Structure

Physi-Chem Properties

Molecular Weight:  792.43
Volume:  787.61
LogP:  3.82
LogD:  3.068
LogS:  -4.719
# Rotatable Bonds:  12
TPSA:  178.04
# H-Bond Aceptor:  14
# H-Bond Donor:  2
# Rings:  7
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.141
Synthetic Accessibility Score:  6.858
Fsp3:  0.881
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.249
MDCK Permeability:  0.00016008545935619622
Pgp-inhibitor:  0.97
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.122

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  54.118064880371094%
Volume Distribution (VD):  1.143
Pgp-substrate:  12.123259544372559%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.979
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.722
CYP2C9-inhibitor:  0.029
CYP2C9-substrate:  0.002
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.081
CYP3A4-inhibitor:  0.817
CYP3A4-substrate:  0.903

ADMET: Excretion

Clearance (CL):  6.066
Half-life (T1/2):  0.269

ADMET: Toxicity

hERG Blockers:  0.926
Human Hepatotoxicity (H-HT):  0.409
Drug-inuced Liver Injury (DILI):  0.69
AMES Toxicity:  0.231
Rat Oral Acute Toxicity:  0.796
Maximum Recommended Daily Dose:  0.043
Skin Sensitization:  0.802
Carcinogencity:  0.118
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.987

Download Data

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

  Natural Product: NPC114306

Natural Product ID:  NPC114306
Common Name*:   Tenacissimoside A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  OHDJGUWKOIBIKY-SGFNNURDSA-N
Standard InCHI:  InChI=1S/C42H64O14/c1-11-20(2)37(47)54-34-35-39(7)15-13-26(53-29-19-28(48-9)32(23(5)50-29)55-38-31(46)33(49-10)30(45)22(4)51-38)18-25(39)12-16-41(35)42(56-41)17-14-27(21(3)43)40(42,8)36(34)52-24(6)44/h11,22-23,25-36,38,45-46H,12-19H2,1-10H3/b20-11+/t22-,23-,25+,26+,27+,28-,29+,30-,31-,32-,33-,34+,35-,36-,38+,39+,40+,41+,42-/m1/s1
SMILES:  CO[C@@H]1C[C@H](O[C@H]2CC[C@]3([C@H](C2)CC[C@@]24[C@@H]3[C@H](OC(=O)/C(=C/C)/C)[C@@H](OC(=O)C)[C@]3([C@]4(O2)CC[C@H]3C(=O)C)C)C)O[C@@H]([C@H]1O[C@@H]1O[C@H](C)[C@H]([C@H]([C@H]1O)OC)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464723
PubChem CID:   44561398
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001691] Steroid esters

*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
NPO23320 Marsdenia tenacissima Species Apocynaceae Eukaryota stems Simao County, Yunnan Province, China 2005-MAR PMID[25215856]
NPO23320 Marsdenia tenacissima Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23320 Marsdenia tenacissima Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]

☑ 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 Inhibition = 50.0 % PMID[471032]
NPT2 Others Unspecified Ratio IC50 = 7.8 n.a. PMID[471032]
NPT2 Others Unspecified Ratio IC50 = 17.9 n.a. PMID[471032]
NPT2 Others Unspecified Ratio IC50 = 10.0 n.a. PMID[471032]
NPT2 Others Unspecified Ratio IC50 = 2.4 n.a. PMID[471032]
NPT2 Others Unspecified Ratio IC50 = 11.2 n.a. PMID[471032]
NPT2 Others Unspecified Ratio IC50 = 7.0 n.a. PMID[471032]
NPT2 Others Unspecified Ratio IC50 = 5.8 n.a. PMID[471032]
NPT2 Others Unspecified Ratio IC50 = 4.7 n.a. PMID[471032]
NPT2 Others Unspecified Ratio IC50 = 1.1 n.a. PMID[471032]
NPT2 Others Unspecified Activity = 3.5 % PMID[471032]
NPT610 Others Molecular identity unknown Activity = 49.3 % PMID[471032]
NPT610 Others Molecular identity unknown Activity = 7.2 % PMID[471032]
NPT610 Others Molecular identity unknown Activity = 32.0 % PMID[471032]
NPT610 Others Molecular identity unknown Activity = 3.0 % PMID[471032]
NPT2 Others Unspecified Activity = 39.8 % PMID[471032]
NPT2 Others Unspecified Activity = 6.8 % PMID[471032]
NPT2 Others Unspecified Activity = 44.2 % PMID[471032]
NPT2 Others Unspecified Activity = 24.9 % PMID[471032]
NPT2 Others Unspecified Activity = 6.3 % PMID[471032]
NPT2 Others Unspecified Activity = 63.6 % PMID[471032]
NPT2 Others Unspecified Activity = 7.6 % PMID[471032]
NPT2 Others Unspecified Activity = 8.9 % PMID[471032]
NPT2 Others Unspecified Activity = 5.1 % PMID[471032]
NPT2 Others Unspecified Activity = 73.0 % PMID[471032]
NPT2 Others Unspecified Activity = 18.0 % PMID[471032]
NPT2 Others Unspecified Activity = 28.0 % PMID[471032]
NPT2 Others Unspecified Activity = 41.0 % PMID[471032]
NPT2 Others Unspecified Inhibition = 50.0 % PMID[471032]
NPT2 Others Unspecified Inhibition = 90.0 % PMID[471032]
NPT2 Others Unspecified Inhibition = 160.0 % PMID[471032]
NPT2 Others Unspecified Inhibition = 180.0 % PMID[471032]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 50.0 % PMID[471032]

☑ 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 NPC114306 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 NPC477490
0.9832 High Similarity NPC477493
0.881 High Similarity NPC93416
0.8803 High Similarity NPC477489
0.879 High Similarity NPC329784
0.879 High Similarity NPC240070
0.874 High Similarity NPC477709
0.874 High Similarity NPC476221
0.873 High Similarity NPC16569
0.873 High Similarity NPC253456
0.873 High Similarity NPC159338
0.8692 High Similarity NPC79250
0.8692 High Similarity NPC290746
0.8682 High Similarity NPC59288
0.8661 High Similarity NPC471855
0.8661 High Similarity NPC42670
0.8661 High Similarity NPC19124
0.8651 High Similarity NPC276838
0.8651 High Similarity NPC125077
0.8651 High Similarity NPC329986
0.8651 High Similarity NPC232785
0.8651 High Similarity NPC140092
0.8651 High Similarity NPC91
0.8651 High Similarity NPC188234
0.8594 High Similarity NPC142756
0.8594 High Similarity NPC32793
0.8594 High Similarity NPC116075
0.8594 High Similarity NPC104585
0.8594 High Similarity NPC298783
0.8594 High Similarity NPC146857
0.8594 High Similarity NPC157817
0.8594 High Similarity NPC247190
0.8594 High Similarity NPC469749
0.8594 High Similarity NPC225385
0.8548 High Similarity NPC27363
0.8527 High Similarity NPC329636
0.8504 High Similarity NPC471407
0.8492 Intermediate Similarity NPC471356
0.8492 Intermediate Similarity NPC117702
0.8492 Intermediate Similarity NPC471357
0.8492 Intermediate Similarity NPC179412
0.8492 Intermediate Similarity NPC146456
0.8492 Intermediate Similarity NPC469757
0.8487 Intermediate Similarity NPC477492
0.8468 Intermediate Similarity NPC28532
0.8462 Intermediate Similarity NPC194716
0.845 Intermediate Similarity NPC316915
0.8438 Intermediate Similarity NPC173347
0.8413 Intermediate Similarity NPC469750
0.8413 Intermediate Similarity NPC250556
0.8397 Intermediate Similarity NPC329675
0.8372 Intermediate Similarity NPC231240
0.8359 Intermediate Similarity NPC180079
0.8359 Intermediate Similarity NPC471358
0.8359 Intermediate Similarity NPC469754
0.8359 Intermediate Similarity NPC476966
0.8359 Intermediate Similarity NPC471361
0.8359 Intermediate Similarity NPC251866
0.8359 Intermediate Similarity NPC9499
0.8359 Intermediate Similarity NPC70542
0.8359 Intermediate Similarity NPC89514
0.8359 Intermediate Similarity NPC10823
0.8359 Intermediate Similarity NPC471360
0.8359 Intermediate Similarity NPC469753
0.8359 Intermediate Similarity NPC6108
0.8359 Intermediate Similarity NPC197707
0.8359 Intermediate Similarity NPC469755
0.8359 Intermediate Similarity NPC471359
0.8359 Intermediate Similarity NPC86159
0.8359 Intermediate Similarity NPC469751
0.8359 Intermediate Similarity NPC219085
0.8359 Intermediate Similarity NPC469752
0.8359 Intermediate Similarity NPC284406
0.8359 Intermediate Similarity NPC471352
0.8359 Intermediate Similarity NPC17896
0.8333 Intermediate Similarity NPC472719
0.8333 Intermediate Similarity NPC207845
0.8321 Intermediate Similarity NPC171619
0.832 Intermediate Similarity NPC264336
0.8306 Intermediate Similarity NPC474466
0.8306 Intermediate Similarity NPC475556
0.8306 Intermediate Similarity NPC475136
0.8306 Intermediate Similarity NPC475629
0.8306 Intermediate Similarity NPC470312
0.8306 Intermediate Similarity NPC281840
0.8281 Intermediate Similarity NPC311534
0.8258 Intermediate Similarity NPC62172
0.8258 Intermediate Similarity NPC289700
0.825 Intermediate Similarity NPC274833
0.824 Intermediate Similarity NPC314535
0.824 Intermediate Similarity NPC173555
0.8231 Intermediate Similarity NPC473519
0.8231 Intermediate Similarity NPC473805
0.8226 Intermediate Similarity NPC30483
0.8226 Intermediate Similarity NPC469756
0.8226 Intermediate Similarity NPC236973
0.8226 Intermediate Similarity NPC329905
0.8226 Intermediate Similarity NPC292467
0.8226 Intermediate Similarity NPC470897
0.8226 Intermediate Similarity NPC55532
0.8226 Intermediate Similarity NPC32177
0.8222 Intermediate Similarity NPC48414
0.8222 Intermediate Similarity NPC5153
0.8217 Intermediate Similarity NPC231529
0.8211 Intermediate Similarity NPC473304
0.8203 Intermediate Similarity NPC42399
0.8203 Intermediate Similarity NPC298841
0.8168 Intermediate Similarity NPC102015
0.816 Intermediate Similarity NPC108072
0.816 Intermediate Similarity NPC72260
0.8154 Intermediate Similarity NPC471170
0.8145 Intermediate Similarity NPC83287
0.814 Intermediate Similarity NPC270109
0.814 Intermediate Similarity NPC245094
0.814 Intermediate Similarity NPC473620
0.8134 Intermediate Similarity NPC75616
0.813 Intermediate Similarity NPC472718
0.813 Intermediate Similarity NPC88945
0.813 Intermediate Similarity NPC471816
0.8125 Intermediate Similarity NPC473635
0.812 Intermediate Similarity NPC190065
0.812 Intermediate Similarity NPC34562
0.812 Intermediate Similarity NPC127656
0.812 Intermediate Similarity NPC141215
0.812 Intermediate Similarity NPC471089
0.811 Intermediate Similarity NPC117445
0.811 Intermediate Similarity NPC208193
0.811 Intermediate Similarity NPC308262
0.8106 Intermediate Similarity NPC248703
0.8102 Intermediate Similarity NPC471172
0.8095 Intermediate Similarity NPC475419
0.8095 Intermediate Similarity NPC40749
0.8095 Intermediate Similarity NPC120390
0.8095 Intermediate Similarity NPC475219
0.8095 Intermediate Similarity NPC231518
0.8095 Intermediate Similarity NPC475590
0.8095 Intermediate Similarity NPC202051
0.8095 Intermediate Similarity NPC474908
0.8092 Intermediate Similarity NPC478154
0.8092 Intermediate Similarity NPC155529
0.8083 Intermediate Similarity NPC8431
0.8077 Intermediate Similarity NPC175186
0.8077 Intermediate Similarity NPC477196
0.8077 Intermediate Similarity NPC104382
0.8065 Intermediate Similarity NPC470778
0.8065 Intermediate Similarity NPC309034
0.8065 Intermediate Similarity NPC78836
0.8065 Intermediate Similarity NPC142066
0.8065 Intermediate Similarity NPC157376
0.8065 Intermediate Similarity NPC471354
0.8065 Intermediate Similarity NPC244402
0.8065 Intermediate Similarity NPC87250
0.8065 Intermediate Similarity NPC473852
0.8065 Intermediate Similarity NPC158344
0.8065 Intermediate Similarity NPC243196
0.8065 Intermediate Similarity NPC471351
0.8065 Intermediate Similarity NPC471355
0.8065 Intermediate Similarity NPC474418
0.8065 Intermediate Similarity NPC196429
0.8065 Intermediate Similarity NPC77319
0.8065 Intermediate Similarity NPC471353
0.8065 Intermediate Similarity NPC34390
0.8065 Intermediate Similarity NPC99728
0.8065 Intermediate Similarity NPC477252
0.8065 Intermediate Similarity NPC27507
0.8065 Intermediate Similarity NPC146432
0.8065 Intermediate Similarity NPC50305
0.8065 Intermediate Similarity NPC290693
0.8065 Intermediate Similarity NPC93883
0.8065 Intermediate Similarity NPC152615
0.8065 Intermediate Similarity NPC84987
0.8062 Intermediate Similarity NPC470516
0.8062 Intermediate Similarity NPC470780
0.8062 Intermediate Similarity NPC287423
0.806 Intermediate Similarity NPC140045
0.806 Intermediate Similarity NPC596
0.806 Intermediate Similarity NPC295885
0.8047 Intermediate Similarity NPC32868
0.8047 Intermediate Similarity NPC318135
0.8047 Intermediate Similarity NPC241456
0.8047 Intermediate Similarity NPC469790
0.8045 Intermediate Similarity NPC262813
0.8045 Intermediate Similarity NPC158350
0.8043 Intermediate Similarity NPC194854
0.8043 Intermediate Similarity NPC48813
0.8033 Intermediate Similarity NPC476964
0.8031 Intermediate Similarity NPC193893
0.8031 Intermediate Similarity NPC474423
0.8031 Intermediate Similarity NPC74259
0.803 Intermediate Similarity NPC88668
0.803 Intermediate Similarity NPC478151
0.8016 Intermediate Similarity NPC471406
0.8016 Intermediate Similarity NPC48692
0.8016 Intermediate Similarity NPC476150
0.8016 Intermediate Similarity NPC476127
0.8016 Intermediate Similarity NPC135369
0.8016 Intermediate Similarity NPC251226
0.8015 Intermediate Similarity NPC478155
0.8015 Intermediate Similarity NPC477197
0.8015 Intermediate Similarity NPC25998

  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 NPC114306 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
0.8413 Intermediate Similarity NPD7507 Approved
0.8359 Intermediate Similarity NPD7319 Approved
0.824 Intermediate Similarity NPD8380 Approved
0.824 Intermediate Similarity NPD8296 Approved
0.824 Intermediate Similarity NPD8379 Approved
0.824 Intermediate Similarity NPD8378 Approved
0.824 Intermediate Similarity NPD8335 Approved
0.8226 Intermediate Similarity NPD7516 Approved
0.816 Intermediate Similarity NPD8377 Approved
0.816 Intermediate Similarity NPD8294 Approved
0.8145 Intermediate Similarity NPD7328 Approved
0.8145 Intermediate Similarity NPD7327 Approved
0.8115 Intermediate Similarity NPD8133 Approved
0.8095 Intermediate Similarity NPD8033 Approved
0.775 Intermediate Similarity NPD8170 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7736 Approved
0.7692 Intermediate Similarity NPD8328 Phase 3
0.7674 Intermediate Similarity NPD7503 Approved
0.7561 Intermediate Similarity NPD6686 Approved
0.748 Intermediate Similarity NPD6412 Phase 2
0.7388 Intermediate Similarity NPD8293 Discontinued
0.7364 Intermediate Similarity NPD7115 Discovery
0.736 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7348 Intermediate Similarity NPD6370 Approved
0.7323 Intermediate Similarity NPD8297 Approved
0.7323 Intermediate Similarity NPD6882 Approved
0.728 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD7492 Approved
0.7231 Intermediate Similarity NPD6009 Approved
0.7231 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD6319 Approved
0.7197 Intermediate Similarity NPD6054 Approved
0.7185 Intermediate Similarity NPD6616 Approved
0.7165 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8516 Approved
0.7143 Intermediate Similarity NPD8515 Approved
0.7143 Intermediate Similarity NPD8513 Phase 3
0.7143 Intermediate Similarity NPD8517 Approved
0.7132 Intermediate Similarity NPD4632 Approved
0.7132 Intermediate Similarity NPD7078 Approved
0.7109 Intermediate Similarity NPD6649 Approved
0.7109 Intermediate Similarity NPD6650 Approved
0.7087 Intermediate Similarity NPD6373 Approved
0.7087 Intermediate Similarity NPD6372 Approved
0.7068 Intermediate Similarity NPD6059 Approved
0.7049 Intermediate Similarity NPD7638 Approved
0.7015 Intermediate Similarity NPD6016 Approved
0.7015 Intermediate Similarity NPD6015 Approved
0.7008 Intermediate Similarity NPD6899 Approved
0.7008 Intermediate Similarity NPD6881 Approved
0.6992 Remote Similarity NPD7640 Approved
0.6992 Remote Similarity NPD7639 Approved
0.6984 Remote Similarity NPD7128 Approved
0.6984 Remote Similarity NPD6675 Approved
0.6984 Remote Similarity NPD6008 Approved
0.6984 Remote Similarity NPD5739 Approved
0.6984 Remote Similarity NPD6402 Approved
0.6977 Remote Similarity NPD8130 Phase 1
0.6963 Remote Similarity NPD5988 Approved
0.6929 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6929 Remote Similarity NPD5697 Approved
0.6917 Remote Similarity NPD8171 Discontinued
0.6912 Remote Similarity NPD7604 Phase 2
0.6899 Remote Similarity NPD7102 Approved
0.6899 Remote Similarity NPD6883 Approved
0.6899 Remote Similarity NPD7290 Approved
0.6875 Remote Similarity NPD7320 Approved
0.6846 Remote Similarity NPD6847 Approved
0.6846 Remote Similarity NPD6617 Approved
0.6846 Remote Similarity NPD6869 Approved
0.6822 Remote Similarity NPD6012 Approved
0.6822 Remote Similarity NPD6013 Approved
0.6822 Remote Similarity NPD6014 Approved
0.6797 Remote Similarity NPD5701 Approved
0.6765 Remote Similarity NPD6921 Approved
0.6765 Remote Similarity NPD5983 Phase 2
0.6744 Remote Similarity NPD6011 Approved
0.6733 Remote Similarity NPD7625 Phase 1
0.6691 Remote Similarity NPD6336 Discontinued
0.6641 Remote Similarity NPD4634 Approved
0.6614 Remote Similarity NPD5211 Phase 2
0.6596 Remote Similarity NPD6033 Approved
0.6591 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6591 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6587 Remote Similarity NPD5285 Approved
0.6587 Remote Similarity NPD5286 Approved
0.6587 Remote Similarity NPD4696 Approved
0.656 Remote Similarity NPD4755 Approved
0.656 Remote Similarity NPD7902 Approved
0.6557 Remote Similarity NPD8034 Phase 2
0.6557 Remote Similarity NPD8035 Phase 2
0.6547 Remote Similarity NPD6067 Discontinued
0.6541 Remote Similarity NPD6053 Discontinued
0.6535 Remote Similarity NPD5344 Discontinued
0.6535 Remote Similarity NPD1700 Approved
0.6519 Remote Similarity NPD6274 Approved
0.6515 Remote Similarity NPD6371 Approved
0.6512 Remote Similarity NPD5141 Approved
0.6496 Remote Similarity NPD7101 Approved
0.6496 Remote Similarity NPD7100 Approved
0.6484 Remote Similarity NPD5224 Approved
0.6484 Remote Similarity NPD4633 Approved
0.6484 Remote Similarity NPD5225 Approved
0.6484 Remote Similarity NPD5226 Approved
0.6484 Remote Similarity NPD7632 Discontinued
0.6457 Remote Similarity NPD4700 Approved
0.6452 Remote Similarity NPD7748 Approved
0.6434 Remote Similarity NPD5174 Approved
0.6434 Remote Similarity NPD5175 Approved
0.6429 Remote Similarity NPD6083 Phase 2
0.6429 Remote Similarity NPD6084 Phase 2
0.6423 Remote Similarity NPD6335 Approved
0.6408 Remote Similarity NPD8074 Phase 3
0.6407 Remote Similarity NPD7799 Discontinued
0.6406 Remote Similarity NPD5223 Approved
0.6378 Remote Similarity NPD4225 Approved
0.6364 Remote Similarity NPD4730 Approved
0.6364 Remote Similarity NPD4729 Approved
0.635 Remote Similarity NPD6317 Approved
0.6341 Remote Similarity NPD46 Approved
0.6341 Remote Similarity NPD6698 Approved
0.6336 Remote Similarity NPD4768 Approved
0.6336 Remote Similarity NPD4767 Approved
0.632 Remote Similarity NPD7900 Approved
0.632 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6304 Remote Similarity NPD6313 Approved
0.6304 Remote Similarity NPD6314 Approved
0.6301 Remote Similarity NPD8338 Approved
0.629 Remote Similarity NPD6079 Approved
0.629 Remote Similarity NPD7515 Phase 2
0.6288 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6286 Remote Similarity NPD6908 Approved
0.6286 Remote Similarity NPD6909 Approved
0.6286 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6277 Remote Similarity NPD6940 Discontinued
0.627 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6269 Remote Similarity NPD5251 Approved
0.6269 Remote Similarity NPD5250 Approved
0.6269 Remote Similarity NPD5248 Approved
0.6269 Remote Similarity NPD5247 Approved
0.6269 Remote Similarity NPD5249 Phase 3
0.626 Remote Similarity NPD5328 Approved
0.625 Remote Similarity NPD5696 Approved
0.625 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6241 Remote Similarity NPD5128 Approved
0.624 Remote Similarity NPD6399 Phase 3
0.624 Remote Similarity NPD4202 Approved
0.6233 Remote Similarity NPD7260 Phase 2
0.6202 Remote Similarity NPD6648 Approved
0.6198 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6197 Remote Similarity NPD7830 Approved
0.6197 Remote Similarity NPD7829 Approved
0.6183 Remote Similarity NPD4754 Approved
0.6179 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6154 Remote Similarity NPD6115 Approved
0.6154 Remote Similarity NPD6697 Approved
0.6154 Remote Similarity NPD6118 Approved
0.6154 Remote Similarity NPD6114 Approved
0.6142 Remote Similarity NPD5695 Phase 3
0.6138 Remote Similarity NPD8336 Approved
0.6138 Remote Similarity NPD8337 Approved
0.6103 Remote Similarity NPD5215 Approved
0.6103 Remote Similarity NPD5216 Approved
0.6103 Remote Similarity NPD5217 Approved
0.6094 Remote Similarity NPD5222 Approved
0.6094 Remote Similarity NPD4697 Phase 3
0.6094 Remote Similarity NPD5221 Approved
0.6094 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6084 Remote Similarity NPD7642 Approved
0.6068 Remote Similarity NPD6116 Phase 1
0.6054 Remote Similarity NPD5956 Approved
0.605 Remote Similarity NPD6928 Phase 2
0.6047 Remote Similarity NPD5173 Approved
0.6043 Remote Similarity NPD6868 Approved
0.6033 Remote Similarity NPD3669 Approved
0.6033 Remote Similarity NPD4788 Approved
0.6033 Remote Similarity NPD3670 Clinical (unspecified phase)
0.6032 Remote Similarity NPD5693 Phase 1
0.6029 Remote Similarity NPD5135 Approved
0.6029 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6029 Remote Similarity NPD5169 Approved
0.6016 Remote Similarity NPD5210 Approved
0.6016 Remote Similarity NPD4629 Approved
0.6016 Remote Similarity NPD7521 Approved
0.6016 Remote Similarity NPD6409 Approved
0.6016 Remote Similarity NPD7334 Approved
0.6016 Remote Similarity NPD6684 Approved
0.6016 Remote Similarity NPD3618 Phase 1
0.6016 Remote Similarity NPD7146 Approved
0.6016 Remote Similarity NPD5330 Approved
0.6013 Remote Similarity NPD7236 Approved
0.6 Remote Similarity NPD1779 Approved
0.6 Remote Similarity NPD4753 Phase 2
0.6 Remote Similarity NPD1780 Approved
0.5985 Remote Similarity NPD5127 Approved
0.5983 Remote Similarity NPD6117 Approved
0.5973 Remote Similarity NPD6845 Suspended
0.5968 Remote Similarity NPD3573 Approved
0.5952 Remote Similarity NPD7838 Discovery

  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