Structure

Physi-Chem Properties

Molecular Weight:  456.36
Volume:  505.751
LogP:  6.158
LogD:  4.502
LogS:  -3.831
# Rotatable Bonds:  1
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.405
Synthetic Accessibility Score:  4.779
Fsp3:  0.9
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.449
MDCK Permeability:  1.0310278412362095e-05
Pgp-inhibitor:  0.326
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.038
20% Bioavailability (F20%):  0.191
30% Bioavailability (F30%):  0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.076
Plasma Protein Binding (PPB):  92.44937896728516%
Volume Distribution (VD):  0.947
Pgp-substrate:  2.8183538913726807%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.619
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.928
CYP2C9-inhibitor:  0.119
CYP2C9-substrate:  0.124
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.036
CYP3A4-inhibitor:  0.275
CYP3A4-substrate:  0.885

ADMET: Excretion

Clearance (CL):  2.894
Half-life (T1/2):  0.076

ADMET: Toxicity

hERG Blockers:  0.024
Human Hepatotoxicity (H-HT):  0.527
Drug-inuced Liver Injury (DILI):  0.015
AMES Toxicity:  0.005
Rat Oral Acute Toxicity:  0.478
Maximum Recommended Daily Dose:  0.908
Skin Sensitization:  0.129
Carcinogencity:  0.186
Eye Corrosion:  0.022
Eye Irritation:  0.059
Respiratory Toxicity:  0.969

Download Data

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

  Natural Product: NPC171789

Natural Product ID:  NPC171789
Common Name*:   Bryonolic Acid
IUPAC Name:   (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,13,14,14b-tetradecahydropicene-2-carboxylic acid
Synonyms:   Bryonolic Acid
Standard InCHIKey:  BHVJSLPLFOAMEV-FPLINDMSSA-N
Standard InCHI:  InChI=1S/C30H48O3/c1-25(2)21-9-8-20-19(28(21,5)12-11-23(25)31)10-13-30(7)22-18-27(4,24(32)33)15-14-26(22,3)16-17-29(20,30)6/h21-23,31H,8-18H2,1-7H3,(H,32,33)/p-1/t21-,22+,23-,26+,27+,28+,29+,30-/m0/s1
SMILES:  CC1(C)[C@@H]2CCC3=C(CC[C@@]4(C)[C@@H]5C[C@@](C)(CC[C@]5(C)CC[C@]34C)C(=O)[O-])[C@@]2(C)CC[C@@H]1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL482596
PubChem CID:   472768
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001292] Cyclic alcohols 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
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. seed n.a. DOI[10.1016/S0031-9422(00)97029-8]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota n.a. stem n.a. PMID[18310955]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota seeds n.a. n.a. PMID[18603435]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota Seeds n.a. n.a. PMID[20469887]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota n.a. n.a. Database[FooDB]
NPO30404 Luffa cylindrica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12328 Ampelopsis japonica Species Vitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12328 Ampelopsis japonica Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12328 Ampelopsis japonica Species Vitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30404 Luffa cylindrica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5105 Lagenaria siceraria Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12328 Ampelopsis japonica Species Vitaceae 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
NPT113 Cell Line RAW264.7 Mus musculus FC = 55.0 n.a. PMID[567357]
NPT113 Cell Line RAW264.7 Mus musculus FC = 3.3 n.a. PMID[567357]
NPT113 Cell Line RAW264.7 Mus musculus FC = 14.0 n.a. PMID[567357]
NPT113 Cell Line RAW264.7 Mus musculus FC = 13.0 n.a. PMID[567357]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 53300.0 nM PMID[567358]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 1.5 % PMID[567358]
NPT113 Cell Line RAW264.7 Mus musculus FC = 4.1 n.a. PMID[567358]
NPT113 Cell Line RAW264.7 Mus musculus FC = 11.3 n.a. PMID[567358]
NPT113 Cell Line RAW264.7 Mus musculus FC = 1.8 n.a. PMID[567358]
NPT1651 Individual Protein Nuclear factor erythroid 2-related factor 2 Mus musculus FC = 11.7 n.a. PMID[567358]
NPT1651 Individual Protein Nuclear factor erythroid 2-related factor 2 Mus musculus FC = 1.7 n.a. PMID[567358]
NPT1651 Individual Protein Nuclear factor erythroid 2-related factor 2 Mus musculus FC = 3.5 n.a. PMID[567358]
NPT1651 Individual Protein Nuclear factor erythroid 2-related factor 2 Mus musculus FC = 1.8 n.a. PMID[567358]
NPT1651 Individual Protein Nuclear factor erythroid 2-related factor 2 Mus musculus FC = 1.5 n.a. PMID[567358]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 72.0 % PMID[567358]
NPT32 Organism Mus musculus Mus musculus ID50 = 376.0 mg.kg-1 PMID[567356]

☑ 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 NPC171789 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
0.9506 High Similarity NPC56588
0.9506 High Similarity NPC72638
0.939 High Similarity NPC307426
0.939 High Similarity NPC293564
0.939 High Similarity NPC142415
0.939 High Similarity NPC171203
0.939 High Similarity NPC51700
0.939 High Similarity NPC71507
0.939 High Similarity NPC242468
0.939 High Similarity NPC18064
0.939 High Similarity NPC98442
0.939 High Similarity NPC68160
0.939 High Similarity NPC88716
0.939 High Similarity NPC102683
0.939 High Similarity NPC130577
0.9277 High Similarity NPC17733
0.9277 High Similarity NPC40552
0.9277 High Similarity NPC474512
0.9277 High Similarity NPC246708
0.9277 High Similarity NPC52169
0.9277 High Similarity NPC470629
0.9277 High Similarity NPC290690
0.9277 High Similarity NPC473242
0.9277 High Similarity NPC182797
0.9277 High Similarity NPC181225
0.9176 High Similarity NPC235704
0.9176 High Similarity NPC301244
0.9167 High Similarity NPC234346
0.9167 High Similarity NPC290972
0.9167 High Similarity NPC59263
0.9167 High Similarity NPC161751
0.9167 High Similarity NPC270768
0.9167 High Similarity NPC198664
0.9167 High Similarity NPC127689
0.9167 High Similarity NPC274330
0.9167 High Similarity NPC121798
0.9167 High Similarity NPC263393
0.9167 High Similarity NPC474972
0.9167 High Similarity NPC474686
0.9167 High Similarity NPC143232
0.9167 High Similarity NPC470588
0.9167 High Similarity NPC95246
0.9167 High Similarity NPC25906
0.9167 High Similarity NPC130520
0.9167 High Similarity NPC61543
0.9167 High Similarity NPC293048
0.9167 High Similarity NPC64872
0.9167 High Similarity NPC225585
0.907 High Similarity NPC133579
0.907 High Similarity NPC474806
0.9059 High Similarity NPC86372
0.9059 High Similarity NPC227467
0.9059 High Similarity NPC49320
0.9059 High Similarity NPC273621
0.9059 High Similarity NPC130278
0.9059 High Similarity NPC120968
0.9059 High Similarity NPC172361
0.9059 High Similarity NPC126369
0.9059 High Similarity NPC290614
0.9059 High Similarity NPC291028
0.9059 High Similarity NPC18872
0.9059 High Similarity NPC111110
0.9059 High Similarity NPC477872
0.9059 High Similarity NPC7260
0.9059 High Similarity NPC470589
0.9059 High Similarity NPC210037
0.8966 High Similarity NPC80365
0.8953 High Similarity NPC228784
0.8953 High Similarity NPC282616
0.8953 High Similarity NPC158030
0.8953 High Similarity NPC71074
0.8953 High Similarity NPC187722
0.8953 High Similarity NPC84319
0.8953 High Similarity NPC52021
0.8953 High Similarity NPC25299
0.8953 High Similarity NPC475708
0.8953 High Similarity NPC300351
0.8953 High Similarity NPC306541
0.8953 High Similarity NPC472149
0.8953 High Similarity NPC233455
0.8953 High Similarity NPC65120
0.8953 High Similarity NPC235884
0.8953 High Similarity NPC324341
0.8953 High Similarity NPC105189
0.8953 High Similarity NPC4036
0.8953 High Similarity NPC145067
0.8953 High Similarity NPC155120
0.8953 High Similarity NPC474525
0.8953 High Similarity NPC966
0.8953 High Similarity NPC288833
0.8941 High Similarity NPC30522
0.8916 High Similarity NPC133954
0.8864 High Similarity NPC32118
0.8851 High Similarity NPC295643
0.8851 High Similarity NPC214756
0.8851 High Similarity NPC49776
0.8851 High Similarity NPC158059
0.8851 High Similarity NPC474436
0.8851 High Similarity NPC86368
0.8851 High Similarity NPC74855
0.8851 High Similarity NPC229281
0.8851 High Similarity NPC63118
0.8851 High Similarity NPC118519
0.8851 High Similarity NPC202728
0.8851 High Similarity NPC298554
0.8851 High Similarity NPC272075
0.8851 High Similarity NPC307335
0.8851 High Similarity NPC136313
0.8851 High Similarity NPC275809
0.8837 High Similarity NPC120840
0.8837 High Similarity NPC193750
0.8837 High Similarity NPC46441
0.8837 High Similarity NPC113989
0.8837 High Similarity NPC474728
0.881 High Similarity NPC73038
0.881 High Similarity NPC55309
0.881 High Similarity NPC477579
0.881 High Similarity NPC235341
0.881 High Similarity NPC325594
0.881 High Similarity NPC213412
0.881 High Similarity NPC28252
0.881 High Similarity NPC475862
0.881 High Similarity NPC95594
0.881 High Similarity NPC74363
0.878 High Similarity NPC73882
0.8764 High Similarity NPC88847
0.875 High Similarity NPC88116
0.875 High Similarity NPC263548
0.875 High Similarity NPC145667
0.875 High Similarity NPC32407
0.875 High Similarity NPC231063
0.875 High Similarity NPC91010
0.875 High Similarity NPC191412
0.875 High Similarity NPC114159
0.875 High Similarity NPC159365
0.875 High Similarity NPC20235
0.875 High Similarity NPC474529
0.875 High Similarity NPC209868
0.875 High Similarity NPC282395
0.875 High Similarity NPC6818
0.875 High Similarity NPC222047
0.875 High Similarity NPC299996
0.8736 High Similarity NPC470590
0.8736 High Similarity NPC60755
0.8736 High Similarity NPC471588
0.8736 High Similarity NPC285184
0.8736 High Similarity NPC38754
0.8736 High Similarity NPC6255
0.8736 High Similarity NPC77099
0.8706 High Similarity NPC474684
0.8706 High Similarity NPC159046
0.8706 High Similarity NPC233836
0.8706 High Similarity NPC142361
0.8706 High Similarity NPC187376
0.8706 High Similarity NPC73064
0.8667 High Similarity NPC21728
0.8659 High Similarity NPC473420
0.8652 High Similarity NPC198245
0.8652 High Similarity NPC96916
0.8652 High Similarity NPC148523
0.8652 High Similarity NPC473240
0.8652 High Similarity NPC474727
0.8652 High Similarity NPC139570
0.8636 High Similarity NPC118490
0.8621 High Similarity NPC20388
0.8605 High Similarity NPC242864
0.8605 High Similarity NPC230387
0.8588 High Similarity NPC158393
0.8588 High Similarity NPC9892
0.8588 High Similarity NPC10005
0.8588 High Similarity NPC91525
0.8588 High Similarity NPC187545
0.8588 High Similarity NPC329943
0.8571 High Similarity NPC180834
0.8556 High Similarity NPC476318
0.8556 High Similarity NPC158371
0.8556 High Similarity NPC230151
0.8556 High Similarity NPC19376
0.8556 High Similarity NPC201657
0.8556 High Similarity NPC132824
0.8556 High Similarity NPC157113
0.8556 High Similarity NPC73004
0.8556 High Similarity NPC173744
0.8556 High Similarity NPC207922
0.8556 High Similarity NPC9487
0.8556 High Similarity NPC98874
0.8556 High Similarity NPC62516
0.8556 High Similarity NPC259733
0.8556 High Similarity NPC327179
0.8556 High Similarity NPC25848
0.8556 High Similarity NPC476327
0.8556 High Similarity NPC116457
0.8556 High Similarity NPC307282
0.8556 High Similarity NPC204961
0.8556 High Similarity NPC305464
0.8539 High Similarity NPC78580
0.8539 High Similarity NPC60692
0.8539 High Similarity NPC296164
0.8539 High Similarity NPC23621
0.8539 High Similarity NPC87095

  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 NPC171789 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
0.8953 High Similarity NPD7515 Phase 2
0.8539 High Similarity NPD7748 Approved
0.8471 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD7902 Approved
0.7976 Intermediate Similarity NPD7645 Phase 2
0.7955 Intermediate Similarity NPD3618 Phase 1
0.7935 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD7900 Approved
0.7931 Intermediate Similarity NPD4786 Approved
0.7907 Intermediate Similarity NPD3667 Approved
0.7889 Intermediate Similarity NPD5328 Approved
0.7889 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7831 Intermediate Similarity NPD6117 Approved
0.7805 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD6116 Phase 1
0.7717 Intermediate Similarity NPD8034 Phase 2
0.7717 Intermediate Similarity NPD8035 Phase 2
0.7717 Intermediate Similarity NPD6079 Approved
0.7647 Intermediate Similarity NPD6114 Approved
0.7647 Intermediate Similarity NPD6697 Approved
0.7647 Intermediate Similarity NPD6118 Approved
0.7647 Intermediate Similarity NPD6115 Approved
0.7634 Intermediate Similarity NPD6399 Phase 3
0.7624 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD3666 Approved
0.7528 Intermediate Similarity NPD3665 Phase 1
0.7528 Intermediate Similarity NPD3133 Approved
0.7447 Intermediate Similarity NPD4202 Approved
0.7423 Intermediate Similarity NPD7638 Approved
0.7396 Intermediate Similarity NPD7614 Phase 1
0.7363 Intermediate Similarity NPD6684 Approved
0.7363 Intermediate Similarity NPD7146 Approved
0.7363 Intermediate Similarity NPD5330 Approved
0.7363 Intermediate Similarity NPD7521 Approved
0.7363 Intermediate Similarity NPD7334 Approved
0.7363 Intermediate Similarity NPD6409 Approved
0.7349 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD7640 Approved
0.7347 Intermediate Similarity NPD7639 Approved
0.734 Intermediate Similarity NPD6411 Approved
0.7327 Intermediate Similarity NPD6402 Approved
0.7327 Intermediate Similarity NPD7128 Approved
0.7327 Intermediate Similarity NPD5739 Approved
0.7327 Intermediate Similarity NPD6675 Approved
0.7317 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD3573 Approved
0.7273 Intermediate Similarity NPD7525 Registered
0.7241 Intermediate Similarity NPD3617 Approved
0.7216 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD5221 Approved
0.7216 Intermediate Similarity NPD4697 Phase 3
0.7216 Intermediate Similarity NPD5222 Approved
0.7204 Intermediate Similarity NPD6903 Approved
0.72 Intermediate Similarity NPD7632 Discontinued
0.7184 Intermediate Similarity NPD7320 Approved
0.7184 Intermediate Similarity NPD6881 Approved
0.7184 Intermediate Similarity NPD6899 Approved
0.7174 Intermediate Similarity NPD5279 Phase 3
0.7143 Intermediate Similarity NPD6083 Phase 2
0.7143 Intermediate Similarity NPD6084 Phase 2
0.7143 Intermediate Similarity NPD4755 Approved
0.7143 Intermediate Similarity NPD3668 Phase 3
0.7143 Intermediate Similarity NPD5173 Approved
0.713 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD6101 Approved
0.7115 Intermediate Similarity NPD6373 Approved
0.7115 Intermediate Similarity NPD6372 Approved
0.7093 Intermediate Similarity NPD3703 Phase 2
0.7093 Intermediate Similarity NPD7339 Approved
0.7093 Intermediate Similarity NPD6942 Approved
0.7087 Intermediate Similarity NPD5697 Approved
0.7087 Intermediate Similarity NPD5701 Approved
0.7048 Intermediate Similarity NPD7290 Approved
0.7048 Intermediate Similarity NPD7102 Approved
0.7048 Intermediate Similarity NPD6883 Approved
0.7041 Intermediate Similarity NPD7732 Phase 3
0.7033 Intermediate Similarity NPD4788 Approved
0.7024 Intermediate Similarity NPD4245 Approved
0.7024 Intermediate Similarity NPD4244 Approved
0.7021 Intermediate Similarity NPD5737 Approved
0.7021 Intermediate Similarity NPD6672 Approved
0.7019 Intermediate Similarity NPD6011 Approved
0.7011 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4692 Approved
0.7 Intermediate Similarity NPD5286 Approved
0.7 Intermediate Similarity NPD4700 Approved
0.7 Intermediate Similarity NPD4696 Approved
0.7 Intermediate Similarity NPD5285 Approved
0.7 Intermediate Similarity NPD4139 Approved
0.6989 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6617 Approved
0.6981 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6981 Remote Similarity NPD6847 Approved
0.6981 Remote Similarity NPD8130 Phase 1
0.6981 Remote Similarity NPD6650 Approved
0.6981 Remote Similarity NPD6869 Approved
0.6981 Remote Similarity NPD6649 Approved
0.6952 Remote Similarity NPD6013 Approved
0.6952 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6952 Remote Similarity NPD6012 Approved
0.6952 Remote Similarity NPD6014 Approved
0.6951 Remote Similarity NPD4224 Phase 2
0.6947 Remote Similarity NPD4753 Phase 2
0.6939 Remote Similarity NPD5695 Phase 3
0.6931 Remote Similarity NPD5223 Approved
0.6923 Remote Similarity NPD4223 Phase 3
0.6923 Remote Similarity NPD4221 Approved
0.6916 Remote Similarity NPD8297 Approved
0.6916 Remote Similarity NPD6882 Approved
0.6905 Remote Similarity NPD3698 Phase 2
0.6889 Remote Similarity NPD4748 Discontinued
0.6889 Remote Similarity NPD4695 Discontinued
0.6882 Remote Similarity NPD5329 Approved
0.6863 Remote Similarity NPD5211 Phase 2
0.6863 Remote Similarity NPD5224 Approved
0.6863 Remote Similarity NPD5225 Approved
0.6863 Remote Similarity NPD4633 Approved
0.6863 Remote Similarity NPD5226 Approved
0.6824 Remote Similarity NPD4789 Approved
0.6818 Remote Similarity NPD7115 Discovery
0.6809 Remote Similarity NPD6098 Approved
0.6804 Remote Similarity NPD5284 Approved
0.6804 Remote Similarity NPD5281 Approved
0.6796 Remote Similarity NPD5174 Approved
0.6796 Remote Similarity NPD4754 Approved
0.6796 Remote Similarity NPD5175 Approved
0.6786 Remote Similarity NPD5360 Phase 3
0.6786 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6774 Remote Similarity NPD4197 Approved
0.6768 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6754 Remote Similarity NPD8328 Phase 3
0.6744 Remote Similarity NPD6081 Approved
0.6744 Remote Similarity NPD5777 Approved
0.6735 Remote Similarity NPD5778 Approved
0.6735 Remote Similarity NPD5779 Approved
0.6733 Remote Similarity NPD5696 Approved
0.6731 Remote Similarity NPD5141 Approved
0.6729 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6868 Approved
0.6702 Remote Similarity NPD1694 Approved
0.6697 Remote Similarity NPD4632 Approved
0.6667 Remote Similarity NPD3671 Phase 1
0.6667 Remote Similarity NPD4768 Approved
0.6667 Remote Similarity NPD4767 Approved
0.6632 Remote Similarity NPD4689 Approved
0.6632 Remote Similarity NPD4138 Approved
0.6632 Remote Similarity NPD4693 Phase 3
0.6632 Remote Similarity NPD4688 Approved
0.6632 Remote Similarity NPD4690 Approved
0.6632 Remote Similarity NPD5280 Approved
0.6632 Remote Similarity NPD5690 Phase 2
0.6632 Remote Similarity NPD4623 Approved
0.6632 Remote Similarity NPD4694 Approved
0.6632 Remote Similarity NPD5205 Approved
0.6632 Remote Similarity NPD4519 Discontinued
0.6627 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6607 Remote Similarity NPD6335 Approved
0.6604 Remote Similarity NPD6412 Phase 2
0.66 Remote Similarity NPD5210 Approved
0.66 Remote Similarity NPD4629 Approved
0.6598 Remote Similarity NPD6673 Approved
0.6598 Remote Similarity NPD6904 Approved
0.6598 Remote Similarity NPD6080 Approved
0.6577 Remote Similarity NPD6274 Approved
0.6569 Remote Similarity NPD4225 Approved
0.6559 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6549 Remote Similarity NPD7100 Approved
0.6549 Remote Similarity NPD7101 Approved
0.6545 Remote Similarity NPD8133 Approved
0.6542 Remote Similarity NPD4729 Approved
0.6542 Remote Similarity NPD5168 Approved
0.6542 Remote Similarity NPD5128 Approved
0.6542 Remote Similarity NPD4730 Approved
0.6522 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6518 Remote Similarity NPD6317 Approved
0.6518 Remote Similarity NPD6009 Approved
0.6517 Remote Similarity NPD8264 Approved
0.6517 Remote Similarity NPD3702 Approved
0.6509 Remote Similarity NPD6008 Approved
0.65 Remote Similarity NPD6001 Approved
0.6495 Remote Similarity NPD5208 Approved
0.6484 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6465 Remote Similarity NPD6050 Approved
0.646 Remote Similarity NPD6314 Approved
0.646 Remote Similarity NPD6313 Approved
0.6452 Remote Similarity NPD8028 Phase 2
0.6449 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6435 Remote Similarity NPD6909 Approved
0.6435 Remote Similarity NPD6908 Approved
0.6429 Remote Similarity NPD7341 Phase 2
0.6422 Remote Similarity NPD5250 Approved
0.6422 Remote Similarity NPD5249 Phase 3
0.6422 Remote Similarity NPD4634 Approved
0.6422 Remote Similarity NPD5247 Approved
0.6422 Remote Similarity NPD5135 Approved
0.6422 Remote Similarity NPD5169 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