Structure

Physi-Chem Properties

Molecular Weight:  264.14
Volume:  275.498
LogP:  0.885
LogD:  0.883
LogS:  -2.296
# Rotatable Bonds:  2
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.749
Synthetic Accessibility Score:  4.349
Fsp3:  0.6
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.073
MDCK Permeability:  1.8531924069975503e-05
Pgp-inhibitor:  0.038
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.128
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.149
Plasma Protein Binding (PPB):  87.01165008544922%
Volume Distribution (VD):  0.266
Pgp-substrate:  17.58831214904785%

ADMET: Metabolism

CYP1A2-inhibitor:  0.027
CYP1A2-substrate:  0.104
CYP2C19-inhibitor:  0.034
CYP2C19-substrate:  0.063
CYP2C9-inhibitor:  0.071
CYP2C9-substrate:  0.101
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.098
CYP3A4-inhibitor:  0.019
CYP3A4-substrate:  0.237

ADMET: Excretion

Clearance (CL):  2.703
Half-life (T1/2):  0.595

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.136
Drug-inuced Liver Injury (DILI):  0.864
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.674
Maximum Recommended Daily Dose:  0.884
Skin Sensitization:  0.632
Carcinogencity:  0.878
Eye Corrosion:  0.041
Eye Irritation:  0.414
Respiratory Toxicity:  0.976

Download Data

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

  Natural Product: NPC476627

Natural Product ID:  NPC476627
Common Name*:   2-[(3R,5R,8S)-3-hydroxy-3,8-dimethyl-1-oxo-2,4,5,6,7,8-hexahydroazulen-5-yl]prop-2-enoic acid
IUPAC Name:   2-[(3R,5R,8S)-3-hydroxy-3,8-dimethyl-1-oxo-2,4,5,6,7,8-hexahydroazulen-5-yl]prop-2-enoic acid
Synonyms:  
Standard InCHIKey:  CNDFIUCLMNGTNC-SVIKCVJRSA-N
Standard InCHI:  InChI=1S/C15H20O4/c1-8-4-5-10(9(2)14(17)18)6-11-13(8)12(16)7-15(11,3)19/h8,10,19H,2,4-7H2,1,3H3,(H,17,18)/t8-,10+,15+/m0/s1
SMILES:  C[C@H]1CC[C@H](CC2=C1C(=O)C[C@@]2(C)O)C(=C)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   n.a.
PubChem CID:   118711727
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
NPO12728 Artemisia rupestris Species Asteraceae Eukaryota Whole plant n.a. n.a. PMID[25127164]
NPO12728 Artemisia rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[25176187]
NPO12728 Artemisia rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26696523]
NPO12728 Artemisia rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12728 Artemisia rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12728 Artemisia rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12728 Artemisia rupestris 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
NPT2 Others Unspecified IC50 = 24700 nM PMID[25127164]
NPT2 Others Unspecified Activity = 77 % PMID[25127164]

☑ 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 NPC476627 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
0.9595 High Similarity NPC476624
0.9595 High Similarity NPC472013
0.9054 High Similarity NPC89374
0.8919 High Similarity NPC7382
0.8875 High Similarity NPC476628
0.8816 High Similarity NPC472014
0.8649 High Similarity NPC29328
0.863 High Similarity NPC67608
0.8571 High Similarity NPC77337
0.8205 Intermediate Similarity NPC182848
0.8158 Intermediate Similarity NPC288667
0.8158 Intermediate Similarity NPC106309
0.8108 Intermediate Similarity NPC476626
0.8025 Intermediate Similarity NPC824
0.8025 Intermediate Similarity NPC138492
0.8025 Intermediate Similarity NPC233352
0.7927 Intermediate Similarity NPC171665
0.7848 Intermediate Similarity NPC77501
0.7831 Intermediate Similarity NPC20262
0.7831 Intermediate Similarity NPC256750
0.7816 Intermediate Similarity NPC268298
0.7792 Intermediate Similarity NPC18543
0.7791 Intermediate Similarity NPC237540
0.7778 Intermediate Similarity NPC192006
0.7765 Intermediate Similarity NPC261380
0.7765 Intermediate Similarity NPC125290
0.7763 Intermediate Similarity NPC476614
0.7738 Intermediate Similarity NPC65350
0.7727 Intermediate Similarity NPC129419
0.7692 Intermediate Similarity NPC9812
0.7683 Intermediate Similarity NPC32758
0.7683 Intermediate Similarity NPC301769
0.7683 Intermediate Similarity NPC471890
0.7683 Intermediate Similarity NPC84185
0.7683 Intermediate Similarity NPC66677
0.7674 Intermediate Similarity NPC472869
0.7667 Intermediate Similarity NPC167219
0.764 Intermediate Similarity NPC300312
0.764 Intermediate Similarity NPC111114
0.764 Intermediate Similarity NPC261607
0.7619 Intermediate Similarity NPC85772
0.7619 Intermediate Similarity NPC133844
0.7614 Intermediate Similarity NPC170775
0.7595 Intermediate Similarity NPC300940
0.759 Intermediate Similarity NPC287817
0.759 Intermediate Similarity NPC74445
0.759 Intermediate Similarity NPC164218
0.7561 Intermediate Similarity NPC169095
0.7558 Intermediate Similarity NPC165162
0.7553 Intermediate Similarity NPC206079
0.7532 Intermediate Similarity NPC476629
0.7528 Intermediate Similarity NPC71533
0.7528 Intermediate Similarity NPC106510
0.7528 Intermediate Similarity NPC472866
0.7528 Intermediate Similarity NPC145666
0.7527 Intermediate Similarity NPC64742
0.7527 Intermediate Similarity NPC244411
0.75 Intermediate Similarity NPC100719
0.75 Intermediate Similarity NPC166791
0.75 Intermediate Similarity NPC72397
0.75 Intermediate Similarity NPC100487
0.75 Intermediate Similarity NPC322035
0.75 Intermediate Similarity NPC470241
0.75 Intermediate Similarity NPC59994
0.75 Intermediate Similarity NPC78677
0.75 Intermediate Similarity NPC308294
0.75 Intermediate Similarity NPC142423
0.75 Intermediate Similarity NPC472870
0.75 Intermediate Similarity NPC47031
0.7473 Intermediate Similarity NPC65829
0.7471 Intermediate Similarity NPC261721
0.7471 Intermediate Similarity NPC476043
0.747 Intermediate Similarity NPC113363
0.7468 Intermediate Similarity NPC469737
0.7442 Intermediate Similarity NPC156485
0.7442 Intermediate Similarity NPC165287
0.7442 Intermediate Similarity NPC472958
0.7442 Intermediate Similarity NPC472865
0.7442 Intermediate Similarity NPC248758
0.7442 Intermediate Similarity NPC19849
0.7442 Intermediate Similarity NPC472957
0.7442 Intermediate Similarity NPC472864
0.7439 Intermediate Similarity NPC97377
0.7412 Intermediate Similarity NPC7414
0.7407 Intermediate Similarity NPC472327
0.7403 Intermediate Similarity NPC278895
0.7386 Intermediate Similarity NPC72513
0.7381 Intermediate Similarity NPC302426
0.7381 Intermediate Similarity NPC45495
0.7381 Intermediate Similarity NPC476625
0.7375 Intermediate Similarity NPC215745
0.7375 Intermediate Similarity NPC12815
0.7375 Intermediate Similarity NPC275098
0.7375 Intermediate Similarity NPC238948
0.7368 Intermediate Similarity NPC474329
0.7368 Intermediate Similarity NPC116139
0.7368 Intermediate Similarity NPC62670
0.7368 Intermediate Similarity NPC474304
0.7363 Intermediate Similarity NPC135776
0.7356 Intermediate Similarity NPC245434
0.7356 Intermediate Similarity NPC142649
0.7349 Intermediate Similarity NPC198240
0.7349 Intermediate Similarity NPC299235
0.7342 Intermediate Similarity NPC280256
0.7342 Intermediate Similarity NPC67183
0.7333 Intermediate Similarity NPC190049
0.7326 Intermediate Similarity NPC49019
0.7326 Intermediate Similarity NPC97913
0.7317 Intermediate Similarity NPC142759
0.7317 Intermediate Similarity NPC215481
0.7317 Intermediate Similarity NPC124289
0.7317 Intermediate Similarity NPC279537
0.7317 Intermediate Similarity NPC141346
0.7317 Intermediate Similarity NPC473437
0.7317 Intermediate Similarity NPC25908
0.7317 Intermediate Similarity NPC115719
0.7303 Intermediate Similarity NPC117122
0.7294 Intermediate Similarity NPC10276
0.7294 Intermediate Similarity NPC325031
0.7294 Intermediate Similarity NPC35089
0.7292 Intermediate Similarity NPC66110
0.7283 Intermediate Similarity NPC469632
0.7283 Intermediate Similarity NPC53685
0.7273 Intermediate Similarity NPC67493
0.7273 Intermediate Similarity NPC107787
0.7263 Intermediate Similarity NPC280963
0.7262 Intermediate Similarity NPC470244
0.7262 Intermediate Similarity NPC201225
0.7262 Intermediate Similarity NPC7232
0.7262 Intermediate Similarity NPC164308
0.7262 Intermediate Similarity NPC469617
0.7262 Intermediate Similarity NPC470239
0.725 Intermediate Similarity NPC319163
0.725 Intermediate Similarity NPC67076
0.7241 Intermediate Similarity NPC115786
0.7241 Intermediate Similarity NPC90446
0.7241 Intermediate Similarity NPC164577
0.7237 Intermediate Similarity NPC53642
0.7237 Intermediate Similarity NPC234767
0.7237 Intermediate Similarity NPC470325
0.7234 Intermediate Similarity NPC477949
0.7229 Intermediate Similarity NPC53581
0.7229 Intermediate Similarity NPC103987
0.7229 Intermediate Similarity NPC15975
0.7229 Intermediate Similarity NPC61952
0.7229 Intermediate Similarity NPC195785
0.7229 Intermediate Similarity NPC316324
0.7229 Intermediate Similarity NPC65603
0.7222 Intermediate Similarity NPC262043
0.7222 Intermediate Similarity NPC205548
0.7222 Intermediate Similarity NPC477215
0.7222 Intermediate Similarity NPC476388
0.7222 Intermediate Similarity NPC232747
0.7215 Intermediate Similarity NPC469914
0.7209 Intermediate Similarity NPC474291
0.7204 Intermediate Similarity NPC474490
0.7204 Intermediate Similarity NPC170120
0.7204 Intermediate Similarity NPC469873
0.7195 Intermediate Similarity NPC199445
0.7195 Intermediate Similarity NPC251435
0.7195 Intermediate Similarity NPC244166
0.7195 Intermediate Similarity NPC474011
0.7195 Intermediate Similarity NPC60718
0.7191 Intermediate Similarity NPC476409
0.7191 Intermediate Similarity NPC136948
0.7191 Intermediate Similarity NPC478145
0.7191 Intermediate Similarity NPC201658
0.7176 Intermediate Similarity NPC115418
0.7176 Intermediate Similarity NPC74673
0.7176 Intermediate Similarity NPC223904
0.7176 Intermediate Similarity NPC271104
0.7176 Intermediate Similarity NPC69271
0.7174 Intermediate Similarity NPC469692
0.7174 Intermediate Similarity NPC469645
0.7174 Intermediate Similarity NPC472871
0.716 Intermediate Similarity NPC35656
0.7159 Intermediate Similarity NPC179006
0.7159 Intermediate Similarity NPC287015
0.7159 Intermediate Similarity NPC78089
0.7159 Intermediate Similarity NPC146850
0.7159 Intermediate Similarity NPC474853
0.7158 Intermediate Similarity NPC141191
0.7143 Intermediate Similarity NPC93763
0.7143 Intermediate Similarity NPC301969
0.7143 Intermediate Similarity NPC309190
0.7143 Intermediate Similarity NPC222210
0.7143 Intermediate Similarity NPC63445
0.7143 Intermediate Similarity NPC74410
0.7143 Intermediate Similarity NPC108816
0.7143 Intermediate Similarity NPC315765
0.7143 Intermediate Similarity NPC37607
0.7143 Intermediate Similarity NPC121200
0.7143 Intermediate Similarity NPC51486
0.7128 Intermediate Similarity NPC184065
0.7128 Intermediate Similarity NPC185553
0.7128 Intermediate Similarity NPC29152
0.7126 Intermediate Similarity NPC258985
0.7126 Intermediate Similarity NPC318468
0.7126 Intermediate Similarity NPC215294
0.7126 Intermediate Similarity NPC477373

  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 NPC476627 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
0.7765 Intermediate Similarity NPD5363 Approved
0.7412 Intermediate Similarity NPD4269 Approved
0.7412 Intermediate Similarity NPD4270 Approved
0.7333 Intermediate Similarity NPD5785 Approved
0.7176 Intermediate Similarity NPD4252 Approved
0.7126 Intermediate Similarity NPD5362 Discontinued
0.7093 Intermediate Similarity NPD5369 Approved
0.7079 Intermediate Similarity NPD5786 Approved
0.7021 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD4800 Clinical (unspecified phase)
0.6961 Remote Similarity NPD6371 Approved
0.6941 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6932 Remote Similarity NPD7154 Phase 3
0.6923 Remote Similarity NPD7341 Phase 2
0.6889 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6835 Remote Similarity NPD7331 Phase 2
0.6832 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6782 Remote Similarity NPD4820 Approved
0.6782 Remote Similarity NPD4819 Approved
0.6782 Remote Similarity NPD4822 Approved
0.6782 Remote Similarity NPD4821 Approved
0.6703 Remote Similarity NPD4623 Approved
0.6703 Remote Similarity NPD4519 Discontinued
0.6702 Remote Similarity NPD5281 Approved
0.6702 Remote Similarity NPD5284 Approved
0.6629 Remote Similarity NPD4221 Approved
0.6629 Remote Similarity NPD4223 Phase 3
0.6629 Remote Similarity NPD5209 Approved
0.6628 Remote Similarity NPD4756 Discovery
0.6591 Remote Similarity NPD5368 Approved
0.6556 Remote Similarity NPD5332 Approved
0.6556 Remote Similarity NPD5331 Approved
0.6552 Remote Similarity NPD4271 Approved
0.6552 Remote Similarity NPD4268 Approved
0.6522 Remote Similarity NPD5690 Phase 2
0.6517 Remote Similarity NPD4790 Discontinued
0.6495 Remote Similarity NPD5695 Phase 3
0.6484 Remote Similarity NPD4197 Approved
0.6444 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6444 Remote Similarity NPD6435 Approved
0.6413 Remote Similarity NPD5329 Approved
0.6404 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6404 Remote Similarity NPD4695 Discontinued
0.6364 Remote Similarity NPD6084 Phase 2
0.6364 Remote Similarity NPD6083 Phase 2
0.6354 Remote Similarity NPD5693 Phase 1
0.6344 Remote Similarity NPD4690 Approved
0.6344 Remote Similarity NPD5205 Approved
0.6344 Remote Similarity NPD4689 Approved
0.6344 Remote Similarity NPD4688 Approved
0.6344 Remote Similarity NPD4138 Approved
0.6344 Remote Similarity NPD4694 Approved
0.6344 Remote Similarity NPD4693 Phase 3
0.6344 Remote Similarity NPD5280 Approved
0.6316 Remote Similarity NPD4753 Phase 2
0.6316 Remote Similarity NPD1695 Approved
0.6316 Remote Similarity NPD6673 Approved
0.6316 Remote Similarity NPD6904 Approved
0.6316 Remote Similarity NPD6080 Approved
0.6316 Remote Similarity NPD5370 Suspended
0.6304 Remote Similarity NPD3133 Approved
0.6304 Remote Similarity NPD3666 Approved
0.6304 Remote Similarity NPD3665 Phase 1
0.63 Remote Similarity NPD5696 Approved
0.6289 Remote Similarity NPD5779 Approved
0.6289 Remote Similarity NPD5778 Approved
0.625 Remote Similarity NPD2664 Clinical (unspecified phase)
0.625 Remote Similarity NPD5692 Phase 3
0.6237 Remote Similarity NPD1694 Approved
0.6224 Remote Similarity NPD5282 Discontinued
0.6211 Remote Similarity NPD5208 Approved
0.6211 Remote Similarity NPD4518 Approved
0.6186 Remote Similarity NPD5694 Approved
0.6186 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6186 Remote Similarity NPD6050 Approved
0.6186 Remote Similarity NPD7983 Approved
0.618 Remote Similarity NPD3617 Approved
0.617 Remote Similarity NPD7334 Approved
0.617 Remote Similarity NPD5330 Approved
0.617 Remote Similarity NPD7146 Approved
0.617 Remote Similarity NPD6409 Approved
0.617 Remote Similarity NPD6684 Approved
0.617 Remote Similarity NPD7521 Approved
0.6162 Remote Similarity NPD4629 Approved
0.6162 Remote Similarity NPD5210 Approved
0.6154 Remote Similarity NPD857 Phase 3
0.6139 Remote Similarity NPD4225 Approved
0.6133 Remote Similarity NPD3172 Approved
0.6126 Remote Similarity NPD7115 Discovery
0.6117 Remote Similarity NPD5211 Phase 2
0.6111 Remote Similarity NPD4195 Approved
0.6082 Remote Similarity NPD5207 Approved
0.6082 Remote Similarity NPD46 Approved
0.6082 Remote Similarity NPD6698 Approved
0.6082 Remote Similarity NPD4096 Approved
0.6078 Remote Similarity NPD6404 Discontinued
0.6064 Remote Similarity NPD1696 Phase 3
0.6064 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6053 Remote Similarity NPD3196 Approved
0.6053 Remote Similarity NPD3194 Approved
0.6053 Remote Similarity NPD3195 Phase 2
0.6053 Remote Similarity NPD4266 Approved
0.6042 Remote Similarity NPD6903 Approved
0.6042 Remote Similarity NPD6672 Approved
0.6042 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6042 Remote Similarity NPD5737 Approved
0.6038 Remote Similarity NPD5697 Approved
0.6022 Remote Similarity NPD4788 Approved
0.602 Remote Similarity NPD7515 Phase 2
0.6 Remote Similarity NPD4249 Approved
0.6 Remote Similarity NPD5279 Phase 3
0.6 Remote Similarity NPD3618 Phase 1
0.6 Remote Similarity NPD6098 Approved
0.6 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6 Remote Similarity NPD5141 Approved
0.5981 Remote Similarity NPD6011 Approved
0.5981 Remote Similarity NPD6881 Approved
0.5981 Remote Similarity NPD6899 Approved
0.5979 Remote Similarity NPD6101 Approved
0.5979 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5979 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5978 Remote Similarity NPD4692 Approved
0.5978 Remote Similarity NPD4139 Approved
0.596 Remote Similarity NPD6399 Phase 3
0.596 Remote Similarity NPD4202 Approved
0.5943 Remote Similarity NPD6402 Approved
0.5943 Remote Similarity NPD6675 Approved
0.5943 Remote Similarity NPD5739 Approved
0.5943 Remote Similarity NPD7128 Approved
0.5941 Remote Similarity NPD7839 Suspended
0.5938 Remote Similarity NPD4250 Approved
0.5938 Remote Similarity NPD3573 Approved
0.5938 Remote Similarity NPD4251 Approved
0.5926 Remote Similarity NPD6014 Approved
0.5926 Remote Similarity NPD6012 Approved
0.5926 Remote Similarity NPD6013 Approved
0.5922 Remote Similarity NPD7640 Approved
0.5922 Remote Similarity NPD5285 Approved
0.5922 Remote Similarity NPD5286 Approved
0.5922 Remote Similarity NPD4696 Approved
0.5922 Remote Similarity NPD7639 Approved
0.5914 Remote Similarity NPD3667 Approved
0.5909 Remote Similarity NPD6053 Discontinued
0.5904 Remote Similarity NPD2685 Clinical (unspecified phase)
0.59 Remote Similarity NPD6001 Approved
0.59 Remote Similarity NPD7748 Approved
0.5895 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5888 Remote Similarity NPD5701 Approved
0.5882 Remote Similarity NPD4755 Approved
0.5872 Remote Similarity NPD6883 Approved
0.5872 Remote Similarity NPD7290 Approved
0.5872 Remote Similarity NPD7102 Approved
0.5865 Remote Similarity NPD5223 Approved
0.5859 Remote Similarity NPD7637 Suspended
0.5859 Remote Similarity NPD6411 Approved
0.5859 Remote Similarity NPD6079 Approved
0.5844 Remote Similarity NPD615 Clinical (unspecified phase)
0.5842 Remote Similarity NPD5654 Approved
0.5833 Remote Similarity NPD634 Phase 3
0.5833 Remote Similarity NPD7320 Approved
0.5825 Remote Similarity NPD7638 Approved
0.5818 Remote Similarity NPD6847 Approved
0.5818 Remote Similarity NPD6649 Approved
0.5818 Remote Similarity NPD6869 Approved
0.5818 Remote Similarity NPD8130 Phase 1
0.5818 Remote Similarity NPD6650 Approved
0.5818 Remote Similarity NPD6617 Approved
0.5816 Remote Similarity NPD5328 Approved
0.581 Remote Similarity NPD5225 Approved
0.581 Remote Similarity NPD4633 Approved
0.581 Remote Similarity NPD5226 Approved
0.581 Remote Similarity NPD5091 Approved
0.581 Remote Similarity NPD5224 Approved
0.58 Remote Similarity NPD5133 Approved
0.5789 Remote Similarity NPD4786 Approved
0.5784 Remote Similarity NPD5222 Approved
0.5784 Remote Similarity NPD7614 Phase 1
0.5784 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5784 Remote Similarity NPD5221 Approved
0.578 Remote Similarity NPD6372 Approved
0.578 Remote Similarity NPD6373 Approved
0.5769 Remote Similarity NPD4700 Approved
0.5766 Remote Similarity NPD8297 Approved
0.5766 Remote Similarity NPD6882 Approved
0.5758 Remote Similarity NPD7838 Discovery
0.5755 Remote Similarity NPD6647 Phase 2
0.5755 Remote Similarity NPD5175 Approved
0.5755 Remote Similarity NPD5174 Approved
0.5747 Remote Similarity NPD4691 Approved
0.5743 Remote Similarity NPD5122 Clinical (unspecified phase)
0.5732 Remote Similarity NPD4192 Approved
0.5732 Remote Similarity NPD4191 Approved
0.5732 Remote Similarity NPD4193 Approved
0.5732 Remote Similarity NPD4194 Approved
0.5728 Remote Similarity NPD5173 Approved
0.5728 Remote Similarity NPD5959 Approved
0.5728 Remote Similarity NPD7902 Approved
0.5727 Remote Similarity NPD4634 Approved
0.5714 Remote Similarity NPD4632 Approved
0.569 Remote Similarity NPD6319 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