Structure

Physi-Chem Properties

Molecular Weight:  498.2
Volume:  480.773
LogP:  0.986
LogD:  1.437
LogS:  -2.454
# Rotatable Bonds:  4
TPSA:  144.71
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  6
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.383
Synthetic Accessibility Score:  4.781
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.967
MDCK Permeability:  1.5539388186880387e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.665
Human Intestinal Absorption (HIA):  0.872
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.382

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.258
Plasma Protein Binding (PPB):  73.31654357910156%
Volume Distribution (VD):  0.997
Pgp-substrate:  30.294395446777344%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.066
CYP2C19-inhibitor:  0.031
CYP2C19-substrate:  0.168
CYP2C9-inhibitor:  0.014
CYP2C9-substrate:  0.163
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.152
CYP3A4-inhibitor:  0.07
CYP3A4-substrate:  0.281

ADMET: Excretion

Clearance (CL):  1.174
Half-life (T1/2):  0.764

ADMET: Toxicity

hERG Blockers:  0.209
Human Hepatotoxicity (H-HT):  0.278
Drug-inuced Liver Injury (DILI):  0.861
AMES Toxicity:  0.502
Rat Oral Acute Toxicity:  0.785
Maximum Recommended Daily Dose:  0.967
Skin Sensitization:  0.089
Carcinogencity:  0.963
Eye Corrosion:  0.003
Eye Irritation:  0.012
Respiratory Toxicity:  0.98

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  Natural Product: NPC174788

Natural Product ID:  NPC174788
Common Name*:   Vincoside Lactam
IUPAC Name:   n.a.
Synonyms:   Vincoside Lactam
Standard InCHIKey:  LBRPLJCNRZUXLS-KUPDLJLDSA-N
Standard InCHI:  InChI=1S/C26H30N2O8/c1-2-12-15-9-18-20-14(13-5-3-4-6-17(13)27-20)7-8-28(18)24(33)16(15)11-34-25(12)36-26-23(32)22(31)21(30)19(10-29)35-26/h2-6,11-12,15,18-19,21-23,25-27,29-32H,1,7-10H2/t12-,15+,18+,19-,21-,22+,23-,25?,26+/m1/s1
SMILES:  OC[C@H]1O[C@@H](OC2OC=C3[C@H]([C@H]2C=C)C[C@@H]2N(C3=O)CCc3c2[nH]c2c3cccc2)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL480522
PubChem CID:   44567645
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0001213] Pyridoindoles
          • [CHEMONTID:0001914] Beta carbolines

*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]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[12628396]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota leaves n.a. n.a. PMID[18588343]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota Hairy roots n.a. n.a. PMID[19271765]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[19331340]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. aerial part n.a. PMID[21070010]
NPO13989 Uncaria macrophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[21070010]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[26285573]
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]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6619887]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[6631435]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264679]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7264682]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[7320741]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14112 Uncaria rhynchophylla Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5881 Catharanthus roseus Species Apocynaceae 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]
NPO5881 Catharanthus roseus Species Apocynaceae 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]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
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]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29352 Uncaria sinensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
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]
NPO5881 Catharanthus roseus Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28864 Nauclea officinalis 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]
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]

☑ 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
NPT2 Others Unspecified Inhibition = 24.3 % PMID[463464]
NPT2 Others Unspecified Inhibition = 71.8 % PMID[463464]
NPT2 Others Unspecified Inhibition = 65.7 % PMID[463464]
NPT2 Others Unspecified Inhibition = 38.6 % PMID[463464]
NPT2 Others Unspecified IC50 = 16400.0 nM PMID[463464]

☑ 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 NPC174788 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
0.9296 High Similarity NPC476114
0.9254 High Similarity NPC52254
0.9204 High Similarity NPC82070
0.8981 High Similarity NPC475271
0.8744 High Similarity NPC476115
0.8614 High Similarity NPC474905
0.8529 High Similarity NPC477548
0.8408 Intermediate Similarity NPC312870
0.8408 Intermediate Similarity NPC199851
0.8408 Intermediate Similarity NPC294909
0.8408 Intermediate Similarity NPC128265
0.8408 Intermediate Similarity NPC254240
0.8325 Intermediate Similarity NPC472112
0.8241 Intermediate Similarity NPC472113
0.8232 Intermediate Similarity NPC469501
0.8232 Intermediate Similarity NPC469470
0.8227 Intermediate Similarity NPC57453
0.8182 Intermediate Similarity NPC175474
0.8112 Intermediate Similarity NPC472108
0.8112 Intermediate Similarity NPC139291
0.809 Intermediate Similarity NPC196251
0.809 Intermediate Similarity NPC111602
0.809 Intermediate Similarity NPC102338
0.809 Intermediate Similarity NPC63199
0.8049 Intermediate Similarity NPC49196
0.8049 Intermediate Similarity NPC249150
0.8049 Intermediate Similarity NPC313985
0.8049 Intermediate Similarity NPC195461
0.8049 Intermediate Similarity NPC79129
0.8049 Intermediate Similarity NPC81654
0.8039 Intermediate Similarity NPC52557
0.8039 Intermediate Similarity NPC50503
0.7889 Intermediate Similarity NPC258480
0.785 Intermediate Similarity NPC234078
0.785 Intermediate Similarity NPC221100
0.7839 Intermediate Similarity NPC472110
0.7839 Intermediate Similarity NPC472109
0.7833 Intermediate Similarity NPC472097
0.7814 Intermediate Similarity NPC313640
0.7811 Intermediate Similarity NPC66210
0.7802 Intermediate Similarity NPC473800
0.7788 Intermediate Similarity NPC281049
0.7767 Intermediate Similarity NPC245916
0.7739 Intermediate Similarity NPC15840
0.7738 Intermediate Similarity NPC21638
0.7723 Intermediate Similarity NPC478077
0.7718 Intermediate Similarity NPC19692
0.7718 Intermediate Similarity NPC220151
0.7692 Intermediate Similarity NPC317430
0.7685 Intermediate Similarity NPC472323
0.7677 Intermediate Similarity NPC24594
0.7677 Intermediate Similarity NPC472122
0.7673 Intermediate Similarity NPC472107
0.7673 Intermediate Similarity NPC79062
0.7665 Intermediate Similarity NPC472123
0.765 Intermediate Similarity NPC472105
0.765 Intermediate Similarity NPC187827
0.758 Intermediate Similarity NPC249428
0.7573 Intermediate Similarity NPC472846
0.7571 Intermediate Similarity NPC160127
0.7571 Intermediate Similarity NPC50997
0.7562 Intermediate Similarity NPC91179
0.7556 Intermediate Similarity NPC33949
0.7548 Intermediate Similarity NPC57994
0.7548 Intermediate Similarity NPC289299
0.7525 Intermediate Similarity NPC113626
0.7523 Intermediate Similarity NPC238457
0.7488 Intermediate Similarity NPC472104
0.7487 Intermediate Similarity NPC161861
0.7463 Intermediate Similarity NPC217372
0.7463 Intermediate Similarity NPC15573
0.7463 Intermediate Similarity NPC183662
0.7455 Intermediate Similarity NPC152768
0.7455 Intermediate Similarity NPC148183
0.7449 Intermediate Similarity NPC21174
0.7449 Intermediate Similarity NPC271797
0.7426 Intermediate Similarity NPC219336
0.7419 Intermediate Similarity NPC162860
0.7419 Intermediate Similarity NPC478158
0.7409 Intermediate Similarity NPC478157
0.7403 Intermediate Similarity NPC184680
0.7402 Intermediate Similarity NPC143533
0.7389 Intermediate Similarity NPC469896
0.738 Intermediate Similarity NPC89987
0.7378 Intermediate Similarity NPC64216
0.7376 Intermediate Similarity NPC326575
0.7376 Intermediate Similarity NPC234987
0.7371 Intermediate Similarity NPC470784
0.7371 Intermediate Similarity NPC470785
0.7366 Intermediate Similarity NPC472119
0.7364 Intermediate Similarity NPC472291
0.7339 Intermediate Similarity NPC475816
0.7339 Intermediate Similarity NPC469743
0.733 Intermediate Similarity NPC133591
0.7327 Intermediate Similarity NPC54420
0.7321 Intermediate Similarity NPC243716
0.7321 Intermediate Similarity NPC472099
0.7308 Intermediate Similarity NPC99891
0.7295 Intermediate Similarity NPC291759
0.7295 Intermediate Similarity NPC207033
0.7295 Intermediate Similarity NPC38823
0.7285 Intermediate Similarity NPC54744
0.7284 Intermediate Similarity NPC191489
0.7282 Intermediate Similarity NPC228835
0.7281 Intermediate Similarity NPC277350
0.7277 Intermediate Similarity NPC329688
0.7277 Intermediate Similarity NPC470499
0.7277 Intermediate Similarity NPC189812
0.7273 Intermediate Similarity NPC473105
0.7273 Intermediate Similarity NPC314333
0.7268 Intermediate Similarity NPC71037
0.7265 Intermediate Similarity NPC472207
0.7265 Intermediate Similarity NPC305984
0.726 Intermediate Similarity NPC17059
0.7255 Intermediate Similarity NPC133261
0.7251 Intermediate Similarity NPC472210
0.7251 Intermediate Similarity NPC247735
0.7251 Intermediate Similarity NPC81802
0.7251 Intermediate Similarity NPC472295
0.7251 Intermediate Similarity NPC269886
0.7243 Intermediate Similarity NPC284685
0.7243 Intermediate Similarity NPC241024
0.724 Intermediate Similarity NPC75634
0.7237 Intermediate Similarity NPC472762
0.7233 Intermediate Similarity NPC325093
0.7233 Intermediate Similarity NPC327373
0.7233 Intermediate Similarity NPC322043
0.7229 Intermediate Similarity NPC321592
0.7229 Intermediate Similarity NPC54803
0.7227 Intermediate Similarity NPC234999
0.7225 Intermediate Similarity NPC182814
0.7222 Intermediate Similarity NPC162730
0.7222 Intermediate Similarity NPC155143
0.7222 Intermediate Similarity NPC476874
0.7212 Intermediate Similarity NPC235684
0.7212 Intermediate Similarity NPC315555
0.721 Intermediate Similarity NPC477549
0.7209 Intermediate Similarity NPC249040
0.7207 Intermediate Similarity NPC229348
0.7204 Intermediate Similarity NPC55493
0.7202 Intermediate Similarity NPC18661
0.7196 Intermediate Similarity NPC149708
0.719 Intermediate Similarity NPC329858
0.7188 Intermediate Similarity NPC312645
0.7183 Intermediate Similarity NPC472116
0.7176 Intermediate Similarity NPC475506
0.7176 Intermediate Similarity NPC471944
0.7176 Intermediate Similarity NPC300183
0.7169 Intermediate Similarity NPC244741
0.7166 Intermediate Similarity NPC315634
0.7166 Intermediate Similarity NPC88923
0.7166 Intermediate Similarity NPC100734
0.7163 Intermediate Similarity NPC318020
0.7163 Intermediate Similarity NPC192674
0.7162 Intermediate Similarity NPC475778
0.7162 Intermediate Similarity NPC111732
0.7156 Intermediate Similarity NPC127647
0.7156 Intermediate Similarity NPC129909
0.7156 Intermediate Similarity NPC303658
0.7155 Intermediate Similarity NPC474192
0.7155 Intermediate Similarity NPC107836
0.7155 Intermediate Similarity NPC475720
0.7154 Intermediate Similarity NPC472845
0.715 Intermediate Similarity NPC19679
0.7143 Intermediate Similarity NPC223409
0.7143 Intermediate Similarity NPC322135
0.7143 Intermediate Similarity NPC474116
0.7143 Intermediate Similarity NPC95240
0.7136 Intermediate Similarity NPC20593
0.7136 Intermediate Similarity NPC194881
0.713 Intermediate Similarity NPC306644
0.713 Intermediate Similarity NPC476492
0.713 Intermediate Similarity NPC236424
0.713 Intermediate Similarity NPC470497
0.713 Intermediate Similarity NPC476491
0.7129 Intermediate Similarity NPC62749
0.7124 Intermediate Similarity NPC284888
0.7123 Intermediate Similarity NPC471191
0.7119 Intermediate Similarity NPC472435
0.7117 Intermediate Similarity NPC320968
0.7115 Intermediate Similarity NPC470003
0.7112 Intermediate Similarity NPC475969
0.7112 Intermediate Similarity NPC475859
0.7111 Intermediate Similarity NPC79386
0.7103 Intermediate Similarity NPC231342
0.7103 Intermediate Similarity NPC472293
0.71 Intermediate Similarity NPC311906
0.71 Intermediate Similarity NPC191382
0.71 Intermediate Similarity NPC100547
0.71 Intermediate Similarity NPC56109
0.7098 Intermediate Similarity NPC274842
0.7095 Intermediate Similarity NPC328798
0.7095 Intermediate Similarity NPC325775
0.7091 Intermediate Similarity NPC270918
0.7087 Intermediate Similarity NPC319232
0.7087 Intermediate Similarity NPC11126
0.7087 Intermediate Similarity NPC24370
0.7085 Intermediate Similarity NPC264176
0.7083 Intermediate Similarity NPC472297
0.7083 Intermediate Similarity NPC100321

  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 NPC174788 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
0.8408 Intermediate Similarity NPD4500 Approved
0.8408 Intermediate Similarity NPD4501 Approved
0.8049 Intermediate Similarity NPD4601 Approved
0.8049 Intermediate Similarity NPD4600 Approved
0.7548 Intermediate Similarity NPD4602 Approved
0.7533 Intermediate Similarity NPD4885 Approved
0.7489 Intermediate Similarity NPD8372 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD7594 Clinical (unspecified phase)
0.7406 Intermediate Similarity NPD6248 Phase 2
0.7406 Intermediate Similarity NPD6249 Phase 2
0.7395 Intermediate Similarity NPD8114 Approved
0.7395 Intermediate Similarity NPD8115 Approved
0.7385 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD7708 Approved
0.7281 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4499 Approved
0.7256 Intermediate Similarity NPD7727 Phase 2
0.7243 Intermediate Similarity NPD7956 Approved
0.7243 Intermediate Similarity NPD7955 Approved
0.7222 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD7952 Approved
0.7198 Intermediate Similarity NPD7791 Approved
0.7198 Intermediate Similarity NPD7953 Approved
0.7198 Intermediate Similarity NPD7951 Approved
0.7198 Intermediate Similarity NPD7789 Approved
0.7198 Intermediate Similarity NPD7950 Approved
0.7198 Intermediate Similarity NPD7790 Approved
0.7188 Intermediate Similarity NPD8326 Phase 3
0.7188 Intermediate Similarity NPD8327 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD8325 Phase 3
0.7166 Intermediate Similarity NPD7803 Approved
0.7163 Intermediate Similarity NPD3800 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD3785 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD2095 Phase 2
0.715 Intermediate Similarity NPD2094 Phase 2
0.715 Intermediate Similarity NPD2092 Phase 2
0.7143 Intermediate Similarity NPD4334 Discontinued
0.7136 Intermediate Similarity NPD7944 Discontinued
0.713 Intermediate Similarity NPD7730 Approved
0.713 Intermediate Similarity NPD7731 Approved
0.7123 Intermediate Similarity NPD7958 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD7957 Phase 1
0.7118 Intermediate Similarity NPD7271 Approved
0.7115 Intermediate Similarity NPD2091 Phase 2
0.7115 Intermediate Similarity NPD2096 Phase 2
0.711 Intermediate Similarity NPD5487 Phase 1
0.7104 Intermediate Similarity NPD4506 Discontinued
0.7104 Intermediate Similarity NPD4520 Approved
0.71 Intermediate Similarity NPD7780 Approved
0.71 Intermediate Similarity NPD7781 Approved
0.7097 Intermediate Similarity NPD7817 Phase 1
0.707 Intermediate Similarity NPD6206 Phase 1
0.7069 Intermediate Similarity NPD7824 Approved
0.7067 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6261 Phase 3
0.7014 Intermediate Similarity NPD6838 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD8289 Discontinued
0.7009 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7717 Approved
0.7 Intermediate Similarity NPD8272 Phase 2
0.7 Intermediate Similarity NPD7716 Approved
0.7 Intermediate Similarity NPD5426 Phase 3
0.6996 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6991 Remote Similarity NPD3393 Approved
0.6991 Remote Similarity NPD5003 Discontinued
0.6991 Remote Similarity NPD3394 Approved
0.6991 Remote Similarity NPD3389 Approved
0.6982 Remote Similarity NPD7947 Clinical (unspecified phase)
0.6974 Remote Similarity NPD6770 Approved
0.6967 Remote Similarity NPD5444 Phase 1
0.6964 Remote Similarity NPD7470 Discontinued
0.6963 Remote Similarity NPD4315 Phase 2
0.6957 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6955 Remote Similarity NPD6176 Phase 1
0.6952 Remote Similarity NPD7483 Phase 2
0.6952 Remote Similarity NPD7482 Phase 2
0.6947 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6942 Remote Similarity NPD482 Approved
0.694 Remote Similarity NPD7426 Phase 1
0.693 Remote Similarity NPD6578 Clinical (unspecified phase)
0.693 Remote Similarity NPD7878 Phase 2
0.6927 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5901 Discontinued
0.692 Remote Similarity NPD7809 Clinical (unspecified phase)
0.6916 Remote Similarity NPD6630 Clinical (unspecified phase)
0.6906 Remote Similarity NPD2916 Discontinued
0.6898 Remote Similarity NPD7618 Phase 3
0.6898 Remote Similarity NPD7619 Phase 3
0.689 Remote Similarity NPD5899 Approved
0.689 Remote Similarity NPD5898 Approved
0.689 Remote Similarity NPD5897 Approved
0.6875 Remote Similarity NPD5835 Phase 3
0.6875 Remote Similarity NPD5834 Phase 3
0.6872 Remote Similarity NPD4897 Phase 2
0.6864 Remote Similarity NPD7796 Approved
0.6864 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6864 Remote Similarity NPD7797 Approved
0.6861 Remote Similarity NPD8493 Clinical (unspecified phase)
0.6856 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6854 Remote Similarity NPD6141 Clinical (unspecified phase)
0.6851 Remote Similarity NPD8374 Phase 3
0.6849 Remote Similarity NPD7621 Clinical (unspecified phase)
0.6837 Remote Similarity NPD5592 Clinical (unspecified phase)
0.683 Remote Similarity NPD7665 Phase 2
0.683 Remote Similarity NPD7666 Phase 3
0.6829 Remote Similarity NPD2844 Phase 3
0.6827 Remote Similarity NPD749 Clinical (unspecified phase)
0.6812 Remote Similarity NPD8406 Clinical (unspecified phase)
0.681 Remote Similarity NPD5473 Discontinued
0.6807 Remote Similarity NPD8329 Phase 3
0.6804 Remote Similarity NPD7777 Approved
0.6804 Remote Similarity NPD53 Approved
0.6804 Remote Similarity NPD7778 Approved
0.6804 Remote Similarity NPD4397 Phase 1
0.6802 Remote Similarity NPD8072 Approved
0.6802 Remote Similarity NPD8370 Discontinued
0.6786 Remote Similarity NPD8322 Phase 2
0.678 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6779 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6771 Remote Similarity NPD7712 Clinical (unspecified phase)
0.6766 Remote Similarity NPD6164 Phase 2
0.6766 Remote Similarity NPD6165 Phase 2
0.6758 Remote Similarity NPD6664 Approved
0.6756 Remote Similarity NPD8399 Phase 1
0.6756 Remote Similarity NPD8423 Phase 2
0.6756 Remote Similarity NPD2509 Approved
0.6756 Remote Similarity NPD2510 Approved
0.6753 Remote Similarity NPD7194 Discontinued
0.674 Remote Similarity NPD6567 Clinical (unspecified phase)
0.674 Remote Similarity NPD8013 Clinical (unspecified phase)
0.674 Remote Similarity NPD7070 Clinical (unspecified phase)
0.6739 Remote Similarity NPD7823 Clinical (unspecified phase)
0.6738 Remote Similarity NPD6995 Phase 1
0.6734 Remote Similarity NPD4926 Clinical (unspecified phase)
0.6732 Remote Similarity NPD5744 Clinical (unspecified phase)
0.6731 Remote Similarity NPD750 Phase 2
0.6731 Remote Similarity NPD43 Approved
0.6731 Remote Similarity NPD6182 Approved
0.6731 Remote Similarity NPD6183 Clinical (unspecified phase)
0.6731 Remote Similarity NPD7181 Phase 3
0.6726 Remote Similarity NPD3777 Phase 3
0.6725 Remote Similarity NPD7970 Approved
0.6725 Remote Similarity NPD7971 Clinical (unspecified phase)
0.6725 Remote Similarity NPD5293 Phase 2
0.6723 Remote Similarity NPD7603 Discontinued
0.6715 Remote Similarity NPD4184 Clinical (unspecified phase)
0.6714 Remote Similarity NPD6178 Phase 3
0.6713 Remote Similarity NPD2564 Approved
0.6713 Remote Similarity NPD2565 Phase 2
0.6699 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6697 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6697 Remote Similarity NPD6999 Discontinued
0.6696 Remote Similarity NPD7218 Clinical (unspecified phase)
0.6695 Remote Similarity NPD5506 Approved
0.6695 Remote Similarity NPD5507 Approved
0.6694 Remote Similarity NPD8375 Approved
0.6694 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6683 Remote Similarity NPD6739 Clinical (unspecified phase)
0.6682 Remote Similarity NPD8073 Approved
0.6682 Remote Similarity NPD5075 Discontinued
0.6681 Remote Similarity NPD3795 Approved
0.6681 Remote Similarity NPD6376 Discontinued
0.6681 Remote Similarity NPD3794 Approved
0.668 Remote Similarity NPD8255 Phase 2
0.6679 Remote Similarity NPD8460 Approved
0.6679 Remote Similarity NPD8459 Approved
0.6667 Remote Similarity NPD7001 Phase 3
0.6667 Remote Similarity NPD5104 Approved
0.6667 Remote Similarity NPD7234 Approved
0.6667 Remote Similarity NPD3003 Approved
0.6667 Remote Similarity NPD7233 Approved
0.6667 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5596 Phase 2
0.6654 Remote Similarity NPD8421 Discontinued
0.6654 Remote Similarity NPD6456 Discontinued
0.6652 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6651 Remote Similarity NPD6665 Discontinued
0.6651 Remote Similarity NPD4426 Clinical (unspecified phase)
0.6651 Remote Similarity NPD5505 Discontinued
0.664 Remote Similarity NPD8371 Clinical (unspecified phase)
0.6639 Remote Similarity NPD6716 Phase 1
0.6639 Remote Similarity NPD6517 Phase 3
0.6638 Remote Similarity NPD7455 Approved
0.6638 Remote Similarity NPD7454 Approved
0.6638 Remote Similarity NPD8093 Discontinued
0.6636 Remote Similarity NPD6449 Clinical (unspecified phase)
0.6636 Remote Similarity NPD7564 Discontinued
0.6635 Remote Similarity NPD2144 Approved
0.6626 Remote Similarity NPD8468 Phase 2
0.6626 Remote Similarity NPD8359 Phase 2
0.6624 Remote Similarity NPD6615 Clinical (unspecified phase)
0.6624 Remote Similarity NPD4086 Phase 1
0.6622 Remote Similarity NPD3947 Discontinued
0.6622 Remote Similarity NPD7308 Discontinued
0.662 Remote Similarity NPD3038 Discontinued
0.6619 Remote Similarity NPD5065 Approved
0.6609 Remote Similarity NPD8094 Discontinued
0.6605 Remote Similarity NPD5555 Phase 1
0.6604 Remote Similarity NPD4079 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