Structure

Physi-Chem Properties

Molecular Weight:  652.16
Volume:  628.696
LogP:  6.384
LogD:  2.441
LogS:  -4.249
# Rotatable Bonds:  1
TPSA:  222.26
# H-Bond Aceptor:  12
# H-Bond Donor:  8
# Rings:  8
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.058
Synthetic Accessibility Score:  4.885
Fsp3:  0.222
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.833
MDCK Permeability:  7.13568260835018e-06
Pgp-inhibitor:  0.077
Pgp-substrate:  0.217
Human Intestinal Absorption (HIA):  0.792
20% Bioavailability (F20%):  0.36
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  84.50364685058594%
Volume Distribution (VD):  0.602
Pgp-substrate:  39.80301284790039%

ADMET: Metabolism

CYP1A2-inhibitor:  0.196
CYP1A2-substrate:  0.294
CYP2C19-inhibitor:  0.136
CYP2C19-substrate:  0.043
CYP2C9-inhibitor:  0.691
CYP2C9-substrate:  0.908
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.149
CYP3A4-inhibitor:  0.037
CYP3A4-substrate:  0.059

ADMET: Excretion

Clearance (CL):  2.823
Half-life (T1/2):  0.684

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.381
Drug-inuced Liver Injury (DILI):  0.991
AMES Toxicity:  0.16
Rat Oral Acute Toxicity:  0.124
Maximum Recommended Daily Dose:  0.964
Skin Sensitization:  0.933
Carcinogencity:  0.034
Eye Corrosion:  0.003
Eye Irritation:  0.901
Respiratory Toxicity:  0.031

Download Data

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

  Natural Product: NPC120102

Natural Product ID:  NPC120102
Common Name*:   Griffipavixanthone
IUPAC Name:   (8S,8aS,12aR)-1,3,6,7-tetrahydroxy-9,9,11-trimethyl-8-(3,4,6,8-tetrahydroxy-9-oxoxanthen-1-yl)-8,8a,10,12a-tetrahydroindeno[1,2-a]xanthen-13-one
Synonyms:  
Standard InCHIKey:  KAPVRSRPLHVWCH-JNFGOLMQSA-N
Standard InCHI:  InChI=1S/C36H28O12/c1-11-4-15-21-26(32(45)33(46)35-27(21)31(44)25-17(40)6-13(38)8-20(25)48-35)22(28(15)36(2,3)10-11)14-9-18(41)29(42)34-23(14)30(43)24-16(39)5-12(37)7-19(24)47-34/h4-9,15,22,28,37-42,45-46H,10H2,1-3H3/t15-,22-,28-/m0/s1
SMILES:  CC1=C[C@H]2c3c([C@H](c4cc(c(c5c4c(=O)c4c(cc(cc4o5)O)O)O)O)[C@H]2C(C)(C)C1)c(c(c1c3c(=O)c2c(cc(cc2o1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3314604
PubChem CID:   60151566
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes
              • [CHEMONTID:0000204] Xanthones

*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
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(74)80113-5]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. whole plant n.a. PMID[10361686]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[16724839]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19113969]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota leaves Bobai, Guangxi Province, China 2005-Dec PMID[24679044]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota Barks n.a. n.a. PMID[24754786]
NPO32711 garcinia esculenta Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[24960143]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6489 Garcinia virgata Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11471 Garcinia oblongifolia Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6948 Davidsoniella virescens Species Ceratocystidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15242 Setosphaeria holmii Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9298 Piper wightii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5276 Zanthoxylum decaryi Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26341 Trifolium resupinatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2812 Lecanora kukunorensis Species Lecanoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6775 Cistanche salsa Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10228 Ascochyta viciae Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1154 Neomeris annulata Species Dasycladaceae 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
NPT65 Cell Line HepG2 Homo sapiens IC50 > 10000.0 nM PMID[456283]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10000.0 nM PMID[456283]
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 > 10000.0 nM PMID[456283]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 41900.0 nM PMID[456283]
NPT27 Others Unspecified IC50 > 10000.0 nM PMID[456283]

☑ 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 NPC120102 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
0.9102 High Similarity NPC187491
0.9102 High Similarity NPC319200
0.908 High Similarity NPC150977
0.8976 High Similarity NPC235448
0.8947 High Similarity NPC17884
0.8947 High Similarity NPC19273
0.8895 High Similarity NPC4200
0.8889 High Similarity NPC188079
0.8882 High Similarity NPC272560
0.8882 High Similarity NPC224851
0.8869 High Similarity NPC472906
0.8851 High Similarity NPC216307
0.883 High Similarity NPC476306
0.8824 High Similarity NPC477840
0.8817 High Similarity NPC206605
0.8817 High Similarity NPC149389
0.8817 High Similarity NPC25152
0.881 High Similarity NPC471973
0.8802 High Similarity NPC161960
0.8802 High Similarity NPC187745
0.8802 High Similarity NPC136674
0.8802 High Similarity NPC304008
0.8786 High Similarity NPC257667
0.8786 High Similarity NPC186847
0.8786 High Similarity NPC472454
0.8779 High Similarity NPC475212
0.8779 High Similarity NPC300307
0.8772 High Similarity NPC320741
0.8772 High Similarity NPC171985
0.8772 High Similarity NPC472449
0.8765 High Similarity NPC152659
0.8765 High Similarity NPC220313
0.8765 High Similarity NPC236521
0.8765 High Similarity NPC146134
0.8765 High Similarity NPC12461
0.8765 High Similarity NPC248638
0.8757 High Similarity NPC234644
0.875 High Similarity NPC100123
0.875 High Similarity NPC46736
0.875 High Similarity NPC185275
0.875 High Similarity NPC197856
0.875 High Similarity NPC324742
0.8743 High Similarity NPC115853
0.8728 High Similarity NPC101107
0.8721 High Similarity NPC474024
0.8721 High Similarity NPC126204
0.8706 High Similarity NPC477841
0.8706 High Similarity NPC470694
0.8698 High Similarity NPC235018
0.8698 High Similarity NPC56085
0.8698 High Similarity NPC188433
0.8698 High Similarity NPC320359
0.8698 High Similarity NPC200746
0.8698 High Similarity NPC297212
0.8698 High Similarity NPC14353
0.8698 High Similarity NPC45146
0.8698 High Similarity NPC228785
0.8698 High Similarity NPC476280
0.8693 High Similarity NPC265380
0.869 High Similarity NPC219867
0.869 High Similarity NPC180011
0.8671 High Similarity NPC475805
0.8671 High Similarity NPC107627
0.8671 High Similarity NPC476637
0.8667 High Similarity NPC151473
0.8663 High Similarity NPC37870
0.8655 High Similarity NPC236132
0.8655 High Similarity NPC189473
0.8655 High Similarity NPC23298
0.8655 High Similarity NPC18100
0.8647 High Similarity NPC278052
0.8647 High Similarity NPC278427
0.8647 High Similarity NPC57715
0.8647 High Similarity NPC32694
0.8647 High Similarity NPC40491
0.8647 High Similarity NPC61010
0.8644 High Similarity NPC476273
0.8631 High Similarity NPC142339
0.8631 High Similarity NPC274730
0.8631 High Similarity NPC470600
0.8623 High Similarity NPC33051
0.8623 High Similarity NPC227337
0.8623 High Similarity NPC273462
0.8623 High Similarity NPC70433
0.8623 High Similarity NPC49402
0.8621 High Similarity NPC102277
0.8621 High Similarity NPC279209
0.8613 High Similarity NPC117854
0.8613 High Similarity NPC477154
0.8613 High Similarity NPC6588
0.8605 High Similarity NPC326520
0.8605 High Similarity NPC472450
0.8605 High Similarity NPC275780
0.8605 High Similarity NPC156432
0.8605 High Similarity NPC239752
0.8605 High Similarity NPC259757
0.8605 High Similarity NPC293319
0.8605 High Similarity NPC473286
0.8605 High Similarity NPC472277
0.8603 High Similarity NPC476170
0.8596 High Similarity NPC474150
0.8596 High Similarity NPC474162
0.8596 High Similarity NPC219927
0.8596 High Similarity NPC15374
0.8596 High Similarity NPC201800
0.8596 High Similarity NPC52204
0.8588 High Similarity NPC312993
0.8588 High Similarity NPC36217
0.8588 High Similarity NPC80375
0.8588 High Similarity NPC119224
0.858 High Similarity NPC300727
0.858 High Similarity NPC199463
0.858 High Similarity NPC165977
0.858 High Similarity NPC111969
0.858 High Similarity NPC474681
0.858 High Similarity NPC241904
0.858 High Similarity NPC218313
0.858 High Similarity NPC99591
0.858 High Similarity NPC236796
0.858 High Similarity NPC217677
0.858 High Similarity NPC37543
0.858 High Similarity NPC112954
0.8571 High Similarity NPC57674
0.8571 High Similarity NPC168247
0.8571 High Similarity NPC230149
0.8571 High Similarity NPC117992
0.8571 High Similarity NPC152951
0.8563 High Similarity NPC288813
0.8556 High Similarity NPC112380
0.8555 High Similarity NPC39091
0.8555 High Similarity NPC170245
0.8555 High Similarity NPC43319
0.8555 High Similarity NPC469394
0.8547 High Similarity NPC7483
0.8547 High Similarity NPC476295
0.8547 High Similarity NPC186686
0.8547 High Similarity NPC273959
0.8547 High Similarity NPC272064
0.8547 High Similarity NPC472281
0.8547 High Similarity NPC207690
0.8547 High Similarity NPC205265
0.8547 High Similarity NPC303460
0.8547 High Similarity NPC132111
0.8547 High Similarity NPC270837
0.8547 High Similarity NPC306321
0.8539 High Similarity NPC244903
0.8539 High Similarity NPC473785
0.8538 High Similarity NPC471211
0.8538 High Similarity NPC266314
0.8538 High Similarity NPC134783
0.8538 High Similarity NPC142252
0.8538 High Similarity NPC189552
0.8538 High Similarity NPC474351
0.8538 High Similarity NPC472275
0.8538 High Similarity NPC301256
0.8538 High Similarity NPC475883
0.8538 High Similarity NPC471212
0.8538 High Similarity NPC34089
0.8538 High Similarity NPC196179
0.8538 High Similarity NPC273467
0.8538 High Similarity NPC312273
0.8531 High Similarity NPC156955
0.8529 High Similarity NPC18699
0.8529 High Similarity NPC85121
0.8529 High Similarity NPC177650
0.8529 High Similarity NPC204879
0.8529 High Similarity NPC105584
0.8529 High Similarity NPC172770
0.8529 High Similarity NPC476242
0.8529 High Similarity NPC55443
0.8529 High Similarity NPC185258
0.8523 High Similarity NPC149846
0.8521 High Similarity NPC5322
0.8521 High Similarity NPC68093
0.8521 High Similarity NPC472907
0.8521 High Similarity NPC6633
0.8521 High Similarity NPC5379
0.8521 High Similarity NPC14561
0.8521 High Similarity NPC77807
0.8521 High Similarity NPC191146
0.8521 High Similarity NPC54830
0.8521 High Similarity NPC133970
0.8521 High Similarity NPC138243
0.8521 High Similarity NPC56049
0.8514 High Similarity NPC476365
0.8512 High Similarity NPC472905
0.8512 High Similarity NPC89474
0.8506 High Similarity NPC472622
0.8506 High Similarity NPC470377
0.8506 High Similarity NPC470374
0.8506 High Similarity NPC218226
0.8506 High Similarity NPC286230
0.8506 High Similarity NPC478059
0.8506 High Similarity NPC14662
0.8506 High Similarity NPC471975
0.8506 High Similarity NPC253730
0.8506 High Similarity NPC478060
0.8497 Intermediate Similarity NPC303174
0.8497 Intermediate Similarity NPC25361
0.8497 Intermediate Similarity NPC7688

  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 NPC120102 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
0.8538 High Similarity NPD6959 Discontinued
0.8497 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD6166 Phase 2
0.8497 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8343 Intermediate Similarity NPD7473 Discontinued
0.8294 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8276 Intermediate Similarity NPD6232 Discontinued
0.8235 Intermediate Similarity NPD1934 Approved
0.8187 Intermediate Similarity NPD2801 Approved
0.8161 Intermediate Similarity NPD5494 Approved
0.8156 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.814 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8101 Intermediate Similarity NPD7074 Phase 3
0.8092 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD3882 Suspended
0.8081 Intermediate Similarity NPD1465 Phase 2
0.8045 Intermediate Similarity NPD7054 Approved
0.8 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7472 Approved
0.7978 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7977 Intermediate Similarity NPD7819 Suspended
0.7976 Intermediate Similarity NPD1511 Approved
0.7944 Intermediate Similarity NPD5844 Phase 1
0.7929 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7889 Intermediate Similarity NPD3818 Discontinued
0.7882 Intermediate Similarity NPD1512 Approved
0.787 Intermediate Similarity NPD7390 Discontinued
0.7869 Intermediate Similarity NPD7808 Phase 3
0.7857 Intermediate Similarity NPD6797 Phase 2
0.7841 Intermediate Similarity NPD3749 Approved
0.7826 Intermediate Similarity NPD8312 Approved
0.7826 Intermediate Similarity NPD8313 Approved
0.7814 Intermediate Similarity NPD7251 Discontinued
0.7809 Intermediate Similarity NPD7199 Phase 2
0.7803 Intermediate Similarity NPD4380 Phase 2
0.7759 Intermediate Similarity NPD7411 Suspended
0.7747 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD7075 Discontinued
0.7738 Intermediate Similarity NPD2800 Approved
0.7727 Intermediate Similarity NPD3817 Phase 2
0.7722 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD7228 Approved
0.7684 Intermediate Similarity NPD7768 Phase 2
0.7676 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD6234 Discontinued
0.7571 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD6100 Approved
0.756 Intermediate Similarity NPD6099 Approved
0.7553 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7539 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD6559 Discontinued
0.7527 Intermediate Similarity NPD3926 Phase 2
0.7515 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD2532 Approved
0.7514 Intermediate Similarity NPD2534 Approved
0.7514 Intermediate Similarity NPD2533 Approved
0.75 Intermediate Similarity NPD8151 Discontinued
0.75 Intermediate Similarity NPD6599 Discontinued
0.75 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD3750 Approved
0.7471 Intermediate Similarity NPD1549 Phase 2
0.7471 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD3226 Approved
0.7418 Intermediate Similarity NPD8127 Discontinued
0.7416 Intermediate Similarity NPD6801 Discontinued
0.7416 Intermediate Similarity NPD37 Approved
0.7389 Intermediate Similarity NPD4966 Approved
0.7389 Intermediate Similarity NPD4967 Phase 2
0.7389 Intermediate Similarity NPD4965 Approved
0.7384 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7381 Intermediate Similarity NPD6651 Approved
0.7365 Intermediate Similarity NPD943 Approved
0.736 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD8150 Discontinued
0.733 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD1510 Phase 2
0.7278 Intermediate Similarity NPD1607 Approved
0.7262 Intermediate Similarity NPD1240 Approved
0.7257 Intermediate Similarity NPD6799 Approved
0.7251 Intermediate Similarity NPD2796 Approved
0.7249 Intermediate Similarity NPD7240 Approved
0.7249 Intermediate Similarity NPD7685 Pre-registration
0.724 Intermediate Similarity NPD8434 Phase 2
0.7228 Intermediate Similarity NPD1247 Approved
0.7219 Intermediate Similarity NPD3751 Discontinued
0.7213 Intermediate Similarity NPD919 Approved
0.7209 Intermediate Similarity NPD2346 Discontinued
0.7193 Intermediate Similarity NPD3748 Approved
0.7189 Intermediate Similarity NPD3787 Discontinued
0.7186 Intermediate Similarity NPD6781 Approved
0.7186 Intermediate Similarity NPD6778 Approved
0.7186 Intermediate Similarity NPD6782 Approved
0.7186 Intermediate Similarity NPD6780 Approved
0.7186 Intermediate Similarity NPD6777 Approved
0.7186 Intermediate Similarity NPD6779 Approved
0.7186 Intermediate Similarity NPD6776 Approved
0.7184 Intermediate Similarity NPD8166 Discontinued
0.7184 Intermediate Similarity NPD7003 Approved
0.7175 Intermediate Similarity NPD6273 Approved
0.7171 Intermediate Similarity NPD7783 Phase 2
0.7171 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7164 Intermediate Similarity NPD7698 Approved
0.7164 Intermediate Similarity NPD7696 Phase 3
0.7164 Intermediate Similarity NPD7697 Approved
0.7151 Intermediate Similarity NPD5404 Approved
0.7151 Intermediate Similarity NPD5406 Approved
0.7151 Intermediate Similarity NPD5405 Approved
0.7151 Intermediate Similarity NPD5408 Approved
0.7151 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5402 Approved
0.7129 Intermediate Similarity NPD7871 Phase 2
0.7129 Intermediate Similarity NPD7870 Phase 2
0.7126 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD2344 Approved
0.7108 Intermediate Similarity NPD7701 Phase 2
0.7097 Intermediate Similarity NPD5711 Approved
0.7097 Intermediate Similarity NPD5710 Approved
0.7093 Intermediate Similarity NPD2799 Discontinued
0.7093 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7088 Intermediate Similarity NPD8455 Phase 2
0.7086 Intermediate Similarity NPD4628 Phase 3
0.7079 Intermediate Similarity NPD7435 Discontinued
0.7062 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD5403 Approved
0.7031 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD1243 Approved
0.7024 Intermediate Similarity NPD4908 Phase 1
0.7017 Intermediate Similarity NPD7028 Phase 2
0.7005 Intermediate Similarity NPD7801 Approved
0.7005 Intermediate Similarity NPD7229 Phase 3
0.7 Intermediate Similarity NPD7699 Phase 2
0.7 Intermediate Similarity NPD7700 Phase 2
0.6995 Remote Similarity NPD5761 Phase 2
0.6995 Remote Similarity NPD5760 Phase 2
0.6995 Remote Similarity NPD7680 Approved
0.699 Remote Similarity NPD4287 Approved
0.6982 Remote Similarity NPD4625 Phase 3
0.6965 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6961 Remote Similarity NPD8319 Approved
0.6961 Remote Similarity NPD8320 Phase 1
0.6959 Remote Similarity NPD3620 Phase 2
0.6959 Remote Similarity NPD1613 Approved
0.6959 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6959 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6957 Remote Similarity NPD7874 Approved
0.6957 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2935 Discontinued
0.695 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6949 Remote Similarity NPD2309 Approved
0.6948 Remote Similarity NPD7907 Approved
0.6946 Remote Similarity NPD6823 Phase 2
0.6935 Remote Similarity NPD6535 Approved
0.6935 Remote Similarity NPD6534 Approved
0.6927 Remote Similarity NPD5401 Approved
0.6927 Remote Similarity NPD5953 Discontinued
0.6919 Remote Similarity NPD447 Suspended
0.6919 Remote Similarity NPD230 Phase 1
0.6901 Remote Similarity NPD8032 Phase 2
0.6897 Remote Similarity NPD2493 Approved
0.6897 Remote Similarity NPD2494 Approved
0.6878 Remote Similarity NPD4582 Approved
0.6878 Remote Similarity NPD4583 Approved
0.6872 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6872 Remote Similarity NPD8054 Approved
0.6872 Remote Similarity NPD8053 Approved
0.6869 Remote Similarity NPD2488 Approved
0.6869 Remote Similarity NPD2490 Approved
0.6859 Remote Similarity NPD7177 Discontinued
0.6857 Remote Similarity NPD1551 Phase 2
0.6854 Remote Similarity NPD4665 Approved
0.6854 Remote Similarity NPD4111 Phase 1
0.6851 Remote Similarity NPD920 Approved
0.6845 Remote Similarity NPD1470 Approved
0.6845 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6829 Remote Similarity NPD4004 Approved
0.6829 Remote Similarity NPD4002 Approved
0.6826 Remote Similarity NPD4749 Approved
0.6821 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6814 Remote Similarity NPD3452 Approved
0.6814 Remote Similarity NPD3450 Approved
0.6807 Remote Similarity NPD1201 Approved
0.6806 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6784 Remote Similarity NPD3027 Phase 3
0.6774 Remote Similarity NPD5977 Approved
0.6774 Remote Similarity NPD5978 Approved
0.6766 Remote Similarity NPD4363 Phase 3
0.6766 Remote Similarity NPD4360 Phase 2
0.6754 Remote Similarity NPD2403 Approved
0.6744 Remote Similarity NPD3764 Approved
0.6744 Remote Similarity NPD2313 Discontinued

  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