Structure

Physi-Chem Properties

Molecular Weight:  530.23
Volume:  515.416
LogP:  0.232
LogD:  1.358
LogS:  -2.189
# Rotatable Bonds:  8
TPSA:  162.73
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.218
Synthetic Accessibility Score:  4.854
Fsp3:  0.519
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:  -5.946
MDCK Permeability:  4.4663072912953794e-05
Pgp-inhibitor:  0.006
Pgp-substrate:  0.99
Human Intestinal Absorption (HIA):  0.925
20% Bioavailability (F20%):  0.012
30% Bioavailability (F30%):  0.939

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.268
Plasma Protein Binding (PPB):  45.45436096191406%
Volume Distribution (VD):  1.049
Pgp-substrate:  47.69072723388672%

ADMET: Metabolism

CYP1A2-inhibitor:  0.044
CYP1A2-substrate:  0.192
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.261
CYP2C9-inhibitor:  0.006
CYP2C9-substrate:  0.077
CYP2D6-inhibitor:  0.023
CYP2D6-substrate:  0.246
CYP3A4-inhibitor:  0.162
CYP3A4-substrate:  0.346

ADMET: Excretion

Clearance (CL):  1.619
Half-life (T1/2):  0.782

ADMET: Toxicity

hERG Blockers:  0.438
Human Hepatotoxicity (H-HT):  0.269
Drug-inuced Liver Injury (DILI):  0.444
AMES Toxicity:  0.553
Rat Oral Acute Toxicity:  0.856
Maximum Recommended Daily Dose:  0.982
Skin Sensitization:  0.224
Carcinogencity:  0.931
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.985

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

  Natural Product: NPC82070

Natural Product ID:  NPC82070
Common Name*:   Strictosidine
IUPAC Name:   methyl (2S,3R,4S)-3-ethenyl-4-[[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]methyl]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
Synonyms:   strictosidine
Standard InCHIKey:  XBAMJZTXGWPTRM-NTXHKPOFSA-N
Standard InCHI:  InChI=1S/C27H34N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,19-20,22-24,26-33H,1,8-11H2,2H3/t13-,16+,19+,20-,22-,23+,24-,26+,27+/m1/s1
SMILES:  OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@H]([C@H]2C=C)C[C@@H]2NCCc3c2[nH]c2c3cccc2)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL402211
PubChem CID:   161336
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides

*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
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[10869194]
NPO3893 Chimarrhis turbinata Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[15568781]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota leaves n.a. n.a. PMID[18588343]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[19331340]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[21070010]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. aerial part n.a. PMID[21070010]
NPO3893 Chimarrhis turbinata Species Rubiaceae Eukaryota leaves n.a. n.a. PMID[21341711]
NPO3893 Chimarrhis turbinata Species Rubiaceae Eukaryota n.a. leaf n.a. PMID[21341711]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27700077]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[28225280]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[31789520]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[31804070]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29352 Uncaria sinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29352 Uncaria sinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29352 Uncaria sinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29352 Uncaria sinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3893 Chimarrhis turbinata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29352 Uncaria sinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14112 Uncaria rhynchophylla Species Rubiaceae 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
NPT3963 Individual Protein Strictosidine beta-glucosidase Catharanthus roseus Km = 220000.0 nM PMID[575342]
NPT3963 Individual Protein Strictosidine beta-glucosidase Catharanthus roseus Vmax = 0.078 mM/min PMID[575342]
NPT3963 Individual Protein Strictosidine beta-glucosidase Catharanthus roseus Ratio = 1.0 /min PMID[575342]
NPT1 Others Radical scavenging activity IC50 = 56000.0 nM PMID[575343]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 > 250.0 ug ml-1 PMID[575344]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC12 = 100.0 ug ml-1 PMID[575344]

☑ 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 NPC82070 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
0.9794 High Similarity NPC476114
0.9747 High Similarity NPC475271
0.9645 High Similarity NPC52254
0.9282 High Similarity NPC474905
0.9204 High Similarity NPC174788
0.9031 High Similarity NPC476115
0.8782 High Similarity NPC128265
0.8782 High Similarity NPC312870
0.8782 High Similarity NPC254240
0.8782 High Similarity NPC199851
0.8782 High Similarity NPC294909
0.8738 High Similarity NPC57453
0.8462 Intermediate Similarity NPC102338
0.8462 Intermediate Similarity NPC111602
0.8462 Intermediate Similarity NPC63199
0.8462 Intermediate Similarity NPC196251
0.8439 Intermediate Similarity NPC477548
0.8274 Intermediate Similarity NPC473800
0.8274 Intermediate Similarity NPC175474
0.8238 Intermediate Similarity NPC313640
0.8232 Intermediate Similarity NPC472112
0.819 Intermediate Similarity NPC221100
0.819 Intermediate Similarity NPC234078
0.8159 Intermediate Similarity NPC220151
0.8159 Intermediate Similarity NPC19692
0.815 Intermediate Similarity NPC472113
0.8137 Intermediate Similarity NPC49196
0.8137 Intermediate Similarity NPC249150
0.8137 Intermediate Similarity NPC79129
0.8137 Intermediate Similarity NPC195461
0.8137 Intermediate Similarity NPC313985
0.8137 Intermediate Similarity NPC81654
0.8119 Intermediate Similarity NPC245916
0.8065 Intermediate Similarity NPC21638
0.8039 Intermediate Similarity NPC52557
0.8039 Intermediate Similarity NPC50503
0.796 Intermediate Similarity NPC469501
0.796 Intermediate Similarity NPC469470
0.7929 Intermediate Similarity NPC139291
0.7929 Intermediate Similarity NPC472108
0.7857 Intermediate Similarity NPC238457
0.7833 Intermediate Similarity NPC472097
0.7826 Intermediate Similarity NPC50997
0.7826 Intermediate Similarity NPC160127
0.78 Intermediate Similarity NPC258480
0.7793 Intermediate Similarity NPC33949
0.7788 Intermediate Similarity NPC281049
0.7783 Intermediate Similarity NPC472762
0.7778 Intermediate Similarity NPC219336
0.7778 Intermediate Similarity NPC148183
0.7778 Intermediate Similarity NPC152768
0.7772 Intermediate Similarity NPC472323
0.775 Intermediate Similarity NPC472109
0.775 Intermediate Similarity NPC472110
0.7739 Intermediate Similarity NPC469896
0.7727 Intermediate Similarity NPC183662
0.7727 Intermediate Similarity NPC15573
0.7727 Intermediate Similarity NPC217372
0.7723 Intermediate Similarity NPC66210
0.7661 Intermediate Similarity NPC312645
0.7661 Intermediate Similarity NPC249428
0.765 Intermediate Similarity NPC15840
0.7636 Intermediate Similarity NPC472099
0.763 Intermediate Similarity NPC476874
0.7621 Intermediate Similarity NPC55493
0.7619 Intermediate Similarity NPC214428
0.7598 Intermediate Similarity NPC328798
0.7598 Intermediate Similarity NPC325775
0.7577 Intermediate Similarity NPC473105
0.7573 Intermediate Similarity NPC191489
0.7573 Intermediate Similarity NPC127647
0.7571 Intermediate Similarity NPC241024
0.7549 Intermediate Similarity NPC235684
0.7548 Intermediate Similarity NPC57994
0.7548 Intermediate Similarity NPC289299
0.7546 Intermediate Similarity NPC234999
0.7533 Intermediate Similarity NPC474192
0.7533 Intermediate Similarity NPC475720
0.7531 Intermediate Similarity NPC284685
0.7525 Intermediate Similarity NPC113626
0.7525 Intermediate Similarity NPC71037
0.7523 Intermediate Similarity NPC18661
0.7523 Intermediate Similarity NPC89508
0.7523 Intermediate Similarity NPC472291
0.7523 Intermediate Similarity NPC229348
0.7513 Intermediate Similarity NPC317430
0.75 Intermediate Similarity NPC472107
0.75 Intermediate Similarity NPC24594
0.75 Intermediate Similarity NPC472122
0.75 Intermediate Similarity NPC469743
0.75 Intermediate Similarity NPC79062
0.7489 Intermediate Similarity NPC274842
0.7487 Intermediate Similarity NPC472123
0.7477 Intermediate Similarity NPC244856
0.7477 Intermediate Similarity NPC475778
0.7476 Intermediate Similarity NPC182814
0.7465 Intermediate Similarity NPC474116
0.7463 Intermediate Similarity NPC315555
0.7456 Intermediate Similarity NPC89987
0.7451 Intermediate Similarity NPC472119
0.7449 Intermediate Similarity NPC88923
0.7449 Intermediate Similarity NPC315634
0.7449 Intermediate Similarity NPC100734
0.7444 Intermediate Similarity NPC2395
0.7443 Intermediate Similarity NPC306644
0.7443 Intermediate Similarity NPC236424
0.7442 Intermediate Similarity NPC277350
0.744 Intermediate Similarity NPC314333
0.7419 Intermediate Similarity NPC478158
0.7416 Intermediate Similarity NPC472295
0.7416 Intermediate Similarity NPC269886
0.7416 Intermediate Similarity NPC81802
0.7416 Intermediate Similarity NPC472210
0.7416 Intermediate Similarity NPC247735
0.7414 Intermediate Similarity NPC475816
0.7409 Intermediate Similarity NPC478157
0.7407 Intermediate Similarity NPC244741
0.7402 Intermediate Similarity NPC472104
0.7402 Intermediate Similarity NPC327373
0.7402 Intermediate Similarity NPC143533
0.7402 Intermediate Similarity NPC322043
0.7402 Intermediate Similarity NPC325093
0.7402 Intermediate Similarity NPC469358
0.7397 Intermediate Similarity NPC111732
0.7389 Intermediate Similarity NPC187827
0.7389 Intermediate Similarity NPC472105
0.7383 Intermediate Similarity NPC162730
0.7381 Intermediate Similarity NPC20593
0.7378 Intermediate Similarity NPC64216
0.7376 Intermediate Similarity NPC326575
0.7376 Intermediate Similarity NPC234987
0.736 Intermediate Similarity NPC21174
0.736 Intermediate Similarity NPC271797
0.7356 Intermediate Similarity NPC329858
0.7355 Intermediate Similarity NPC472846
0.7349 Intermediate Similarity NPC476098
0.7349 Intermediate Similarity NPC165599
0.7345 Intermediate Similarity NPC235885
0.733 Intermediate Similarity NPC477979
0.733 Intermediate Similarity NPC318020
0.7318 Intermediate Similarity NPC151976
0.7317 Intermediate Similarity NPC472444
0.7313 Intermediate Similarity NPC79107
0.7313 Intermediate Similarity NPC475424
0.7311 Intermediate Similarity NPC476516
0.7308 Intermediate Similarity NPC46413
0.7295 Intermediate Similarity NPC62749
0.7295 Intermediate Similarity NPC478077
0.7285 Intermediate Similarity NPC54744
0.7277 Intermediate Similarity NPC329688
0.7277 Intermediate Similarity NPC189812
0.7273 Intermediate Similarity NPC476514
0.7264 Intermediate Similarity NPC231342
0.7264 Intermediate Similarity NPC472293
0.7261 Intermediate Similarity NPC472435
0.726 Intermediate Similarity NPC162860
0.7253 Intermediate Similarity NPC184680
0.7248 Intermediate Similarity NPC46225
0.7243 Intermediate Similarity NPC192674
0.7243 Intermediate Similarity NPC472297
0.7243 Intermediate Similarity NPC472436
0.7243 Intermediate Similarity NPC472296
0.7241 Intermediate Similarity NPC267885
0.724 Intermediate Similarity NPC207020
0.724 Intermediate Similarity NPC75634
0.724 Intermediate Similarity NPC264176
0.7238 Intermediate Similarity NPC129909
0.7234 Intermediate Similarity NPC99891
0.7232 Intermediate Similarity NPC469594
0.7229 Intermediate Similarity NPC321592
0.7229 Intermediate Similarity NPC54803
0.7222 Intermediate Similarity NPC470785
0.7222 Intermediate Similarity NPC193761
0.7222 Intermediate Similarity NPC470784
0.722 Intermediate Similarity NPC204491
0.722 Intermediate Similarity NPC91179
0.7215 Intermediate Similarity NPC127677
0.7206 Intermediate Similarity NPC111275
0.7205 Intermediate Similarity NPC57690
0.7204 Intermediate Similarity NPC472292
0.7202 Intermediate Similarity NPC474145
0.7202 Intermediate Similarity NPC475841
0.7202 Intermediate Similarity NPC309498
0.7196 Intermediate Similarity NPC324245
0.7196 Intermediate Similarity NPC320748
0.7196 Intermediate Similarity NPC470499
0.7196 Intermediate Similarity NPC149708
0.7193 Intermediate Similarity NPC141428
0.7192 Intermediate Similarity NPC110500
0.7192 Intermediate Similarity NPC203468
0.7192 Intermediate Similarity NPC472586
0.7192 Intermediate Similarity NPC149155
0.7183 Intermediate Similarity NPC472116
0.7183 Intermediate Similarity NPC102592
0.7183 Intermediate Similarity NPC79356
0.7176 Intermediate Similarity NPC32451
0.7176 Intermediate Similarity NPC328559
0.7175 Intermediate Similarity NPC471284
0.7171 Intermediate Similarity NPC126709
0.7171 Intermediate Similarity NPC248041

  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 NPC82070 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
0.8782 High Similarity NPD4501 Approved
0.8782 High Similarity NPD4500 Approved
0.8137 Intermediate Similarity NPD4600 Approved
0.8137 Intermediate Similarity NPD4601 Approved
0.7661 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD8326 Phase 3
0.7661 Intermediate Similarity NPD8325 Phase 3
0.7581 Intermediate Similarity NPD4506 Discontinued
0.7573 Intermediate Similarity NPD7708 Approved
0.7571 Intermediate Similarity NPD6248 Phase 2
0.7571 Intermediate Similarity NPD6249 Phase 2
0.7566 Intermediate Similarity NPD8372 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD4602 Approved
0.7531 Intermediate Similarity NPD7955 Approved
0.7531 Intermediate Similarity NPD7956 Approved
0.7476 Intermediate Similarity NPD5003 Discontinued
0.7465 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.7449 Intermediate Similarity NPD7803 Approved
0.7442 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD7957 Phase 1
0.744 Intermediate Similarity NPD4499 Approved
0.7402 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD2094 Phase 2
0.7402 Intermediate Similarity NPD2095 Phase 2
0.7402 Intermediate Similarity NPD2092 Phase 2
0.738 Intermediate Similarity NPD4885 Approved
0.7373 Intermediate Similarity NPD7947 Clinical (unspecified phase)
0.7366 Intermediate Similarity NPD2096 Phase 2
0.7366 Intermediate Similarity NPD2091 Phase 2
0.7361 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD6770 Approved
0.7294 Intermediate Similarity NPD8399 Phase 1
0.7294 Intermediate Similarity NPD8423 Phase 2
0.7273 Intermediate Similarity NPD7470 Discontinued
0.7269 Intermediate Similarity NPD5487 Phase 1
0.7252 Intermediate Similarity NPD8112 Clinical (unspecified phase)
0.7243 Intermediate Similarity NPD3800 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD3785 Clinical (unspecified phase)
0.7225 Intermediate Similarity NPD4334 Discontinued
0.722 Intermediate Similarity NPD3394 Approved
0.722 Intermediate Similarity NPD3389 Approved
0.722 Intermediate Similarity NPD3393 Approved
0.7215 Intermediate Similarity NPD2509 Approved
0.7215 Intermediate Similarity NPD2510 Approved
0.7202 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD482 Approved
0.719 Intermediate Similarity NPD2565 Phase 2
0.719 Intermediate Similarity NPD2564 Approved
0.7189 Intermediate Similarity NPD8072 Approved
0.7178 Intermediate Similarity NPD6739 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7727 Phase 2
0.7164 Intermediate Similarity NPD2844 Phase 3
0.7163 Intermediate Similarity NPD6661 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD5901 Discontinued
0.7156 Intermediate Similarity NPD6630 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD6206 Phase 1
0.7136 Intermediate Similarity NPD5899 Approved
0.7136 Intermediate Similarity NPD5898 Approved
0.7136 Intermediate Similarity NPD5897 Approved
0.7116 Intermediate Similarity NPD53 Approved
0.7116 Intermediate Similarity NPD6261 Phase 3
0.7116 Intermediate Similarity NPD7777 Approved
0.7116 Intermediate Similarity NPD7778 Approved
0.7104 Intermediate Similarity NPD4520 Approved
0.708 Intermediate Similarity NPD5632 Approved
0.7078 Intermediate Similarity NPD8115 Approved
0.7078 Intermediate Similarity NPD8114 Approved
0.7064 Intermediate Similarity NPD8073 Approved
0.7054 Intermediate Similarity NPD3795 Approved
0.7054 Intermediate Similarity NPD3794 Approved
0.7048 Intermediate Similarity NPD5444 Phase 1
0.7045 Intermediate Similarity NPD3003 Approved
0.7042 Intermediate Similarity NPD8468 Phase 2
0.7042 Intermediate Similarity NPD4315 Phase 2
0.7039 Intermediate Similarity NPD6642 Approved
0.7039 Intermediate Similarity NPD6641 Approved
0.7032 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD6176 Phase 1
0.7004 Intermediate Similarity NPD7878 Phase 2
0.7 Intermediate Similarity NPD8283 Approved
0.7 Intermediate Similarity NPD56 Approved
0.7 Intermediate Similarity NPD5075 Discontinued
0.7 Intermediate Similarity NPD8282 Approved
0.6996 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6996 Remote Similarity NPD7998 Clinical (unspecified phase)
0.699 Remote Similarity NPD5104 Approved
0.6981 Remote Similarity NPD7234 Approved
0.6981 Remote Similarity NPD7233 Approved
0.6976 Remote Similarity NPD6183 Clinical (unspecified phase)
0.6976 Remote Similarity NPD750 Phase 2
0.6976 Remote Similarity NPD43 Approved
0.6976 Remote Similarity NPD6182 Approved
0.6972 Remote Similarity NPD6479 Discontinued
0.6959 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6959 Remote Similarity NPD4397 Phase 1
0.6957 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6955 Remote Similarity NPD5482 Discontinued
0.6951 Remote Similarity NPD6529 Discontinued
0.6951 Remote Similarity NPD5835 Phase 3
0.6951 Remote Similarity NPD5834 Phase 3
0.6947 Remote Similarity NPD4897 Phase 2
0.6941 Remote Similarity NPD7817 Phase 1
0.6927 Remote Similarity NPD1768 Approved
0.692 Remote Similarity NPD7809 Clinical (unspecified phase)
0.6914 Remote Similarity NPD8466 Approved
0.6914 Remote Similarity NPD8467 Approved
0.6914 Remote Similarity NPD8465 Approved
0.691 Remote Similarity NPD7731 Approved
0.691 Remote Similarity NPD7730 Approved
0.6907 Remote Similarity NPD7790 Approved
0.6907 Remote Similarity NPD7952 Approved
0.6907 Remote Similarity NPD7950 Approved
0.6907 Remote Similarity NPD7953 Approved
0.6907 Remote Similarity NPD7789 Approved
0.6907 Remote Similarity NPD7951 Approved
0.6907 Remote Similarity NPD7791 Approved
0.6907 Remote Similarity NPD7558 Phase 2
0.69 Remote Similarity NPD7194 Discontinued
0.6898 Remote Similarity NPD7944 Discontinued
0.6897 Remote Similarity NPD2915 Discontinued
0.6897 Remote Similarity NPD7271 Approved
0.6892 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6883 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6881 Remote Similarity NPD7946 Pre-registration
0.688 Remote Similarity NPD7780 Approved
0.688 Remote Similarity NPD7781 Approved
0.6878 Remote Similarity NPD2920 Discontinued
0.6878 Remote Similarity NPD4184 Clinical (unspecified phase)
0.6877 Remote Similarity NPD8363 Approved
0.6877 Remote Similarity NPD8364 Approved
0.6872 Remote Similarity NPD5903 Approved
0.6872 Remote Similarity NPD5902 Approved
0.6867 Remote Similarity NPD8289 Discontinued
0.6864 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6861 Remote Similarity NPD6838 Clinical (unspecified phase)
0.686 Remote Similarity NPD5483 Clinical (unspecified phase)
0.6856 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6851 Remote Similarity NPD8374 Phase 3
0.6851 Remote Similarity NPD7824 Approved
0.6849 Remote Similarity NPD7621 Clinical (unspecified phase)
0.6847 Remote Similarity NPD8272 Phase 2
0.6847 Remote Similarity NPD5426 Phase 3
0.6833 Remote Similarity NPD2921 Clinical (unspecified phase)
0.6824 Remote Similarity NPD8365 Clinical (unspecified phase)
0.6822 Remote Similarity NPD1534 Approved
0.6818 Remote Similarity NPD484 Approved
0.6815 Remote Similarity NPD8255 Phase 2
0.6814 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6814 Remote Similarity NPD7070 Clinical (unspecified phase)
0.6814 Remote Similarity NPD8013 Clinical (unspecified phase)
0.6812 Remote Similarity NPD8406 Clinical (unspecified phase)
0.6808 Remote Similarity NPD8426 Approved
0.6808 Remote Similarity NPD8459 Approved
0.6808 Remote Similarity NPD8425 Approved
0.6808 Remote Similarity NPD8460 Approved
0.6807 Remote Similarity NPD8329 Phase 3
0.6802 Remote Similarity NPD3777 Phase 3
0.6797 Remote Similarity NPD3280 Approved
0.6796 Remote Similarity NPD1325 Approved
0.6796 Remote Similarity NPD1326 Approved
0.6793 Remote Similarity NPD7796 Approved
0.6793 Remote Similarity NPD7797 Approved
0.6792 Remote Similarity NPD6178 Phase 3
0.6792 Remote Similarity NPD3436 Approved
0.6783 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6783 Remote Similarity NPD8428 Approved
0.6783 Remote Similarity NPD8429 Approved
0.6783 Remote Similarity NPD8427 Approved
0.6781 Remote Similarity NPD7717 Approved
0.6781 Remote Similarity NPD7716 Approved
0.6779 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6778 Remote Similarity NPD8421 Discontinued
0.6777 Remote Similarity NPD6716 Phase 1
0.6771 Remote Similarity NPD3947 Discontinued
0.6771 Remote Similarity NPD8098 Approved
0.677 Remote Similarity NPD7825 Clinical (unspecified phase)
0.6769 Remote Similarity NPD7218 Clinical (unspecified phase)
0.6767 Remote Similarity NPD5506 Approved
0.6767 Remote Similarity NPD5507 Approved
0.6765 Remote Similarity NPD4373 Phase 2
0.6756 Remote Similarity NPD2916 Discontinued
0.6754 Remote Similarity NPD7571 Clinical (unspecified phase)
0.6745 Remote Similarity NPD5596 Phase 2
0.6743 Remote Similarity NPD7619 Phase 3
0.6743 Remote Similarity NPD4427 Phase 2
0.6743 Remote Similarity NPD7618 Phase 3
0.6739 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6738 Remote Similarity NPD6995 Phase 1
0.6734 Remote Similarity NPD8463 Approved
0.6734 Remote Similarity NPD8370 Discontinued
0.6733 Remote Similarity NPD6531 Approved
0.6733 Remote Similarity NPD6530 Approved
0.673 Remote Similarity NPD8464 Clinical (unspecified phase)
0.673 Remote Similarity NPD5473 Discontinued
0.6714 Remote Similarity NPD2144 Approved
0.6714 Remote Similarity NPD7865 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