Structure

Physi-Chem Properties

Molecular Weight:  332.16
Volume:  336.36
LogP:  1.113
LogD:  1.245
LogS:  -3.425
# Rotatable Bonds:  1
TPSA:  87.74
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.766
Synthetic Accessibility Score:  4.923
Fsp3:  0.684
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.001
MDCK Permeability:  1.0333396858186461e-05
Pgp-inhibitor:  0.009
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.59
30% Bioavailability (F30%):  0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.726
Plasma Protein Binding (PPB):  87.92092895507812%
Volume Distribution (VD):  0.817
Pgp-substrate:  11.441777229309082%

ADMET: Metabolism

CYP1A2-inhibitor:  0.033
CYP1A2-substrate:  0.569
CYP2C19-inhibitor:  0.047
CYP2C19-substrate:  0.368
CYP2C9-inhibitor:  0.042
CYP2C9-substrate:  0.049
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.235
CYP3A4-inhibitor:  0.393
CYP3A4-substrate:  0.3

ADMET: Excretion

Clearance (CL):  10.09
Half-life (T1/2):  0.419

ADMET: Toxicity

hERG Blockers:  0.033
Human Hepatotoxicity (H-HT):  0.205
Drug-inuced Liver Injury (DILI):  0.06
AMES Toxicity:  0.018
Rat Oral Acute Toxicity:  0.987
Maximum Recommended Daily Dose:  0.781
Skin Sensitization:  0.105
Carcinogencity:  0.966
Eye Corrosion:  0.003
Eye Irritation:  0.017
Respiratory Toxicity:  0.954

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

  Natural Product: NPC471996

Natural Product ID:  NPC471996
Common Name*:   YJYCGDAWLMWZRS-WUDVTJOCSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  YJYCGDAWLMWZRS-WUDVTJOCSA-N
Standard InCHI:  InChI=1S/C19H24O5/c1-11-16(22)14(21)7-17(2)15-4-3-12-8-24-9-13(12)18(15,10-20)5-6-19(11,17)23/h8-9,15,20,22-23H,3-7,10H2,1-2H3/t15-,17-,18-,19?/m1/s1
SMILES:  CC1=C(C(=O)CC2(C1(CCC3(C2CCC4=COC=C43)CO)O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3315157
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0002550] Isocopalane and spongiane diterpenoids

*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
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. Tongoa, Vanuatu Islands 1996 PMID[10757711]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[12662110]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[15497946]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. Tong-Yong City in the South Sea, Korea n.a. PMID[16905319]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[17567172]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[17988093]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. n.a. n.a. PMID[18407692]
NPO33376 Spongia sp. Species Spongiidae Eukaryota n.a. Indonesian n.a. PMID[24992702]

☑ 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
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens IC50 = 34400.0 nM PMID[490393]
NPT365 Individual Protein NAD(P)H dehydrogenase [quinone] 1 Mus musculus CD = 11.2 uM PMID[490393]
NPT983 Protein Complex Nuclear factor NF-kappa-B complex Homo sapiens ED50 = 50.0 uM PMID[490393]

☑ 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 NPC471996 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
0.9538 High Similarity NPC471995
0.9065 High Similarity NPC243577
0.9044 High Similarity NPC4764
0.8857 High Similarity NPC62103
0.8857 High Similarity NPC20578
0.8849 High Similarity NPC67003
0.8714 High Similarity NPC90296
0.8702 High Similarity NPC272899
0.8696 High Similarity NPC46896
0.8671 High Similarity NPC41182
0.8662 High Similarity NPC64568
0.8662 High Similarity NPC103134
0.8649 High Similarity NPC472785
0.8633 High Similarity NPC310043
0.8623 High Similarity NPC158525
0.8611 High Similarity NPC97904
0.8603 High Similarity NPC61788
0.8601 High Similarity NPC251865
0.8593 High Similarity NPC223063
0.8593 High Similarity NPC120836
0.8592 High Similarity NPC121158
0.8592 High Similarity NPC263337
0.8562 High Similarity NPC470998
0.8561 High Similarity NPC214572
0.8552 High Similarity NPC471174
0.8551 High Similarity NPC471998
0.8542 High Similarity NPC5676
0.8533 High Similarity NPC249021
0.8523 High Similarity NPC35000
0.8514 High Similarity NPC246164
0.8514 High Similarity NPC475777
0.8511 High Similarity NPC90953
0.8487 Intermediate Similarity NPC5079
0.8456 Intermediate Similarity NPC114880
0.8456 Intermediate Similarity NPC178932
0.8456 Intermediate Similarity NPC30222
0.8446 Intermediate Similarity NPC472787
0.8446 Intermediate Similarity NPC272590
0.8435 Intermediate Similarity NPC211625
0.8433 Intermediate Similarity NPC303010
0.8431 Intermediate Similarity NPC51568
0.8431 Intermediate Similarity NPC224394
0.8431 Intermediate Similarity NPC663
0.8431 Intermediate Similarity NPC234660
0.8425 Intermediate Similarity NPC216755
0.8421 Intermediate Similarity NPC477402
0.8414 Intermediate Similarity NPC185456
0.8411 Intermediate Similarity NPC261597
0.8403 Intermediate Similarity NPC476946
0.84 Intermediate Similarity NPC214541
0.84 Intermediate Similarity NPC44675
0.84 Intermediate Similarity NPC92979
0.84 Intermediate Similarity NPC469336
0.84 Intermediate Similarity NPC472786
0.84 Intermediate Similarity NPC75310
0.8389 Intermediate Similarity NPC469503
0.8378 Intermediate Similarity NPC196846
0.8377 Intermediate Similarity NPC276551
0.8377 Intermediate Similarity NPC470940
0.837 Intermediate Similarity NPC23086
0.8366 Intermediate Similarity NPC69028
0.8366 Intermediate Similarity NPC82851
0.8366 Intermediate Similarity NPC329938
0.8358 Intermediate Similarity NPC130275
0.8357 Intermediate Similarity NPC476947
0.8355 Intermediate Similarity NPC477403
0.8355 Intermediate Similarity NPC475967
0.8345 Intermediate Similarity NPC218838
0.8345 Intermediate Similarity NPC476944
0.8333 Intermediate Similarity NPC57998
0.8333 Intermediate Similarity NPC52412
0.8333 Intermediate Similarity NPC282445
0.8323 Intermediate Similarity NPC470875
0.8322 Intermediate Similarity NPC473681
0.8322 Intermediate Similarity NPC218204
0.8322 Intermediate Similarity NPC61157
0.8321 Intermediate Similarity NPC198904
0.8312 Intermediate Similarity NPC469338
0.8312 Intermediate Similarity NPC477405
0.8312 Intermediate Similarity NPC292389
0.8311 Intermediate Similarity NPC472654
0.8311 Intermediate Similarity NPC195325
0.8311 Intermediate Similarity NPC125182
0.8311 Intermediate Similarity NPC69647
0.8301 Intermediate Similarity NPC335761
0.8299 Intermediate Similarity NPC255414
0.8299 Intermediate Similarity NPC250228
0.8299 Intermediate Similarity NPC302987
0.8296 Intermediate Similarity NPC230979
0.8289 Intermediate Similarity NPC472772
0.8289 Intermediate Similarity NPC304692
0.8289 Intermediate Similarity NPC36655
0.8278 Intermediate Similarity NPC296807
0.8278 Intermediate Similarity NPC141538
0.8278 Intermediate Similarity NPC155939
0.8267 Intermediate Similarity NPC75906
0.8267 Intermediate Similarity NPC33938
0.8267 Intermediate Similarity NPC470996
0.8258 Intermediate Similarity NPC476857
0.8258 Intermediate Similarity NPC469849
0.8258 Intermediate Similarity NPC476856
0.8258 Intermediate Similarity NPC476858
0.8255 Intermediate Similarity NPC228842
0.8255 Intermediate Similarity NPC470997
0.8255 Intermediate Similarity NPC212257
0.8248 Intermediate Similarity NPC329707
0.8247 Intermediate Similarity NPC193798
0.8244 Intermediate Similarity NPC212918
0.8243 Intermediate Similarity NPC471007
0.8231 Intermediate Similarity NPC470999
0.8231 Intermediate Similarity NPC346
0.8224 Intermediate Similarity NPC469485
0.8224 Intermediate Similarity NPC41880
0.8224 Intermediate Similarity NPC104736
0.8224 Intermediate Similarity NPC209364
0.8222 Intermediate Similarity NPC178382
0.8217 Intermediate Similarity NPC471397
0.8214 Intermediate Similarity NPC293253
0.8207 Intermediate Similarity NPC473152
0.8205 Intermediate Similarity NPC23387
0.8201 Intermediate Similarity NPC89133
0.8194 Intermediate Similarity NPC18904
0.8194 Intermediate Similarity NPC134254
0.8194 Intermediate Similarity NPC39986
0.8194 Intermediate Similarity NPC302369
0.8188 Intermediate Similarity NPC234494
0.8182 Intermediate Similarity NPC25255
0.8182 Intermediate Similarity NPC472653
0.817 Intermediate Similarity NPC45101
0.817 Intermediate Similarity NPC173544
0.817 Intermediate Similarity NPC187149
0.817 Intermediate Similarity NPC194499
0.817 Intermediate Similarity NPC286722
0.817 Intermediate Similarity NPC470118
0.8158 Intermediate Similarity NPC264943
0.8153 Intermediate Similarity NPC472774
0.8153 Intermediate Similarity NPC476853
0.8153 Intermediate Similarity NPC472282
0.8153 Intermediate Similarity NPC476861
0.8153 Intermediate Similarity NPC472775
0.8153 Intermediate Similarity NPC173516
0.8153 Intermediate Similarity NPC476850
0.8146 Intermediate Similarity NPC44577
0.8146 Intermediate Similarity NPC268905
0.8146 Intermediate Similarity NPC294511
0.8146 Intermediate Similarity NPC121615
0.8141 Intermediate Similarity NPC476860
0.8141 Intermediate Similarity NPC123088
0.8133 Intermediate Similarity NPC196864
0.8133 Intermediate Similarity NPC477404
0.8133 Intermediate Similarity NPC469335
0.8133 Intermediate Similarity NPC159927
0.8129 Intermediate Similarity NPC200782
0.8129 Intermediate Similarity NPC290400
0.8129 Intermediate Similarity NPC263432
0.8129 Intermediate Similarity NPC472771
0.8129 Intermediate Similarity NPC149896
0.8129 Intermediate Similarity NPC117986
0.8129 Intermediate Similarity NPC96443
0.8125 Intermediate Similarity NPC202260
0.8121 Intermediate Similarity NPC19747
0.8117 Intermediate Similarity NPC474611
0.8117 Intermediate Similarity NPC472823
0.8117 Intermediate Similarity NPC473473
0.8117 Intermediate Similarity NPC307383
0.8117 Intermediate Similarity NPC475295
0.8116 Intermediate Similarity NPC279877
0.8116 Intermediate Similarity NPC26532
0.8116 Intermediate Similarity NPC112706
0.8116 Intermediate Similarity NPC207294
0.8108 Intermediate Similarity NPC62799
0.8105 Intermediate Similarity NPC60973
0.8105 Intermediate Similarity NPC107646
0.8089 Intermediate Similarity NPC475779
0.8089 Intermediate Similarity NPC478178
0.8077 Intermediate Similarity NPC472773
0.8077 Intermediate Similarity NPC283209
0.8074 Intermediate Similarity NPC36255
0.8069 Intermediate Similarity NPC56197
0.8067 Intermediate Similarity NPC471001
0.8065 Intermediate Similarity NPC287559
0.8065 Intermediate Similarity NPC470789
0.8054 Intermediate Similarity NPC221809
0.8052 Intermediate Similarity NPC195954
0.8052 Intermediate Similarity NPC197137
0.8052 Intermediate Similarity NPC88007
0.8052 Intermediate Similarity NPC299038
0.8052 Intermediate Similarity NPC472283
0.805 Intermediate Similarity NPC470995
0.8043 Intermediate Similarity NPC290955
0.8043 Intermediate Similarity NPC246392
0.8039 Intermediate Similarity NPC469850
0.8038 Intermediate Similarity NPC478179
0.8038 Intermediate Similarity NPC472651
0.8038 Intermediate Similarity NPC472784
0.8027 Intermediate Similarity NPC205071
0.8026 Intermediate Similarity NPC472672
0.8026 Intermediate Similarity NPC476940
0.8026 Intermediate Similarity NPC476939
0.8025 Intermediate Similarity NPC271657

  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 NPC471996 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
0.84 Intermediate Similarity NPD5760 Phase 2
0.84 Intermediate Similarity NPD5761 Phase 2
0.7831 Intermediate Similarity NPD8434 Phase 2
0.7636 Intermediate Similarity NPD6765 Approved
0.7636 Intermediate Similarity NPD6764 Approved
0.761 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD6785 Approved
0.7456 Intermediate Similarity NPD6784 Approved
0.74 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD2800 Approved
0.7255 Intermediate Similarity NPD4628 Phase 3
0.7179 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD1471 Phase 3
0.7105 Intermediate Similarity NPD6100 Approved
0.7105 Intermediate Similarity NPD6099 Approved
0.7078 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD2532 Approved
0.707 Intermediate Similarity NPD2534 Approved
0.707 Intermediate Similarity NPD2533 Approved
0.7032 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6273 Approved
0.7 Intermediate Similarity NPD3226 Approved
0.6962 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6948 Remote Similarity NPD2344 Approved
0.6948 Remote Similarity NPD2346 Discontinued
0.6943 Remote Similarity NPD7236 Approved
0.6923 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6919 Remote Similarity NPD6559 Discontinued
0.6852 Remote Similarity NPD6599 Discontinued
0.6848 Remote Similarity NPD3882 Suspended
0.6829 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7819 Suspended
0.6818 Remote Similarity NPD2799 Discontinued
0.6815 Remote Similarity NPD3750 Approved
0.6807 Remote Similarity NPD3749 Approved
0.6797 Remote Similarity NPD6651 Approved
0.6788 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6786 Remote Similarity NPD6959 Discontinued
0.6772 Remote Similarity NPD2309 Approved
0.6771 Remote Similarity NPD8404 Phase 2
0.677 Remote Similarity NPD920 Approved
0.6755 Remote Similarity NPD3764 Approved
0.6755 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6755 Remote Similarity NPD2313 Discontinued
0.675 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6005 Phase 3
0.6731 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6731 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6731 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6004 Phase 3
0.6731 Remote Similarity NPD6002 Phase 3
0.6728 Remote Similarity NPD7239 Suspended
0.6727 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6726 Remote Similarity NPD5494 Approved
0.6709 Remote Similarity NPD7003 Approved
0.6707 Remote Similarity NPD7075 Discontinued
0.6688 Remote Similarity NPD1549 Phase 2
0.6687 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6687 Remote Similarity NPD5616 Clinical (unspecified phase)
0.6687 Remote Similarity NPD7458 Discontinued
0.6686 Remote Similarity NPD8127 Discontinued
0.6686 Remote Similarity NPD1247 Approved
0.6667 Remote Similarity NPD1608 Approved
0.6667 Remote Similarity NPD1934 Approved
0.6667 Remote Similarity NPD3972 Approved
0.6667 Remote Similarity NPD6166 Phase 2
0.6667 Remote Similarity NPD6801 Discontinued
0.6667 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2796 Approved
0.6667 Remote Similarity NPD37 Approved
0.6667 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6647 Remote Similarity NPD4965 Approved
0.6647 Remote Similarity NPD5844 Phase 1
0.6647 Remote Similarity NPD4966 Approved
0.6647 Remote Similarity NPD4967 Phase 2
0.6646 Remote Similarity NPD642 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4380 Phase 2
0.6645 Remote Similarity NPD3268 Approved
0.6645 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6627 Remote Similarity NPD2801 Approved
0.6623 Remote Similarity NPD6355 Discontinued
0.6613 Remote Similarity NPD3057 Approved
0.6606 Remote Similarity NPD7411 Suspended
0.6605 Remote Similarity NPD1512 Approved
0.6603 Remote Similarity NPD7033 Discontinued
0.6603 Remote Similarity NPD1510 Phase 2
0.6603 Remote Similarity NPD3748 Approved
0.6601 Remote Similarity NPD8032 Phase 2
0.659 Remote Similarity NPD3818 Discontinued
0.6587 Remote Similarity NPD5402 Approved
0.6587 Remote Similarity NPD3817 Phase 2
0.6584 Remote Similarity NPD6799 Approved
0.6582 Remote Similarity NPD970 Clinical (unspecified phase)
0.6577 Remote Similarity NPD6696 Suspended
0.657 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6568 Remote Similarity NPD919 Approved
0.6561 Remote Similarity NPD1551 Phase 2
0.6558 Remote Similarity NPD4140 Approved
0.6552 Remote Similarity NPD7804 Clinical (unspecified phase)
0.655 Remote Similarity NPD5710 Approved
0.655 Remote Similarity NPD5711 Approved
0.6548 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6545 Remote Similarity NPD7028 Phase 2
0.6533 Remote Similarity NPD2797 Approved
0.6532 Remote Similarity NPD7473 Discontinued
0.6524 Remote Similarity NPD2972 Approved
0.6524 Remote Similarity NPD3533 Approved
0.6522 Remote Similarity NPD643 Clinical (unspecified phase)
0.6519 Remote Similarity NPD5762 Approved
0.6519 Remote Similarity NPD5763 Approved
0.6512 Remote Similarity NPD3926 Phase 2
0.6509 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6497 Remote Similarity NPD4308 Phase 3
0.6497 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6494 Remote Similarity NPD3751 Discontinued
0.6494 Remote Similarity NPD7799 Discontinued
0.649 Remote Similarity NPD6917 Clinical (unspecified phase)
0.649 Remote Similarity NPD2798 Approved
0.6484 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6481 Remote Similarity NPD1511 Approved
0.6481 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6477 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6474 Remote Similarity NPD1607 Approved
0.6471 Remote Similarity NPD7095 Approved
0.6471 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6234 Discontinued
0.6467 Remote Similarity NPD1876 Approved
0.6463 Remote Similarity NPD2932 Approved
0.6463 Remote Similarity NPD1778 Approved
0.6463 Remote Similarity NPD5403 Approved
0.6463 Remote Similarity NPD17 Approved
0.6461 Remote Similarity NPD8313 Approved
0.6461 Remote Similarity NPD8312 Approved
0.6456 Remote Similarity NPD2935 Discontinued
0.6453 Remote Similarity NPD6232 Discontinued
0.6453 Remote Similarity NPD7229 Phase 3
0.6452 Remote Similarity NPD1240 Approved
0.6452 Remote Similarity NPD4060 Phase 1
0.645 Remote Similarity NPD7768 Phase 2
0.645 Remote Similarity NPD7058 Phase 2
0.645 Remote Similarity NPD7057 Phase 3
0.6447 Remote Similarity NPD2861 Phase 2
0.6442 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6438 Remote Similarity NPD1243 Approved
0.6436 Remote Similarity NPD2491 Approved
0.6434 Remote Similarity NPD1241 Discontinued
0.6429 Remote Similarity NPD6798 Discontinued
0.6429 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6424 Remote Similarity NPD1049 Clinical (unspecified phase)
0.641 Remote Similarity NPD5124 Phase 1
0.641 Remote Similarity NPD5123 Clinical (unspecified phase)
0.641 Remote Similarity NPD5735 Approved
0.64 Remote Similarity NPD7893 Clinical (unspecified phase)
0.64 Remote Similarity NPD4749 Approved
0.64 Remote Similarity NPD7177 Discontinued
0.6398 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6398 Remote Similarity NPD4110 Phase 3
0.6398 Remote Similarity NPD8166 Discontinued
0.6384 Remote Similarity NPD6797 Phase 2
0.6382 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6379 Remote Similarity NPD2403 Approved
0.6379 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6376 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6375 Remote Similarity NPD2424 Discontinued
0.6364 Remote Similarity NPD4665 Approved
0.6364 Remote Similarity NPD4111 Phase 1
0.6358 Remote Similarity NPD1283 Approved
0.6358 Remote Similarity NPD8651 Approved
0.6358 Remote Similarity NPD3787 Discontinued
0.6354 Remote Similarity NPD8150 Discontinued
0.6351 Remote Similarity NPD3019 Approved
0.6349 Remote Similarity NPD3448 Approved
0.6348 Remote Similarity NPD7251 Discontinued
0.6348 Remote Similarity NPD3658 Clinical (unspecified phase)
0.6346 Remote Similarity NPD2979 Phase 3
0.6341 Remote Similarity NPD5401 Approved
0.634 Remote Similarity NPD5676 Approved
0.6333 Remote Similarity NPD8407 Phase 2
0.633 Remote Similarity NPD4107 Approved
0.6328 Remote Similarity NPD7074 Phase 3
0.6323 Remote Similarity NPD7985 Registered
0.6323 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6322 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6319 Remote Similarity NPD3300 Phase 2
0.6316 Remote Similarity NPD3267 Approved
0.6316 Remote Similarity NPD3266 Approved
0.6316 Remote Similarity NPD1470 Approved
0.6313 Remote Similarity NPD7808 Phase 3
0.6313 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6307 Remote Similarity NPD7228 Approved
0.6303 Remote Similarity NPD5049 Phase 3
0.6301 Remote Similarity NPD7199 Phase 2
0.6299 Remote Similarity NPD4908 Phase 1
0.6296 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6294 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6294 Remote Similarity NPD2296 Approved
0.6291 Remote Similarity NPD5327 Phase 3
0.6284 Remote Similarity NPD1651 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