Structure

Physi-Chem Properties

Molecular Weight:  766.45
Volume:  766.797
LogP:  2.111
LogD:  2.963
LogS:  -3.295
# Rotatable Bonds:  8
TPSA:  215.83
# H-Bond Aceptor:  13
# H-Bond Donor:  8
# Rings:  7
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.132
Synthetic Accessibility Score:  5.843
Fsp3:  0.927
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.739
MDCK Permeability:  1.8680973880691454e-05
Pgp-inhibitor:  0.931
Pgp-substrate:  0.003
Human Intestinal Absorption (HIA):  0.891
20% Bioavailability (F20%):  0.192
30% Bioavailability (F30%):  0.935

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.015
Plasma Protein Binding (PPB):  80.51549530029297%
Volume Distribution (VD):  0.443
Pgp-substrate:  6.729678630828857%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.845
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.572
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.038
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.108
CYP3A4-inhibitor:  0.047
CYP3A4-substrate:  0.023

ADMET: Excretion

Clearance (CL):  0.815
Half-life (T1/2):  0.72

ADMET: Toxicity

hERG Blockers:  0.175
Human Hepatotoxicity (H-HT):  0.206
Drug-inuced Liver Injury (DILI):  0.007
AMES Toxicity:  0.065
Rat Oral Acute Toxicity:  0.051
Maximum Recommended Daily Dose:  0.062
Skin Sensitization:  0.7
Carcinogencity:  0.009
Eye Corrosion:  0.003
Eye Irritation:  0.015
Respiratory Toxicity:  0.182

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

  Natural Product: NPC5194

Natural Product ID:  NPC5194
Common Name*:   Hymenistatin 1
IUPAC Name:   n.a.
Synonyms:   Hymenistatin 1
Standard InCHIKey:  NACGNHONDBBQGE-MXKYYYADSA-N
Standard InCHI:  InChI=1S/C47H72N8O9/c1-9-28(7)38-44(61)52-39(29(8)10-2)47(64)55-23-13-16-36(55)45(62)53-21-11-14-34(53)42(59)49-33(25-30-17-19-31(56)20-18-30)41(58)50-37(27(5)6)46(63)54-22-12-15-35(54)43(60)48-32(24-26(3)4)40(57)51-38/h17-20,26-29,32-39,56H,9-16,21-25H2,1-8H3,(H,48,60)(H,49,59)(H,50,58)(H,51,57)(H,52,61)/t28-,29-,32-,33-,34-,35-,36-,37-,38-,39-/m0/s1
SMILES:  CC[C@@H]([C@@H]1N=C(O)[C@H](CC(C)C)N=C(O)[C@@H]2CCCN2C(=O)[C@@H](N=C(O)[C@@H](N=C([C@H]2N(C(=O)[C@H]3N(C(=O)[C@@H](N=C1O)[C@H](CC)C)CCC3)CCC2)O)Cc1ccc(cc1)O)C(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2370330
PubChem CID:   10102206
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000348] Peptides
            • [CHEMONTID:0004831] Oligopeptides

*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
NPO14751 Anisodoris nobilis Species Discodorididae Eukaryota n.a. n.a. n.a. PMID[7241154]
NPO17477 Potentilla indica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17233 Picrodendron baccatum Species Picrodendraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17233 Picrodendron baccatum Species Picrodendraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO757 Dorycnium graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11480 Haematomma puniceum Species Haematommataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17477 Potentilla indica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13830 Alcaligenes faecalis Species Alcaligenaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16589 Clitocybe conglobata Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17935 Pedicularis lasiophrys Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12664 Haplanthus tentaculatus n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13365 Helminthosporium euchlaenae Species Massarinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16723 Gascardia madagascariensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17016 Cassinia aculeata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17160 Dimerostemma lippioides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14751 Anisodoris nobilis Species Discodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16836 Polyporus picipes Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21698 Crinum augustum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9435 Acacia georginae Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15034 Intsia bijuga Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6751 Clusia grandiflora Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17695 Calyptranthes tricona Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11799 Ursinia saxatilis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28868 Pardachirus pavoninus Species Soleidae 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
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 = 40000.0 nM PMID[568639]
NPT399 Cell Line SF-295 Homo sapiens GI50 = 300000.0 nM PMID[568639]
NPT376 Cell Line A498 Homo sapiens GI50 = 700000.0 nM PMID[568639]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 300000.0 nM PMID[568639]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 = 100000.0 nM PMID[568639]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 = 600000.0 nM PMID[568639]

☑ 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 NPC5194 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 NPC261934
0.9444 High Similarity NPC262166
0.931 High Similarity NPC202198
0.931 High Similarity NPC56685
0.9272 High Similarity NPC302597
0.9272 High Similarity NPC141957
0.9262 High Similarity NPC241794
0.8966 High Similarity NPC16188
0.8881 High Similarity NPC476989
0.8851 High Similarity NPC233702
0.8734 High Similarity NPC136797
0.8658 High Similarity NPC473491
0.8553 High Similarity NPC244509
0.8483 Intermediate Similarity NPC313694
0.8483 Intermediate Similarity NPC242159
0.8481 Intermediate Similarity NPC129486
0.8442 Intermediate Similarity NPC326349
0.8442 Intermediate Similarity NPC323336
0.8428 Intermediate Similarity NPC475204
0.8428 Intermediate Similarity NPC475123
0.8408 Intermediate Similarity NPC472923
0.8387 Intermediate Similarity NPC244336
0.8375 Intermediate Similarity NPC328494
0.8354 Intermediate Similarity NPC61004
0.8323 Intermediate Similarity NPC137627
0.8323 Intermediate Similarity NPC475532
0.8302 Intermediate Similarity NPC328649
0.8272 Intermediate Similarity NPC26108
0.8272 Intermediate Similarity NPC165285
0.8194 Intermediate Similarity NPC130309
0.8194 Intermediate Similarity NPC476268
0.8176 Intermediate Similarity NPC63931
0.8086 Intermediate Similarity NPC198254
0.8086 Intermediate Similarity NPC274198
0.8086 Intermediate Similarity NPC46009
0.8077 Intermediate Similarity NPC473580
0.8075 Intermediate Similarity NPC107938
0.8075 Intermediate Similarity NPC294516
0.8049 Intermediate Similarity NPC17698
0.8049 Intermediate Similarity NPC471165
0.8037 Intermediate Similarity NPC230611
0.8026 Intermediate Similarity NPC81026
0.8 Intermediate Similarity NPC200589
0.7988 Intermediate Similarity NPC306804
0.7987 Intermediate Similarity NPC469243
0.7975 Intermediate Similarity NPC276506
0.7975 Intermediate Similarity NPC40234
0.7961 Intermediate Similarity NPC266741
0.7961 Intermediate Similarity NPC313867
0.7961 Intermediate Similarity NPC316008
0.7959 Intermediate Similarity NPC287401
0.7939 Intermediate Similarity NPC473402
0.7939 Intermediate Similarity NPC279871
0.7908 Intermediate Similarity NPC314358
0.7895 Intermediate Similarity NPC315283
0.7895 Intermediate Similarity NPC314388
0.7892 Intermediate Similarity NPC196243
0.7892 Intermediate Similarity NPC50016
0.7879 Intermediate Similarity NPC273755
0.7875 Intermediate Similarity NPC475544
0.784 Intermediate Similarity NPC223207
0.7831 Intermediate Similarity NPC473354
0.7831 Intermediate Similarity NPC155506
0.7831 Intermediate Similarity NPC159767
0.7831 Intermediate Similarity NPC476227
0.7818 Intermediate Similarity NPC89831
0.7805 Intermediate Similarity NPC280022
0.7798 Intermediate Similarity NPC194671
0.7798 Intermediate Similarity NPC269750
0.7798 Intermediate Similarity NPC45037
0.7791 Intermediate Similarity NPC471771
0.7791 Intermediate Similarity NPC254700
0.7791 Intermediate Similarity NPC304074
0.7791 Intermediate Similarity NPC290755
0.7785 Intermediate Similarity NPC39431
0.777 Intermediate Similarity NPC257390
0.7765 Intermediate Similarity NPC167763
0.7765 Intermediate Similarity NPC470903
0.7765 Intermediate Similarity NPC470112
0.7746 Intermediate Similarity NPC200964
0.7708 Intermediate Similarity NPC6975
0.7707 Intermediate Similarity NPC324081
0.7706 Intermediate Similarity NPC473404
0.7703 Intermediate Similarity NPC255447
0.7702 Intermediate Similarity NPC287757
0.7702 Intermediate Similarity NPC319320
0.7684 Intermediate Similarity NPC329295
0.7669 Intermediate Similarity NPC191863
0.7669 Intermediate Similarity NPC289776
0.7669 Intermediate Similarity NPC133470
0.7665 Intermediate Similarity NPC248670
0.7662 Intermediate Similarity NPC476978
0.7647 Intermediate Similarity NPC153554
0.7643 Intermediate Similarity NPC317254
0.7635 Intermediate Similarity NPC300315
0.7632 Intermediate Similarity NPC89489
0.7627 Intermediate Similarity NPC477638
0.7627 Intermediate Similarity NPC477632
0.7616 Intermediate Similarity NPC294951
0.7602 Intermediate Similarity NPC477637
0.7602 Intermediate Similarity NPC476321
0.76 Intermediate Similarity NPC477636
0.7593 Intermediate Similarity NPC469898
0.759 Intermediate Similarity NPC186617
0.7588 Intermediate Similarity NPC97526
0.7588 Intermediate Similarity NPC475421
0.7588 Intermediate Similarity NPC119652
0.7586 Intermediate Similarity NPC46427
0.758 Intermediate Similarity NPC240848
0.7569 Intermediate Similarity NPC202521
0.7568 Intermediate Similarity NPC473322
0.7566 Intermediate Similarity NPC109580
0.7558 Intermediate Similarity NPC471526
0.7545 Intermediate Similarity NPC473693
0.7545 Intermediate Similarity NPC471568
0.7533 Intermediate Similarity NPC326966
0.7517 Intermediate Similarity NPC252878
0.7516 Intermediate Similarity NPC469903
0.7514 Intermediate Similarity NPC477631
0.75 Intermediate Similarity NPC315266
0.75 Intermediate Similarity NPC476990
0.7486 Intermediate Similarity NPC329731
0.7486 Intermediate Similarity NPC4910
0.7483 Intermediate Similarity NPC470546
0.7453 Intermediate Similarity NPC473002
0.7451 Intermediate Similarity NPC6570
0.7443 Intermediate Similarity NPC102959
0.7442 Intermediate Similarity NPC475564
0.7442 Intermediate Similarity NPC475409
0.7442 Intermediate Similarity NPC170302
0.7442 Intermediate Similarity NPC32064
0.7439 Intermediate Similarity NPC469902
0.7439 Intermediate Similarity NPC473003
0.7434 Intermediate Similarity NPC141050
0.7431 Intermediate Similarity NPC283760
0.743 Intermediate Similarity NPC184933
0.743 Intermediate Similarity NPC59827
0.7425 Intermediate Similarity NPC209463
0.7414 Intermediate Similarity NPC471050
0.7414 Intermediate Similarity NPC471048
0.7414 Intermediate Similarity NPC471049
0.7413 Intermediate Similarity NPC470545
0.7412 Intermediate Similarity NPC164608
0.7412 Intermediate Similarity NPC158277
0.7401 Intermediate Similarity NPC240130
0.7401 Intermediate Similarity NPC61332
0.7401 Intermediate Similarity NPC60516
0.7401 Intermediate Similarity NPC473305
0.7401 Intermediate Similarity NPC163961
0.74 Intermediate Similarity NPC478147
0.7389 Intermediate Similarity NPC477639
0.7386 Intermediate Similarity NPC94862
0.7383 Intermediate Similarity NPC319766
0.7372 Intermediate Similarity NPC91953
0.7371 Intermediate Similarity NPC299806
0.7368 Intermediate Similarity NPC244866
0.7365 Intermediate Similarity NPC171372
0.7355 Intermediate Similarity NPC48202
0.7343 Intermediate Similarity NPC470544
0.7342 Intermediate Similarity NPC262077
0.7341 Intermediate Similarity NPC39822
0.7338 Intermediate Similarity NPC471264
0.7338 Intermediate Similarity NPC471265
0.7337 Intermediate Similarity NPC196091
0.7333 Intermediate Similarity NPC296712
0.7333 Intermediate Similarity NPC469666
0.7333 Intermediate Similarity NPC469901
0.7326 Intermediate Similarity NPC473546
0.7321 Intermediate Similarity NPC473502
0.7317 Intermediate Similarity NPC324850
0.7312 Intermediate Similarity NPC2501
0.731 Intermediate Similarity NPC319950
0.7308 Intermediate Similarity NPC477527
0.7308 Intermediate Similarity NPC197921
0.7296 Intermediate Similarity NPC311658
0.7279 Intermediate Similarity NPC474862
0.7278 Intermediate Similarity NPC473000
0.7278 Intermediate Similarity NPC302715
0.7278 Intermediate Similarity NPC5620
0.7278 Intermediate Similarity NPC65714
0.7273 Intermediate Similarity NPC138083
0.7267 Intermediate Similarity NPC7817
0.7267 Intermediate Similarity NPC475168
0.7263 Intermediate Similarity NPC473378
0.7263 Intermediate Similarity NPC473407
0.7261 Intermediate Similarity NPC469360
0.7261 Intermediate Similarity NPC251439
0.7248 Intermediate Similarity NPC101719
0.7247 Intermediate Similarity NPC234069
0.7244 Intermediate Similarity NPC163392
0.7244 Intermediate Similarity NPC239762
0.7232 Intermediate Similarity NPC276120
0.7222 Intermediate Similarity NPC239357
0.7215 Intermediate Similarity NPC52748
0.7214 Intermediate Similarity NPC258056
0.7208 Intermediate Similarity NPC248283
0.7207 Intermediate Similarity NPC174122
0.7207 Intermediate Similarity NPC64140
0.7203 Intermediate Similarity NPC118202
0.7198 Intermediate Similarity NPC473371

  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 NPC5194 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
0.8933 High Similarity NPD7118 Clinical (unspecified phase)
0.8471 Intermediate Similarity NPD8303 Discontinued
0.7622 Intermediate Similarity NPD2098 Approved
0.7547 Intermediate Similarity NPD7303 Discontinued
0.7545 Intermediate Similarity NPD4652 Approved
0.75 Intermediate Similarity NPD2097 Approved
0.7483 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD7450 Phase 2
0.7417 Intermediate Similarity NPD1330 Phase 2
0.7417 Intermediate Similarity NPD1329 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD7979 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7523 Phase 3
0.7391 Intermediate Similarity NPD7131 Phase 3
0.7351 Intermediate Similarity NPD3136 Phase 2
0.7338 Intermediate Similarity NPD8172 Phase 2
0.7338 Intermediate Similarity NPD8173 Phase 2
0.7315 Intermediate Similarity NPD2585 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD6860 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD5339 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD7978 Discontinued
0.7248 Intermediate Similarity NPD3125 Approved
0.7207 Intermediate Similarity NPD7617 Discontinued
0.7176 Intermediate Similarity NPD7484 Phase 3
0.7176 Intermediate Similarity NPD7485 Phase 3
0.7169 Intermediate Similarity NPD8019 Approved
0.7169 Intermediate Similarity NPD7495 Discontinued
0.7161 Intermediate Similarity NPD7113 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD5200 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD2890 Approved
0.7076 Intermediate Similarity NPD2017 Approved
0.7076 Intermediate Similarity NPD2888 Approved
0.7076 Intermediate Similarity NPD2889 Approved
0.7044 Intermediate Similarity NPD8076 Discontinued
0.7025 Intermediate Similarity NPD6866 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6867 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD7728 Clinical (unspecified phase)
0.6994 Remote Similarity NPD6682 Clinical (unspecified phase)
0.6994 Remote Similarity NPD5137 Approved
0.6948 Remote Similarity NPD4125 Approved
0.6928 Remote Similarity NPD7451 Discontinued
0.6923 Remote Similarity NPD5745 Approved
0.6909 Remote Similarity NPD7613 Discontinued
0.6903 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6899 Remote Similarity NPD4782 Clinical (unspecified phase)
0.6887 Remote Similarity NPD2584 Suspended
0.6887 Remote Similarity NPD3071 Approved
0.6887 Remote Similarity NPD3072 Approved
0.6887 Remote Similarity NPD3073 Approved
0.6879 Remote Similarity NPD8416 Discontinued
0.6879 Remote Similarity NPD6346 Approved
0.6879 Remote Similarity NPD4791 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4676 Approved
0.6839 Remote Similarity NPD7608 Discontinued
0.6835 Remote Similarity NPD8643 Discontinued
0.6829 Remote Similarity NPD8290 Clinical (unspecified phase)
0.6826 Remote Similarity NPD6670 Clinical (unspecified phase)
0.6821 Remote Similarity NPD4761 Approved
0.6821 Remote Similarity NPD4762 Approved
0.6813 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6807 Remote Similarity NPD6078 Clinical (unspecified phase)
0.6798 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6795 Remote Similarity NPD5746 Approved
0.679 Remote Similarity NPD6681 Discovery
0.6779 Remote Similarity NPD5303 Approved
0.6779 Remote Similarity NPD5304 Approved
0.677 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6757 Remote Similarity NPD3123 Discovery
0.674 Remote Similarity NPD7280 Phase 3
0.674 Remote Similarity NPD7281 Phase 3
0.6732 Remote Similarity NPD4659 Approved
0.6732 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6731 Remote Similarity NPD5263 Approved
0.6728 Remote Similarity NPD2022 Approved
0.6727 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6716 Remote Similarity NPD8292 Phase 2
0.671 Remote Similarity NPD3588 Discontinued
0.6707 Remote Similarity NPD7066 Clinical (unspecified phase)
0.6688 Remote Similarity NPD2044 Approved
0.6688 Remote Similarity NPD2048 Approved
0.6688 Remote Similarity NPD2051 Approved
0.6688 Remote Similarity NPD2047 Approved
0.6688 Remote Similarity NPD2046 Approved
0.6688 Remote Similarity NPD21 Approved
0.6688 Remote Similarity NPD2050 Clinical (unspecified phase)
0.6688 Remote Similarity NPD2043 Approved
0.6688 Remote Similarity NPD2049 Clinical (unspecified phase)
0.6688 Remote Similarity NPD2045 Approved
0.6687 Remote Similarity NPD5725 Approved
0.6687 Remote Similarity NPD5341 Clinical (unspecified phase)
0.6685 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2228 Approved
0.6667 Remote Similarity NPD4177 Approved
0.6667 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4175 Approved
0.6667 Remote Similarity NPD2234 Approved
0.6667 Remote Similarity NPD2229 Approved
0.6649 Remote Similarity NPD6256 Approved
0.6649 Remote Similarity NPD6255 Approved
0.6649 Remote Similarity NPD6254 Approved
0.6646 Remote Similarity NPD6901 Phase 3
0.6644 Remote Similarity NPD9568 Approved
0.6628 Remote Similarity NPD5773 Approved
0.6628 Remote Similarity NPD5772 Approved
0.6626 Remote Similarity NPD2088 Approved
0.6626 Remote Similarity NPD6809 Clinical (unspecified phase)
0.6626 Remote Similarity NPD2087 Approved
0.6624 Remote Similarity NPD4207 Discontinued
0.6611 Remote Similarity NPD5484 Approved
0.6611 Remote Similarity NPD5485 Approved
0.6607 Remote Similarity NPD6390 Discontinued
0.6606 Remote Similarity NPD6676 Phase 2
0.6606 Remote Similarity NPD5481 Discontinued
0.6603 Remote Similarity NPD3608 Clinical (unspecified phase)
0.6601 Remote Similarity NPD4706 Clinical (unspecified phase)
0.6597 Remote Similarity NPD6253 Approved
0.659 Remote Similarity NPD5967 Approved
0.6587 Remote Similarity NPD3988 Approved
0.6587 Remote Similarity NPD6631 Clinical (unspecified phase)
0.6587 Remote Similarity NPD3987 Approved
0.6587 Remote Similarity NPD7892 Clinical (unspecified phase)
0.6585 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6584 Remote Similarity NPD6073 Approved
0.6582 Remote Similarity NPD4497 Clinical (unspecified phase)
0.657 Remote Similarity NPD7011 Discontinued
0.6568 Remote Similarity NPD1670 Discontinued
0.6566 Remote Similarity NPD8323 Discontinued
0.6562 Remote Similarity NPD5323 Approved
0.6558 Remote Similarity NPD2562 Approved
0.6558 Remote Similarity NPD2561 Approved
0.6556 Remote Similarity NPD1759 Phase 1
0.6554 Remote Similarity NPD2517 Approved
0.6548 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6543 Remote Similarity NPD4126 Approved
0.6541 Remote Similarity NPD3632 Clinical (unspecified phase)
0.6541 Remote Similarity NPD2078 Clinical (unspecified phase)
0.6538 Remote Similarity NPD4103 Phase 2
0.6538 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6536 Remote Similarity NPD3421 Phase 3
0.6534 Remote Similarity NPD7133 Discontinued
0.6532 Remote Similarity NPD4566 Approved
0.6532 Remote Similarity NPD4567 Approved
0.6529 Remote Similarity NPD8315 Phase 1
0.6527 Remote Similarity NPD5308 Clinical (unspecified phase)
0.6524 Remote Similarity NPD6505 Approved
0.6524 Remote Similarity NPD6504 Approved
0.6522 Remote Similarity NPD4757 Clinical (unspecified phase)
0.6514 Remote Similarity NPD8031 Discontinued
0.6506 Remote Similarity NPD1967 Approved
0.6506 Remote Similarity NPD1968 Approved
0.65 Remote Similarity NPD7634 Clinical (unspecified phase)
0.65 Remote Similarity NPD8022 Clinical (unspecified phase)
0.65 Remote Similarity NPD7086 Phase 2
0.6497 Remote Similarity NPD2516 Approved
0.649 Remote Similarity NPD317 Approved
0.649 Remote Similarity NPD318 Approved
0.649 Remote Similarity NPD1758 Phase 1
0.649 Remote Similarity NPD16 Approved
0.649 Remote Similarity NPD856 Approved
0.6488 Remote Similarity NPD5613 Approved
0.6488 Remote Similarity NPD5614 Approved
0.6485 Remote Similarity NPD2437 Approved
0.6485 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6485 Remote Similarity NPD2436 Approved
0.648 Remote Similarity NPD8124 Phase 3
0.648 Remote Similarity NPD8126 Clinical (unspecified phase)
0.6467 Remote Similarity NPD256 Approved
0.6467 Remote Similarity NPD5309 Clinical (unspecified phase)
0.6467 Remote Similarity NPD255 Approved
0.6458 Remote Similarity NPD7811 Phase 3
0.6458 Remote Similarity NPD7810 Phase 3
0.6456 Remote Similarity NPD5759 Approved
0.6452 Remote Similarity NPD6089 Clinical (unspecified phase)
0.6442 Remote Similarity NPD3552 Approved
0.6442 Remote Similarity NPD3555 Approved
0.6442 Remote Similarity NPD3553 Approved
0.6442 Remote Similarity NPD3554 Approved
0.6438 Remote Similarity NPD5299 Approved
0.6433 Remote Similarity NPD3053 Approved
0.6433 Remote Similarity NPD3055 Approved
0.6432 Remote Similarity NPD6557 Phase 2
0.6424 Remote Similarity NPD7720 Phase 2
0.6414 Remote Similarity NPD1445 Approved
0.6414 Remote Similarity NPD1444 Approved
0.6407 Remote Similarity NPD3400 Discontinued
0.6405 Remote Similarity NPD4093 Discontinued
0.6402 Remote Similarity NPD3480 Approved
0.64 Remote Similarity NPD1791 Approved
0.64 Remote Similarity NPD1793 Approved
0.6398 Remote Similarity NPD5747 Discontinued
0.6398 Remote Similarity NPD2245 Discovery
0.6393 Remote Similarity NPD6297 Approved
0.6393 Remote Similarity NPD5445 Approved
0.6389 Remote Similarity NPD7965 Phase 2
0.6389 Remote Similarity NPD7964 Clinical (unspecified phase)
0.6389 Remote Similarity NPD9610 Approved
0.6389 Remote Similarity NPD9608 Approved
0.638 Remote Similarity NPD2568 Approved
0.6379 Remote Similarity NPD7248 Discontinued
0.6374 Remote Similarity NPD6020 Phase 2
0.6369 Remote Similarity NPD6325 Discontinued

  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