Structure

Physi-Chem Properties

Molecular Weight:  654.27
Volume:  658.215
LogP:  5.212
LogD:  4.14
LogS:  -5.705
# Rotatable Bonds:  8
TPSA:  132.89
# H-Bond Aceptor:  10
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.294
Synthetic Accessibility Score:  5.214
Fsp3:  0.514
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:  -4.978
MDCK Permeability:  1.6050909835030325e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.765

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.345
Plasma Protein Binding (PPB):  97.68910217285156%
Volume Distribution (VD):  0.787
Pgp-substrate:  1.4973307847976685%

ADMET: Metabolism

CYP1A2-inhibitor:  0.035
CYP1A2-substrate:  0.115
CYP2C19-inhibitor:  0.915
CYP2C19-substrate:  0.791
CYP2C9-inhibitor:  0.932
CYP2C9-substrate:  0.19
CYP2D6-inhibitor:  0.191
CYP2D6-substrate:  0.277
CYP3A4-inhibitor:  0.956
CYP3A4-substrate:  0.773

ADMET: Excretion

Clearance (CL):  5.144
Half-life (T1/2):  0.117

ADMET: Toxicity

hERG Blockers:  0.359
Human Hepatotoxicity (H-HT):  0.907
Drug-inuced Liver Injury (DILI):  0.922
AMES Toxicity:  0.07
Rat Oral Acute Toxicity:  0.825
Maximum Recommended Daily Dose:  0.141
Skin Sensitization:  0.196
Carcinogencity:  0.12
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.026

Download Data

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

  Natural Product: NPC271958

Natural Product ID:  NPC271958
Common Name*:   Cryptophycin 327
IUPAC Name:   (3S,6R,10R,13Z,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-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 327
Standard InCHIKey:  PSNOPSMXOBPNNV-GKPRUIBSSA-N
Standard InCHI:  InChI=1S/C35H43ClN2O8/c1-20(2)16-29-35(42)44-27(22(4)31-32(46-31)24-10-7-6-8-11-24)12-9-13-30(39)38-26(33(40)37-19-21(3)34(41)45-29)18-23-14-15-28(43-5)25(36)17-23/h6-11,13-15,17,20-22,26-27,29,31-32H,12,16,18-19H2,1-5H3,(H,37,40)(H,38,39)/b13-9-/t21-,22+,26-,27+,29+,31-,32-/m1/s1
SMILES:  COc1ccc(cc1Cl)C[C@H]1N=C(O)/C=CC[C@H](OC(=O)[C@@H](OC(=O)[C@@H](CN=C1O)C)CC(C)C)[C@@H]([C@H]1O[C@@H]1c1ccccc1)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL452448
PubChem CID:   11422411
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]
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[TCMID]
NPO8945 Grevillea robusta Species Proteaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
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]
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]
NPO3613 Eriobotrya deflexa Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4541 Capnella lacertiliensis Species Nephtheidae 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 = 14100.0 nM PMID[456489]

☑ 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 NPC271958 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 NPC134413
1.0 High Similarity NPC45112
1.0 High Similarity NPC263507
0.9755 High Similarity NPC86678
0.9627 High Similarity NPC227778
0.9563 High Similarity NPC151030
0.9563 High Similarity NPC269383
0.9325 High Similarity NPC49315
0.9 High Similarity NPC207675
0.9 High Similarity NPC212699
0.8562 High Similarity NPC132771
0.7572 Intermediate Similarity NPC56635
0.7435 Intermediate Similarity NPC473371
0.7323 Intermediate Similarity NPC219350
0.7323 Intermediate Similarity NPC194699
0.7321 Intermediate Similarity NPC86087
0.731 Intermediate Similarity NPC313414
0.7293 Intermediate Similarity NPC196091
0.7289 Intermediate Similarity NPC6570
0.7278 Intermediate Similarity NPC473502
0.7234 Intermediate Similarity NPC315542
0.7219 Intermediate Similarity NPC91953
0.7212 Intermediate Similarity NPC470392
0.7193 Intermediate Similarity NPC182475
0.7178 Intermediate Similarity NPC277306
0.7178 Intermediate Similarity NPC469442
0.716 Intermediate Similarity NPC197921
0.7143 Intermediate Similarity NPC186617
0.7108 Intermediate Similarity NPC471953
0.7108 Intermediate Similarity NPC25539
0.7104 Intermediate Similarity NPC473693
0.7104 Intermediate Similarity NPC471568
0.7067 Intermediate Similarity NPC274268
0.7059 Intermediate Similarity NPC475421
0.7048 Intermediate Similarity NPC45191
0.7043 Intermediate Similarity NPC477115
0.7018 Intermediate Similarity NPC212850
0.7018 Intermediate Similarity NPC83289
0.7018 Intermediate Similarity NPC189724
0.7018 Intermediate Similarity NPC469360
0.7006 Intermediate Similarity NPC244866
0.7005 Intermediate Similarity NPC213529
0.6994 Remote Similarity NPC63628
0.6994 Remote Similarity NPC178466
0.6983 Remote Similarity NPC305700
0.6983 Remote Similarity NPC10221
0.6983 Remote Similarity NPC187028
0.6983 Remote Similarity NPC140915
0.6983 Remote Similarity NPC18249
0.6983 Remote Similarity NPC197741
0.6978 Remote Similarity NPC472923
0.6971 Remote Similarity NPC245974
0.697 Remote Similarity NPC296712
0.6954 Remote Similarity NPC247298
0.6949 Remote Similarity NPC182119
0.6947 Remote Similarity NPC470903
0.6947 Remote Similarity NPC167763
0.6947 Remote Similarity NPC470112
0.6946 Remote Similarity NPC30390
0.6946 Remote Similarity NPC326966
0.6935 Remote Similarity NPC469443
0.6923 Remote Similarity NPC472623
0.6914 Remote Similarity NPC474862
0.689 Remote Similarity NPC95733
0.689 Remote Similarity NPC62101
0.6884 Remote Similarity NPC316461
0.6875 Remote Similarity NPC299806
0.6872 Remote Similarity NPC473407
0.6872 Remote Similarity NPC473378
0.6848 Remote Similarity NPC254700
0.6848 Remote Similarity NPC29477
0.6845 Remote Similarity NPC48909
0.6832 Remote Similarity NPC43275
0.6829 Remote Similarity NPC211218
0.6828 Remote Similarity NPC40234
0.6809 Remote Similarity NPC476227
0.6802 Remote Similarity NPC14600
0.6802 Remote Similarity NPC204848
0.6802 Remote Similarity NPC41473
0.6802 Remote Similarity NPC160607
0.6802 Remote Similarity NPC312770
0.679 Remote Similarity NPC263835
0.6788 Remote Similarity NPC474498
0.677 Remote Similarity NPC314743
0.6765 Remote Similarity NPC76453
0.6763 Remote Similarity NPC299583
0.676 Remote Similarity NPC139699
0.676 Remote Similarity NPC114659
0.6758 Remote Similarity NPC319320
0.6758 Remote Similarity NPC287757
0.6757 Remote Similarity NPC15506
0.6755 Remote Similarity NPC248670
0.6746 Remote Similarity NPC275538
0.6746 Remote Similarity NPC114102
0.6743 Remote Similarity NPC222039
0.6743 Remote Similarity NPC100478
0.6738 Remote Similarity NPC90984
0.6732 Remote Similarity NPC220060
0.6726 Remote Similarity NPC325651
0.6724 Remote Similarity NPC477837
0.6724 Remote Similarity NPC477838
0.6723 Remote Similarity NPC5462
0.6722 Remote Similarity NPC478189
0.6721 Remote Similarity NPC476194
0.672 Remote Similarity NPC26108
0.672 Remote Similarity NPC473354
0.672 Remote Similarity NPC474953
0.672 Remote Similarity NPC471165
0.6711 Remote Similarity NPC319774
0.6707 Remote Similarity NPC301713
0.6706 Remote Similarity NPC214869
0.6699 Remote Similarity NPC469444
0.6697 Remote Similarity NPC3921
0.6687 Remote Similarity NPC47667
0.6686 Remote Similarity NPC204546
0.6686 Remote Similarity NPC52029
0.6686 Remote Similarity NPC35961
0.6686 Remote Similarity NPC195749
0.6685 Remote Similarity NPC156348
0.6684 Remote Similarity NPC471395
0.6684 Remote Similarity NPC50016
0.6684 Remote Similarity NPC475794
0.6683 Remote Similarity NPC326333
0.6667 Remote Similarity NPC251571
0.6667 Remote Similarity NPC179250
0.6667 Remote Similarity NPC50380
0.6667 Remote Similarity NPC106688
0.665 Remote Similarity NPC51047
0.6649 Remote Similarity NPC474607
0.6648 Remote Similarity NPC277857
0.6648 Remote Similarity NPC324081
0.6648 Remote Similarity NPC115144
0.6633 Remote Similarity NPC328763
0.6632 Remote Similarity NPC158277
0.6632 Remote Similarity NPC164608
0.6631 Remote Similarity NPC107938
0.6631 Remote Similarity NPC209463
0.6631 Remote Similarity NPC294516
0.6629 Remote Similarity NPC304956
0.6627 Remote Similarity NPC476260
0.6627 Remote Similarity NPC476241
0.6627 Remote Similarity NPC155838
0.6619 Remote Similarity NPC326027
0.6615 Remote Similarity NPC474650
0.6611 Remote Similarity NPC470935
0.6611 Remote Similarity NPC471032
0.661 Remote Similarity NPC81026
0.6609 Remote Similarity NPC471201
0.6608 Remote Similarity NPC274732
0.6606 Remote Similarity NPC160493
0.6603 Remote Similarity NPC469445
0.6596 Remote Similarity NPC208280
0.6596 Remote Similarity NPC470936
0.6593 Remote Similarity NPC127402
0.6592 Remote Similarity NPC53884
0.6592 Remote Similarity NPC258671
0.6591 Remote Similarity NPC195814
0.659 Remote Similarity NPC6913
0.6588 Remote Similarity NPC246991
0.6587 Remote Similarity NPC476179
0.6587 Remote Similarity NPC476125
0.6585 Remote Similarity NPC476183
0.6584 Remote Similarity NPC323662
0.6582 Remote Similarity NPC276120
0.658 Remote Similarity NPC32064
0.6579 Remote Similarity NPC273755
0.6571 Remote Similarity NPC281780
0.6568 Remote Similarity NPC186898
0.6566 Remote Similarity NPC64140
0.6566 Remote Similarity NPC90577
0.6566 Remote Similarity NPC471315
0.6566 Remote Similarity NPC471314
0.6566 Remote Similarity NPC174122
0.6557 Remote Similarity NPC275027
0.6556 Remote Similarity NPC476743
0.6554 Remote Similarity NPC266741
0.6552 Remote Similarity NPC113295
0.6548 Remote Similarity NPC232872
0.6548 Remote Similarity NPC34780
0.6546 Remote Similarity NPC329816
0.6546 Remote Similarity NPC476321
0.6545 Remote Similarity NPC476281
0.6545 Remote Similarity NPC476184
0.6545 Remote Similarity NPC279871
0.6543 Remote Similarity NPC238430
0.6538 Remote Similarity NPC39431
0.6537 Remote Similarity NPC311357
0.6535 Remote Similarity NPC144314
0.6533 Remote Similarity NPC477526
0.6529 Remote Similarity NPC478147
0.6526 Remote Similarity NPC230611
0.6526 Remote Similarity NPC89831
0.6524 Remote Similarity NPC319950
0.6522 Remote Similarity NPC282294
0.6519 Remote Similarity NPC143892
0.6519 Remote Similarity NPC476744
0.6519 Remote Similarity NPC283081
0.6519 Remote Similarity NPC299090
0.6519 Remote Similarity NPC153644
0.6519 Remote Similarity NPC221383

  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 NPC271958 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
1.0 High Similarity NPD7959 Clinical (unspecified phase)
0.9938 High Similarity NPD8014 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD4018 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD3465 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD3274 Phase 2
0.7443 Intermediate Similarity NPD2379 Clinical (unspecified phase)
0.7382 Intermediate Similarity NPD6312 Discontinued
0.7312 Intermediate Similarity NPD3936 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD7972 Discontinued
0.7283 Intermediate Similarity NPD5096 Phase 3
0.7283 Intermediate Similarity NPD5095 Phase 3
0.7278 Intermediate Similarity NPD7596 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD3819 Phase 2
0.7189 Intermediate Similarity NPD3933 Discontinued
0.7176 Intermediate Similarity NPD5958 Discontinued
0.7176 Intermediate Similarity NPD4534 Discontinued
0.7158 Intermediate Similarity NPD3857 Clinical (unspecified phase)
0.712 Intermediate Similarity NPD5822 Clinical (unspecified phase)
0.7102 Intermediate Similarity NPD2370 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD3676 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7608 Discontinued
0.7006 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.6989 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6989 Remote Similarity NPD6390 Discontinued
0.6978 Remote Similarity NPD7975 Clinical (unspecified phase)
0.697 Remote Similarity NPD454 Approved
0.6946 Remote Similarity NPD1048 Approved
0.6932 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6932 Remote Similarity NPD3536 Discontinued
0.6919 Remote Similarity NPD7978 Discontinued
0.6893 Remote Similarity NPD52 Approved
0.6893 Remote Similarity NPD7526 Approved
0.6893 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6889 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6886 Remote Similarity NPD3136 Phase 2
0.6884 Remote Similarity NPD7565 Approved
0.6854 Remote Similarity NPD7131 Phase 3
0.6833 Remote Similarity NPD6502 Phase 2
0.6833 Remote Similarity NPD4972 Discontinued
0.6824 Remote Similarity NPD6355 Discontinued
0.6813 Remote Similarity NPD7460 Discontinued
0.6811 Remote Similarity NPD6746 Phase 2
0.6789 Remote Similarity NPD5557 Phase 1
0.6774 Remote Similarity NPD5649 Clinical (unspecified phase)
0.6772 Remote Similarity NPD3909 Discontinued
0.6763 Remote Similarity NPD6032 Approved
0.6761 Remote Similarity NPD3887 Approved
0.6758 Remote Similarity NPD7029 Discontinued
0.6758 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6738 Remote Similarity NPD7315 Approved
0.6722 Remote Similarity NPD4003 Phase 3
0.6721 Remote Similarity NPD5563 Clinical (unspecified phase)
0.672 Remote Similarity NPD3365 Discontinued
0.6706 Remote Similarity NPD6233 Phase 2
0.6706 Remote Similarity NPD7477 Discontinued
0.6705 Remote Similarity NPD3400 Discontinued
0.6703 Remote Similarity NPD4064 Discontinued
0.67 Remote Similarity NPD4971 Clinical (unspecified phase)
0.6686 Remote Similarity NPD2808 Discontinued
0.6686 Remote Similarity NPD2598 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4433 Discontinued
0.6667 Remote Similarity NPD1501 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2354 Approved
0.6667 Remote Similarity NPD3823 Discontinued
0.6667 Remote Similarity NPD5709 Phase 3
0.6648 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6648 Remote Similarity NPD4739 Approved
0.6647 Remote Similarity NPD6798 Discontinued
0.6636 Remote Similarity NPD7805 Phase 3
0.6632 Remote Similarity NPD3366 Approved
0.6631 Remote Similarity NPD4666 Phase 3
0.663 Remote Similarity NPD5773 Approved
0.663 Remote Similarity NPD5772 Approved
0.6629 Remote Similarity NPD6666 Approved
0.6629 Remote Similarity NPD6667 Approved
0.6613 Remote Similarity NPD8031 Discontinued
0.6612 Remote Similarity NPD6677 Suspended
0.6612 Remote Similarity NPD6072 Discontinued
0.6612 Remote Similarity NPD4424 Discontinued
0.661 Remote Similarity NPD6658 Clinical (unspecified phase)
0.661 Remote Similarity NPD6331 Phase 2
0.6608 Remote Similarity NPD5745 Approved
0.6596 Remote Similarity NPD5623 Approved
0.6587 Remote Similarity NPD3098 Discontinued
0.6571 Remote Similarity NPD2239 Approved
0.6571 Remote Similarity NPD2240 Approved
0.657 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6557 Remote Similarity NPD3579 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6556 Remote Similarity NPD4123 Phase 3
0.6552 Remote Similarity NPD4536 Approved
0.6552 Remote Similarity NPD4538 Approved
0.6552 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6548 Remote Similarity NPD987 Approved
0.6545 Remote Similarity NPD3847 Discontinued
0.6543 Remote Similarity NPD7129 Suspended
0.6541 Remote Similarity NPD7089 Clinical (unspecified phase)
0.6536 Remote Similarity NPD6815 Approved
0.6534 Remote Similarity NPD2353 Approved
0.6534 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6532 Remote Similarity NPD1184 Approved
0.6529 Remote Similarity NPD2614 Approved
0.6524 Remote Similarity NPD8070 Approved
0.6522 Remote Similarity NPD958 Approved
0.6514 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6514 Remote Similarity NPD6866 Clinical (unspecified phase)
0.6514 Remote Similarity NPD5960 Phase 3
0.6512 Remote Similarity NPD4062 Phase 3
0.6508 Remote Similarity NPD7485 Phase 3
0.6508 Remote Similarity NPD7484 Phase 3
0.6503 Remote Similarity NPD6056 Approved
0.6503 Remote Similarity NPD6057 Approved
0.6497 Remote Similarity NPD2897 Discontinued
0.6491 Remote Similarity NPD5163 Phase 2
0.6491 Remote Similarity NPD5746 Approved
0.6491 Remote Similarity NPD7095 Approved
0.6486 Remote Similarity NPD5356 Approved
0.6486 Remote Similarity NPD5355 Approved
0.6485 Remote Similarity NPD2668 Approved
0.6485 Remote Similarity NPD2667 Approved
0.648 Remote Similarity NPD3973 Approved
0.6477 Remote Similarity NPD1519 Approved
0.6477 Remote Similarity NPD2161 Phase 2
0.6477 Remote Similarity NPD1538 Phase 1
0.6477 Remote Similarity NPD1537 Approved
0.6474 Remote Similarity NPD4060 Phase 1
0.6467 Remote Similarity NPD1715 Phase 1
0.6467 Remote Similarity NPD4675 Approved
0.6467 Remote Similarity NPD1714 Approved
0.6467 Remote Similarity NPD4678 Approved
0.6467 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6461 Remote Similarity NPD1416 Approved
0.6457 Remote Similarity NPD1536 Approved
0.6448 Remote Similarity NPD957 Approved
0.6442 Remote Similarity NPD6905 Phase 2
0.6441 Remote Similarity NPD3656 Approved
0.6441 Remote Similarity NPD5865 Clinical (unspecified phase)
0.6432 Remote Similarity NPD6386 Approved
0.6432 Remote Similarity NPD6385 Approved
0.6429 Remote Similarity NPD3685 Discontinued
0.6429 Remote Similarity NPD7314 Clinical (unspecified phase)
0.6429 Remote Similarity NPD1669 Approved
0.6425 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6421 Remote Similarity NPD2821 Approved
0.642 Remote Similarity NPD4108 Discontinued
0.642 Remote Similarity NPD5588 Approved
0.6417 Remote Similarity NPD4874 Phase 2
0.6416 Remote Similarity NPD840 Approved
0.6416 Remote Similarity NPD839 Approved
0.6416 Remote Similarity NPD1423 Approved
0.6413 Remote Similarity NPD4005 Discontinued
0.6413 Remote Similarity NPD3455 Phase 2
0.6409 Remote Similarity NPD6682 Clinical (unspecified phase)
0.6406 Remote Similarity NPD6981 Phase 2
0.6404 Remote Similarity NPD7153 Discontinued
0.6402 Remote Similarity NPD6315 Phase 2
0.6398 Remote Similarity NPD8019 Approved
0.6395 Remote Similarity NPD1024 Discontinued
0.6393 Remote Similarity NPD7523 Phase 3
0.6392 Remote Similarity NPD3965 Phase 1
0.6391 Remote Similarity NPD196 Phase 1
0.6384 Remote Similarity NPD4476 Approved
0.6384 Remote Similarity NPD1522 Approved
0.6384 Remote Similarity NPD2438 Suspended
0.6384 Remote Similarity NPD4477 Approved
0.6384 Remote Similarity NPD1523 Approved
0.6379 Remote Similarity NPD6346 Approved
0.6369 Remote Similarity NPD4487 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1520 Approved
0.6364 Remote Similarity NPD7097 Phase 1
0.6364 Remote Similarity NPD1521 Approved
0.6364 Remote Similarity NPD5688 Approved
0.6364 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5689 Approved
0.6364 Remote Similarity NPD6556 Clinical (unspecified phase)
0.6359 Remote Similarity NPD3687 Approved
0.6359 Remote Similarity NPD3686 Approved
0.6359 Remote Similarity NPD5542 Phase 2
0.6358 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6358 Remote Similarity NPD3374 Clinical (unspecified phase)
0.6354 Remote Similarity NPD5058 Phase 3
0.6344 Remote Similarity NPD2541 Clinical (unspecified phase)
0.634 Remote Similarity NPD6620 Discovery
0.6339 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6333 Remote Similarity NPD4535 Phase 3
0.6333 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6333 Remote Similarity NPD4110 Phase 3
0.6332 Remote Similarity NPD5565 Discontinued
0.6324 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6324 Remote Similarity NPD4361 Phase 2
0.6322 Remote Similarity NPD2674 Phase 3
0.6321 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6319 Remote Similarity NPD7041 Phase 2
0.6319 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6313 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6313 Remote Similarity NPD2030 Discontinued
0.631 Remote Similarity NPD7495 Discontinued
0.631 Remote Similarity NPD3812 Clinical (unspecified phase)
0.6307 Remote Similarity NPD3052 Approved
0.6307 Remote Similarity NPD4579 Clinical (unspecified phase)

  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