.7619 Intermediate Similarity NPC145879
0.7614 Intermediate Similarity NPC292793
0.7595 Intermediate Similarity NPC472746
0.7595 Intermediate Similarity NPC197659
0.7595 Intermediate Similarity NPC470428
0.7595 Intermediate Similarity NPC238227
0.7595 Intermediate Similarity NPC74995
0.759 Intermediate Similarity NPC85774
0.759 Intermediate Similarity NPC263974
0.759 Intermediate Similarity NPC214043
0.759 Intermediate Similarity NPC82902
0.759 Intermediate Similarity NPC165064
0.759 Intermediate Similarity NPC473246
0.7586 Intermediate Similarity NPC476168
0.7586 Intermediate Similarity NPC297265
0.7586 Intermediate Similarity NPC23434
0.7586 Intermediate Similarity NPC299185
0.7564 Intermediate Similarity NPC114236
0.7561 Intermediate Similarity NPC48362
0.7561 Intermediate Similarity NPC93590
0.7558 Intermediate Similarity NPC116146
0.7558 Intermediate Similarity NPC472970
0.7558 Intermediate Similarity NPC86319
0.7558 Intermediate Similarity NPC472971
0.7558 Intermediate Similarity NPC57954
0.7558 Intermediate Similarity NPC102414
0.7558 Intermediate Similarity NPC213832
0.7558 Intermediate Similarity NPC128496
0.7558 Intermediate Similarity NPC309603
0.7558 Intermediate Similarity NPC119416
0.7558 Intermediate Similarity NPC475921
0.7558 Intermediate Similarity NPC220498
0.7558 Intermediate Similarity NPC473999
0.7558 Intermediate Similarity NPC275740
0.7558 Intermediate Similarity NPC77168
0.7558 Intermediate Similarity NPC84271
0.7558 Intermediate Similarity NPC24772
0.7558 Intermediate Similarity NPC474704
0.7532 Intermediate Similarity NPC244708
0.7532 Intermediate Similarity NPC330659
0.7532 Intermediate Similarity NPC161187
0.7531 Intermediate Similarity NPC104120
0.7531 Intermediate Similarity NPC148685
0.7531 Intermediate Similarity NPC172013
0.7531 Intermediate Similarity NPC157895
0.7531 Intermediate Similarity NPC472478
0.7529 Intermediate Similarity NPC472493
0.7529 Intermediate Similarity NPC470012
0.7529 Intermediate Similarity NPC181103
0.7529 Intermediate Similarity NPC58063
0.7529 Intermediate Similarity NPC136548
0.7529 Intermediate Similarity NPC475740
0.7529 Intermediate Similarity NPC141292
0.7529 Intermediate Similarity NPC305029
0.75 Intermediate Similarity NPC474083
0.75 Intermediate Similarity NPC470375
0.75 Intermediate Similarity NPC244356
0.75 Intermediate Similarity NPC247783
0.75 Intermediate Similarity NPC253561
0.75 Intermediate Similarity NPC181594
0.75 Intermediate Similarity NPC224060
0.75 Intermediate Similarity NPC294263
0.75 Intermediate Similarity NPC144739
0.75 Intermediate Similarity NPC178852

  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 NPC199316 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
0.7927 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD3618 Phase 1
0.7805 Intermediate Similarity NPD4786 Approved
0.7778 Intermediate Similarity NPD3667 Approved
0.764 Intermediate Similarity NPD4697 Phase 3
0.7558 Intermediate Similarity NPD5328 Approved
0.747 Intermediate Similarity NPD4788 Approved
0.7412 Intermediate Similarity NPD5279 Phase 3
0.7403 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD8034 Phase 2
0.7386 Intermediate Similarity NPD8035 Phase 2
0.7386 Intermediate Similarity NPD6079 Approved
0.7381 Intermediate Similarity NPD3133 Approved
0.7381 Intermediate Similarity NPD3666 Approved
0.7381 Intermediate Similarity NPD3665 Phase 1
0.7368 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD4202 Approved
0.7297 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD6399 Phase 3
0.7065 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD5222 Approved
0.7065 Intermediate Similarity NPD5221 Approved
0.7037 Intermediate Similarity NPD6117 Approved
0.6989 Remote Similarity NPD4755 Approved
0.6989 Remote Similarity NPD5173 Approved
0.6977 Remote Similarity NPD3668 Phase 3
0.6966 Remote Similarity NPD4753 Phase 2
0.6951 Remote Similarity NPD6116 Phase 1
0.6941 Remote Similarity NPD4223 Phase 3
0.6941 Remote Similarity NPD4221 Approved
0.6923 Remote Similarity NPD3698 Phase 2
0.6914 Remote Similarity NPD7339 Approved
0.6914 Remote Similarity NPD3703 Phase 2
0.6914 Remote Similarity NPD6942 Approved
0.6905 Remote Similarity NPD7525 Registered
0.6867 Remote Similarity NPD6115 Approved
0.6867 Remote Similarity NPD6118 Approved
0.6867 Remote Similarity NPD6114 Approved
0.6867 Remote Similarity NPD6697 Approved
0.6842 Remote Similarity NPD5285 Approved
0.6842 Remote Similarity NPD4700 Approved
0.6842 Remote Similarity NPD5286 Approved
0.6842 Remote Similarity NPD4696 Approved
0.6835 Remote Similarity NPD4244 Approved
0.6835 Remote Similarity NPD4245 Approved
0.6835 Remote Similarity NPD4789 Approved
0.6829 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6813 Remote Similarity NPD7515 Phase 2
0.6795 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6795 Remote Similarity NPD5360 Phase 3
0.679 Remote Similarity NPD6924 Approved
0.679 Remote Similarity NPD6926 Approved
0.6782 Remote Similarity NPD4197 Approved
0.6774 Remote Similarity NPD4629 Approved
0.6774 Remote Similarity NPD5210 Approved
0.6771 Remote Similarity NPD5223 Approved
0.6705 Remote Similarity NPD5329 Approved
0.6701 Remote Similarity NPD5211 Phase 2
0.6701 Remote Similarity NPD5226 Approved
0.6701 Remote Similarity NPD4633 Approved
0.6701 Remote Similarity NPD5225 Approved
0.6701 Remote Similarity NPD5224 Approved
0.6667 Remote Similarity NPD3671 Phase 1
0.6667 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3617 Approved
0.6633 Remote Similarity NPD5174 Approved
0.6633 Remote Similarity NPD5175 Approved
0.6633 Remote Similarity NPD4754 Approved
0.6629 Remote Similarity NPD4138 Approved
0.6629 Remote Similarity NPD5205 Approved
0.6629 Remote Similarity NPD5280 Approved
0.6629 Remote Similarity NPD4693 Phase 3
0.6629 Remote Similarity NPD4689 Approved
0.6629 Remote Similarity NPD4690 Approved
0.6629 Remote Similarity NPD5690 Phase 2
0.6629 Remote Similarity NPD4688 Approved
0.6629 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6629 Remote Similarity NPD4694 Approved
0.6628 Remote Similarity NPD4692 Approved
0.6628 Remote Similarity NPD4139 Approved
0.6627 Remote Similarity NPD6933 Approved
0.6566 Remote Similarity NPD5141 Approved
0.6543 Remote Similarity NPD4758 Discontinued
0.6543 Remote Similarity NPD7151 Approved
0.6543 Remote Similarity NPD7152 Approved
0.6543 Remote Similarity NPD7150 Approved
0.6538 Remote Similarity NPD4224 Phase 2
0.6512 Remote Similarity NPD4695 Discontinued
0.6512 Remote Similarity NPD4748 Discontinued
0.65 Remote Similarity NPD6922 Approved
0.65 Remote Similarity NPD5739 Approved
0.65 Remote Similarity NPD4768 Approved
0.65 Remote Similarity NPD6402 Approved
0.65 Remote Similarity NPD7128 Approved
0.65 Remote Similarity NPD6675 Approved
0.65 Remote Similarity NPD4767 Approved
0.65 Remote Similarity NPD6923 Approved
0.6489 Remote Similarity NPD7748 Approved
0.6471 Remote Similarity NPD6372 Approved
0.6471 Remote Similarity NPD6373 Approved
0.6458 Remote Similarity NPD6083 Phase 2
0.6458 Remote Similarity NPD6084 Phase 2
0.6458 Remote Similarity NPD7902 Approved
0.6452 Remote Similarity NPD5281 Approved
0.6452 Remote Similarity NPD5284 Approved
0.6444 Remote Similarity NPD7334 Approved
0.6444 Remote Similarity NPD6409 Approved
0.6444 Remote Similarity NPD5330 Approved
0.6444 Remote Similarity NPD7146 Approved
0.6444 Remote Similarity NPD7521 Approved
0.6444 Remote Similarity NPD6684 Approved
0.6436 Remote Similarity NPD5697 Approved
0.6436 Remote Similarity NPD5701 Approved
0.6421 Remote Similarity NPD5695 Phase 3
0.642 Remote Similarity NPD7144 Approved
0.642 Remote Similarity NPD7143 Approved
0.6395 Remote Similarity NPD7645 Phase 2
0.6395 Remote Similarity NPD6929 Approved
0.6392 Remote Similarity NPD5696 Approved
0.6392 Remote Similarity NPD7638 Approved
0.6373 Remote Similarity NPD5128 Approved
0.6373 Remote Similarity NPD6899 Approved
0.6373 Remote Similarity NPD7320 Approved
0.6373 Remote Similarity NPD5168 Approved
0.6373 Remote Similarity NPD6011 Approved
0.6373 Remote Similarity NPD4730 Approved
0.6373 Remote Similarity NPD6881 Approved
0.6373 Remote Similarity NPD4729 Approved
0.6346 Remote Similarity NPD6649 Approved
0.6346 Remote Similarity NPD6650 Approved
0.6344 Remote Similarity NPD4096 Approved
0.6327 Remote Similarity NPD7640 Approved
0.6327 Remote Similarity NPD7639 Approved
0.6322 Remote Similarity NPD6930 Phase 2
0.6322 Remote Similarity NPD6931 Approved
0.6322 Remote Similarity NPD7509 Discontinued
0.6311 Remote Similarity NPD6012 Approved
0.6311 Remote Similarity NPD6013 Approved
0.6311 Remote Similarity NPD6014 Approved
0.631 Remote Similarity NPD3702 Approved
0.6304 Remote Similarity NPD6903 Approved
0.6304 Remote Similarity NPD6672 Approved
0.6304 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6304 Remote Similarity NPD5737 Approved
0.6292 Remote Similarity NPD5362 Discontinued
0.6277 Remote Similarity NPD6411 Approved
0.6264 Remote Similarity NPD4519 Discontinued
0.6264 Remote Similarity NPD4623 Approved
0.625 Remote Similarity NPD7102 Approved
0.625 Remote Similarity NPD6883 Approved
0.625 Remote Similarity NPD5251 Approved
0.625 Remote Similarity NPD5250 Approved
0.625 Remote Similarity NPD7290 Approved
0.625 Remote Similarity NPD5369 Approved
0.625 Remote Similarity NPD5247 Approved
0.625 Remote Similarity NPD4634 Approved
0.625 Remote Similarity NPD5248 Approved
0.625 Remote Similarity NPD5169 Approved
0.625 Remote Similarity NPD5249 Phase 3
0.625 Remote Similarity NPD5135 Approved
0.625 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6224 Remote Similarity NPD4225 Approved
0.622 Remote Similarity NPD4747 Approved
0.6207 Remote Similarity NPD4195 Approved
0.6196 Remote Similarity NPD4751 Clinical (unspecified phase)
0.619 Remote Similarity NPD6617 Approved
0.619 Remote Similarity NPD6847 Approved
0.619 Remote Similarity NPD8130 Phase 1
0.619 Remote Similarity NPD5217 Approved
0.619 Remote Similarity NPD5127 Approved
0.619 Remote Similarity NPD6869 Approved
0.619 Remote Similarity NPD5216 Approved
0.619 Remote Similarity NPD6401 Clinical (unspecified phase)
0.619 Remote Similarity NPD5215 Approved
0.6184 Remote Similarity NPD3198 Approved
0.618 Remote Similarity NPD4752 Clinical (unspecified phase)
0.618 Remote Similarity NPD4270 Approved
0.618 Remote Similarity NPD4269 Approved
0.6163 Remote Similarity NPD6932 Approved
0.6163 Remote Similarity NPD6925 Approved
0.6163 Remote Similarity NPD5776 Phase 2
0.6154 Remote Similarity NPD1696 Phase 3
0.6154 Remote Similarity NPD1694 Approved
0.6146 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6146 Remote Similarity NPD7900 Approved
0.6145 Remote Similarity NPD5276 Approved
0.6145 Remote Similarity NPD6081 Approved
0.6145 Remote Similarity NPD4243 Approved
0.6136 Remote Similarity NPD5368 Approved
0.6136 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6132 Remote Similarity NPD6882 Approved
0.6132 Remote Similarity NPD8297 Approved
0.6129 Remote Similarity NPD4518 Approved
0.6118 Remote Similarity NPD8264 Approved
0.6111 Remote Similarity NPD6695 Phase 3
0.6098 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6098 Remote Similarity NPD4137 Phase 3

  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