Structure

Physi-Chem Properties

Molecular Weight:  344.2
Volume:  362.161
LogP:  4.07
LogD:  3.69
LogS:  -4.476
# Rotatable Bonds:  2
TPSA:  59.67
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.738
Synthetic Accessibility Score:  4.655
Fsp3:  0.667
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:  -4.868
MDCK Permeability:  2.1828891476616263e-05
Pgp-inhibitor:  0.257
Pgp-substrate:  0.049
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.225
30% Bioavailability (F30%):  0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.058
Plasma Protein Binding (PPB):  95.49586486816406%
Volume Distribution (VD):  1.208
Pgp-substrate:  5.23335599899292%

ADMET: Metabolism

CYP1A2-inhibitor:  0.298
CYP1A2-substrate:  0.958
CYP2C19-inhibitor:  0.306
CYP2C19-substrate:  0.845
CYP2C9-inhibitor:  0.418
CYP2C9-substrate:  0.239
CYP2D6-inhibitor:  0.024
CYP2D6-substrate:  0.124
CYP3A4-inhibitor:  0.826
CYP3A4-substrate:  0.771

ADMET: Excretion

Clearance (CL):  10.493
Half-life (T1/2):  0.414

ADMET: Toxicity

hERG Blockers:  0.356
Human Hepatotoxicity (H-HT):  0.695
Drug-inuced Liver Injury (DILI):  0.271
AMES Toxicity:  0.04
Rat Oral Acute Toxicity:  0.738
Maximum Recommended Daily Dose:  0.821
Skin Sensitization:  0.625
Carcinogencity:  0.847
Eye Corrosion:  0.004
Eye Irritation:  0.02
Respiratory Toxicity:  0.965

Download Data

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

  Natural Product: NPC472302

Natural Product ID:  NPC472302
Common Name*:   MKJJWVLPTZDSTH-PCKVVBOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MKJJWVLPTZDSTH-PCKVVBOYSA-N
Standard InCHI:  InChI=1S/C21H28O4/c1-12-13-6-7-17-20(2,8-5-9-21(17,3)19(23)24-4)15(13)11-16-14(12)10-18(22)25-16/h10-13,15,17H,5-9H2,1-4H3/t12-,13+,15+,17-,20-,21-/m1/s1
SMILES:  CC1C2CCC3C(C2C=C4C1=CC(=O)O4)(CCCC3(C)C(=O)OC)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3358073
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001634] Naphthofurans

*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
NPO32931 pterolobium macropterum Species Fabaceae Eukaryota Root Bark n.a. n.a. PMID[25337628]

☑ 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
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 94410.0 nM PMID[547831]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 47580.0 nM PMID[547831]

☑ 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 NPC472302 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
0.8941 High Similarity NPC189311
0.8864 High Similarity NPC212679
0.8864 High Similarity NPC220454
0.8864 High Similarity NPC469595
0.881 High Similarity NPC200513
0.8736 High Similarity NPC477228
0.8681 High Similarity NPC295347
0.8659 High Similarity NPC54996
0.8636 High Similarity NPC226863
0.8539 High Similarity NPC5509
0.8539 High Similarity NPC284561
0.8506 High Similarity NPC65661
0.8495 Intermediate Similarity NPC208094
0.8488 Intermediate Similarity NPC193198
0.8462 Intermediate Similarity NPC472303
0.8444 Intermediate Similarity NPC469372
0.8444 Intermediate Similarity NPC8062
0.8434 Intermediate Similarity NPC472300
0.8434 Intermediate Similarity NPC316500
0.8421 Intermediate Similarity NPC168319
0.8421 Intermediate Similarity NPC194028
0.8387 Intermediate Similarity NPC112654
0.8372 Intermediate Similarity NPC268122
0.837 Intermediate Similarity NPC84893
0.837 Intermediate Similarity NPC477129
0.837 Intermediate Similarity NPC477130
0.8352 Intermediate Similarity NPC289479
0.8333 Intermediate Similarity NPC173042
0.8333 Intermediate Similarity NPC174342
0.8315 Intermediate Similarity NPC163016
0.8315 Intermediate Similarity NPC75315
0.8295 Intermediate Similarity NPC86316
0.8295 Intermediate Similarity NPC106416
0.828 Intermediate Similarity NPC209355
0.8276 Intermediate Similarity NPC118423
0.8276 Intermediate Similarity NPC22611
0.8261 Intermediate Similarity NPC475657
0.8261 Intermediate Similarity NPC1108
0.8256 Intermediate Similarity NPC40228
0.8256 Intermediate Similarity NPC282293
0.8242 Intermediate Similarity NPC51486
0.8242 Intermediate Similarity NPC101651
0.8242 Intermediate Similarity NPC280592
0.8242 Intermediate Similarity NPC253177
0.8242 Intermediate Similarity NPC159748
0.8242 Intermediate Similarity NPC213636
0.8222 Intermediate Similarity NPC24816
0.8202 Intermediate Similarity NPC168248
0.8202 Intermediate Similarity NPC220478
0.8191 Intermediate Similarity NPC319692
0.8191 Intermediate Similarity NPC325960
0.8182 Intermediate Similarity NPC149869
0.8182 Intermediate Similarity NPC318515
0.8182 Intermediate Similarity NPC30486
0.8182 Intermediate Similarity NPC71626
0.8172 Intermediate Similarity NPC38830
0.8161 Intermediate Similarity NPC94200
0.8161 Intermediate Similarity NPC186276
0.8152 Intermediate Similarity NPC296114
0.8152 Intermediate Similarity NPC471329
0.814 Intermediate Similarity NPC195424
0.8125 Intermediate Similarity NPC477720
0.8125 Intermediate Similarity NPC54705
0.8118 Intermediate Similarity NPC4827
0.8118 Intermediate Similarity NPC471220
0.8111 Intermediate Similarity NPC125925
0.8111 Intermediate Similarity NPC312561
0.8111 Intermediate Similarity NPC181327
0.8105 Intermediate Similarity NPC38530
0.8105 Intermediate Similarity NPC84335
0.8105 Intermediate Similarity NPC476768
0.8105 Intermediate Similarity NPC110937
0.8095 Intermediate Similarity NPC899
0.809 Intermediate Similarity NPC474013
0.809 Intermediate Similarity NPC323765
0.8085 Intermediate Similarity NPC33473
0.8085 Intermediate Similarity NPC171395
0.8081 Intermediate Similarity NPC34768
0.8081 Intermediate Similarity NPC266570
0.8068 Intermediate Similarity NPC474976
0.8068 Intermediate Similarity NPC474790
0.8065 Intermediate Similarity NPC139692
0.8065 Intermediate Similarity NPC115021
0.8046 Intermediate Similarity NPC474955
0.8046 Intermediate Similarity NPC14203
0.8046 Intermediate Similarity NPC229584
0.8043 Intermediate Similarity NPC476437
0.8043 Intermediate Similarity NPC476369
0.8043 Intermediate Similarity NPC232426
0.8043 Intermediate Similarity NPC280149
0.8043 Intermediate Similarity NPC221111
0.8043 Intermediate Similarity NPC477782
0.8043 Intermediate Similarity NPC281942
0.8023 Intermediate Similarity NPC150646
0.8022 Intermediate Similarity NPC196407
0.8022 Intermediate Similarity NPC477128
0.8021 Intermediate Similarity NPC181147
0.802 Intermediate Similarity NPC228477
0.802 Intermediate Similarity NPC137911
0.8 Intermediate Similarity NPC260796
0.8 Intermediate Similarity NPC195640
0.8 Intermediate Similarity NPC302788
0.8 Intermediate Similarity NPC179380
0.8 Intermediate Similarity NPC473825
0.7979 Intermediate Similarity NPC476415
0.7978 Intermediate Similarity NPC475100
0.7976 Intermediate Similarity NPC65650
0.7959 Intermediate Similarity NPC469606
0.7959 Intermediate Similarity NPC31058
0.7959 Intermediate Similarity NPC273005
0.7957 Intermediate Similarity NPC477783
0.7957 Intermediate Similarity NPC49420
0.7957 Intermediate Similarity NPC472814
0.7957 Intermediate Similarity NPC177037
0.7957 Intermediate Similarity NPC65513
0.7957 Intermediate Similarity NPC141831
0.7957 Intermediate Similarity NPC473986
0.7957 Intermediate Similarity NPC474018
0.7955 Intermediate Similarity NPC471218
0.7938 Intermediate Similarity NPC476767
0.7938 Intermediate Similarity NPC117685
0.7938 Intermediate Similarity NPC474012
0.7938 Intermediate Similarity NPC476299
0.7935 Intermediate Similarity NPC168131
0.7935 Intermediate Similarity NPC285982
0.7935 Intermediate Similarity NPC251528
0.7935 Intermediate Similarity NPC280833
0.7935 Intermediate Similarity NPC177141
0.7935 Intermediate Similarity NPC118011
0.7935 Intermediate Similarity NPC474844
0.7935 Intermediate Similarity NPC36668
0.7931 Intermediate Similarity NPC474956
0.7931 Intermediate Similarity NPC268827
0.7917 Intermediate Similarity NPC204054
0.7917 Intermediate Similarity NPC476253
0.7917 Intermediate Similarity NPC2049
0.7917 Intermediate Similarity NPC257726
0.7917 Intermediate Similarity NPC53844
0.79 Intermediate Similarity NPC189863
0.79 Intermediate Similarity NPC478052
0.7895 Intermediate Similarity NPC127197
0.7889 Intermediate Similarity NPC474680
0.7889 Intermediate Similarity NPC2709
0.7889 Intermediate Similarity NPC470048
0.7889 Intermediate Similarity NPC472442
0.7889 Intermediate Similarity NPC30984
0.7882 Intermediate Similarity NPC40353
0.7872 Intermediate Similarity NPC263780
0.7872 Intermediate Similarity NPC169343
0.7872 Intermediate Similarity NPC472871
0.7865 Intermediate Similarity NPC472440
0.7865 Intermediate Similarity NPC470046
0.7865 Intermediate Similarity NPC470047
0.7865 Intermediate Similarity NPC477124
0.7857 Intermediate Similarity NPC166797
0.7857 Intermediate Similarity NPC20025
0.7857 Intermediate Similarity NPC306928
0.7857 Intermediate Similarity NPC310981
0.7849 Intermediate Similarity NPC198818
0.7849 Intermediate Similarity NPC474842
0.7849 Intermediate Similarity NPC475965
0.7841 Intermediate Similarity NPC278459
0.7835 Intermediate Similarity NPC108368
0.7835 Intermediate Similarity NPC98868
0.7835 Intermediate Similarity NPC57079
0.7835 Intermediate Similarity NPC176845
0.7831 Intermediate Similarity NPC181587
0.7826 Intermediate Similarity NPC215831
0.7826 Intermediate Similarity NPC478259
0.7826 Intermediate Similarity NPC472220
0.7826 Intermediate Similarity NPC97884
0.7826 Intermediate Similarity NPC471956
0.7826 Intermediate Similarity NPC72397
0.7826 Intermediate Similarity NPC478261
0.7826 Intermediate Similarity NPC472870
0.7826 Intermediate Similarity NPC478260
0.7812 Intermediate Similarity NPC242848
0.7812 Intermediate Similarity NPC29952
0.7812 Intermediate Similarity NPC134072
0.7812 Intermediate Similarity NPC16967
0.7812 Intermediate Similarity NPC234993
0.7802 Intermediate Similarity NPC470050
0.7802 Intermediate Similarity NPC470051
0.78 Intermediate Similarity NPC472868
0.78 Intermediate Similarity NPC189616
0.7791 Intermediate Similarity NPC189206
0.7791 Intermediate Similarity NPC165711
0.7791 Intermediate Similarity NPC61952
0.7789 Intermediate Similarity NPC470697
0.7789 Intermediate Similarity NPC191521
0.7778 Intermediate Similarity NPC474359
0.7778 Intermediate Similarity NPC155332
0.7778 Intermediate Similarity NPC32577
0.7778 Intermediate Similarity NPC114540
0.7778 Intermediate Similarity NPC248758
0.7778 Intermediate Similarity NPC476769
0.7767 Intermediate Similarity NPC16270
0.7766 Intermediate Similarity NPC470036
0.7766 Intermediate Similarity NPC174167
0.7766 Intermediate Similarity NPC166110

  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 NPC472302 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
0.881 High Similarity NPD4752 Clinical (unspecified phase)
0.8152 Intermediate Similarity NPD5693 Phase 1
0.8022 Intermediate Similarity NPD6672 Approved
0.8022 Intermediate Similarity NPD5737 Approved
0.8 Intermediate Similarity NPD7521 Approved
0.8 Intermediate Similarity NPD7146 Approved
0.8 Intermediate Similarity NPD6684 Approved
0.8 Intermediate Similarity NPD5330 Approved
0.8 Intermediate Similarity NPD6409 Approved
0.8 Intermediate Similarity NPD7334 Approved
0.7849 Intermediate Similarity NPD5692 Phase 3
0.7826 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD6903 Approved
0.7766 Intermediate Similarity NPD5694 Approved
0.7766 Intermediate Similarity NPD6050 Approved
0.7742 Intermediate Similarity NPD6080 Approved
0.7742 Intermediate Similarity NPD6673 Approved
0.7742 Intermediate Similarity NPD6904 Approved
0.7692 Intermediate Similarity NPD1694 Approved
0.766 Intermediate Similarity NPD5207 Approved
0.7634 Intermediate Similarity NPD5208 Approved
0.7558 Intermediate Similarity NPD8039 Approved
0.7553 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD3573 Approved
0.7526 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7638 Approved
0.7423 Intermediate Similarity NPD7748 Approved
0.7423 Intermediate Similarity NPD7900 Approved
0.7423 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6098 Approved
0.74 Intermediate Similarity NPD7640 Approved
0.74 Intermediate Similarity NPD7639 Approved
0.7396 Intermediate Similarity NPD5281 Approved
0.7396 Intermediate Similarity NPD5284 Approved
0.7374 Intermediate Similarity NPD6084 Phase 2
0.7374 Intermediate Similarity NPD6083 Phase 2
0.7368 Intermediate Similarity NPD6051 Approved
0.7347 Intermediate Similarity NPD5654 Approved
0.7347 Intermediate Similarity NPD5695 Phase 3
0.7333 Intermediate Similarity NPD4695 Discontinued
0.732 Intermediate Similarity NPD6399 Phase 3
0.73 Intermediate Similarity NPD5696 Approved
0.7245 Intermediate Similarity NPD6001 Approved
0.7241 Intermediate Similarity NPD4058 Approved
0.7238 Intermediate Similarity NPD6686 Approved
0.7234 Intermediate Similarity NPD4623 Approved
0.7234 Intermediate Similarity NPD4519 Discontinued
0.7216 Intermediate Similarity NPD7515 Phase 2
0.7204 Intermediate Similarity NPD3133 Approved
0.7204 Intermediate Similarity NPD3665 Phase 1
0.7204 Intermediate Similarity NPD3666 Approved
0.72 Intermediate Similarity NPD5959 Approved
0.72 Intermediate Similarity NPD7902 Approved
0.7176 Intermediate Similarity NPD4137 Phase 3
0.7174 Intermediate Similarity NPD4221 Approved
0.7174 Intermediate Similarity NPD4223 Phase 3
0.7143 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD3617 Approved
0.7093 Intermediate Similarity NPD4747 Approved
0.7093 Intermediate Similarity NPD4691 Approved
0.7053 Intermediate Similarity NPD5280 Approved
0.7053 Intermediate Similarity NPD5279 Phase 3
0.7053 Intermediate Similarity NPD4694 Approved
0.7053 Intermediate Similarity NPD3618 Phase 1
0.7045 Intermediate Similarity NPD5733 Approved
0.7045 Intermediate Similarity NPD4687 Approved
0.7021 Intermediate Similarity NPD3668 Phase 3
0.7021 Intermediate Similarity NPD4197 Approved
0.7011 Intermediate Similarity NPD5276 Approved
0.701 Intermediate Similarity NPD4753 Phase 2
0.7009 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.6989 Remote Similarity NPD3667 Approved
0.6989 Remote Similarity NPD5209 Approved
0.6961 Remote Similarity NPD4225 Approved
0.6947 Remote Similarity NPD5329 Approved
0.6944 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6931 Remote Similarity NPD7732 Phase 3
0.6893 Remote Similarity NPD6404 Discontinued
0.6887 Remote Similarity NPD6402 Approved
0.6887 Remote Similarity NPD6008 Approved
0.6887 Remote Similarity NPD5739 Approved
0.6887 Remote Similarity NPD7128 Approved
0.6887 Remote Similarity NPD6675 Approved
0.6875 Remote Similarity NPD5205 Approved
0.6875 Remote Similarity NPD4138 Approved
0.6875 Remote Similarity NPD4690 Approved
0.6875 Remote Similarity NPD7115 Discovery
0.6875 Remote Similarity NPD4688 Approved
0.6875 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6875 Remote Similarity NPD4693 Phase 3
0.6875 Remote Similarity NPD4689 Approved
0.6869 Remote Similarity NPD6411 Approved
0.6857 Remote Similarity NPD6052 Approved
0.6842 Remote Similarity NPD4786 Approved
0.6837 Remote Similarity NPD5328 Approved
0.6822 Remote Similarity NPD5701 Approved
0.6822 Remote Similarity NPD5697 Approved
0.6818 Remote Similarity NPD6053 Discontinued
0.6762 Remote Similarity NPD7632 Discontinued
0.6759 Remote Similarity NPD6899 Approved
0.6759 Remote Similarity NPD6881 Approved
0.6759 Remote Similarity NPD7320 Approved
0.6759 Remote Similarity NPD6011 Approved
0.6701 Remote Similarity NPD5690 Phase 2
0.67 Remote Similarity NPD6079 Approved
0.6697 Remote Similarity NPD6013 Approved
0.6697 Remote Similarity NPD6014 Approved
0.6697 Remote Similarity NPD6373 Approved
0.6697 Remote Similarity NPD6372 Approved
0.6697 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4629 Approved
0.6667 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5210 Approved
0.6667 Remote Similarity NPD6614 Approved
0.6667 Remote Similarity NPD6101 Approved
0.6636 Remote Similarity NPD5909 Discontinued
0.6636 Remote Similarity NPD6883 Approved
0.6636 Remote Similarity NPD7102 Approved
0.6636 Remote Similarity NPD7290 Approved
0.6634 Remote Similarity NPD5779 Approved
0.6634 Remote Similarity NPD4202 Approved
0.6634 Remote Similarity NPD5778 Approved
0.663 Remote Similarity NPD4756 Discovery
0.6607 Remote Similarity NPD6858 Approved
0.6607 Remote Similarity NPD7094 Approved
0.6602 Remote Similarity NPD7614 Phase 1
0.6602 Remote Similarity NPD4697 Phase 3
0.6602 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6602 Remote Similarity NPD5222 Approved
0.6602 Remote Similarity NPD5221 Approved
0.66 Remote Similarity NPD4096 Approved
0.6588 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6581 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6577 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6577 Remote Similarity NPD6847 Approved
0.6577 Remote Similarity NPD6649 Approved
0.6577 Remote Similarity NPD8130 Phase 1
0.6577 Remote Similarity NPD6650 Approved
0.6577 Remote Similarity NPD6869 Approved
0.6577 Remote Similarity NPD6617 Approved
0.6538 Remote Similarity NPD5173 Approved
0.6538 Remote Similarity NPD4755 Approved
0.6535 Remote Similarity NPD7637 Suspended
0.6535 Remote Similarity NPD8035 Phase 2
0.6535 Remote Similarity NPD8034 Phase 2
0.6518 Remote Similarity NPD6882 Approved
0.6518 Remote Similarity NPD8297 Approved
0.6514 Remote Similarity NPD6412 Phase 2
0.6496 Remote Similarity NPD7503 Approved
0.6495 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6489 Remote Similarity NPD4195 Approved
0.6471 Remote Similarity NPD5133 Approved
0.6449 Remote Similarity NPD5211 Phase 2
0.6436 Remote Similarity NPD5785 Approved
0.6429 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6417 Remote Similarity NPD7507 Approved
0.6415 Remote Similarity NPD5285 Approved
0.6415 Remote Similarity NPD5286 Approved
0.6415 Remote Similarity NPD4700 Approved
0.6415 Remote Similarity NPD4696 Approved
0.64 Remote Similarity NPD4518 Approved
0.6392 Remote Similarity NPD7154 Phase 3
0.6392 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6392 Remote Similarity NPD4788 Approved
0.6355 Remote Similarity NPD5223 Approved
0.6348 Remote Similarity NPD6274 Approved
0.6348 Remote Similarity NPD6868 Approved
0.6346 Remote Similarity NPD1698 Clinical (unspecified phase)
0.633 Remote Similarity NPD5141 Approved
0.6322 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4632 Approved
0.6296 Remote Similarity NPD5226 Approved
0.6296 Remote Similarity NPD5224 Approved
0.6296 Remote Similarity NPD4633 Approved
0.6296 Remote Similarity NPD5225 Approved
0.6293 Remote Similarity NPD6317 Approved
0.629 Remote Similarity NPD7260 Phase 2
0.6286 Remote Similarity NPD5349 Clinical (unspecified phase)
0.6275 Remote Similarity NPD46 Approved
0.6275 Remote Similarity NPD6698 Approved
0.6264 Remote Similarity NPD5777 Approved
0.626 Remote Similarity NPD7319 Approved
0.6239 Remote Similarity NPD6314 Approved
0.6239 Remote Similarity NPD5174 Approved
0.6239 Remote Similarity NPD6335 Approved
0.6239 Remote Similarity NPD4754 Approved
0.6239 Remote Similarity NPD5175 Approved
0.6239 Remote Similarity NPD6313 Approved
0.6211 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6195 Remote Similarity NPD2067 Discontinued
0.6186 Remote Similarity NPD7101 Approved
0.6186 Remote Similarity NPD7100 Approved
0.6186 Remote Similarity NPD4692 Approved
0.6186 Remote Similarity NPD4139 Approved
0.617 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6163 Remote Similarity NPD4193 Approved
0.6163 Remote Similarity NPD4191 Approved
0.6163 Remote Similarity NPD4192 Approved
0.6163 Remote Similarity NPD4194 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