Structure

Physi-Chem Properties

Molecular Weight:  534.21
Volume:  513.64
LogP:  1.112
LogD:  1.003
LogS:  -3.947
# Rotatable Bonds:  5
TPSA:  162.73
# H-Bond Aceptor:  11
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.224
Synthetic Accessibility Score:  6.799
Fsp3:  0.741
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.207
MDCK Permeability:  0.00010310934885637835
Pgp-inhibitor:  1.0
Pgp-substrate:  0.025
Human Intestinal Absorption (HIA):  0.903
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.86
Plasma Protein Binding (PPB):  55.11798858642578%
Volume Distribution (VD):  0.662
Pgp-substrate:  31.984949111938477%

ADMET: Metabolism

CYP1A2-inhibitor:  0.004
CYP1A2-substrate:  0.698
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.681
CYP2C9-inhibitor:  0.014
CYP2C9-substrate:  0.041
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.091
CYP3A4-inhibitor:  0.416
CYP3A4-substrate:  0.293

ADMET: Excretion

Clearance (CL):  3.776
Half-life (T1/2):  0.047

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.689
Drug-inuced Liver Injury (DILI):  0.901
AMES Toxicity:  0.014
Rat Oral Acute Toxicity:  0.823
Maximum Recommended Daily Dose:  0.42
Skin Sensitization:  0.025
Carcinogencity:  0.024
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.065

Download Data

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

  Natural Product: NPC109607

Natural Product ID:  NPC109607
Common Name*:   VKCVPDRXEYKUOZ-JXMROGBWSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  VKCVPDRXEYKUOZ-JXMROGBWSA-N
Standard InCHI:  InChI=1S/C27H34O11/c1-7-10(2)22(32)37-17-15-11(3)8-14(29)20(31)25(15,6)24-26-9-35-27(24,34)19(30)12(4)16(26)18(36-13(5)28)23(33)38-21(17)26/h7-8,12,15-21,24,30-31,34H,9H2,1-6H3/b10-7+
SMILES:  C/C=C(C)/C(=O)OC1C2C(=CC(=O)C(C2(C)C2C34COC2(C(C(C)C3C(C(=O)OC14)OC(=O)C)O)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2006033
PubChem CID:   5476831
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0002119] Quassinoids

*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
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[16872768]
NPO26237 Piper longum Species Piperaceae Eukaryota fruits n.a. n.a. PMID[20839888]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. PMID[23434420]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO878 Hannoa undulata Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26237 Piper longum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO878 Hannoa undulata Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26237 Piper longum Species Piperaceae 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
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 43.05 nM PMID[464239]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 74.13 nM PMID[464239]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 194.98 nM PMID[464239]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 38.82 nM PMID[464239]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 61.09 nM PMID[464239]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 1054.39 nM PMID[464239]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 39.63 nM PMID[464239]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 111.17 nM PMID[464239]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 59.43 nM PMID[464239]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 39.63 nM PMID[464239]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 107.4 nM PMID[464239]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 110.15 nM PMID[464239]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 37.5 nM PMID[464239]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 37.67 nM PMID[464239]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 47.1 nM PMID[464239]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 87.3 nM PMID[464239]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 38.9 nM PMID[464239]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 41.5 nM PMID[464239]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 74.13 nM PMID[464239]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 44.36 nM PMID[464239]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 46.03 nM PMID[464239]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 143.88 nM PMID[464239]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 197.24 nM PMID[464239]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 319.15 nM PMID[464239]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 40.18 nM PMID[464239]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 48.31 nM PMID[464239]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 38.55 nM PMID[464239]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 37.5 nM PMID[464239]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 81.1 nM PMID[464239]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 71.94 nM PMID[464239]

☑ 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 NPC109607 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 NPC107338
0.9909 High Similarity NPC476529
0.9909 High Similarity NPC475775
0.9649 High Similarity NPC470922
0.955 High Similarity NPC473968
0.9545 High Similarity NPC18547
0.9545 High Similarity NPC474906
0.9459 High Similarity NPC134869
0.9459 High Similarity NPC235539
0.9459 High Similarity NPC152199
0.9369 High Similarity NPC470919
0.9369 High Similarity NPC469877
0.9364 High Similarity NPC11252
0.9364 High Similarity NPC289312
0.9292 High Similarity NPC297179
0.9286 High Similarity NPC474046
0.9286 High Similarity NPC259306
0.9286 High Similarity NPC470628
0.9279 High Similarity NPC51978
0.9273 High Similarity NPC201992
0.9204 High Similarity NPC473590
0.9189 High Similarity NPC302146
0.9145 High Similarity NPC24651
0.9115 High Similarity NPC251236
0.9115 High Similarity NPC96312
0.9115 High Similarity NPC40632
0.9115 High Similarity NPC328374
0.906 High Similarity NPC18945
0.906 High Similarity NPC91693
0.906 High Similarity NPC67251
0.906 High Similarity NPC105926
0.906 High Similarity NPC265557
0.9027 High Similarity NPC473798
0.9 High Similarity NPC293850
0.8983 High Similarity NPC476729
0.8974 High Similarity NPC312833
0.8966 High Similarity NPC112038
0.8957 High Similarity NPC204552
0.8957 High Similarity NPC188667
0.8947 High Similarity NPC474734
0.8938 High Similarity NPC49451
0.8919 High Similarity NPC472534
0.8919 High Similarity NPC143706
0.8889 High Similarity NPC470779
0.8879 High Similarity NPC122971
0.8879 High Similarity NPC469488
0.887 High Similarity NPC309433
0.8852 High Similarity NPC471855
0.8852 High Similarity NPC478153
0.8852 High Similarity NPC478152
0.8852 High Similarity NPC478150
0.88 High Similarity NPC596
0.8793 High Similarity NPC17772
0.878 High Similarity NPC478151
0.877 High Similarity NPC301639
0.877 High Similarity NPC45346
0.877 High Similarity NPC475377
0.877 High Similarity NPC478065
0.877 High Similarity NPC477197
0.877 High Similarity NPC475167
0.877 High Similarity NPC172374
0.877 High Similarity NPC25998
0.877 High Similarity NPC173435
0.877 High Similarity NPC134914
0.877 High Similarity NPC262796
0.877 High Similarity NPC478064
0.877 High Similarity NPC329993
0.877 High Similarity NPC478155
0.877 High Similarity NPC264566
0.877 High Similarity NPC476074
0.8739 High Similarity NPC3316
0.8739 High Similarity NPC144854
0.8729 High Similarity NPC477046
0.8729 High Similarity NPC102822
0.872 High Similarity NPC141215
0.872 High Similarity NPC190065
0.872 High Similarity NPC471089
0.8718 High Similarity NPC470777
0.8707 High Similarity NPC122033
0.8707 High Similarity NPC474654
0.8707 High Similarity NPC287343
0.8707 High Similarity NPC470854
0.8707 High Similarity NPC97908
0.8699 High Similarity NPC478154
0.8689 High Similarity NPC477079
0.8689 High Similarity NPC477076
0.8689 High Similarity NPC477077
0.8689 High Similarity NPC471407
0.8689 High Similarity NPC477196
0.8689 High Similarity NPC470913
0.8684 High Similarity NPC194951
0.8684 High Similarity NPC474516
0.8684 High Similarity NPC12046
0.8678 High Similarity NPC470780
0.8661 High Similarity NPC154608
0.8661 High Similarity NPC192813
0.8661 High Similarity NPC189075
0.8661 High Similarity NPC277017
0.8661 High Similarity NPC275539
0.8651 High Similarity NPC295885
0.8651 High Similarity NPC140045
0.864 High Similarity NPC262813
0.8632 High Similarity NPC470776
0.8632 High Similarity NPC251310
0.8629 High Similarity NPC168879
0.8609 High Similarity NPC208998
0.8609 High Similarity NPC157441
0.8609 High Similarity NPC7921
0.8609 High Similarity NPC25909
0.8607 High Similarity NPC475281
0.8607 High Similarity NPC477078
0.8607 High Similarity NPC477075
0.8607 High Similarity NPC329923
0.8607 High Similarity NPC477194
0.8607 High Similarity NPC477191
0.8607 High Similarity NPC477192
0.8607 High Similarity NPC477193
0.8584 High Similarity NPC141350
0.8584 High Similarity NPC27814
0.8583 High Similarity NPC227397
0.8571 High Similarity NPC202051
0.8571 High Similarity NPC110496
0.8571 High Similarity NPC251998
0.8559 High Similarity NPC127530
0.8559 High Similarity NPC77689
0.8559 High Similarity NPC19028
0.8559 High Similarity NPC473636
0.8559 High Similarity NPC9674
0.8559 High Similarity NPC473920
0.8548 High Similarity NPC477195
0.8548 High Similarity NPC102316
0.8548 High Similarity NPC46823
0.8548 High Similarity NPC30279
0.8548 High Similarity NPC192765
0.8548 High Similarity NPC473918
0.8548 High Similarity NPC71391
0.8548 High Similarity NPC277212
0.8548 High Similarity NPC178264
0.8548 High Similarity NPC476776
0.8547 High Similarity NPC474483
0.8547 High Similarity NPC146432
0.8547 High Similarity NPC470775
0.8547 High Similarity NPC176513
0.8547 High Similarity NPC470778
0.8547 High Similarity NPC134430
0.8537 High Similarity NPC88311
0.8537 High Similarity NPC115656
0.8537 High Similarity NPC472267
0.8537 High Similarity NPC97918
0.8537 High Similarity NPC107536
0.8537 High Similarity NPC141600
0.8537 High Similarity NPC269484
0.8537 High Similarity NPC11577
0.8537 High Similarity NPC470912
0.8537 High Similarity NPC305793
0.8537 High Similarity NPC252289
0.8537 High Similarity NPC244296
0.8537 High Similarity NPC280029
0.8537 High Similarity NPC9470
0.8537 High Similarity NPC1314
0.8537 High Similarity NPC470518
0.8537 High Similarity NPC252657
0.8537 High Similarity NPC82380
0.8537 High Similarity NPC273878
0.8534 High Similarity NPC243354
0.8525 High Similarity NPC476008
0.8522 High Similarity NPC269530
0.8509 High Similarity NPC5103
0.8509 High Similarity NPC83005
0.8487 Intermediate Similarity NPC48692
0.8482 Intermediate Similarity NPC102352
0.848 Intermediate Similarity NPC225791
0.8468 Intermediate Similarity NPC476774
0.8468 Intermediate Similarity NPC476775
0.8468 Intermediate Similarity NPC476780
0.8468 Intermediate Similarity NPC271610
0.8468 Intermediate Similarity NPC476852
0.8462 Intermediate Similarity NPC16081
0.8462 Intermediate Similarity NPC89929
0.8462 Intermediate Similarity NPC213084
0.8462 Intermediate Similarity NPC190185
0.8462 Intermediate Similarity NPC173686
0.8462 Intermediate Similarity NPC44170
0.8462 Intermediate Similarity NPC268954
0.8462 Intermediate Similarity NPC471816
0.8455 Intermediate Similarity NPC473620
0.8455 Intermediate Similarity NPC476859
0.8455 Intermediate Similarity NPC311534
0.8455 Intermediate Similarity NPC245094
0.8448 Intermediate Similarity NPC469496
0.8448 Intermediate Similarity NPC194273
0.8448 Intermediate Similarity NPC311592
0.8448 Intermediate Similarity NPC469454
0.8448 Intermediate Similarity NPC255017
0.8448 Intermediate Similarity NPC94509
0.8448 Intermediate Similarity NPC469463
0.8448 Intermediate Similarity NPC75167
0.8443 Intermediate Similarity NPC285091
0.8443 Intermediate Similarity NPC477745
0.8443 Intermediate Similarity NPC225049

  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 NPC109607 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
0.8333 Intermediate Similarity NPD6686 Approved
0.8279 Intermediate Similarity NPD8328 Phase 3
0.8145 Intermediate Similarity NPD7507 Approved
0.8065 Intermediate Similarity NPD7492 Approved
0.8051 Intermediate Similarity NPD8297 Approved
0.8051 Intermediate Similarity NPD6882 Approved
0.8033 Intermediate Similarity NPD6319 Approved
0.8033 Intermediate Similarity NPD6054 Approved
0.8016 Intermediate Similarity NPD7736 Approved
0.8 Intermediate Similarity NPD6616 Approved
0.7953 Intermediate Similarity NPD7319 Approved
0.7937 Intermediate Similarity NPD7078 Approved
0.7934 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7934 Intermediate Similarity NPD6009 Approved
0.7903 Intermediate Similarity NPD6370 Approved
0.7886 Intermediate Similarity NPD6059 Approved
0.7863 Intermediate Similarity NPD6899 Approved
0.7863 Intermediate Similarity NPD6881 Approved
0.7863 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7845 Intermediate Similarity NPD6402 Approved
0.7845 Intermediate Similarity NPD5739 Approved
0.7845 Intermediate Similarity NPD7128 Approved
0.7845 Intermediate Similarity NPD6675 Approved
0.7833 Intermediate Similarity NPD4632 Approved
0.7823 Intermediate Similarity NPD6016 Approved
0.7823 Intermediate Similarity NPD6015 Approved
0.7815 Intermediate Similarity NPD6649 Approved
0.7815 Intermediate Similarity NPD6650 Approved
0.7797 Intermediate Similarity NPD6373 Approved
0.7797 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7797 Intermediate Similarity NPD6372 Approved
0.7797 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7795 Intermediate Similarity NPD8293 Discontinued
0.7787 Intermediate Similarity NPD7115 Discovery
0.7778 Intermediate Similarity NPD5697 Approved
0.7778 Intermediate Similarity NPD6412 Phase 2
0.776 Intermediate Similarity NPD5988 Approved
0.7731 Intermediate Similarity NPD7102 Approved
0.7731 Intermediate Similarity NPD6883 Approved
0.7731 Intermediate Similarity NPD7290 Approved
0.7712 Intermediate Similarity NPD7320 Approved
0.7667 Intermediate Similarity NPD6869 Approved
0.7667 Intermediate Similarity NPD8130 Phase 1
0.7667 Intermediate Similarity NPD6847 Approved
0.7667 Intermediate Similarity NPD6617 Approved
0.7661 Intermediate Similarity NPD7516 Approved
0.7647 Intermediate Similarity NPD6012 Approved
0.7647 Intermediate Similarity NPD6014 Approved
0.7647 Intermediate Similarity NPD6013 Approved
0.7632 Intermediate Similarity NPD4225 Approved
0.7632 Intermediate Similarity NPD7638 Approved
0.7627 Intermediate Similarity NPD5701 Approved
0.7583 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7581 Intermediate Similarity NPD7328 Approved
0.7581 Intermediate Similarity NPD7327 Approved
0.7565 Intermediate Similarity NPD7640 Approved
0.7565 Intermediate Similarity NPD7639 Approved
0.7563 Intermediate Similarity NPD6011 Approved
0.7559 Intermediate Similarity NPD7604 Phase 2
0.754 Intermediate Similarity NPD5983 Phase 2
0.754 Intermediate Similarity NPD8513 Phase 3
0.754 Intermediate Similarity NPD8517 Approved
0.754 Intermediate Similarity NPD8516 Approved
0.754 Intermediate Similarity NPD8515 Approved
0.754 Intermediate Similarity NPD8033 Approved
0.754 Intermediate Similarity NPD7503 Approved
0.746 Intermediate Similarity NPD8294 Approved
0.746 Intermediate Similarity NPD8377 Approved
0.7442 Intermediate Similarity NPD6336 Discontinued
0.7402 Intermediate Similarity NPD8380 Approved
0.7402 Intermediate Similarity NPD8378 Approved
0.7402 Intermediate Similarity NPD8379 Approved
0.7402 Intermediate Similarity NPD8296 Approved
0.7402 Intermediate Similarity NPD8335 Approved
0.7398 Intermediate Similarity NPD8133 Approved
0.7377 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD6033 Approved
0.7321 Intermediate Similarity NPD46 Approved
0.7321 Intermediate Similarity NPD6698 Approved
0.7295 Intermediate Similarity NPD4634 Approved
0.7293 Intermediate Similarity NPD7260 Phase 2
0.7288 Intermediate Similarity NPD5211 Phase 2
0.7281 Intermediate Similarity NPD7748 Approved
0.728 Intermediate Similarity NPD6274 Approved
0.7266 Intermediate Similarity NPD6921 Approved
0.7265 Intermediate Similarity NPD5286 Approved
0.7265 Intermediate Similarity NPD4696 Approved
0.7265 Intermediate Similarity NPD5285 Approved
0.7257 Intermediate Similarity NPD7515 Phase 2
0.725 Intermediate Similarity NPD6008 Approved
0.7244 Intermediate Similarity NPD7100 Approved
0.7244 Intermediate Similarity NPD7101 Approved
0.7241 Intermediate Similarity NPD6084 Phase 2
0.7241 Intermediate Similarity NPD7902 Approved
0.7241 Intermediate Similarity NPD6083 Phase 2
0.7241 Intermediate Similarity NPD4755 Approved
0.7167 Intermediate Similarity NPD5141 Approved
0.7165 Intermediate Similarity NPD6335 Approved
0.7155 Intermediate Similarity NPD5221 Approved
0.7155 Intermediate Similarity NPD5222 Approved
0.7155 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5225 Approved
0.7143 Intermediate Similarity NPD5226 Approved
0.7143 Intermediate Similarity NPD4633 Approved
0.7143 Intermediate Similarity NPD5224 Approved
0.7143 Intermediate Similarity NPD6868 Approved
0.7121 Intermediate Similarity NPD8074 Phase 3
0.7119 Intermediate Similarity NPD4700 Approved
0.7111 Intermediate Similarity NPD6845 Suspended
0.7105 Intermediate Similarity NPD6079 Approved
0.7094 Intermediate Similarity NPD5173 Approved
0.7087 Intermediate Similarity NPD6317 Approved
0.7083 Intermediate Similarity NPD5175 Approved
0.7083 Intermediate Similarity NPD5174 Approved
0.708 Intermediate Similarity NPD5328 Approved
0.7059 Intermediate Similarity NPD5344 Discontinued
0.7059 Intermediate Similarity NPD5223 Approved
0.7054 Intermediate Similarity NPD3573 Approved
0.7049 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD6399 Phase 3
0.704 Intermediate Similarity NPD6053 Discontinued
0.7031 Intermediate Similarity NPD6313 Approved
0.7031 Intermediate Similarity NPD6314 Approved
0.7009 Intermediate Similarity NPD4697 Phase 3
0.7 Intermediate Similarity NPD6908 Approved
0.7 Intermediate Similarity NPD6909 Approved
0.7 Intermediate Similarity NPD7632 Discontinued
0.6992 Remote Similarity NPD4730 Approved
0.6992 Remote Similarity NPD4729 Approved
0.6991 Remote Similarity NPD6672 Approved
0.6991 Remote Similarity NPD5737 Approved
0.6983 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6983 Remote Similarity NPD7900 Approved
0.6967 Remote Similarity NPD4768 Approved
0.6967 Remote Similarity NPD4767 Approved
0.6923 Remote Similarity NPD5695 Phase 3
0.6894 Remote Similarity NPD6067 Discontinued
0.6891 Remote Similarity NPD5696 Approved
0.688 Remote Similarity NPD5250 Approved
0.688 Remote Similarity NPD5251 Approved
0.688 Remote Similarity NPD5248 Approved
0.688 Remote Similarity NPD5249 Phase 3
0.688 Remote Similarity NPD6371 Approved
0.688 Remote Similarity NPD5247 Approved
0.6875 Remote Similarity NPD1694 Approved
0.687 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6855 Remote Similarity NPD5128 Approved
0.6814 Remote Similarity NPD3618 Phase 1
0.681 Remote Similarity NPD6411 Approved
0.681 Remote Similarity NPD5693 Phase 1
0.6803 Remote Similarity NPD4754 Approved
0.6786 Remote Similarity NPD7966 Clinical (unspecified phase)
0.678 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6757 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6752 Remote Similarity NPD5779 Approved
0.6752 Remote Similarity NPD5778 Approved
0.675 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6724 Remote Similarity NPD7838 Discovery
0.6715 Remote Similarity NPD5956 Approved
0.6714 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6696 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6694 Remote Similarity NPD6648 Approved
0.6693 Remote Similarity NPD5217 Approved
0.6693 Remote Similarity NPD5215 Approved
0.6693 Remote Similarity NPD5216 Approved
0.6687 Remote Similarity NPD7799 Discontinued
0.6667 Remote Similarity NPD7521 Approved
0.6667 Remote Similarity NPD7146 Approved
0.6667 Remote Similarity NPD5330 Approved
0.6667 Remote Similarity NPD7983 Approved
0.6667 Remote Similarity NPD7334 Approved
0.6667 Remote Similarity NPD6684 Approved
0.6667 Remote Similarity NPD6409 Approved
0.6643 Remote Similarity NPD8415 Approved
0.6638 Remote Similarity NPD4753 Phase 2
0.6638 Remote Similarity NPD6904 Approved
0.6638 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6101 Approved
0.6638 Remote Similarity NPD6080 Approved
0.6638 Remote Similarity NPD6673 Approved
0.6638 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6637 Remote Similarity NPD4786 Approved
0.6622 Remote Similarity NPD7236 Approved
0.6614 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6614 Remote Similarity NPD5135 Approved
0.6614 Remote Similarity NPD5169 Approved
0.6613 Remote Similarity NPD8170 Clinical (unspecified phase)
0.661 Remote Similarity NPD4202 Approved
0.6607 Remote Similarity NPD3667 Approved
0.6587 Remote Similarity NPD5168 Approved
0.6577 Remote Similarity NPD4695 Discontinued
0.6562 Remote Similarity NPD5127 Approved
0.6555 Remote Similarity NPD5282 Discontinued
0.6552 Remote Similarity NPD6903 Approved
0.6525 Remote Similarity NPD8035 Phase 2
0.6525 Remote Similarity NPD8034 Phase 2
0.6513 Remote Similarity NPD7239 Suspended
0.6506 Remote Similarity NPD8407 Phase 2

  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