Structure

Physi-Chem Properties

Molecular Weight:  626.24
Volume:  623.623
LogP:  4.696
LogD:  4.251
LogS:  -4.712
# Rotatable Bonds:  7
TPSA:  143.89
# H-Bond Aceptor:  10
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.327
Synthetic Accessibility Score:  5.237
Fsp3:  0.485
Lipinski Rule-of-5:  Accepted
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:  -4.756
MDCK Permeability:  2.009911258937791e-05
Pgp-inhibitor:  0.988
Pgp-substrate:  0.014
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.029
30% Bioavailability (F30%):  0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.106
Plasma Protein Binding (PPB):  94.99913024902344%
Volume Distribution (VD):  0.66
Pgp-substrate:  2.6706862449645996%

ADMET: Metabolism

CYP1A2-inhibitor:  0.036
CYP1A2-substrate:  0.061
CYP2C19-inhibitor:  0.731
CYP2C19-substrate:  0.072
CYP2C9-inhibitor:  0.848
CYP2C9-substrate:  0.883
CYP2D6-inhibitor:  0.067
CYP2D6-substrate:  0.147
CYP3A4-inhibitor:  0.92
CYP3A4-substrate:  0.626

ADMET: Excretion

Clearance (CL):  6.66
Half-life (T1/2):  0.521

ADMET: Toxicity

hERG Blockers:  0.062
Human Hepatotoxicity (H-HT):  0.848
Drug-inuced Liver Injury (DILI):  0.924
AMES Toxicity:  0.09
Rat Oral Acute Toxicity:  0.822
Maximum Recommended Daily Dose:  0.399
Skin Sensitization:  0.246
Carcinogencity:  0.199
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.029

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

  Natural Product: NPC227778

Natural Product ID:  NPC227778
Common Name*:   Cryptophycin 176
IUPAC Name:   (3S,10R,13E,16S)-10-[(3-chloro-4-hydroxyphenyl)methyl]-3-(2-methylpropyl)-16-[(1S)-1-[(2R,3R)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
Synonyms:   Cryptophycin 176
Standard InCHIKey:  ZOBPQYRFOOKIQZ-JZZSZVNESA-N
Standard InCHI:  InChI=1S/C33H39ClN2O8/c1-19(2)16-27-33(41)43-26(20(3)30-31(44-30)22-8-5-4-6-9-22)10-7-11-28(38)36-24(32(40)35-15-14-29(39)42-27)18-21-12-13-25(37)23(34)17-21/h4-9,11-13,17,19-20,24,26-27,30-31,37H,10,14-16,18H2,1-3H3,(H,35,40)(H,36,38)/b11-7+/t20-,24+,26-,27-,30+,31+/m0/s1
SMILES:  CC(C)C[C@H]1C(=O)O[C@@H](C/C=C/C(=N[C@H](Cc2ccc(c(c2)Cl)O)C(=NCCC(=O)O1)O)O)[C@H](C)[C@@H]1[C@@H](c2ccccc2)O1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL452431
PubChem CID:   21591965
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0002010] Hybrid peptides

*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
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. aerial part n.a. DOI[10.1021/jo00416a020]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. PMID[11473413]
NPO4541 Capnella lacertiliensis Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[12608844]
NPO40970 0stoc sp. GSV 224 Strain 0stocaceae Bacteria n.a. n.a. n.a. PMID[15332864]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota leaves n.a. n.a. PMID[17243726]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24476550]
NPO40970 0stoc sp. GSV 224 Strain 0stocaceae Bacteria n.a. n.a. n.a. PMID[9090872]
NPO8305 Katsuwonus pelamis Species Scombridae Eukaryota n.a. n.a. Database[FooDB]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1969 Streptomyces pilosus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8811 Cytisus prolifer Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28833 Eleutherococcus sieboldianus Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19804 Lycopodium saururus Species Lycopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5335 0stoc sp Species 0stocaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO834 Peperomia clusiifolia Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8623 Anneissia japonica Species Comatulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18618 Neurolaena lobata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7788 Rana catesbeiana Species Ranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9705 Meyerozyma guilliermondii Species Debaryomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4541 Capnella lacertiliensis Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19541 Smilax moranensis Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8305 Katsuwonus pelamis Species Scombridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1537 Vaccinium arctostaphylos Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8426 Tinospora rumphii Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7240 Osteospermum oppositifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10879 Lasius meridionalis Species Formicidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4198 Ungernia vvedenskyi Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12744 Ajuga nipponensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23436 Cladrastis sikokiana Species Fabaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 1.3 nM PMID[565713]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 1.3 nM PMID[565713]
NPT114 Cell Line LoVo Homo sapiens IC50 = 1.3 nM PMID[565713]

☑ 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 NPC227778 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
0.9627 High Similarity NPC134413
0.9627 High Similarity NPC45112
0.9627 High Similarity NPC263507
0.9627 High Similarity NPC271958
0.939 High Similarity NPC86678
0.9193 High Similarity NPC151030
0.9193 High Similarity NPC269383
0.8963 High Similarity NPC49315
0.875 High Similarity NPC212699
0.875 High Similarity NPC207675
0.8313 Intermediate Similarity NPC132771
0.7688 Intermediate Similarity NPC473371
0.7578 Intermediate Similarity NPC6570
0.75 Intermediate Similarity NPC91953
0.7442 Intermediate Similarity NPC56635
0.7439 Intermediate Similarity NPC197921
0.7289 Intermediate Similarity NPC469360
0.7284 Intermediate Similarity NPC244866
0.725 Intermediate Similarity NPC296712
0.7222 Intermediate Similarity NPC45191
0.7222 Intermediate Similarity NPC326966
0.7197 Intermediate Similarity NPC474862
0.7175 Intermediate Similarity NPC472623
0.7165 Intermediate Similarity NPC469443
0.7117 Intermediate Similarity NPC48909
0.7117 Intermediate Similarity NPC30390
0.7076 Intermediate Similarity NPC313414
0.7072 Intermediate Similarity NPC40234
0.7072 Intermediate Similarity NPC196091
0.7056 Intermediate Similarity NPC473502
0.7049 Intermediate Similarity NPC476227
0.7035 Intermediate Similarity NPC219350
0.7035 Intermediate Similarity NPC194699
0.7021 Intermediate Similarity NPC315542
0.7012 Intermediate Similarity NPC275538
0.7 Intermediate Similarity NPC15506
0.6995 Remote Similarity NPC248670
0.6994 Remote Similarity NPC325651
0.6982 Remote Similarity NPC86087
0.697 Remote Similarity NPC470392
0.6966 Remote Similarity NPC476194
0.6957 Remote Similarity NPC26108
0.6957 Remote Similarity NPC473354
0.6957 Remote Similarity NPC471165
0.695 Remote Similarity NPC220060
0.6928 Remote Similarity NPC76453
0.6927 Remote Similarity NPC156348
0.6923 Remote Similarity NPC106688
0.6923 Remote Similarity NPC186617
0.6919 Remote Similarity NPC50016
0.6915 Remote Similarity NPC469444
0.6897 Remote Similarity NPC469442
0.6897 Remote Similarity NPC277306
0.6885 Remote Similarity NPC471568
0.6885 Remote Similarity NPC473693
0.6875 Remote Similarity NPC51047
0.6868 Remote Similarity NPC107938
0.6868 Remote Similarity NPC294516
0.6868 Remote Similarity NPC209463
0.6867 Remote Similarity NPC471953
0.6865 Remote Similarity NPC158277
0.6864 Remote Similarity NPC471201
0.686 Remote Similarity NPC81026
0.686 Remote Similarity NPC182475
0.6856 Remote Similarity NPC328763
0.6852 Remote Similarity NPC47667
0.6845 Remote Similarity NPC475421
0.6845 Remote Similarity NPC6913
0.6829 Remote Similarity NPC25539
0.6828 Remote Similarity NPC477115
0.682 Remote Similarity NPC213529
0.6814 Remote Similarity NPC469445
0.6811 Remote Similarity NPC273755
0.6802 Remote Similarity NPC323662
0.6802 Remote Similarity NPC266741
0.68 Remote Similarity NPC476743
0.6794 Remote Similarity NPC274268
0.6792 Remote Similarity NPC319950
0.679 Remote Similarity NPC476241
0.679 Remote Similarity NPC476260
0.6788 Remote Similarity NPC478147
0.6784 Remote Similarity NPC212850
0.6784 Remote Similarity NPC189724
0.6784 Remote Similarity NPC83289
0.678 Remote Similarity NPC39431
0.6776 Remote Similarity NPC238430
0.6774 Remote Similarity NPC279871
0.6772 Remote Similarity NPC476321
0.677 Remote Similarity NPC160493
0.6768 Remote Similarity NPC476353
0.6766 Remote Similarity NPC108553
0.6763 Remote Similarity NPC63628
0.6763 Remote Similarity NPC178466
0.6761 Remote Similarity NPC476744
0.676 Remote Similarity NPC187028
0.676 Remote Similarity NPC10221
0.676 Remote Similarity NPC197741
0.676 Remote Similarity NPC140915
0.676 Remote Similarity NPC305700
0.676 Remote Similarity NPC18249
0.6758 Remote Similarity NPC472923
0.6757 Remote Similarity NPC230611
0.6757 Remote Similarity NPC89831
0.6753 Remote Similarity NPC473407
0.6753 Remote Similarity NPC473378
0.6752 Remote Similarity NPC317254
0.675 Remote Similarity NPC476183
0.6748 Remote Similarity NPC476179
0.6748 Remote Similarity NPC476125
0.6746 Remote Similarity NPC64205
0.6743 Remote Similarity NPC245974
0.6737 Remote Similarity NPC470903
0.6737 Remote Similarity NPC471526
0.6737 Remote Similarity NPC167763
0.6737 Remote Similarity NPC470112
0.6724 Remote Similarity NPC247298
0.6723 Remote Similarity NPC182119
0.672 Remote Similarity NPC137627
0.672 Remote Similarity NPC306804
0.6708 Remote Similarity NPC476184
0.6708 Remote Similarity NPC476281
0.6703 Remote Similarity NPC475204
0.6703 Remote Similarity NPC475123
0.6702 Remote Similarity NPC294951
0.6698 Remote Similarity NPC316461
0.6685 Remote Similarity NPC471203
0.6685 Remote Similarity NPC476742
0.6684 Remote Similarity NPC473402
0.6684 Remote Similarity NPC155506
0.6684 Remote Similarity NPC159767
0.6667 Remote Similarity NPC322526
0.6667 Remote Similarity NPC27581
0.6667 Remote Similarity NPC194671
0.6667 Remote Similarity NPC312770
0.6667 Remote Similarity NPC142577
0.6667 Remote Similarity NPC311737
0.6667 Remote Similarity NPC41473
0.6667 Remote Similarity NPC38458
0.6667 Remote Similarity NPC160607
0.6667 Remote Similarity NPC470728
0.6667 Remote Similarity NPC204848
0.6667 Remote Similarity NPC269750
0.6667 Remote Similarity NPC45037
0.6667 Remote Similarity NPC63931
0.6667 Remote Similarity NPC299806
0.6667 Remote Similarity NPC14600
0.6648 Remote Similarity NPC476741
0.6646 Remote Similarity NPC95733
0.6646 Remote Similarity NPC4974
0.6646 Remote Similarity NPC190663
0.6646 Remote Similarity NPC62101
0.663 Remote Similarity NPC61004
0.663 Remote Similarity NPC254700
0.6628 Remote Similarity NPC299583
0.6626 Remote Similarity NPC476278
0.6615 Remote Similarity NPC471050
0.6615 Remote Similarity NPC471049
0.6615 Remote Similarity NPC471048
0.6613 Remote Similarity NPC90984
0.6613 Remote Similarity NPC46009
0.661 Remote Similarity NPC473491
0.6609 Remote Similarity NPC106183
0.6609 Remote Similarity NPC222039
0.6609 Remote Similarity NPC100478
0.6608 Remote Similarity NPC473052
0.6608 Remote Similarity NPC473055
0.6607 Remote Similarity NPC114102
0.6606 Remote Similarity NPC29477
0.6604 Remote Similarity NPC82963
0.6593 Remote Similarity NPC314743
0.6591 Remote Similarity NPC5462
0.659 Remote Similarity NPC477838
0.659 Remote Similarity NPC477837
0.6585 Remote Similarity NPC211218
0.6585 Remote Similarity NPC14141
0.6584 Remote Similarity NPC283760
0.6584 Remote Similarity NPC43275
0.6582 Remote Similarity NPC118202
0.658 Remote Similarity NPC474498
0.6571 Remote Similarity NPC262216
0.6568 Remote Similarity NPC214869
0.6568 Remote Similarity NPC328070
0.6564 Remote Similarity NPC295287
0.6548 Remote Similarity NPC195749
0.6548 Remote Similarity NPC52029
0.6548 Remote Similarity NPC35961
0.6545 Remote Similarity NPC33402
0.6543 Remote Similarity NPC45777
0.6543 Remote Similarity NPC263835
0.6543 Remote Similarity NPC477061
0.6541 Remote Similarity NPC50380
0.6541 Remote Similarity NPC179250
0.6538 Remote Similarity NPC474149
0.6538 Remote Similarity NPC319320
0.6538 Remote Similarity NPC287757
0.6536 Remote Similarity NPC114659
0.6536 Remote Similarity NPC139699
0.6535 Remote Similarity NPC319774
0.6534 Remote Similarity NPC16188
0.6532 Remote Similarity NPC279676

  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 NPC227778 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
0.9627 High Similarity NPD7959 Clinical (unspecified phase)
0.9568 High Similarity NPD8014 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4018 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD3465 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD3274 Phase 2
0.7216 Intermediate Similarity NPD2379 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7978 Discontinued
0.7173 Intermediate Similarity NPD6312 Discontinued
0.716 Intermediate Similarity NPD3136 Phase 2
0.7097 Intermediate Similarity NPD3936 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD3819 Phase 2
0.7065 Intermediate Similarity NPD5095 Phase 3
0.7065 Intermediate Similarity NPD5096 Phase 3
0.7062 Intermediate Similarity NPD7972 Discontinued
0.7041 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.6973 Remote Similarity NPD3933 Discontinued
0.6966 Remote Similarity NPD7460 Discontinued
0.6959 Remote Similarity NPD3400 Discontinued
0.6947 Remote Similarity NPD3857 Clinical (unspecified phase)
0.6941 Remote Similarity NPD4534 Discontinued
0.6941 Remote Similarity NPD5958 Discontinued
0.691 Remote Similarity NPD7029 Discontinued
0.6902 Remote Similarity NPD5822 Clinical (unspecified phase)
0.6875 Remote Similarity NPD2370 Clinical (unspecified phase)
0.68 Remote Similarity NPD3536 Discontinued
0.6793 Remote Similarity NPD7608 Discontinued
0.679 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6776 Remote Similarity NPD7129 Suspended
0.6765 Remote Similarity NPD6866 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6761 Remote Similarity NPD6390 Discontinued
0.6761 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6758 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6748 Remote Similarity NPD3098 Discontinued
0.6742 Remote Similarity NPD6056 Approved
0.6742 Remote Similarity NPD6057 Approved
0.6707 Remote Similarity NPD1048 Approved
0.6705 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6683 Remote Similarity NPD7565 Approved
0.6667 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7526 Approved
0.6667 Remote Similarity NPD52 Approved
0.6648 Remote Similarity NPD3455 Phase 2
0.6648 Remote Similarity NPD6682 Clinical (unspecified phase)
0.663 Remote Similarity NPD8019 Approved
0.6629 Remote Similarity NPD3973 Approved
0.6629 Remote Similarity NPD7131 Phase 3
0.6629 Remote Similarity NPD7523 Phase 3
0.6627 Remote Similarity NPD454 Approved
0.6627 Remote Similarity NPD6346 Approved
0.6626 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6611 Remote Similarity NPD4972 Discontinued
0.6611 Remote Similarity NPD6502 Phase 2
0.6608 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6595 Remote Similarity NPD3365 Discontinued
0.6595 Remote Similarity NPD6746 Phase 2
0.6588 Remote Similarity NPD6355 Discontinued
0.6579 Remote Similarity NPD5557 Phase 1
0.6561 Remote Similarity NPD3909 Discontinued
0.6559 Remote Similarity NPD5649 Clinical (unspecified phase)
0.6557 Remote Similarity NPD4874 Phase 2
0.6548 Remote Similarity NPD2372 Approved
0.6541 Remote Similarity NPD5709 Phase 3
0.6538 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6538 Remote Similarity NPD7495 Discontinued
0.6534 Remote Similarity NPD3887 Approved
0.6532 Remote Similarity NPD7450 Phase 2
0.6532 Remote Similarity NPD6032 Approved
0.6524 Remote Similarity NPD7315 Approved
0.6505 Remote Similarity NPD4666 Phase 3
0.6503 Remote Similarity NPD5563 Clinical (unspecified phase)
0.6502 Remote Similarity NPD4971 Clinical (unspecified phase)
0.65 Remote Similarity NPD4003 Phase 3
0.6486 Remote Similarity NPD4064 Discontinued
0.6485 Remote Similarity NPD4914 Approved
0.648 Remote Similarity NPD3364 Phase 3
0.6471 Remote Similarity NPD7477 Discontinued
0.6471 Remote Similarity NPD6233 Phase 2
0.6467 Remote Similarity NPD7451 Discontinued
0.6458 Remote Similarity NPD3823 Discontinued
0.6457 Remote Similarity NPD2808 Discontinued
0.645 Remote Similarity NPD2598 Clinical (unspecified phase)
0.6449 Remote Similarity NPD7805 Phase 3
0.6448 Remote Similarity NPD4433 Discontinued
0.6441 Remote Similarity NPD2354 Approved
0.6437 Remote Similarity NPD1501 Clinical (unspecified phase)
0.6433 Remote Similarity NPD8265 Approved
0.6425 Remote Similarity NPD4739 Approved
0.6421 Remote Similarity NPD3366 Approved
0.642 Remote Similarity NPD2976 Clinical (unspecified phase)
0.642 Remote Similarity NPD1759 Phase 1
0.6413 Remote Similarity NPD5773 Approved
0.6413 Remote Similarity NPD5772 Approved
0.6412 Remote Similarity NPD6798 Discontinued
0.6404 Remote Similarity NPD6666 Approved
0.6404 Remote Similarity NPD6667 Approved
0.6398 Remote Similarity NPD8031 Discontinued
0.6393 Remote Similarity NPD6677 Suspended
0.6393 Remote Similarity NPD6072 Discontinued
0.6393 Remote Similarity NPD4424 Discontinued
0.6389 Remote Similarity NPD7613 Discontinued
0.6384 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6384 Remote Similarity NPD6331 Phase 2
0.6383 Remote Similarity NPD5623 Approved
0.6374 Remote Similarity NPD5745 Approved
0.6358 Remote Similarity NPD1758 Phase 1
0.6345 Remote Similarity NPD8424 Clinical (unspecified phase)
0.6343 Remote Similarity NPD1537 Approved
0.6343 Remote Similarity NPD1538 Phase 1
0.6343 Remote Similarity NPD1519 Approved
0.6343 Remote Similarity NPD2239 Approved
0.6343 Remote Similarity NPD2240 Approved
0.6339 Remote Similarity NPD3579 Clinical (unspecified phase)
0.6337 Remote Similarity NPD1555 Discontinued
0.6337 Remote Similarity NPD8485 Approved
0.6337 Remote Similarity NPD4060 Phase 1
0.6337 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6333 Remote Similarity NPD4123 Phase 3
0.6324 Remote Similarity NPD7089 Clinical (unspecified phase)
0.6322 Remote Similarity NPD4538 Approved
0.6322 Remote Similarity NPD4536 Approved
0.6322 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6322 Remote Similarity NPD3554 Approved
0.6322 Remote Similarity NPD3552 Approved
0.6322 Remote Similarity NPD3553 Approved
0.6322 Remote Similarity NPD3555 Approved
0.6319 Remote Similarity NPD2617 Discontinued
0.6313 Remote Similarity NPD6815 Approved
0.631 Remote Similarity NPD8070 Approved
0.631 Remote Similarity NPD987 Approved
0.6307 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6307 Remote Similarity NPD2353 Approved
0.6304 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6303 Remote Similarity NPD3847 Discontinued
0.6301 Remote Similarity NPD555 Phase 2
0.6296 Remote Similarity NPD7484 Phase 3
0.6296 Remote Similarity NPD7485 Phase 3
0.6294 Remote Similarity NPD2614 Approved
0.6287 Remote Similarity NPD4659 Approved
0.6286 Remote Similarity NPD5960 Phase 3
0.6279 Remote Similarity NPD4062 Phase 3
0.6275 Remote Similarity NPD5544 Approved
0.6271 Remote Similarity NPD2897 Discontinued
0.627 Remote Similarity NPD5355 Approved
0.627 Remote Similarity NPD5356 Approved
0.6262 Remote Similarity NPD4387 Approved
0.6262 Remote Similarity NPD4386 Approved
0.6257 Remote Similarity NPD7095 Approved
0.6257 Remote Similarity NPD5746 Approved
0.6257 Remote Similarity NPD5163 Phase 2
0.6257 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6257 Remote Similarity NPD4738 Phase 2
0.625 Remote Similarity NPD1523 Approved
0.625 Remote Similarity NPD1522 Approved
0.625 Remote Similarity NPD4675 Approved
0.625 Remote Similarity NPD1715 Phase 1
0.625 Remote Similarity NPD6905 Phase 2
0.625 Remote Similarity NPD4678 Approved
0.625 Remote Similarity NPD1714 Approved
0.625 Remote Similarity NPD5667 Approved
0.625 Remote Similarity NPD2161 Phase 2
0.6244 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6244 Remote Similarity NPD5946 Clinical (unspecified phase)
0.6243 Remote Similarity NPD825 Approved
0.6243 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6243 Remote Similarity NPD826 Approved
0.6242 Remote Similarity NPD2668 Approved
0.6242 Remote Similarity NPD2667 Approved
0.6237 Remote Similarity NPD7695 Clinical (unspecified phase)
0.623 Remote Similarity NPD1972 Approved
0.623 Remote Similarity NPD1973 Approved
0.623 Remote Similarity NPD1969 Clinical (unspecified phase)
0.6229 Remote Similarity NPD1536 Approved
0.6229 Remote Similarity NPD6852 Discontinued
0.622 Remote Similarity NPD2218 Phase 2
0.622 Remote Similarity NPD2217 Approved
0.6218 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6216 Remote Similarity NPD958 Approved
0.6216 Remote Similarity NPD6386 Approved
0.6216 Remote Similarity NPD6385 Approved
0.6215 Remote Similarity NPD3656 Approved
0.6215 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6213 Remote Similarity NPD4103 Phase 2
0.6213 Remote Similarity NPD4104 Clinical (unspecified phase)
0.6211 Remote Similarity NPD2821 Approved
0.6211 Remote Similarity NPD2228 Approved
0.6211 Remote Similarity NPD2234 Approved
0.6211 Remote Similarity NPD2229 Approved
0.6209 Remote Similarity NPD4731 Phase 3
0.6209 Remote Similarity NPD6689 Clinical (unspecified phase)
0.6209 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6207 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6207 Remote Similarity NPD1184 Approved
0.6207 Remote Similarity NPD4361 Phase 2
0.6205 Remote Similarity NPD3421 Phase 3
0.6201 Remote Similarity NPD2575 Approved
0.62 Remote Similarity NPD8361 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