Structure

Physi-Chem Properties

Molecular Weight:  242.13
Volume:  264.021
LogP:  3.569
LogD:  3.17
LogS:  -2.947
# Rotatable Bonds:  0
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.685
Synthetic Accessibility Score:  4.098
Fsp3:  0.375
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:  -4.835
MDCK Permeability:  1.952010097738821e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.15
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.941
30% Bioavailability (F30%):  0.424

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.038
Plasma Protein Binding (PPB):  96.1736831665039%
Volume Distribution (VD):  1.482
Pgp-substrate:  3.644057273864746%

ADMET: Metabolism

CYP1A2-inhibitor:  0.975
CYP1A2-substrate:  0.753
CYP2C19-inhibitor:  0.234
CYP2C19-substrate:  0.403
CYP2C9-inhibitor:  0.316
CYP2C9-substrate:  0.862
CYP2D6-inhibitor:  0.652
CYP2D6-substrate:  0.071
CYP3A4-inhibitor:  0.73
CYP3A4-substrate:  0.517

ADMET: Excretion

Clearance (CL):  11.262
Half-life (T1/2):  0.835

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.339
Drug-inuced Liver Injury (DILI):  0.061
AMES Toxicity:  0.476
Rat Oral Acute Toxicity:  0.731
Maximum Recommended Daily Dose:  0.716
Skin Sensitization:  0.666
Carcinogencity:  0.763
Eye Corrosion:  0.684
Eye Irritation:  0.793
Respiratory Toxicity:  0.979

Download Data

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

  Natural Product: NPC188292

Natural Product ID:  NPC188292
Common Name*:   Cordiachrome B
IUPAC Name:   (8aS,10aS)-10a-methyl-8-methylidene-5,6,7,8a,9,10-hexahydroanthracene-1,4-dione
Synonyms:  
Standard InCHIKey:  BJEHSIIPDRQCJK-BBRMVZONSA-N
Standard InCHI:  InChI=1S/C16H18O2/c1-10-4-3-7-16(2)9-12-11(8-13(10)16)14(17)5-6-15(12)18/h5-6,13H,1,3-4,7-9H2,2H3/t13-,16-/m0/s1
SMILES:  O=C1C=CC(=O)C2=C1C[C@]1(C)CCCC(=C)[C@@H]1C2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL401659
PubChem CID:   24761029
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*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
NPO6865 Cordia fragrantissima Species Cordiaceae Eukaryota n.a. Myanmar n.a. PMID[18088097]
NPO22854 Cordia globifera Species Cordiaceae Eukaryota n.a. n.a. n.a. PMID[19368377]
NPO22854 Cordia globifera Species Cordiaceae Eukaryota n.a. n.a. n.a. PMID[20384317]
NPO6865 Cordia fragrantissima Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22854 Cordia globifera Species Cordiaceae 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
NPT1229 Cell Line Huh-7 Homo sapiens IC50 = 71.5 ug.mL-1 PMID[468968]
NPT189 Cell Line Vero Chlorocebus aethiops IC50 = 1.7 ug.mL-1 PMID[468969]
NPT91 Cell Line KB Homo sapiens IC50 = 6.0 ug.mL-1 PMID[468969]
NPT639 Cell Line NCI-H187 Homo sapiens IC50 = 0.4 ug.mL-1 PMID[468969]
NPT841 Organism Leishmania major Leishmania major IC50 = 2.5 ug.mL-1 PMID[468968]
NPT27 Others Unspecified IC50 = 14.6 ug.mL-1 PMID[468968]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 12.5 ug.mL-1 PMID[468969]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 = 1.5 ug.mL-1 PMID[468969]
NPT20 Organism Candida albicans Candida albicans IC50 = 7.7 ug.mL-1 PMID[468969]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 6.4 ug.mL-1 PMID[468969]

☑ 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 NPC188292 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
1.0 High Similarity NPC260474
0.9688 High Similarity NPC87141
0.9524 High Similarity NPC251118
0.9385 High Similarity NPC310992
0.9254 High Similarity NPC54123
0.9242 High Similarity NPC256846
0.9206 High Similarity NPC288253
0.9118 High Similarity NPC470045
0.9118 High Similarity NPC470044
0.9104 High Similarity NPC251929
0.9104 High Similarity NPC265782
0.9104 High Similarity NPC2634
0.9062 High Similarity NPC469662
0.9 High Similarity NPC1254
0.8955 High Similarity NPC139397
0.8906 High Similarity NPC197238
0.8906 High Similarity NPC202118
0.8889 High Similarity NPC127582
0.8841 High Similarity NPC251705
0.8841 High Similarity NPC303613
0.8841 High Similarity NPC474228
0.8824 High Similarity NPC260040
0.8824 High Similarity NPC307176
0.8806 High Similarity NPC155198
0.8769 High Similarity NPC285371
0.8769 High Similarity NPC475124
0.8732 High Similarity NPC69408
0.873 High Similarity NPC472304
0.873 High Similarity NPC276764
0.8714 High Similarity NPC309852
0.8696 High Similarity NPC190035
0.8696 High Similarity NPC234707
0.8696 High Similarity NPC305501
0.8696 High Similarity NPC115023
0.8696 High Similarity NPC5701
0.8696 High Similarity NPC225467
0.8592 High Similarity NPC476346
0.8592 High Similarity NPC293803
0.8592 High Similarity NPC473171
0.8571 High Similarity NPC27610
0.8571 High Similarity NPC56905
0.8571 High Similarity NPC311852
0.8551 High Similarity NPC159577
0.8551 High Similarity NPC282593
0.8551 High Similarity NPC35734
0.8507 High Similarity NPC323005
0.8493 Intermediate Similarity NPC189485
0.8485 Intermediate Similarity NPC212210
0.8462 Intermediate Similarity NPC60565
0.8451 Intermediate Similarity NPC474797
0.8451 Intermediate Similarity NPC255021
0.8451 Intermediate Similarity NPC474796
0.8451 Intermediate Similarity NPC219232
0.8451 Intermediate Similarity NPC329866
0.8451 Intermediate Similarity NPC128346
0.8429 Intermediate Similarity NPC474562
0.8429 Intermediate Similarity NPC181204
0.8413 Intermediate Similarity NPC115385
0.8406 Intermediate Similarity NPC286814
0.8406 Intermediate Similarity NPC182815
0.84 Intermediate Similarity NPC475833
0.8382 Intermediate Similarity NPC290350
0.8382 Intermediate Similarity NPC4370
0.8378 Intermediate Similarity NPC170793
0.8378 Intermediate Similarity NPC27817
0.8378 Intermediate Similarity NPC90965
0.8333 Intermediate Similarity NPC255650
0.831 Intermediate Similarity NPC130016
0.831 Intermediate Similarity NPC180015
0.831 Intermediate Similarity NPC109576
0.831 Intermediate Similarity NPC56747
0.8281 Intermediate Similarity NPC60772
0.8267 Intermediate Similarity NPC108955
0.8267 Intermediate Similarity NPC474509
0.8267 Intermediate Similarity NPC476809
0.8261 Intermediate Similarity NPC82477
0.8261 Intermediate Similarity NPC39157
0.8261 Intermediate Similarity NPC142754
0.8261 Intermediate Similarity NPC296697
0.8261 Intermediate Similarity NPC20610
0.8243 Intermediate Similarity NPC115515
0.8235 Intermediate Similarity NPC92327
0.8219 Intermediate Similarity NPC469796
0.8219 Intermediate Similarity NPC469793
0.8209 Intermediate Similarity NPC4638
0.8209 Intermediate Similarity NPC6697
0.8194 Intermediate Similarity NPC211641
0.8182 Intermediate Similarity NPC213152
0.8169 Intermediate Similarity NPC223187
0.8169 Intermediate Similarity NPC470078
0.8158 Intermediate Similarity NPC99308
0.8158 Intermediate Similarity NPC474085
0.8158 Intermediate Similarity NPC55869
0.8158 Intermediate Similarity NPC116797
0.8116 Intermediate Similarity NPC475523
0.8116 Intermediate Similarity NPC193770
0.8116 Intermediate Similarity NPC176107
0.8116 Intermediate Similarity NPC220210
0.8116 Intermediate Similarity NPC20181
0.8108 Intermediate Similarity NPC472300
0.8095 Intermediate Similarity NPC200258
0.8088 Intermediate Similarity NPC470329
0.8082 Intermediate Similarity NPC65650
0.806 Intermediate Similarity NPC165695
0.8056 Intermediate Similarity NPC474488
0.8052 Intermediate Similarity NPC142253
0.8052 Intermediate Similarity NPC3511
0.8028 Intermediate Similarity NPC40574
0.8026 Intermediate Similarity NPC26139
0.8 Intermediate Similarity NPC170799
0.8 Intermediate Similarity NPC74410
0.8 Intermediate Similarity NPC471409
0.8 Intermediate Similarity NPC308108
0.8 Intermediate Similarity NPC469996
0.8 Intermediate Similarity NPC275494
0.7975 Intermediate Similarity NPC474537
0.7973 Intermediate Similarity NPC180886
0.7973 Intermediate Similarity NPC110725
0.7971 Intermediate Similarity NPC176171
0.7945 Intermediate Similarity NPC20025
0.7937 Intermediate Similarity NPC5626
0.7922 Intermediate Similarity NPC225515
0.7922 Intermediate Similarity NPC278459
0.7917 Intermediate Similarity NPC21944
0.7917 Intermediate Similarity NPC133253
0.7895 Intermediate Similarity NPC472490
0.7895 Intermediate Similarity NPC476177
0.7879 Intermediate Similarity NPC259261
0.7867 Intermediate Similarity NPC165711
0.7848 Intermediate Similarity NPC87552
0.7846 Intermediate Similarity NPC192427
0.7821 Intermediate Similarity NPC238991
0.7821 Intermediate Similarity NPC302661
0.7821 Intermediate Similarity NPC472239
0.7821 Intermediate Similarity NPC103486
0.7821 Intermediate Similarity NPC472867
0.7794 Intermediate Similarity NPC32285
0.7792 Intermediate Similarity NPC2482
0.7792 Intermediate Similarity NPC472478
0.7792 Intermediate Similarity NPC469637
0.7792 Intermediate Similarity NPC287063
0.7778 Intermediate Similarity NPC14002
0.7778 Intermediate Similarity NPC214770
0.7778 Intermediate Similarity NPC246722
0.7778 Intermediate Similarity NPC477856
0.7778 Intermediate Similarity NPC151045
0.7778 Intermediate Similarity NPC23117
0.7778 Intermediate Similarity NPC268564
0.7763 Intermediate Similarity NPC82635
0.7763 Intermediate Similarity NPC470052
0.7761 Intermediate Similarity NPC25853
0.775 Intermediate Similarity NPC29447
0.775 Intermediate Similarity NPC8518
0.775 Intermediate Similarity NPC133652
0.775 Intermediate Similarity NPC263997
0.775 Intermediate Similarity NPC132228
0.775 Intermediate Similarity NPC8571
0.775 Intermediate Similarity NPC476426
0.775 Intermediate Similarity NPC33663
0.7733 Intermediate Similarity NPC40353
0.7733 Intermediate Similarity NPC92080
0.7733 Intermediate Similarity NPC474463
0.7733 Intermediate Similarity NPC470525
0.7733 Intermediate Similarity NPC19907
0.7727 Intermediate Similarity NPC266295
0.7727 Intermediate Similarity NPC30215
0.7727 Intermediate Similarity NPC94991
0.7722 Intermediate Similarity NPC118423
0.7722 Intermediate Similarity NPC41539
0.7722 Intermediate Similarity NPC53733
0.7722 Intermediate Similarity NPC49019
0.7703 Intermediate Similarity NPC251970
0.7703 Intermediate Similarity NPC476046
0.7703 Intermediate Similarity NPC241854
0.7692 Intermediate Similarity NPC473217
0.7692 Intermediate Similarity NPC149237
0.7692 Intermediate Similarity NPC121984
0.7692 Intermediate Similarity NPC470034
0.7692 Intermediate Similarity NPC475863
0.7692 Intermediate Similarity NPC471898
0.7681 Intermediate Similarity NPC52449
0.7681 Intermediate Similarity NPC169275
0.7654 Intermediate Similarity NPC222613
0.7654 Intermediate Similarity NPC118648
0.7654 Intermediate Similarity NPC475022
0.7647 Intermediate Similarity NPC97322
0.7647 Intermediate Similarity NPC475795
0.7639 Intermediate Similarity NPC477857
0.7632 Intermediate Similarity NPC91665
0.7632 Intermediate Similarity NPC257666
0.7632 Intermediate Similarity NPC266193
0.7632 Intermediate Similarity NPC97377
0.7625 Intermediate Similarity NPC473246
0.7612 Intermediate Similarity NPC96551
0.7612 Intermediate Similarity NPC285594
0.76 Intermediate Similarity NPC279666
0.76 Intermediate Similarity NPC192540
0.7595 Intermediate Similarity NPC469805
0.7595 Intermediate Similarity NPC193347
0.7595 Intermediate Similarity NPC469799

  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 NPC188292 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
0.9104 High Similarity NPD4691 Approved
0.8986 High Similarity NPD4058 Approved
0.8986 High Similarity NPD4687 Approved
0.8955 High Similarity NPD4137 Phase 3
0.8824 High Similarity NPD4747 Approved
0.8714 High Similarity NPD5733 Approved
0.8696 High Similarity NPD5276 Approved
0.8261 Intermediate Similarity NPD3621 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD3527 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD287 Approved
0.7922 Intermediate Similarity NPD8028 Phase 2
0.7875 Intermediate Similarity NPD5690 Phase 2
0.7792 Intermediate Similarity NPD4695 Discontinued
0.7595 Intermediate Similarity NPD4221 Approved
0.7595 Intermediate Similarity NPD4223 Phase 3
0.7561 Intermediate Similarity NPD3573 Approved
0.7439 Intermediate Similarity NPD4519 Discontinued
0.7439 Intermediate Similarity NPD4694 Approved
0.7439 Intermediate Similarity NPD5280 Approved
0.7439 Intermediate Similarity NPD4623 Approved
0.7407 Intermediate Similarity NPD3665 Phase 1
0.7407 Intermediate Similarity NPD3133 Approved
0.7407 Intermediate Similarity NPD4197 Approved
0.7407 Intermediate Similarity NPD3666 Approved
0.7317 Intermediate Similarity NPD5329 Approved
0.7308 Intermediate Similarity NPD3617 Approved
0.7294 Intermediate Similarity NPD5207 Approved
0.7229 Intermediate Similarity NPD4690 Approved
0.7229 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7229 Intermediate Similarity NPD5279 Phase 3
0.7229 Intermediate Similarity NPD7334 Approved
0.7229 Intermediate Similarity NPD7146 Approved
0.7229 Intermediate Similarity NPD5330 Approved
0.7229 Intermediate Similarity NPD6409 Approved
0.7229 Intermediate Similarity NPD3618 Phase 1
0.7229 Intermediate Similarity NPD5205 Approved
0.7229 Intermediate Similarity NPD4138 Approved
0.7229 Intermediate Similarity NPD4688 Approved
0.7229 Intermediate Similarity NPD4689 Approved
0.7229 Intermediate Similarity NPD7521 Approved
0.7229 Intermediate Similarity NPD4693 Phase 3
0.7229 Intermediate Similarity NPD6684 Approved
0.7215 Intermediate Similarity NPD4195 Approved
0.7209 Intermediate Similarity NPD5284 Approved
0.7209 Intermediate Similarity NPD6079 Approved
0.7209 Intermediate Similarity NPD5694 Approved
0.7209 Intermediate Similarity NPD5281 Approved
0.716 Intermediate Similarity NPD3667 Approved
0.7093 Intermediate Similarity NPD5692 Phase 3
0.7059 Intermediate Similarity NPD6672 Approved
0.7059 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6903 Approved
0.7059 Intermediate Similarity NPD5208 Approved
0.7059 Intermediate Similarity NPD5737 Approved
0.7011 Intermediate Similarity NPD6050 Approved
0.6988 Remote Similarity NPD4786 Approved
0.6988 Remote Similarity NPD3668 Phase 3
0.6977 Remote Similarity NPD4753 Phase 2
0.6977 Remote Similarity NPD6904 Approved
0.6977 Remote Similarity NPD6080 Approved
0.6977 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6977 Remote Similarity NPD5328 Approved
0.6977 Remote Similarity NPD6673 Approved
0.6966 Remote Similarity NPD5210 Approved
0.6966 Remote Similarity NPD4629 Approved
0.6897 Remote Similarity NPD4096 Approved
0.6889 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6889 Remote Similarity NPD5222 Approved
0.6889 Remote Similarity NPD5221 Approved
0.686 Remote Similarity NPD4518 Approved
0.6829 Remote Similarity NPD4139 Approved
0.6829 Remote Similarity NPD4692 Approved
0.6824 Remote Similarity NPD6098 Approved
0.6818 Remote Similarity NPD7515 Phase 2
0.6818 Remote Similarity NPD5693 Phase 1
0.6813 Remote Similarity NPD3495 Discontinued
0.6813 Remote Similarity NPD5173 Approved
0.6778 Remote Similarity NPD5695 Phase 3
0.6757 Remote Similarity NPD7331 Phase 2
0.6747 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6742 Remote Similarity NPD5133 Approved
0.6742 Remote Similarity NPD4202 Approved
0.6707 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6706 Remote Similarity NPD1694 Approved
0.6703 Remote Similarity NPD7614 Phase 1
0.6703 Remote Similarity NPD7732 Phase 3
0.6667 Remote Similarity NPD6001 Approved
0.6667 Remote Similarity NPD5286 Approved
0.6667 Remote Similarity NPD7900 Approved
0.6667 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD5285 Approved
0.6667 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7748 Approved
0.6596 Remote Similarity NPD5223 Approved
0.6593 Remote Similarity NPD5654 Approved
0.6593 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7631 Approved
0.6526 Remote Similarity NPD5091 Approved
0.6526 Remote Similarity NPD5224 Approved
0.6526 Remote Similarity NPD5225 Approved
0.6526 Remote Similarity NPD4633 Approved
0.6526 Remote Similarity NPD5226 Approved
0.6526 Remote Similarity NPD5211 Phase 2
0.6522 Remote Similarity NPD4697 Phase 3
0.6471 Remote Similarity NPD4788 Approved
0.6458 Remote Similarity NPD5174 Approved
0.6458 Remote Similarity NPD5175 Approved
0.6452 Remote Similarity NPD5959 Approved
0.6452 Remote Similarity NPD7902 Approved
0.6452 Remote Similarity NPD6084 Phase 2
0.6452 Remote Similarity NPD4755 Approved
0.6452 Remote Similarity NPD6083 Phase 2
0.6444 Remote Similarity NPD7609 Phase 3
0.6438 Remote Similarity NPD4191 Approved
0.6438 Remote Similarity NPD4194 Approved
0.6438 Remote Similarity NPD4193 Approved
0.6438 Remote Similarity NPD4192 Approved
0.64 Remote Similarity NPD7341 Phase 2
0.6392 Remote Similarity NPD5141 Approved
0.6383 Remote Similarity NPD5696 Approved
0.6374 Remote Similarity NPD6399 Phase 3
0.6316 Remote Similarity NPD4700 Approved
0.6316 Remote Similarity NPD6404 Discontinued
0.6316 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6263 Remote Similarity NPD6614 Approved
0.6263 Remote Similarity NPD5697 Approved
0.6224 Remote Similarity NPD7812 Clinical (unspecified phase)
0.62 Remote Similarity NPD5168 Approved
0.62 Remote Similarity NPD4729 Approved
0.62 Remote Similarity NPD6011 Approved
0.62 Remote Similarity NPD4730 Approved
0.62 Remote Similarity NPD6881 Approved
0.62 Remote Similarity NPD6899 Approved
0.619 Remote Similarity NPD1799 Clinical (unspecified phase)
0.618 Remote Similarity NPD650 Approved
0.6173 Remote Similarity NPD4784 Approved
0.6173 Remote Similarity NPD4785 Approved
0.6139 Remote Similarity NPD6012 Approved
0.6139 Remote Similarity NPD6014 Approved
0.6139 Remote Similarity NPD6013 Approved
0.6133 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6125 Remote Similarity NPD4243 Approved
0.6122 Remote Similarity NPD6052 Approved
0.6122 Remote Similarity NPD4754 Approved
0.6119 Remote Similarity NPD8262 Approved
0.6098 Remote Similarity NPD8039 Approved
0.6087 Remote Similarity NPD6411 Approved
0.6078 Remote Similarity NPD5250 Approved
0.6078 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6078 Remote Similarity NPD5249 Phase 3
0.6078 Remote Similarity NPD5248 Approved
0.6078 Remote Similarity NPD4634 Approved
0.6078 Remote Similarity NPD7290 Approved
0.6078 Remote Similarity NPD7102 Approved
0.6078 Remote Similarity NPD5135 Approved
0.6078 Remote Similarity NPD5169 Approved
0.6078 Remote Similarity NPD5251 Approved
0.6078 Remote Similarity NPD6883 Approved
0.6078 Remote Similarity NPD5247 Approved
0.6056 Remote Similarity NPD4627 Clinical (unspecified phase)
0.604 Remote Similarity NPD5128 Approved
0.6024 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6019 Remote Similarity NPD5215 Approved
0.6019 Remote Similarity NPD5216 Approved
0.6019 Remote Similarity NPD6650 Approved
0.6019 Remote Similarity NPD5127 Approved
0.6019 Remote Similarity NPD6869 Approved
0.6019 Remote Similarity NPD8130 Phase 1
0.6019 Remote Similarity NPD6847 Approved
0.6019 Remote Similarity NPD6649 Approved
0.6019 Remote Similarity NPD5217 Approved
0.6019 Remote Similarity NPD6617 Approved
0.6 Remote Similarity NPD6008 Approved
0.6 Remote Similarity NPD6675 Approved
0.6 Remote Similarity NPD5739 Approved
0.6 Remote Similarity NPD4768 Approved
0.6 Remote Similarity NPD7128 Approved
0.6 Remote Similarity NPD6402 Approved
0.6 Remote Similarity NPD4767 Approved
0.5962 Remote Similarity NPD6882 Approved
0.5962 Remote Similarity NPD8297 Approved
0.5957 Remote Similarity NPD5769 Clinical (unspecified phase)
0.5955 Remote Similarity NPD1696 Phase 3
0.5941 Remote Similarity NPD5701 Approved
0.5941 Remote Similarity NPD6412 Phase 2
0.5905 Remote Similarity NPD4632 Approved
0.5904 Remote Similarity NPD8264 Approved
0.5904 Remote Similarity NPD5275 Approved
0.5904 Remote Similarity NPD7339 Approved
0.5904 Remote Similarity NPD6942 Approved
0.5904 Remote Similarity NPD4190 Phase 3
0.5882 Remote Similarity NPD7320 Approved
0.5882 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5876 Remote Similarity NPD5290 Discontinued
0.587 Remote Similarity NPD5764 Clinical (unspecified phase)
0.587 Remote Similarity NPD6101 Approved
0.5849 Remote Similarity NPD5167 Approved
0.5844 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5825 Remote Similarity NPD6373 Approved
0.5825 Remote Similarity NPD6372 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