Structure

Physi-Chem Properties

Molecular Weight:  470.34
Volume:  511.905
LogP:  3.619
LogD:  3.341
LogS:  -3.992
# Rotatable Bonds:  0
TPSA:  71.44
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.487
Synthetic Accessibility Score:  5.191
Fsp3:  0.9
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:  -5.144
MDCK Permeability:  1.5779056411702186e-05
Pgp-inhibitor:  0.847
Pgp-substrate:  0.01
Human Intestinal Absorption (HIA):  0.038
20% Bioavailability (F20%):  0.873
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.977
Plasma Protein Binding (PPB):  73.34160614013672%
Volume Distribution (VD):  0.703
Pgp-substrate:  20.242401123046875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.532
CYP2C19-inhibitor:  0.039
CYP2C19-substrate:  0.932
CYP2C9-inhibitor:  0.11
CYP2C9-substrate:  0.066
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.063
CYP3A4-inhibitor:  0.88
CYP3A4-substrate:  0.758

ADMET: Excretion

Clearance (CL):  11.696
Half-life (T1/2):  0.691

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.443
Drug-inuced Liver Injury (DILI):  0.046
AMES Toxicity:  0.037
Rat Oral Acute Toxicity:  0.892
Maximum Recommended Daily Dose:  0.776
Skin Sensitization:  0.14
Carcinogencity:  0.49
Eye Corrosion:  0.012
Eye Irritation:  0.019
Respiratory Toxicity:  0.98

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC108840

Natural Product ID:  NPC108840
Common Name*:   (4As,6Ar,6Bs,8R,8As,9R,12As,12Br,14As,14Bs)-8-Hydroxy-2,2,4A,6A,8A,9,12B,14A-Octamethylhexadecahydropicene-3,5,10(6Bh,11H,14Bh)-Trione
IUPAC Name:   (4aS,6aR,6aR,6bS,8R,8aS,9R,12aS,14aS,14bS)-8-hydroxy-2,2,4a,6a,6a,8a,9,14a-octamethyl-4,6,6b,7,8,9,11,12,12a,13,14,14b-dodecahydro-1H-picene-3,5,10-trione
Synonyms:  
Standard InCHIKey:  AQSQZYRCGPMIGT-ABAOYDBWSA-N
Standard InCHI:  InChI=1S/C30H46O4/c1-17-18(31)9-10-19-26(4)11-12-28(6)21-14-25(2,3)23(33)15-27(21,5)24(34)16-29(28,7)20(26)13-22(32)30(17,19)8/h17,19-22,32H,9-16H2,1-8H3/t17-,19-,20-,21+,22+,26-,27-,28-,29+,30+/m0/s1
SMILES:  O=C1CC[C@@H]2[C@]([C@H]1C)(C)[C@H](O)C[C@H]1[C@@]2(C)CC[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC(C)(C)C(=O)C1)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL490988
PubChem CID:   15109247
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0031-9422(90)85349-K]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. DOI[10.1186/1471-2202-6-1]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10579865]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[10716597]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10757718]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11374948]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11561442]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[12579877]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1375626]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1602302]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[16864458]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota roots n.a. n.a. PMID[16989518]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[17250858]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[17265278]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. leaf n.a. PMID[1823717]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[18554602]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[18996177]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota root n.a. n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[21486005]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[21514608]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota dried roots purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China) n.a. PMID[22148431]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota leaves n.a. n.a. PMID[23268606]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[23852638]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24549173]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[24963543]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[25237706]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. bark n.a. PMID[2534610]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. PMID[2816380]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[29355322]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota Leaves n.a. n.a. PMID[31556299]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7102323]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7304185]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8699928]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[8722541]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. root n.a. Database[Article]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13661 Tripterygium wilfordii Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13661 Tripterygium wilfordii Species Celastraceae 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
NPT759 Cell Line H9 Homo sapiens IC50 = 106000.0 nM PMID[507977]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 ED50 > 106.0 uM PMID[507977]

☑ 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 NPC108840 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
0.9714 High Similarity NPC168511
0.9714 High Similarity NPC159325
0.9571 High Similarity NPC282905
0.9571 High Similarity NPC68426
0.9571 High Similarity NPC477229
0.9306 High Similarity NPC267753
0.9189 High Similarity NPC472608
0.9167 High Similarity NPC130011
0.9 High Similarity NPC2568
0.9 High Similarity NPC260319
0.9 High Similarity NPC103647
0.9 High Similarity NPC180777
0.8933 High Similarity NPC26029
0.8831 High Similarity NPC50658
0.88 High Similarity NPC23884
0.8784 High Similarity NPC97534
0.8784 High Similarity NPC174964
0.8784 High Similarity NPC195155
0.8767 High Similarity NPC81759
0.8734 High Similarity NPC25037
0.8734 High Similarity NPC34984
0.8684 High Similarity NPC243594
0.8684 High Similarity NPC31031
0.8667 High Similarity NPC5767
0.8667 High Similarity NPC475742
0.863 High Similarity NPC247195
0.863 High Similarity NPC290058
0.863 High Similarity NPC89310
0.8625 High Similarity NPC62572
0.859 High Similarity NPC280781
0.859 High Similarity NPC476071
0.859 High Similarity NPC48756
0.8553 High Similarity NPC221420
0.8514 High Similarity NPC232112
0.85 High Similarity NPC105895
0.8472 Intermediate Similarity NPC475977
0.8421 Intermediate Similarity NPC472486
0.8421 Intermediate Similarity NPC472487
0.8378 Intermediate Similarity NPC151018
0.8378 Intermediate Similarity NPC58057
0.8378 Intermediate Similarity NPC320549
0.8378 Intermediate Similarity NPC156277
0.8356 Intermediate Similarity NPC213178
0.8356 Intermediate Similarity NPC131892
0.8356 Intermediate Similarity NPC6120
0.8356 Intermediate Similarity NPC327728
0.8333 Intermediate Similarity NPC472984
0.8312 Intermediate Similarity NPC298168
0.8312 Intermediate Similarity NPC143133
0.8289 Intermediate Similarity NPC21220
0.8289 Intermediate Similarity NPC273366
0.8289 Intermediate Similarity NPC125767
0.8286 Intermediate Similarity NPC292419
0.8286 Intermediate Similarity NPC290791
0.825 Intermediate Similarity NPC289486
0.825 Intermediate Similarity NPC30583
0.825 Intermediate Similarity NPC61107
0.8219 Intermediate Similarity NPC100917
0.8219 Intermediate Similarity NPC31187
0.8219 Intermediate Similarity NPC469724
0.8219 Intermediate Similarity NPC474954
0.8219 Intermediate Similarity NPC281203
0.8182 Intermediate Similarity NPC4209
0.8158 Intermediate Similarity NPC254340
0.8148 Intermediate Similarity NPC269684
0.8125 Intermediate Similarity NPC474870
0.8125 Intermediate Similarity NPC271572
0.8101 Intermediate Similarity NPC320144
0.8101 Intermediate Similarity NPC73013
0.8095 Intermediate Similarity NPC473319
0.8095 Intermediate Similarity NPC3032
0.8095 Intermediate Similarity NPC131104
0.8082 Intermediate Similarity NPC204233
0.8077 Intermediate Similarity NPC112463
0.8077 Intermediate Similarity NPC207010
0.8077 Intermediate Similarity NPC475031
0.8077 Intermediate Similarity NPC317913
0.8077 Intermediate Similarity NPC472746
0.8072 Intermediate Similarity NPC74363
0.8072 Intermediate Similarity NPC187545
0.8072 Intermediate Similarity NPC475862
0.8052 Intermediate Similarity NPC159789
0.8052 Intermediate Similarity NPC212733
0.8049 Intermediate Similarity NPC475745
0.8049 Intermediate Similarity NPC237938
0.8049 Intermediate Similarity NPC474482
0.8049 Intermediate Similarity NPC219535
0.8049 Intermediate Similarity NPC473299
0.8026 Intermediate Similarity NPC310766
0.8026 Intermediate Similarity NPC475230
0.8025 Intermediate Similarity NPC268040
0.8 Intermediate Similarity NPC261616
0.8 Intermediate Similarity NPC67653
0.8 Intermediate Similarity NPC470609
0.8 Intermediate Similarity NPC471459
0.7976 Intermediate Similarity NPC73064
0.7975 Intermediate Similarity NPC324700
0.7975 Intermediate Similarity NPC171426
0.7975 Intermediate Similarity NPC34046
0.7975 Intermediate Similarity NPC185465
0.7975 Intermediate Similarity NPC80089
0.7975 Intermediate Similarity NPC224802
0.7973 Intermediate Similarity NPC469987
0.7973 Intermediate Similarity NPC475893
0.7952 Intermediate Similarity NPC133954
0.7931 Intermediate Similarity NPC472147
0.7931 Intermediate Similarity NPC472148
0.7927 Intermediate Similarity NPC475726
0.7927 Intermediate Similarity NPC472743
0.7922 Intermediate Similarity NPC133922
0.7922 Intermediate Similarity NPC280026
0.7922 Intermediate Similarity NPC167702
0.7907 Intermediate Similarity NPC88337
0.7907 Intermediate Similarity NPC472146
0.7907 Intermediate Similarity NPC475211
0.7907 Intermediate Similarity NPC291028
0.7907 Intermediate Similarity NPC185529
0.7901 Intermediate Similarity NPC469745
0.7901 Intermediate Similarity NPC328264
0.7882 Intermediate Similarity NPC230387
0.7882 Intermediate Similarity NPC474719
0.7875 Intermediate Similarity NPC201276
0.7875 Intermediate Similarity NPC80891
0.7867 Intermediate Similarity NPC321732
0.7867 Intermediate Similarity NPC324607
0.7857 Intermediate Similarity NPC472738
0.7857 Intermediate Similarity NPC213412
0.7857 Intermediate Similarity NPC83242
0.7831 Intermediate Similarity NPC474996
0.7821 Intermediate Similarity NPC179858
0.7816 Intermediate Similarity NPC105189
0.7808 Intermediate Similarity NPC80463
0.7808 Intermediate Similarity NPC260116
0.7805 Intermediate Similarity NPC328007
0.7805 Intermediate Similarity NPC317066
0.7738 Intermediate Similarity NPC292553
0.7738 Intermediate Similarity NPC131350
0.7733 Intermediate Similarity NPC473225
0.7711 Intermediate Similarity NPC327451
0.7703 Intermediate Similarity NPC142712
0.7701 Intermediate Similarity NPC193750
0.7701 Intermediate Similarity NPC290614
0.7701 Intermediate Similarity NPC7260
0.7701 Intermediate Similarity NPC227467
0.7701 Intermediate Similarity NPC120968
0.7701 Intermediate Similarity NPC18872
0.7701 Intermediate Similarity NPC210037
0.7701 Intermediate Similarity NPC18536
0.7701 Intermediate Similarity NPC50443
0.7701 Intermediate Similarity NPC477872
0.7701 Intermediate Similarity NPC273621
0.7683 Intermediate Similarity NPC12933
0.7683 Intermediate Similarity NPC58631
0.7674 Intermediate Similarity NPC472739
0.7674 Intermediate Similarity NPC52169
0.7674 Intermediate Similarity NPC182797
0.7667 Intermediate Similarity NPC163685
0.7662 Intermediate Similarity NPC126642
0.7647 Intermediate Similarity NPC477579
0.7647 Intermediate Similarity NPC235341
0.7647 Intermediate Similarity NPC2783
0.7647 Intermediate Similarity NPC95594
0.7647 Intermediate Similarity NPC471737
0.7647 Intermediate Similarity NPC56588
0.7647 Intermediate Similarity NPC248216
0.7647 Intermediate Similarity NPC120395
0.7647 Intermediate Similarity NPC72638
0.7625 Intermediate Similarity NPC264602
0.7619 Intermediate Similarity NPC181871
0.7619 Intermediate Similarity NPC171789
0.7619 Intermediate Similarity NPC74595
0.7619 Intermediate Similarity NPC264665
0.7619 Intermediate Similarity NPC9060
0.7619 Intermediate Similarity NPC471044
0.7619 Intermediate Similarity NPC473336
0.7619 Intermediate Similarity NPC180834
0.7619 Intermediate Similarity NPC474233
0.7619 Intermediate Similarity NPC50438
0.7614 Intermediate Similarity NPC38754
0.7614 Intermediate Similarity NPC4036
0.7614 Intermediate Similarity NPC145067
0.7614 Intermediate Similarity NPC235704
0.7614 Intermediate Similarity NPC158030
0.7614 Intermediate Similarity NPC187722
0.7614 Intermediate Similarity NPC65120
0.7614 Intermediate Similarity NPC474525
0.7614 Intermediate Similarity NPC233455
0.76 Intermediate Similarity NPC41542
0.76 Intermediate Similarity NPC48079
0.759 Intermediate Similarity NPC121121
0.7586 Intermediate Similarity NPC127689
0.7586 Intermediate Similarity NPC225585
0.7586 Intermediate Similarity NPC270768
0.7586 Intermediate Similarity NPC274330
0.7586 Intermediate Similarity NPC290972
0.7586 Intermediate Similarity NPC293048
0.7586 Intermediate Similarity NPC69627
0.7586 Intermediate Similarity NPC263393
0.7586 Intermediate Similarity NPC121798
0.7586 Intermediate Similarity NPC143232

  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 NPC108840 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
0.8378 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.8378 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.8356 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.8356 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD6117 Approved
0.8077 Intermediate Similarity NPD6116 Phase 1
0.8052 Intermediate Similarity NPD3703 Phase 2
0.8 Intermediate Similarity NPD4244 Approved
0.8 Intermediate Similarity NPD4245 Approved
0.7975 Intermediate Similarity NPD6115 Approved
0.7975 Intermediate Similarity NPD6114 Approved
0.7975 Intermediate Similarity NPD6697 Approved
0.7975 Intermediate Similarity NPD6118 Approved
0.7922 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD3698 Phase 2
0.7763 Intermediate Similarity NPD4789 Approved
0.7733 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD5360 Phase 3
0.7614 Intermediate Similarity NPD7515 Phase 2
0.7568 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD3671 Phase 1
0.7529 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7416 Intermediate Similarity NPD8035 Phase 2
0.7416 Intermediate Similarity NPD8034 Phase 2
0.7391 Intermediate Similarity NPD7902 Approved
0.7253 Intermediate Similarity NPD7748 Approved
0.7237 Intermediate Similarity NPD4224 Phase 2
0.7215 Intermediate Similarity NPD6081 Approved
0.7215 Intermediate Similarity NPD4758 Discontinued
0.7179 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD5364 Discontinued
0.7065 Intermediate Similarity NPD7900 Approved
0.7065 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD3618 Phase 1
0.7 Intermediate Similarity NPD5777 Approved
0.6824 Remote Similarity NPD7645 Phase 2
0.6818 Remote Similarity NPD4786 Approved
0.6813 Remote Similarity NPD5328 Approved
0.6782 Remote Similarity NPD3667 Approved
0.6737 Remote Similarity NPD4697 Phase 3
0.6705 Remote Similarity NPD4788 Approved
0.6667 Remote Similarity NPD4787 Phase 1
0.6667 Remote Similarity NPD6079 Approved
0.6596 Remote Similarity NPD6399 Phase 3
0.6548 Remote Similarity NPD3702 Approved
0.6505 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6444 Remote Similarity NPD3666 Approved
0.6444 Remote Similarity NPD3133 Approved
0.6444 Remote Similarity NPD3665 Phase 1
0.6438 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6438 Remote Similarity NPD615 Clinical (unspecified phase)
0.6436 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6421 Remote Similarity NPD4202 Approved
0.6392 Remote Similarity NPD5222 Approved
0.6392 Remote Similarity NPD5221 Approved
0.6392 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6364 Remote Similarity NPD8418 Phase 2
0.6364 Remote Similarity NPD7525 Registered
0.6327 Remote Similarity NPD5173 Approved
0.6327 Remote Similarity NPD4755 Approved
0.6304 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6277 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6264 Remote Similarity NPD3668 Phase 3
0.6214 Remote Similarity NPD6920 Discontinued
0.62 Remote Similarity NPD5286 Approved
0.62 Remote Similarity NPD4700 Approved
0.62 Remote Similarity NPD4696 Approved
0.62 Remote Similarity NPD5285 Approved
0.619 Remote Similarity NPD6373 Approved
0.619 Remote Similarity NPD6372 Approved
0.618 Remote Similarity NPD6928 Phase 2
0.6143 Remote Similarity NPD385 Approved
0.6143 Remote Similarity NPD384 Approved
0.6139 Remote Similarity NPD5223 Approved
0.6136 Remote Similarity NPD3617 Approved
0.6105 Remote Similarity NPD4753 Phase 2
0.61 Remote Similarity NPD7638 Approved
0.6095 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6091 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6078 Remote Similarity NPD5211 Phase 2
0.6078 Remote Similarity NPD4633 Approved
0.6078 Remote Similarity NPD5225 Approved
0.6078 Remote Similarity NPD5224 Approved
0.6078 Remote Similarity NPD5226 Approved
0.6075 Remote Similarity NPD6650 Approved
0.6075 Remote Similarity NPD6649 Approved
0.6058 Remote Similarity NPD6675 Approved
0.6058 Remote Similarity NPD6402 Approved
0.6058 Remote Similarity NPD7128 Approved
0.6058 Remote Similarity NPD5739 Approved
0.604 Remote Similarity NPD7639 Approved
0.604 Remote Similarity NPD7640 Approved
0.6026 Remote Similarity NPD3198 Approved
0.6019 Remote Similarity NPD5174 Approved
0.6019 Remote Similarity NPD4754 Approved
0.6019 Remote Similarity NPD5175 Approved
0.6 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6 Remote Similarity NPD4695 Discontinued
0.5962 Remote Similarity NPD5141 Approved
0.596 Remote Similarity NPD4629 Approved
0.596 Remote Similarity NPD5210 Approved
0.5957 Remote Similarity NPD5279 Phase 3
0.5943 Remote Similarity NPD7320 Approved
0.5943 Remote Similarity NPD6899 Approved
0.5943 Remote Similarity NPD6881 Approved
0.5943 Remote Similarity NPD6415 Discontinued
0.5926 Remote Similarity NPD7909 Approved
0.5922 Remote Similarity NPD7632 Discontinued
0.5913 Remote Similarity NPD8328 Phase 3
0.5905 Remote Similarity NPD4767 Approved
0.5905 Remote Similarity NPD4768 Approved
0.59 Remote Similarity NPD7614 Phase 1
0.587 Remote Similarity NPD4221 Approved
0.587 Remote Similarity NPD4223 Phase 3
0.5851 Remote Similarity NPD5329 Approved
0.5849 Remote Similarity NPD5697 Approved
0.5849 Remote Similarity NPD5701 Approved
0.5842 Remote Similarity NPD6084 Phase 2
0.5842 Remote Similarity NPD6083 Phase 2
0.5833 Remote Similarity NPD7290 Approved
0.5833 Remote Similarity NPD7102 Approved
0.5833 Remote Similarity NPD6883 Approved
0.5818 Remote Similarity NPD8133 Approved
0.5806 Remote Similarity NPD3669 Approved
0.5806 Remote Similarity NPD3670 Clinical (unspecified phase)
0.5804 Remote Similarity NPD7115 Discovery
0.5795 Remote Similarity NPD7339 Approved
0.5795 Remote Similarity NPD6942 Approved
0.5794 Remote Similarity NPD4730 Approved
0.5794 Remote Similarity NPD5168 Approved
0.5794 Remote Similarity NPD6011 Approved
0.5794 Remote Similarity NPD4729 Approved
0.5794 Remote Similarity NPD5128 Approved
0.5789 Remote Similarity NPD6684 Approved
0.5789 Remote Similarity NPD7146 Approved
0.5789 Remote Similarity NPD7521 Approved
0.5789 Remote Similarity NPD5330 Approved
0.5789 Remote Similarity NPD6409 Approved
0.5789 Remote Similarity NPD7334 Approved
0.578 Remote Similarity NPD6401 Clinical (unspecified phase)
0.578 Remote Similarity NPD8130 Phase 1
0.578 Remote Similarity NPD6869 Approved
0.578 Remote Similarity NPD6847 Approved
0.578 Remote Similarity NPD6617 Approved
0.5761 Remote Similarity NPD4139 Approved
0.5761 Remote Similarity NPD4692 Approved
0.5758 Remote Similarity NPD8171 Discontinued
0.5745 Remote Similarity NPD4197 Approved
0.5741 Remote Similarity NPD6012 Approved
0.5741 Remote Similarity NPD6013 Approved
0.5741 Remote Similarity NPD6014 Approved
0.573 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5729 Remote Similarity NPD3573 Approved
0.5727 Remote Similarity NPD8297 Approved
0.5727 Remote Similarity NPD6882 Approved
0.5714 Remote Similarity NPD6700 Approved
0.5714 Remote Similarity NPD6701 Clinical (unspecified phase)
0.5701 Remote Similarity NPD6412 Phase 2
0.5688 Remote Similarity NPD5250 Approved
0.5688 Remote Similarity NPD5134 Clinical (unspecified phase)
0.5688 Remote Similarity NPD5251 Approved
0.5688 Remote Similarity NPD5169 Approved
0.5688 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5688 Remote Similarity NPD5247 Approved
0.5688 Remote Similarity NPD4634 Approved
0.5688 Remote Similarity NPD5135 Approved
0.5688 Remote Similarity NPD5249 Phase 3
0.5688 Remote Similarity NPD5248 Approved
0.5676 Remote Similarity NPD8298 Phase 2
0.567 Remote Similarity NPD6903 Approved
0.567 Remote Similarity NPD5737 Approved
0.567 Remote Similarity NPD6672 Approved
0.5657 Remote Similarity NPD6411 Approved
0.5657 Remote Similarity NPD6703 Approved
0.5657 Remote Similarity NPD6702 Approved
0.5647 Remote Similarity NPD229 Approved
0.5647 Remote Similarity NPD6705 Phase 1
0.5644 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5636 Remote Similarity NPD5127 Approved
0.5636 Remote Similarity NPD5215 Approved
0.5636 Remote Similarity NPD5216 Approved
0.5636 Remote Similarity NPD5217 Approved
0.5631 Remote Similarity NPD5696 Approved
0.5625 Remote Similarity NPD4138 Approved
0.5625 Remote Similarity NPD4519 Discontinued
0.5625 Remote Similarity NPD4623 Approved
0.5625 Remote Similarity NPD4688 Approved
0.5625 Remote Similarity NPD4689 Approved
0.5625 Remote Similarity NPD4690 Approved
0.5625 Remote Similarity NPD4693 Phase 3
0.5625 Remote Similarity NPD5205 Approved
0.5604 Remote Similarity NPD4802 Phase 2
0.5604 Remote Similarity NPD4238 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