Structure

Physi-Chem Properties

Molecular Weight:  220.18
Volume:  248.481
LogP:  3.514
LogD:  3.553
LogS:  -4.455
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.672
Synthetic Accessibility Score:  5.51
Fsp3:  0.867
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.557
MDCK Permeability:  1.0872519851545803e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.709
30% Bioavailability (F30%):  0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.719
Plasma Protein Binding (PPB):  51.49054718017578%
Volume Distribution (VD):  1.252
Pgp-substrate:  42.41127014160156%

ADMET: Metabolism

CYP1A2-inhibitor:  0.238
CYP1A2-substrate:  0.251
CYP2C19-inhibitor:  0.07
CYP2C19-substrate:  0.762
CYP2C9-inhibitor:  0.083
CYP2C9-substrate:  0.217
CYP2D6-inhibitor:  0.028
CYP2D6-substrate:  0.518
CYP3A4-inhibitor:  0.258
CYP3A4-substrate:  0.284

ADMET: Excretion

Clearance (CL):  9.698
Half-life (T1/2):  0.099

ADMET: Toxicity

hERG Blockers:  0.025
Human Hepatotoxicity (H-HT):  0.259
Drug-inuced Liver Injury (DILI):  0.056
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.097
Maximum Recommended Daily Dose:  0.923
Skin Sensitization:  0.823
Carcinogencity:  0.334
Eye Corrosion:  0.892
Eye Irritation:  0.98
Respiratory Toxicity:  0.954

Download Data

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

  Natural Product: NPC147524

Natural Product ID:  NPC147524
Common Name*:   Khusimol
IUPAC Name:   n.a.
Synonyms:   Khusimol
Standard InCHIKey:  OOYRHNIVDZZGQV-BHPKHCPMSA-N
Standard InCHI:  InChI=1S/C15H24O/c1-10-13-5-4-12(9-16)15(13)7-6-11(8-15)14(10,2)3/h11-13,16H,1,4-9H2,2-3H3/t11-,12-,13-,15+/m1/s1
SMILES:  OC[C@H]1CC[C@H]2[C@@]31CC[C@H](C3)C(C2=C)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL511334
PubChem CID:   167519
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
NPO24490 Cussonia bancoensis Species Araliaceae Eukaryota n.a. n.a. n.a. PMID[14510614]
NPO24490 Cussonia bancoensis Species Araliaceae Eukaryota n.a. stem n.a. PMID[21443171]
NPO21741 Araucaria angustifolia Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24869 Nicotiana rustica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21741 Araucaria angustifolia Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24869 Nicotiana rustica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24490 Cussonia bancoensis Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21741 Araucaria angustifolia Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24869 Nicotiana rustica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22352 Lysimachia heterogenea Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24869 Nicotiana rustica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23737 Allium turcomanicum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24110 Lippia alba Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12731 Porodaedalea pini Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24684 Eremanthus crotonoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21741 Araucaria angustifolia Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2617 Dracocephalum multicaule Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14889 Vachellia farnesiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23423 Phellopterus littoralis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24716 Pulvinula constellatio Species Pyronemataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24490 Cussonia bancoensis Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19677 Cephalaria transsylvanica Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22021 Teucrium spinosum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25027 Cynoglossum creticum Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23283 Triptilion benaventei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21168 Erylus lendenfeldi Species Geodiidae 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
NPT4680 Individual Protein Vasopressin V1a receptor Rattus norvegicus IC50 = 125000.0 nM PMID[452441]
NPT4680 Individual Protein Vasopressin V1a receptor Rattus norvegicus Ki = 41000.0 nM PMID[452441]
NPT4680 Individual Protein Vasopressin V1a receptor Rattus norvegicus Ki = 53000.0 nM PMID[452441]

☑ 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 NPC147524 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
0.9194 High Similarity NPC308522
0.9194 High Similarity NPC74885
0.8571 High Similarity NPC476737
0.8571 High Similarity NPC27243
0.8462 Intermediate Similarity NPC160209
0.8413 Intermediate Similarity NPC219940
0.8281 Intermediate Similarity NPC300442
0.8088 Intermediate Similarity NPC111234
0.7971 Intermediate Similarity NPC195489
0.7971 Intermediate Similarity NPC474140
0.7941 Intermediate Similarity NPC45296
0.7879 Intermediate Similarity NPC162309
0.7869 Intermediate Similarity NPC39068
0.7869 Intermediate Similarity NPC264779
0.7857 Intermediate Similarity NPC196358
0.7857 Intermediate Similarity NPC5046
0.7857 Intermediate Similarity NPC145552
0.7857 Intermediate Similarity NPC192638
0.7857 Intermediate Similarity NPC254509
0.7857 Intermediate Similarity NPC49168
0.7857 Intermediate Similarity NPC62657
0.7857 Intermediate Similarity NPC25511
0.7846 Intermediate Similarity NPC101128
0.7846 Intermediate Similarity NPC68656
0.7826 Intermediate Similarity NPC164045
0.7746 Intermediate Similarity NPC231256
0.7746 Intermediate Similarity NPC212879
0.7746 Intermediate Similarity NPC162742
0.7746 Intermediate Similarity NPC200243
0.7746 Intermediate Similarity NPC121744
0.7746 Intermediate Similarity NPC136188
0.7746 Intermediate Similarity NPC22105
0.7746 Intermediate Similarity NPC230301
0.7746 Intermediate Similarity NPC185536
0.7746 Intermediate Similarity NPC322353
0.7746 Intermediate Similarity NPC471468
0.7746 Intermediate Similarity NPC104387
0.7746 Intermediate Similarity NPC240235
0.7746 Intermediate Similarity NPC304309
0.7746 Intermediate Similarity NPC118508
0.7746 Intermediate Similarity NPC134847
0.7746 Intermediate Similarity NPC28657
0.7746 Intermediate Similarity NPC288035
0.7746 Intermediate Similarity NPC70982
0.7746 Intermediate Similarity NPC471723
0.7746 Intermediate Similarity NPC230704
0.7746 Intermediate Similarity NPC178383
0.7746 Intermediate Similarity NPC141071
0.7746 Intermediate Similarity NPC313185
0.7746 Intermediate Similarity NPC3403
0.7746 Intermediate Similarity NPC257347
0.7746 Intermediate Similarity NPC285893
0.7727 Intermediate Similarity NPC2728
0.7727 Intermediate Similarity NPC60837
0.7727 Intermediate Similarity NPC282619
0.7727 Intermediate Similarity NPC11555
0.7727 Intermediate Similarity NPC208198
0.7727 Intermediate Similarity NPC172613
0.7727 Intermediate Similarity NPC258595
0.7714 Intermediate Similarity NPC472506
0.7656 Intermediate Similarity NPC47840
0.7656 Intermediate Similarity NPC135648
0.7656 Intermediate Similarity NPC234264
0.7639 Intermediate Similarity NPC78067
0.7639 Intermediate Similarity NPC470362
0.7639 Intermediate Similarity NPC107059
0.7639 Intermediate Similarity NPC321381
0.7639 Intermediate Similarity NPC244488
0.7639 Intermediate Similarity NPC46160
0.7639 Intermediate Similarity NPC91573
0.7639 Intermediate Similarity NPC93662
0.7639 Intermediate Similarity NPC14112
0.7639 Intermediate Similarity NPC129165
0.7639 Intermediate Similarity NPC113733
0.7639 Intermediate Similarity NPC240604
0.7639 Intermediate Similarity NPC321016
0.7639 Intermediate Similarity NPC189883
0.7639 Intermediate Similarity NPC202642
0.7639 Intermediate Similarity NPC278091
0.7639 Intermediate Similarity NPC86305
0.7639 Intermediate Similarity NPC73875
0.7639 Intermediate Similarity NPC237460
0.7639 Intermediate Similarity NPC300324
0.7639 Intermediate Similarity NPC247325
0.7639 Intermediate Similarity NPC134330
0.7619 Intermediate Similarity NPC189290
0.7619 Intermediate Similarity NPC474769
0.7612 Intermediate Similarity NPC475897
0.7612 Intermediate Similarity NPC473929
0.7606 Intermediate Similarity NPC476736
0.7606 Intermediate Similarity NPC472503
0.7606 Intermediate Similarity NPC309178
0.7606 Intermediate Similarity NPC308440
0.7576 Intermediate Similarity NPC144650
0.7576 Intermediate Similarity NPC475704
0.7541 Intermediate Similarity NPC202146
0.7541 Intermediate Similarity NPC32222
0.7541 Intermediate Similarity NPC286752
0.7538 Intermediate Similarity NPC15152
0.7536 Intermediate Similarity NPC475952
0.7534 Intermediate Similarity NPC248830
0.7534 Intermediate Similarity NPC198968
0.7534 Intermediate Similarity NPC331618
0.7534 Intermediate Similarity NPC214570
0.7534 Intermediate Similarity NPC202540
0.7534 Intermediate Similarity NPC34019
0.7534 Intermediate Similarity NPC318495
0.7534 Intermediate Similarity NPC212241
0.7534 Intermediate Similarity NPC119355
0.7534 Intermediate Similarity NPC257191
0.7534 Intermediate Similarity NPC155986
0.75 Intermediate Similarity NPC253303
0.75 Intermediate Similarity NPC269077
0.75 Intermediate Similarity NPC197805
0.75 Intermediate Similarity NPC171225
0.75 Intermediate Similarity NPC185874
0.75 Intermediate Similarity NPC103822
0.75 Intermediate Similarity NPC139207
0.75 Intermediate Similarity NPC309825
0.7465 Intermediate Similarity NPC201373
0.7465 Intermediate Similarity NPC474743
0.7465 Intermediate Similarity NPC14352
0.7465 Intermediate Similarity NPC234527
0.7463 Intermediate Similarity NPC238352
0.7463 Intermediate Similarity NPC477009
0.746 Intermediate Similarity NPC29976
0.746 Intermediate Similarity NPC150713
0.7432 Intermediate Similarity NPC275910
0.7432 Intermediate Similarity NPC18603
0.7432 Intermediate Similarity NPC186191
0.7432 Intermediate Similarity NPC301707
0.7432 Intermediate Similarity NPC477817
0.7432 Intermediate Similarity NPC6978
0.7432 Intermediate Similarity NPC302041
0.7432 Intermediate Similarity NPC42853
0.7432 Intermediate Similarity NPC65897
0.7432 Intermediate Similarity NPC307965
0.7432 Intermediate Similarity NPC87604
0.7432 Intermediate Similarity NPC31828
0.7432 Intermediate Similarity NPC244385
0.7432 Intermediate Similarity NPC205455
0.7432 Intermediate Similarity NPC472342
0.7432 Intermediate Similarity NPC138621
0.7432 Intermediate Similarity NPC85346
0.7432 Intermediate Similarity NPC473943
0.7432 Intermediate Similarity NPC102708
0.7432 Intermediate Similarity NPC285761
0.7432 Intermediate Similarity NPC477514
0.7432 Intermediate Similarity NPC76931
0.7432 Intermediate Similarity NPC474216
0.7432 Intermediate Similarity NPC477819
0.7432 Intermediate Similarity NPC167037
0.7432 Intermediate Similarity NPC477522
0.7429 Intermediate Similarity NPC133873
0.7429 Intermediate Similarity NPC475728
0.7424 Intermediate Similarity NPC124112
0.7419 Intermediate Similarity NPC84824
0.7419 Intermediate Similarity NPC67508
0.7397 Intermediate Similarity NPC38141
0.7397 Intermediate Similarity NPC96319
0.7391 Intermediate Similarity NPC216460
0.7391 Intermediate Similarity NPC208999
0.7391 Intermediate Similarity NPC244790
0.7391 Intermediate Similarity NPC276616
0.7391 Intermediate Similarity NPC245795
0.7368 Intermediate Similarity NPC87439
0.7361 Intermediate Similarity NPC475517
0.7361 Intermediate Similarity NPC469533
0.7361 Intermediate Similarity NPC102313
0.7361 Intermediate Similarity NPC469593
0.7361 Intermediate Similarity NPC474524
0.7361 Intermediate Similarity NPC199316
0.7361 Intermediate Similarity NPC27395
0.7361 Intermediate Similarity NPC329090
0.7361 Intermediate Similarity NPC469534
0.7353 Intermediate Similarity NPC135650
0.7353 Intermediate Similarity NPC222366
0.7353 Intermediate Similarity NPC286669
0.7353 Intermediate Similarity NPC476406
0.7353 Intermediate Similarity NPC149680
0.7353 Intermediate Similarity NPC476039
0.7344 Intermediate Similarity NPC476735
0.7333 Intermediate Similarity NPC84694
0.7333 Intermediate Similarity NPC273410
0.7333 Intermediate Similarity NPC1319
0.7333 Intermediate Similarity NPC109546
0.7333 Intermediate Similarity NPC209430
0.7333 Intermediate Similarity NPC49627
0.7333 Intermediate Similarity NPC30986
0.7333 Intermediate Similarity NPC81306
0.7333 Intermediate Similarity NPC116119
0.7333 Intermediate Similarity NPC472742
0.7333 Intermediate Similarity NPC475727
0.7333 Intermediate Similarity NPC201459
0.7333 Intermediate Similarity NPC49599
0.7333 Intermediate Similarity NPC80530
0.7333 Intermediate Similarity NPC28862
0.7333 Intermediate Similarity NPC47982
0.7333 Intermediate Similarity NPC80297
0.7333 Intermediate Similarity NPC143182

  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 NPC147524 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
0.7746 Intermediate Similarity NPD6942 Approved
0.7746 Intermediate Similarity NPD7339 Approved
0.7397 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD6926 Approved
0.7361 Intermediate Similarity NPD6924 Approved
0.7324 Intermediate Similarity NPD4243 Approved
0.7286 Intermediate Similarity NPD6922 Approved
0.7286 Intermediate Similarity NPD6923 Approved
0.7237 Intermediate Similarity NPD7525 Registered
0.7183 Intermediate Similarity NPD7143 Approved
0.7183 Intermediate Similarity NPD7144 Approved
0.7162 Intermediate Similarity NPD6933 Approved
0.7123 Intermediate Similarity NPD4784 Approved
0.7123 Intermediate Similarity NPD4785 Approved
0.7083 Intermediate Similarity NPD7152 Approved
0.7083 Intermediate Similarity NPD7151 Approved
0.7083 Intermediate Similarity NPD7150 Approved
0.7027 Intermediate Similarity NPD5275 Approved
0.7027 Intermediate Similarity NPD4190 Phase 3
0.6962 Remote Similarity NPD4788 Approved
0.6883 Remote Similarity NPD6929 Approved
0.6875 Remote Similarity NPD4786 Approved
0.6835 Remote Similarity NPD3667 Approved
0.6795 Remote Similarity NPD6930 Phase 2
0.6795 Remote Similarity NPD4748 Discontinued
0.6795 Remote Similarity NPD6931 Approved
0.679 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6714 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3133 Approved
0.6667 Remote Similarity NPD4195 Approved
0.6667 Remote Similarity NPD3665 Phase 1
0.6667 Remote Similarity NPD3666 Approved
0.6627 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6623 Remote Similarity NPD6932 Approved
0.6623 Remote Similarity NPD6925 Approved
0.6623 Remote Similarity NPD5776 Phase 2
0.6615 Remote Similarity NPD342 Phase 1
0.6582 Remote Similarity NPD7509 Discontinued
0.6543 Remote Similarity NPD6695 Phase 3
0.6538 Remote Similarity NPD7145 Approved
0.6506 Remote Similarity NPD5279 Phase 3
0.6506 Remote Similarity NPD3618 Phase 1
0.6471 Remote Similarity NPD4753 Phase 2
0.6471 Remote Similarity NPD5328 Approved
0.6463 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6456 Remote Similarity NPD6683 Phase 2
0.6456 Remote Similarity NPD7645 Phase 2
0.6438 Remote Similarity NPD6705 Phase 1
0.642 Remote Similarity NPD4223 Phase 3
0.642 Remote Similarity NPD4221 Approved
0.6393 Remote Similarity NPD384 Approved
0.6393 Remote Similarity NPD385 Approved
0.6386 Remote Similarity NPD6893 Approved
0.6375 Remote Similarity NPD7514 Phase 3
0.6351 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6329 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6322 Remote Similarity NPD6079 Approved
0.6296 Remote Similarity NPD6902 Approved
0.6271 Remote Similarity NPD1799 Clinical (unspecified phase)
0.6267 Remote Similarity NPD4789 Approved
0.6267 Remote Similarity NPD4787 Phase 1
0.6265 Remote Similarity NPD4197 Approved
0.625 Remote Similarity NPD4202 Approved
0.6235 Remote Similarity NPD7750 Discontinued
0.6235 Remote Similarity NPD7524 Approved
0.619 Remote Similarity NPD5329 Approved
0.6184 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6184 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6173 Remote Similarity NPD7332 Phase 2
0.6143 Remote Similarity NPD1145 Discontinued
0.6136 Remote Similarity NPD8035 Phase 2
0.6136 Remote Similarity NPD8034 Phase 2
0.6133 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6133 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6133 Remote Similarity NPD3698 Phase 2
0.6125 Remote Similarity NPD3617 Approved
0.6118 Remote Similarity NPD4690 Approved
0.6118 Remote Similarity NPD4693 Phase 3
0.6118 Remote Similarity NPD5205 Approved
0.6118 Remote Similarity NPD5690 Phase 2
0.6118 Remote Similarity NPD4138 Approved
0.6118 Remote Similarity NPD4694 Approved
0.6118 Remote Similarity NPD4689 Approved
0.6118 Remote Similarity NPD4688 Approved
0.6118 Remote Similarity NPD5280 Approved
0.6111 Remote Similarity NPD5210 Approved
0.6111 Remote Similarity NPD4629 Approved
0.6098 Remote Similarity NPD4139 Approved
0.6098 Remote Similarity NPD4692 Approved
0.6098 Remote Similarity NPD6898 Phase 1
0.6071 Remote Similarity NPD3668 Phase 3
0.6067 Remote Similarity NPD6399 Phase 3
0.6056 Remote Similarity NPD368 Approved
0.6053 Remote Similarity NPD4245 Approved
0.6053 Remote Similarity NPD4244 Approved
0.6044 Remote Similarity NPD5221 Approved
0.6044 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6044 Remote Similarity NPD4697 Phase 3
0.6044 Remote Similarity NPD5222 Approved
0.6026 Remote Similarity NPD6113 Clinical (unspecified phase)
0.5978 Remote Similarity NPD4755 Approved
0.5978 Remote Similarity NPD6083 Phase 2
0.5978 Remote Similarity NPD6084 Phase 2
0.5978 Remote Similarity NPD5173 Approved
0.5977 Remote Similarity NPD6903 Approved
0.5977 Remote Similarity NPD4722 Approved
0.5977 Remote Similarity NPD4723 Approved
0.5955 Remote Similarity NPD7087 Discontinued
0.5949 Remote Similarity NPD8264 Approved
0.5934 Remote Similarity NPD5695 Phase 3
0.5875 Remote Similarity NPD1346 Approved
0.5875 Remote Similarity NPD6117 Approved
0.5851 Remote Similarity NPD5285 Approved
0.5851 Remote Similarity NPD4696 Approved
0.5851 Remote Similarity NPD5286 Approved
0.5851 Remote Similarity NPD4700 Approved
0.5802 Remote Similarity NPD6116 Phase 1
0.5797 Remote Similarity NPD4219 Approved
0.5795 Remote Similarity NPD5737 Approved
0.5795 Remote Similarity NPD6672 Approved
0.5789 Remote Similarity NPD5223 Approved
0.5789 Remote Similarity NPD5360 Phase 3
0.5789 Remote Similarity NPD5361 Clinical (unspecified phase)
0.5783 Remote Similarity NPD6928 Phase 2
0.5778 Remote Similarity NPD5281 Approved
0.5778 Remote Similarity NPD5284 Approved
0.5765 Remote Similarity NPD5332 Approved
0.5765 Remote Similarity NPD5331 Approved
0.5758 Remote Similarity NPD7320 Approved
0.575 Remote Similarity NPD3703 Phase 2
0.575 Remote Similarity NPD3702 Approved
0.5747 Remote Similarity NPD7521 Approved
0.5747 Remote Similarity NPD5330 Approved
0.5747 Remote Similarity NPD7334 Approved
0.5747 Remote Similarity NPD6409 Approved
0.5747 Remote Similarity NPD7146 Approved
0.5747 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5747 Remote Similarity NPD6684 Approved
0.5745 Remote Similarity NPD5696 Approved
0.5745 Remote Similarity NPD7638 Approved
0.5745 Remote Similarity NPD5290 Discontinued
0.5733 Remote Similarity NPD4224 Phase 2
0.5732 Remote Similarity NPD6697 Approved
0.5732 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5732 Remote Similarity NPD6115 Approved
0.5732 Remote Similarity NPD6114 Approved
0.5732 Remote Similarity NPD6118 Approved
0.573 Remote Similarity NPD6051 Approved
0.5729 Remote Similarity NPD5226 Approved
0.5729 Remote Similarity NPD5224 Approved
0.5729 Remote Similarity NPD5225 Approved
0.5729 Remote Similarity NPD5211 Phase 2
0.5729 Remote Similarity NPD4633 Approved
0.5714 Remote Similarity NPD388 Approved
0.5714 Remote Similarity NPD386 Approved
0.5714 Remote Similarity NPD4790 Discontinued
0.5684 Remote Similarity NPD7640 Approved
0.5684 Remote Similarity NPD7639 Approved
0.567 Remote Similarity NPD5175 Approved
0.567 Remote Similarity NPD4754 Approved
0.567 Remote Similarity NPD5174 Approved
0.5667 Remote Similarity NPD4096 Approved
0.5641 Remote Similarity NPD4747 Approved
0.5632 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5618 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5612 Remote Similarity NPD5141 Approved
0.5604 Remote Similarity NPD7637 Suspended
0.5604 Remote Similarity NPD7515 Phase 2

  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