Structure

Physi-Chem Properties

Molecular Weight:  488.39
Volume:  540.394
LogP:  5.752
LogD:  4.458
LogS:  -4.961
# Rotatable Bonds:  5
TPSA:  69.92
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.421
Synthetic Accessibility Score:  5.357
Fsp3:  0.871
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:  -4.787
MDCK Permeability:  1.8052185623673722e-05
Pgp-inhibitor:  0.985
Pgp-substrate:  0.089
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.44
30% Bioavailability (F30%):  0.793

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.314
Plasma Protein Binding (PPB):  90.5491943359375%
Volume Distribution (VD):  1.111
Pgp-substrate:  7.248220443725586%

ADMET: Metabolism

CYP1A2-inhibitor:  0.013
CYP1A2-substrate:  0.181
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.896
CYP2C9-inhibitor:  0.17
CYP2C9-substrate:  0.198
CYP2D6-inhibitor:  0.032
CYP2D6-substrate:  0.378
CYP3A4-inhibitor:  0.732
CYP3A4-substrate:  0.562

ADMET: Excretion

Clearance (CL):  7.089
Half-life (T1/2):  0.113

ADMET: Toxicity

hERG Blockers:  0.395
Human Hepatotoxicity (H-HT):  0.214
Drug-inuced Liver Injury (DILI):  0.045
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.986
Maximum Recommended Daily Dose:  0.983
Skin Sensitization:  0.167
Carcinogencity:  0.045
Eye Corrosion:  0.003
Eye Irritation:  0.011
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: NPC295668

Natural Product ID:  NPC295668
Common Name*:   (3S,7S,8R,9S,10S,12R,13R,14S,17R)-17-[(E,2R)-6-Hydroxy-6-Methylhept-4-En-2-Yl]-7-Methoxy-4,4,9,13,14-Pentamethyl-2,3,7,8,10,11,12,15,16,17-Decahydro-1H-Cyclopenta[A]Phenanthrene-3,12-Diol
IUPAC Name:   (3S,7S,8R,9S,10S,12R,13R,14S,17R)-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-7-methoxy-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,12-diol
Synonyms:  
Standard InCHIKey:  OSNWCRUHKQXEMA-KOBRMIIQSA-N
Standard InCHI:  InChI=1S/C31H52O4/c1-19(11-10-15-27(2,3)34)20-14-16-30(7)26-23(35-9)17-22-21(12-13-24(32)28(22,4)5)29(26,6)18-25(33)31(20,30)8/h10,15,17,19-21,23-26,32-34H,11-14,16,18H2,1-9H3/b15-10+/t19-,20-,21-,23+,24+,25-,26-,29+,30+,31+/m1/s1
SMILES:  CO[C@H]1C=C2[C@H]([C@]3([C@@H]1[C@]1(C)CC[C@@H]([C@]1([C@@H](C3)O)C)[C@@H](C/C=C/C(O)(C)C)C)C)CC[C@@H](C2(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1253844
PubChem CID:   44607451
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001686] Cucurbitacins

*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
NPO22328 Momordica balsamina Species Cucurbitaceae Eukaryota n.a. African n.a. PMID[19795842]
NPO22328 Momordica balsamina Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[20541427]
NPO22328 Momordica balsamina Species Cucurbitaceae Eukaryota n.a. n.a. n.a. PMID[31339732]
NPO22328 Momordica balsamina Species Cucurbitaceae 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
NPT83 Cell Line MCF7 Homo sapiens IC50 = 55400.0 nM PMID[464562]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 17700.0 nM PMID[464562]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 28300.0 nM PMID[464562]
NPT2 Others Unspecified Selectivity Index = 3.1 n.a. PMID[464562]
NPT2 Others Unspecified Selectivity Index = 2.0 n.a. PMID[464562]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 46300.0 nM PMID[464563]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 44400.0 nM PMID[464563]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 568.6 n.a. PMID[464563]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 585.0 n.a. PMID[464563]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 249.6 n.a. PMID[464563]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Activity = 235.8 n.a. PMID[464563]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Flu intensity = 27.2 n.a. PMID[464563]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Flu intensity = 391.6 n.a. PMID[464563]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 2.7 n.a. PMID[464563]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Ratio = 38.2 n.a. PMID[464563]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens CI = 0.393 n.a. PMID[464563]

☑ 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 NPC295668 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
0.9524 High Similarity NPC261266
0.9412 High Similarity NPC149224
0.9405 High Similarity NPC274448
0.9294 High Similarity NPC6391
0.9286 High Similarity NPC470077
0.9222 High Similarity NPC288970
0.9213 High Similarity NPC144202
0.9176 High Similarity NPC157257
0.9176 High Similarity NPC266511
0.9101 High Similarity NPC27531
0.9059 High Similarity NPC205845
0.9048 High Similarity NPC470049
0.9048 High Similarity NPC49964
0.9048 High Similarity NPC50964
0.9011 High Similarity NPC72204
0.9 High Similarity NPC65402
0.9 High Similarity NPC127718
0.8989 High Similarity NPC41554
0.8989 High Similarity NPC97404
0.8953 High Similarity NPC470360
0.8941 High Similarity NPC470558
0.8929 High Similarity NPC7505
0.8929 High Similarity NPC264245
0.8929 High Similarity NPC23852
0.8929 High Similarity NPC474752
0.8929 High Similarity NPC209620
0.8929 High Similarity NPC474683
0.8929 High Similarity NPC474759
0.8929 High Similarity NPC82986
0.8929 High Similarity NPC474731
0.8901 High Similarity NPC8774
0.8876 High Similarity NPC291484
0.8876 High Similarity NPC204188
0.8876 High Similarity NPC3345
0.8876 High Similarity NPC80561
0.8876 High Similarity NPC11216
0.8876 High Similarity NPC329596
0.8864 High Similarity NPC133588
0.8864 High Similarity NPC474668
0.8851 High Similarity NPC299068
0.8851 High Similarity NPC152808
0.8851 High Similarity NPC293287
0.8824 High Similarity NPC87489
0.8824 High Similarity NPC296701
0.8824 High Similarity NPC218616
0.8824 High Similarity NPC101462
0.881 High Similarity NPC164840
0.881 High Similarity NPC241290
0.881 High Similarity NPC209944
0.881 High Similarity NPC234193
0.8804 High Similarity NPC12103
0.8804 High Similarity NPC227583
0.8804 High Similarity NPC98457
0.8778 High Similarity NPC234335
0.8764 High Similarity NPC470361
0.8736 High Similarity NPC318390
0.8721 High Similarity NPC475789
0.8721 High Similarity NPC474634
0.8706 High Similarity NPC476646
0.8706 High Similarity NPC47761
0.869 High Similarity NPC143182
0.869 High Similarity NPC28862
0.869 High Similarity NPC81306
0.869 High Similarity NPC109546
0.869 High Similarity NPC30986
0.869 High Similarity NPC47982
0.869 High Similarity NPC84694
0.869 High Similarity NPC209430
0.8652 High Similarity NPC471952
0.8636 High Similarity NPC139724
0.8621 High Similarity NPC231310
0.8621 High Similarity NPC238485
0.8621 High Similarity NPC185568
0.8621 High Similarity NPC124172
0.8621 High Similarity NPC474047
0.8602 High Similarity NPC276103
0.8602 High Similarity NPC54248
0.8588 High Similarity NPC96362
0.8587 High Similarity NPC474922
0.8571 High Similarity NPC474216
0.8571 High Similarity NPC177641
0.8571 High Similarity NPC87604
0.8557 High Similarity NPC473543
0.8542 High Similarity NPC471482
0.8542 High Similarity NPC300399
0.8511 High Similarity NPC261807
0.8511 High Similarity NPC126815
0.8506 High Similarity NPC317458
0.8506 High Similarity NPC82623
0.8488 Intermediate Similarity NPC470383
0.8488 Intermediate Similarity NPC249423
0.8478 Intermediate Similarity NPC310013
0.8462 Intermediate Similarity NPC470390
0.8462 Intermediate Similarity NPC270511
0.8462 Intermediate Similarity NPC14380
0.8462 Intermediate Similarity NPC192437
0.8462 Intermediate Similarity NPC245410
0.8454 Intermediate Similarity NPC471888
0.8454 Intermediate Similarity NPC471887
0.8454 Intermediate Similarity NPC471885
0.8454 Intermediate Similarity NPC473523
0.8454 Intermediate Similarity NPC471886
0.8452 Intermediate Similarity NPC91594
0.8452 Intermediate Similarity NPC155986
0.8452 Intermediate Similarity NPC471798
0.8452 Intermediate Similarity NPC198968
0.8452 Intermediate Similarity NPC318495
0.8444 Intermediate Similarity NPC280556
0.8438 Intermediate Similarity NPC475617
0.8427 Intermediate Similarity NPC94462
0.8427 Intermediate Similarity NPC24277
0.8421 Intermediate Similarity NPC218107
0.8409 Intermediate Similarity NPC474493
0.8409 Intermediate Similarity NPC475798
0.8409 Intermediate Similarity NPC209802
0.8409 Intermediate Similarity NPC127606
0.8409 Intermediate Similarity NPC83702
0.8404 Intermediate Similarity NPC210717
0.8404 Intermediate Similarity NPC103165
0.8391 Intermediate Similarity NPC470614
0.8391 Intermediate Similarity NPC189972
0.8391 Intermediate Similarity NPC248886
0.8391 Intermediate Similarity NPC1272
0.8391 Intermediate Similarity NPC30166
0.8391 Intermediate Similarity NPC155521
0.8391 Intermediate Similarity NPC202389
0.8387 Intermediate Similarity NPC119562
0.8387 Intermediate Similarity NPC279410
0.8372 Intermediate Similarity NPC322313
0.8372 Intermediate Similarity NPC236237
0.8372 Intermediate Similarity NPC102253
0.8372 Intermediate Similarity NPC26117
0.837 Intermediate Similarity NPC210268
0.837 Intermediate Similarity NPC275671
0.8353 Intermediate Similarity NPC275910
0.8353 Intermediate Similarity NPC473943
0.8353 Intermediate Similarity NPC285761
0.8352 Intermediate Similarity NPC101886
0.8351 Intermediate Similarity NPC476471
0.8351 Intermediate Similarity NPC475344
0.8351 Intermediate Similarity NPC37207
0.8351 Intermediate Similarity NPC471889
0.8333 Intermediate Similarity NPC129165
0.8333 Intermediate Similarity NPC300324
0.8333 Intermediate Similarity NPC240604
0.8333 Intermediate Similarity NPC321016
0.8333 Intermediate Similarity NPC107059
0.8333 Intermediate Similarity NPC244488
0.8333 Intermediate Similarity NPC476948
0.8333 Intermediate Similarity NPC189883
0.8333 Intermediate Similarity NPC253190
0.8333 Intermediate Similarity NPC247325
0.8333 Intermediate Similarity NPC134330
0.8333 Intermediate Similarity NPC113733
0.8333 Intermediate Similarity NPC265588
0.8333 Intermediate Similarity NPC321381
0.8316 Intermediate Similarity NPC291634
0.8316 Intermediate Similarity NPC99726
0.8316 Intermediate Similarity NPC476893
0.8298 Intermediate Similarity NPC476894
0.8298 Intermediate Similarity NPC477969
0.8298 Intermediate Similarity NPC135224
0.8295 Intermediate Similarity NPC141941
0.8295 Intermediate Similarity NPC134481
0.8295 Intermediate Similarity NPC477818
0.8295 Intermediate Similarity NPC470384
0.8295 Intermediate Similarity NPC110778
0.8295 Intermediate Similarity NPC193870
0.8276 Intermediate Similarity NPC474531
0.8265 Intermediate Similarity NPC474124
0.8265 Intermediate Similarity NPC36688
0.8265 Intermediate Similarity NPC471450
0.8256 Intermediate Similarity NPC1319
0.8256 Intermediate Similarity NPC472463
0.8256 Intermediate Similarity NPC328714
0.8256 Intermediate Similarity NPC80530
0.8256 Intermediate Similarity NPC273410
0.8247 Intermediate Similarity NPC295110
0.8247 Intermediate Similarity NPC25177
0.8247 Intermediate Similarity NPC268829
0.8247 Intermediate Similarity NPC222875
0.8247 Intermediate Similarity NPC247701
0.8242 Intermediate Similarity NPC212596
0.8242 Intermediate Similarity NPC67872
0.8242 Intermediate Similarity NPC470542
0.8242 Intermediate Similarity NPC475605
0.8242 Intermediate Similarity NPC4574
0.8235 Intermediate Similarity NPC214570
0.8235 Intermediate Similarity NPC470758
0.8235 Intermediate Similarity NPC470711
0.8229 Intermediate Similarity NPC476895
0.8222 Intermediate Similarity NPC474970
0.8222 Intermediate Similarity NPC6605
0.8222 Intermediate Similarity NPC201273
0.8214 Intermediate Similarity NPC28657
0.8214 Intermediate Similarity NPC471723
0.8214 Intermediate Similarity NPC22105
0.8214 Intermediate Similarity NPC257347
0.8214 Intermediate Similarity NPC285893
0.8214 Intermediate Similarity NPC134847

  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 NPC295668 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
0.8372 Intermediate Similarity NPD7525 Registered
0.8333 Intermediate Similarity NPD4751 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD7339 Approved
0.8214 Intermediate Similarity NPD6942 Approved
0.8144 Intermediate Similarity NPD7640 Approved
0.8144 Intermediate Similarity NPD7639 Approved
0.809 Intermediate Similarity NPD6695 Phase 3
0.8041 Intermediate Similarity NPD7638 Approved
0.8 Intermediate Similarity NPD7338 Clinical (unspecified phase)
0.7955 Intermediate Similarity NPD6930 Phase 2
0.7955 Intermediate Similarity NPD7514 Phase 3
0.7955 Intermediate Similarity NPD6931 Approved
0.7907 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7841 Intermediate Similarity NPD6929 Approved
0.7753 Intermediate Similarity NPD7332 Phase 2
0.7742 Intermediate Similarity NPD7524 Approved
0.7742 Intermediate Similarity NPD7750 Discontinued
0.7727 Intermediate Similarity NPD7145 Approved
0.7674 Intermediate Similarity NPD4785 Approved
0.7674 Intermediate Similarity NPD4784 Approved
0.7674 Intermediate Similarity NPD6924 Approved
0.7674 Intermediate Similarity NPD6926 Approved
0.7667 Intermediate Similarity NPD6902 Approved
0.764 Intermediate Similarity NPD7645 Phase 2
0.7614 Intermediate Similarity NPD6932 Approved
0.7614 Intermediate Similarity NPD5776 Phase 2
0.7614 Intermediate Similarity NPD6925 Approved
0.7609 Intermediate Similarity NPD4786 Approved
0.7528 Intermediate Similarity NPD7322 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD6893 Approved
0.75 Intermediate Similarity NPD6933 Approved
0.7451 Intermediate Similarity NPD7632 Discontinued
0.7442 Intermediate Similarity NPD4243 Approved
0.7442 Intermediate Similarity NPD7151 Approved
0.7442 Intermediate Similarity NPD7152 Approved
0.7442 Intermediate Similarity NPD7150 Approved
0.7423 Intermediate Similarity NPD7087 Discontinued
0.7423 Intermediate Similarity NPD6079 Approved
0.7396 Intermediate Similarity NPD5328 Approved
0.7396 Intermediate Similarity NPD6051 Approved
0.7391 Intermediate Similarity NPD3667 Approved
0.7386 Intermediate Similarity NPD8264 Approved
0.7364 Intermediate Similarity NPD7115 Discovery
0.7363 Intermediate Similarity NPD4748 Discontinued
0.7326 Intermediate Similarity NPD7143 Approved
0.7326 Intermediate Similarity NPD7144 Approved
0.7283 Intermediate Similarity NPD6898 Phase 1
0.7282 Intermediate Similarity NPD5211 Phase 2
0.7263 Intermediate Similarity NPD3618 Phase 1
0.7253 Intermediate Similarity NPD6683 Phase 2
0.7245 Intermediate Similarity NPD7637 Suspended
0.7209 Intermediate Similarity NPD6922 Approved
0.7209 Intermediate Similarity NPD6923 Approved
0.7174 Intermediate Similarity NPD7509 Discontinued
0.7172 Intermediate Similarity NPD6399 Phase 3
0.7172 Intermediate Similarity NPD4202 Approved
0.7143 Intermediate Similarity NPD7328 Approved
0.7143 Intermediate Similarity NPD7327 Approved
0.7143 Intermediate Similarity NPD5141 Approved
0.7129 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD5222 Approved
0.7129 Intermediate Similarity NPD5221 Approved
0.7105 Intermediate Similarity NPD7503 Approved
0.7105 Intermediate Similarity NPD8033 Approved
0.7087 Intermediate Similarity NPD5285 Approved
0.7087 Intermediate Similarity NPD5286 Approved
0.7087 Intermediate Similarity NPD4696 Approved
0.708 Intermediate Similarity NPD7516 Approved
0.7065 Intermediate Similarity NPD4195 Approved
0.7059 Intermediate Similarity NPD5173 Approved
0.7059 Intermediate Similarity NPD4755 Approved
0.7019 Intermediate Similarity NPD5223 Approved
0.7019 Intermediate Similarity NPD4159 Approved
0.7018 Intermediate Similarity NPD8294 Approved
0.7018 Intermediate Similarity NPD8377 Approved
0.7 Intermediate Similarity NPD5275 Approved
0.7 Intermediate Similarity NPD4190 Phase 3
0.699 Remote Similarity NPD4225 Approved
0.6961 Remote Similarity NPD4697 Phase 3
0.6957 Remote Similarity NPD8335 Approved
0.6957 Remote Similarity NPD8380 Approved
0.6957 Remote Similarity NPD8296 Approved
0.6957 Remote Similarity NPD8378 Approved
0.6957 Remote Similarity NPD8379 Approved
0.6952 Remote Similarity NPD5224 Approved
0.6952 Remote Similarity NPD5225 Approved
0.6952 Remote Similarity NPD4633 Approved
0.6952 Remote Similarity NPD5226 Approved
0.6944 Remote Similarity NPD6881 Approved
0.6944 Remote Similarity NPD6899 Approved
0.6937 Remote Similarity NPD4632 Approved
0.6923 Remote Similarity NPD4700 Approved
0.6916 Remote Similarity NPD7128 Approved
0.6916 Remote Similarity NPD5739 Approved
0.6916 Remote Similarity NPD6675 Approved
0.6916 Remote Similarity NPD6402 Approved
0.6887 Remote Similarity NPD5175 Approved
0.6887 Remote Similarity NPD5174 Approved
0.6875 Remote Similarity NPD3666 Approved
0.6875 Remote Similarity NPD3668 Phase 3
0.6875 Remote Similarity NPD3133 Approved
0.6875 Remote Similarity NPD3665 Phase 1
0.687 Remote Similarity NPD7741 Discontinued
0.6869 Remote Similarity NPD4753 Phase 2
0.6857 Remote Similarity NPD5344 Discontinued
0.6852 Remote Similarity NPD5697 Approved
0.6818 Remote Similarity NPD7102 Approved
0.6818 Remote Similarity NPD4634 Approved
0.6818 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6818 Remote Similarity NPD6883 Approved
0.6818 Remote Similarity NPD7290 Approved
0.6804 Remote Similarity NPD7520 Clinical (unspecified phase)
0.68 Remote Similarity NPD7136 Phase 2
0.6789 Remote Similarity NPD6011 Approved
0.6789 Remote Similarity NPD7320 Approved
0.6759 Remote Similarity NPD6008 Approved
0.6757 Remote Similarity NPD6617 Approved
0.6757 Remote Similarity NPD6869 Approved
0.6757 Remote Similarity NPD6649 Approved
0.6757 Remote Similarity NPD6847 Approved
0.6757 Remote Similarity NPD6650 Approved
0.6757 Remote Similarity NPD8130 Phase 1
0.6754 Remote Similarity NPD6009 Approved
0.6733 Remote Similarity NPD7515 Phase 2
0.6731 Remote Similarity NPD6083 Phase 2
0.6731 Remote Similarity NPD6084 Phase 2
0.6729 Remote Similarity NPD4754 Approved
0.6727 Remote Similarity NPD6014 Approved
0.6727 Remote Similarity NPD6373 Approved
0.6727 Remote Similarity NPD6372 Approved
0.6727 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6013 Approved
0.6727 Remote Similarity NPD6012 Approved
0.6724 Remote Similarity NPD6054 Approved
0.6723 Remote Similarity NPD7507 Approved
0.6699 Remote Similarity NPD5210 Approved
0.6699 Remote Similarity NPD4629 Approved
0.6697 Remote Similarity NPD5701 Approved
0.6696 Remote Similarity NPD6053 Discontinued
0.6696 Remote Similarity NPD6882 Approved
0.6696 Remote Similarity NPD8297 Approved
0.6667 Remote Similarity NPD4223 Phase 3
0.6667 Remote Similarity NPD4221 Approved
0.6667 Remote Similarity NPD5290 Discontinued
0.6636 Remote Similarity NPD4729 Approved
0.6636 Remote Similarity NPD4730 Approved
0.6633 Remote Similarity NPD5329 Approved
0.661 Remote Similarity NPD6370 Approved
0.6607 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6606 Remote Similarity NPD4768 Approved
0.6606 Remote Similarity NPD4767 Approved
0.6606 Remote Similarity NPD6640 Phase 3
0.6604 Remote Similarity NPD6648 Approved
0.6602 Remote Similarity NPD7748 Approved
0.6588 Remote Similarity NPD368 Approved
0.6581 Remote Similarity NPD6319 Approved
0.6581 Remote Similarity NPD6059 Approved
0.6569 Remote Similarity NPD8034 Phase 2
0.6569 Remote Similarity NPD8035 Phase 2
0.6566 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6566 Remote Similarity NPD5279 Phase 3
0.6566 Remote Similarity NPD4519 Discontinued
0.6566 Remote Similarity NPD4623 Approved
0.6557 Remote Similarity NPD7319 Approved
0.6555 Remote Similarity NPD7604 Phase 2
0.6545 Remote Similarity NPD6412 Phase 2
0.6531 Remote Similarity NPD4197 Approved
0.6525 Remote Similarity NPD5983 Phase 2
0.6525 Remote Similarity NPD6015 Approved
0.6525 Remote Similarity NPD6016 Approved
0.6518 Remote Similarity NPD5135 Approved
0.6518 Remote Similarity NPD5250 Approved
0.6518 Remote Similarity NPD5249 Phase 3
0.6518 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6518 Remote Similarity NPD5169 Approved
0.6518 Remote Similarity NPD5248 Approved
0.6518 Remote Similarity NPD5251 Approved
0.6518 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6518 Remote Similarity NPD5247 Approved
0.6505 Remote Similarity NPD5779 Approved
0.6505 Remote Similarity NPD5778 Approved
0.65 Remote Similarity NPD7492 Approved
0.6486 Remote Similarity NPD5128 Approved
0.6486 Remote Similarity NPD5168 Approved
0.6486 Remote Similarity NPD6686 Approved
0.6471 Remote Similarity NPD5988 Approved
0.646 Remote Similarity NPD5127 Approved
0.646 Remote Similarity NPD5215 Approved
0.646 Remote Similarity NPD5217 Approved
0.646 Remote Similarity NPD5216 Approved
0.6446 Remote Similarity NPD6336 Discontinued
0.6446 Remote Similarity NPD6616 Approved
0.6436 Remote Similarity NPD6672 Approved
0.6436 Remote Similarity NPD5737 Approved
0.6429 Remote Similarity NPD5362 Discontinued
0.6429 Remote Similarity NPD4788 Approved
0.6421 Remote Similarity NPD6115 Approved
0.6421 Remote Similarity NPD6697 Approved
0.6421 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6421 Remote Similarity NPD6118 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