Structure

Physi-Chem Properties

Molecular Weight:  330.22
Volume:  356.008
LogP:  2.952
LogD:  3.165
LogS:  -4.232
# Rotatable Bonds:  0
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.529
Synthetic Accessibility Score:  4.689
Fsp3:  0.762
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -4.594
MDCK Permeability:  2.6750531105790287e-05
Pgp-inhibitor:  0.869
Pgp-substrate:  0.395
Human Intestinal Absorption (HIA):  0.606
20% Bioavailability (F20%):  0.958
30% Bioavailability (F30%):  0.902

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.527
Plasma Protein Binding (PPB):  91.82588195800781%
Volume Distribution (VD):  0.737
Pgp-substrate:  5.30985164642334%

ADMET: Metabolism

CYP1A2-inhibitor:  0.037
CYP1A2-substrate:  0.521
CYP2C19-inhibitor:  0.103
CYP2C19-substrate:  0.83
CYP2C9-inhibitor:  0.042
CYP2C9-substrate:  0.079
CYP2D6-inhibitor:  0.012
CYP2D6-substrate:  0.106
CYP3A4-inhibitor:  0.591
CYP3A4-substrate:  0.31

ADMET: Excretion

Clearance (CL):  9.202
Half-life (T1/2):  0.271

ADMET: Toxicity

hERG Blockers:  0.094
Human Hepatotoxicity (H-HT):  0.501
Drug-inuced Liver Injury (DILI):  0.324
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.75
Maximum Recommended Daily Dose:  0.882
Skin Sensitization:  0.365
Carcinogencity:  0.895
Eye Corrosion:  0.006
Eye Irritation:  0.045
Respiratory Toxicity:  0.975

Download Data

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

  Natural Product: NPC109305

Natural Product ID:  NPC109305
Common Name*:   E-Volkendousin
IUPAC Name:   (3S,4R,8R,9S,10R,13S,14S,17E)-17-ethylidene-3,4-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-16-one
Synonyms:   E-Volkendousin
Standard InCHIKey:  QAKWWXLYSGFAQN-CGQGDFJRSA-N
Standard InCHI:  InChI=1S/C21H30O3/c1-4-13-18(23)11-16-12-5-6-15-19(24)17(22)8-10-21(15,3)14(12)7-9-20(13,16)2/h4,6,12,14,16-17,19,22,24H,5,7-11H2,1-3H3/b13-4-/t12-,14+,16+,17+,19-,20-,21-/m1/s1
SMILES:  C/C=C1/C(=O)C[C@H]2[C@@H]3CC=C4[C@H]([C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL233040
PubChem CID:   10853919
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0003568] Androstane steroids
          • [CHEMONTID:0001467] Androgens and derivatives

*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
NPO10872 Aglaia ponapensis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[17055270]
NPO10872 Aglaia ponapensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10872 Aglaia ponapensis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10872 Aglaia ponapensis Species Meliaceae 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
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 4.6 ug ml-1 PMID[466470]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 4.7 ug ml-1 PMID[466470]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 4.2 ug ml-1 PMID[466470]

☑ 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 NPC109305 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
0.9326 High Similarity NPC474736
0.9205 High Similarity NPC473999
0.9205 High Similarity NPC309603
0.9101 High Similarity NPC48010
0.9022 High Similarity NPC117133
0.9 High Similarity NPC473998
0.9 High Similarity NPC475806
0.8864 High Similarity NPC474732
0.8864 High Similarity NPC31564
0.8864 High Similarity NPC474733
0.8864 High Similarity NPC145879
0.8864 High Similarity NPC474778
0.8837 High Similarity NPC151519
0.8817 High Similarity NPC471463
0.8804 High Similarity NPC472976
0.8804 High Similarity NPC8993
0.8804 High Similarity NPC472977
0.8791 High Similarity NPC155304
0.8778 High Similarity NPC119416
0.8764 High Similarity NPC58063
0.8764 High Similarity NPC475740
0.875 High Similarity NPC470574
0.875 High Similarity NPC471224
0.875 High Similarity NPC473424
0.875 High Similarity NPC477915
0.8723 High Similarity NPC474938
0.8723 High Similarity NPC474785
0.871 High Similarity NPC271195
0.8696 High Similarity NPC69454
0.8673 High Similarity NPC149047
0.8667 High Similarity NPC471722
0.8667 High Similarity NPC158778
0.8667 High Similarity NPC328539
0.8652 High Similarity NPC472974
0.8652 High Similarity NPC472985
0.8652 High Similarity NPC472986
0.8636 High Similarity NPC321187
0.8636 High Similarity NPC161423
0.8636 High Similarity NPC227064
0.8636 High Similarity NPC85774
0.8636 High Similarity NPC221758
0.8636 High Similarity NPC59453
0.8636 High Similarity NPC214043
0.8636 High Similarity NPC329043
0.8636 High Similarity NPC472265
0.8636 High Similarity NPC58841
0.8632 High Similarity NPC103051
0.8602 High Similarity NPC299100
0.8602 High Similarity NPC474690
0.86 High Similarity NPC214644
0.8587 High Similarity NPC233116
0.8587 High Similarity NPC272746
0.8587 High Similarity NPC63748
0.8586 High Similarity NPC475060
0.8586 High Similarity NPC220229
0.8571 High Similarity NPC469319
0.8571 High Similarity NPC26959
0.8571 High Similarity NPC31985
0.8571 High Similarity NPC268406
0.8571 High Similarity NPC209502
0.8571 High Similarity NPC186688
0.8571 High Similarity NPC204833
0.8571 High Similarity NPC1015
0.8571 High Similarity NPC472973
0.8571 High Similarity NPC77263
0.8571 High Similarity NPC229871
0.8571 High Similarity NPC250592
0.8571 High Similarity NPC32830
0.8539 High Similarity NPC476426
0.8539 High Similarity NPC474083
0.8539 High Similarity NPC469948
0.8526 High Similarity NPC253826
0.8523 High Similarity NPC317458
0.8523 High Similarity NPC169941
0.8523 High Similarity NPC251475
0.8511 High Similarity NPC259286
0.8511 High Similarity NPC473170
0.8511 High Similarity NPC180950
0.85 High Similarity NPC217201
0.8488 Intermediate Similarity NPC308038
0.8485 Intermediate Similarity NPC49958
0.8485 Intermediate Similarity NPC48733
0.8485 Intermediate Similarity NPC50692
0.8485 Intermediate Similarity NPC296945
0.8485 Intermediate Similarity NPC260268
0.8485 Intermediate Similarity NPC171137
0.8485 Intermediate Similarity NPC152695
0.8485 Intermediate Similarity NPC319077
0.8485 Intermediate Similarity NPC302607
0.8485 Intermediate Similarity NPC85829
0.8485 Intermediate Similarity NPC214264
0.8485 Intermediate Similarity NPC476027
0.8485 Intermediate Similarity NPC97202
0.8485 Intermediate Similarity NPC202167
0.8485 Intermediate Similarity NPC150531
0.8478 Intermediate Similarity NPC191684
0.8478 Intermediate Similarity NPC473099
0.8478 Intermediate Similarity NPC126993
0.8478 Intermediate Similarity NPC85173
0.8462 Intermediate Similarity NPC474677
0.8444 Intermediate Similarity NPC194417
0.8444 Intermediate Similarity NPC20688
0.8444 Intermediate Similarity NPC222613
0.8444 Intermediate Similarity NPC179591
0.8444 Intermediate Similarity NPC327115
0.8444 Intermediate Similarity NPC118648
0.8444 Intermediate Similarity NPC475022
0.8444 Intermediate Similarity NPC51014
0.8444 Intermediate Similarity NPC469994
0.8444 Intermediate Similarity NPC72133
0.8427 Intermediate Similarity NPC476412
0.8427 Intermediate Similarity NPC33913
0.8427 Intermediate Similarity NPC473157
0.8427 Intermediate Similarity NPC473246
0.8427 Intermediate Similarity NPC237712
0.8421 Intermediate Similarity NPC250757
0.8421 Intermediate Similarity NPC249954
0.8421 Intermediate Similarity NPC301534
0.8416 Intermediate Similarity NPC11710
0.8409 Intermediate Similarity NPC93590
0.8404 Intermediate Similarity NPC473162
0.8404 Intermediate Similarity NPC196485
0.8404 Intermediate Similarity NPC245972
0.84 Intermediate Similarity NPC83744
0.84 Intermediate Similarity NPC477916
0.8391 Intermediate Similarity NPC2482
0.8391 Intermediate Similarity NPC472478
0.8387 Intermediate Similarity NPC189520
0.8387 Intermediate Similarity NPC168027
0.8387 Intermediate Similarity NPC116726
0.8387 Intermediate Similarity NPC472978
0.8387 Intermediate Similarity NPC131872
0.8387 Intermediate Similarity NPC185936
0.8372 Intermediate Similarity NPC475994
0.837 Intermediate Similarity NPC275740
0.837 Intermediate Similarity NPC472475
0.837 Intermediate Similarity NPC2983
0.837 Intermediate Similarity NPC472983
0.837 Intermediate Similarity NPC146554
0.837 Intermediate Similarity NPC472240
0.837 Intermediate Similarity NPC473100
0.837 Intermediate Similarity NPC262858
0.837 Intermediate Similarity NPC86319
0.837 Intermediate Similarity NPC472477
0.8352 Intermediate Similarity NPC93778
0.8352 Intermediate Similarity NPC141292
0.8352 Intermediate Similarity NPC90652
0.8351 Intermediate Similarity NPC154072
0.8333 Intermediate Similarity NPC161147
0.8333 Intermediate Similarity NPC320306
0.8333 Intermediate Similarity NPC197823
0.8333 Intermediate Similarity NPC108078
0.8317 Intermediate Similarity NPC329417
0.8316 Intermediate Similarity NPC53565
0.8316 Intermediate Similarity NPC472932
0.8316 Intermediate Similarity NPC476174
0.83 Intermediate Similarity NPC323834
0.83 Intermediate Similarity NPC166607
0.8298 Intermediate Similarity NPC475255
0.8298 Intermediate Similarity NPC12722
0.8298 Intermediate Similarity NPC134826
0.8298 Intermediate Similarity NPC472930
0.8295 Intermediate Similarity NPC136150
0.8295 Intermediate Similarity NPC121984
0.8283 Intermediate Similarity NPC249187
0.8283 Intermediate Similarity NPC311612
0.8283 Intermediate Similarity NPC247957
0.8283 Intermediate Similarity NPC475050
0.828 Intermediate Similarity NPC69622
0.8276 Intermediate Similarity NPC170394
0.8276 Intermediate Similarity NPC281138
0.8265 Intermediate Similarity NPC476897
0.8265 Intermediate Similarity NPC81530
0.8261 Intermediate Similarity NPC206060
0.8261 Intermediate Similarity NPC292491
0.8261 Intermediate Similarity NPC328313
0.8261 Intermediate Similarity NPC470417
0.8261 Intermediate Similarity NPC471724
0.8261 Intermediate Similarity NPC310752
0.8261 Intermediate Similarity NPC143767
0.8261 Intermediate Similarity NPC131470
0.8247 Intermediate Similarity NPC114274
0.8247 Intermediate Similarity NPC235464
0.8247 Intermediate Similarity NPC197386
0.8247 Intermediate Similarity NPC478056
0.8247 Intermediate Similarity NPC166745
0.8242 Intermediate Similarity NPC470955
0.8242 Intermediate Similarity NPC94666
0.8242 Intermediate Similarity NPC82979
0.8242 Intermediate Similarity NPC473168
0.8242 Intermediate Similarity NPC155011
0.8229 Intermediate Similarity NPC472941
0.8229 Intermediate Similarity NPC473158
0.8229 Intermediate Similarity NPC456
0.8222 Intermediate Similarity NPC82902
0.8211 Intermediate Similarity NPC292793
0.8211 Intermediate Similarity NPC87095
0.8211 Intermediate Similarity NPC111015
0.8211 Intermediate Similarity NPC196227
0.8202 Intermediate Similarity NPC212083

  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 NPC109305 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
0.8864 High Similarity NPD3618 Phase 1
0.8837 High Similarity NPD3667 Approved
0.8636 High Similarity NPD4786 Approved
0.8636 High Similarity NPD3665 Phase 1
0.8636 High Similarity NPD3133 Approved
0.8636 High Similarity NPD3666 Approved
0.8587 High Similarity NPD6079 Approved
0.8571 High Similarity NPD5328 Approved
0.8298 Intermediate Similarity NPD4202 Approved
0.8229 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.8229 Intermediate Similarity NPD5222 Approved
0.8229 Intermediate Similarity NPD5221 Approved
0.8182 Intermediate Similarity NPD5211 Phase 2
0.8144 Intermediate Similarity NPD5173 Approved
0.8043 Intermediate Similarity NPD5279 Phase 3
0.8041 Intermediate Similarity NPD4697 Phase 3
0.8022 Intermediate Similarity NPD3668 Phase 3
0.802 Intermediate Similarity NPD5141 Approved
0.8 Intermediate Similarity NPD4221 Approved
0.8 Intermediate Similarity NPD4223 Phase 3
0.798 Intermediate Similarity NPD4696 Approved
0.798 Intermediate Similarity NPD5286 Approved
0.798 Intermediate Similarity NPD5285 Approved
0.7979 Intermediate Similarity NPD4753 Phase 2
0.7959 Intermediate Similarity NPD4755 Approved
0.79 Intermediate Similarity NPD5223 Approved
0.787 Intermediate Similarity NPD7115 Discovery
0.7849 Intermediate Similarity NPD4623 Approved
0.7849 Intermediate Similarity NPD4519 Discontinued
0.7849 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD4197 Approved
0.7822 Intermediate Similarity NPD5224 Approved
0.7822 Intermediate Similarity NPD4633 Approved
0.7822 Intermediate Similarity NPD5226 Approved
0.7822 Intermediate Similarity NPD5225 Approved
0.7812 Intermediate Similarity NPD7515 Phase 2
0.78 Intermediate Similarity NPD4700 Approved
0.7778 Intermediate Similarity NPD4695 Discontinued
0.7755 Intermediate Similarity NPD5210 Approved
0.7755 Intermediate Similarity NPD4629 Approved
0.7753 Intermediate Similarity NPD3617 Approved
0.7745 Intermediate Similarity NPD5174 Approved
0.7745 Intermediate Similarity NPD5175 Approved
0.7742 Intermediate Similarity NPD5329 Approved
0.7732 Intermediate Similarity NPD6399 Phase 3
0.7727 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD4689 Approved
0.766 Intermediate Similarity NPD4690 Approved
0.766 Intermediate Similarity NPD7334 Approved
0.766 Intermediate Similarity NPD5690 Phase 2
0.766 Intermediate Similarity NPD6409 Approved
0.766 Intermediate Similarity NPD5205 Approved
0.766 Intermediate Similarity NPD4688 Approved
0.766 Intermediate Similarity NPD4693 Phase 3
0.766 Intermediate Similarity NPD4138 Approved
0.766 Intermediate Similarity NPD5330 Approved
0.766 Intermediate Similarity NPD7146 Approved
0.766 Intermediate Similarity NPD6684 Approved
0.766 Intermediate Similarity NPD7521 Approved
0.7642 Intermediate Similarity NPD4634 Approved
0.7624 Intermediate Similarity NPD7640 Approved
0.7624 Intermediate Similarity NPD7639 Approved
0.7614 Intermediate Similarity NPD7339 Approved
0.7614 Intermediate Similarity NPD6942 Approved
0.7573 Intermediate Similarity NPD4754 Approved
0.7558 Intermediate Similarity NPD4691 Approved
0.7527 Intermediate Similarity NPD4788 Approved
0.7525 Intermediate Similarity NPD7638 Approved
0.7525 Intermediate Similarity NPD4225 Approved
0.7524 Intermediate Similarity NPD5697 Approved
0.75 Intermediate Similarity NPD6903 Approved
0.75 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7748 Approved
0.7474 Intermediate Similarity NPD5280 Approved
0.7474 Intermediate Similarity NPD4694 Approved
0.7473 Intermediate Similarity NPD4195 Approved
0.7453 Intermediate Similarity NPD5128 Approved
0.7453 Intermediate Similarity NPD6011 Approved
0.7453 Intermediate Similarity NPD5168 Approved
0.7453 Intermediate Similarity NPD4730 Approved
0.7453 Intermediate Similarity NPD6899 Approved
0.7453 Intermediate Similarity NPD6881 Approved
0.7453 Intermediate Similarity NPD4729 Approved
0.7442 Intermediate Similarity NPD4137 Phase 3
0.7431 Intermediate Similarity NPD4632 Approved
0.7429 Intermediate Similarity NPD4768 Approved
0.7429 Intermediate Similarity NPD6675 Approved
0.7429 Intermediate Similarity NPD7128 Approved
0.7429 Intermediate Similarity NPD4767 Approved
0.7429 Intermediate Similarity NPD6402 Approved
0.7429 Intermediate Similarity NPD5739 Approved
0.7426 Intermediate Similarity NPD6083 Phase 2
0.7426 Intermediate Similarity NPD6084 Phase 2
0.7396 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD6012 Approved
0.7383 Intermediate Similarity NPD6014 Approved
0.7383 Intermediate Similarity NPD6013 Approved
0.7368 Intermediate Similarity NPD1696 Phase 3
0.7368 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6412 Phase 2
0.7358 Intermediate Similarity NPD5701 Approved
0.7356 Intermediate Similarity NPD4747 Approved
0.7339 Intermediate Similarity NPD8297 Approved
0.732 Intermediate Similarity NPD6672 Approved
0.732 Intermediate Similarity NPD5737 Approved
0.7315 Intermediate Similarity NPD6883 Approved
0.7315 Intermediate Similarity NPD7102 Approved
0.7315 Intermediate Similarity NPD5247 Approved
0.7315 Intermediate Similarity NPD5248 Approved
0.7315 Intermediate Similarity NPD5249 Phase 3
0.7315 Intermediate Similarity NPD7290 Approved
0.7315 Intermediate Similarity NPD5135 Approved
0.7315 Intermediate Similarity NPD5251 Approved
0.7315 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD5169 Approved
0.7315 Intermediate Similarity NPD5250 Approved
0.7303 Intermediate Similarity NPD4058 Approved
0.729 Intermediate Similarity NPD7320 Approved
0.7255 Intermediate Similarity NPD7902 Approved
0.7248 Intermediate Similarity NPD6649 Approved
0.7248 Intermediate Similarity NPD5216 Approved
0.7248 Intermediate Similarity NPD6847 Approved
0.7248 Intermediate Similarity NPD6617 Approved
0.7248 Intermediate Similarity NPD5215 Approved
0.7248 Intermediate Similarity NPD5127 Approved
0.7248 Intermediate Similarity NPD8130 Phase 1
0.7248 Intermediate Similarity NPD6650 Approved
0.7248 Intermediate Similarity NPD6869 Approved
0.7248 Intermediate Similarity NPD5217 Approved
0.7241 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD5695 Phase 3
0.7222 Intermediate Similarity NPD6372 Approved
0.7222 Intermediate Similarity NPD6373 Approved
0.7204 Intermediate Similarity NPD7525 Registered
0.7184 Intermediate Similarity NPD5696 Approved
0.7184 Intermediate Similarity NPD5290 Discontinued
0.7182 Intermediate Similarity NPD6882 Approved
0.7143 Intermediate Similarity NPD6933 Approved
0.71 Intermediate Similarity NPD5281 Approved
0.71 Intermediate Similarity NPD5284 Approved
0.7091 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD6009 Approved
0.7079 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD5167 Approved
0.7053 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD6319 Approved
0.7041 Intermediate Similarity NPD3573 Approved
0.701 Intermediate Similarity NPD5363 Approved
0.701 Intermediate Similarity NPD1694 Approved
0.7 Intermediate Similarity NPD5785 Approved
0.7 Intermediate Similarity NPD4096 Approved
0.6991 Remote Similarity NPD6274 Approved
0.6991 Remote Similarity NPD6868 Approved
0.6989 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6981 Remote Similarity NPD7632 Discontinued
0.6972 Remote Similarity NPD6686 Approved
0.697 Remote Similarity NPD4518 Approved
0.697 Remote Similarity NPD5208 Approved
0.6961 Remote Similarity NPD7900 Approved
0.6961 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6952 Remote Similarity NPD6404 Discontinued
0.6947 Remote Similarity NPD4692 Approved
0.6947 Remote Similarity NPD4139 Approved
0.6944 Remote Similarity NPD6008 Approved
0.6932 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6931 Remote Similarity NPD5693 Phase 1
0.693 Remote Similarity NPD6317 Approved
0.6923 Remote Similarity NPD4687 Approved
0.6923 Remote Similarity NPD6926 Approved
0.6923 Remote Similarity NPD6924 Approved
0.6923 Remote Similarity NPD5733 Approved
0.6915 Remote Similarity NPD6929 Approved
0.6915 Remote Similarity NPD7645 Phase 2
0.69 Remote Similarity NPD6080 Approved
0.69 Remote Similarity NPD6673 Approved
0.69 Remote Similarity NPD7285 Clinical (unspecified phase)
0.69 Remote Similarity NPD6904 Approved
0.6897 Remote Similarity NPD6054 Approved
0.6893 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6889 Remote Similarity NPD5276 Approved
0.687 Remote Similarity NPD6313 Approved
0.687 Remote Similarity NPD6314 Approved
0.687 Remote Similarity NPD6335 Approved
0.6869 Remote Similarity NPD7524 Approved
0.6863 Remote Similarity NPD5133 Approved
0.6854 Remote Similarity NPD3698 Phase 2
0.6848 Remote Similarity NPD3703 Phase 2
0.6848 Remote Similarity NPD8264 Approved
0.6842 Remote Similarity NPD6930 Phase 2
0.6842 Remote Similarity NPD4748 Discontinued
0.6842 Remote Similarity NPD6931 Approved
0.6842 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6838 Remote Similarity NPD6015 Approved
0.6838 Remote Similarity NPD6016 Approved
0.6838 Remote Similarity NPD5983 Phase 2
0.6822 Remote Similarity NPD5091 Approved
0.681 Remote Similarity NPD7101 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