Structure

Physi-Chem Properties

Molecular Weight:  622.08
Volume:  583.313
LogP:  7.29
LogD:  3.163
LogS:  -5.614
# Rotatable Bonds:  4
TPSA:  160.07
# H-Bond Aceptor:  9
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.1
Synthetic Accessibility Score:  3.477
Fsp3:  0.125
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:  -5.734
MDCK Permeability:  7.785693924233783e-06
Pgp-inhibitor:  0.137
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.97
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  95.16590118408203%
Volume Distribution (VD):  0.292
Pgp-substrate:  12.725875854492188%

ADMET: Metabolism

CYP1A2-inhibitor:  0.702
CYP1A2-substrate:  0.555
CYP2C19-inhibitor:  0.175
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.607
CYP2C9-substrate:  0.801
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.279
CYP3A4-inhibitor:  0.013
CYP3A4-substrate:  0.056

ADMET: Excretion

Clearance (CL):  4.681
Half-life (T1/2):  0.364

ADMET: Toxicity

hERG Blockers:  0.005
Human Hepatotoxicity (H-HT):  0.033
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.18
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.964
Skin Sensitization:  0.911
Carcinogencity:  0.022
Eye Corrosion:  0.003
Eye Irritation:  0.926
Respiratory Toxicity:  0.094

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

  Natural Product: NPC191606

Natural Product ID:  NPC191606
Common Name*:   Neobulgarone G
IUPAC Name:   (10S)-4-chloro-10-[(9S)-1-chloro-2,4-dihydroxy-7-(hydroxymethyl)-5-methoxy-10-oxo-9H-anthracen-9-yl]-1,3-dihydroxy-8-methoxy-6-methyl-10H-anthracen-9-one
Synonyms:   Neobulgarone G
Standard InCHIKey:  MQMWBFUKNWTRJV-DNQXCXABSA-N
Standard InCHI:  InChI=1S/C32H24Cl2O9/c1-11-4-13-21(19(5-11)42-2)31(40)25-15(36)8-17(38)29(33)27(25)23(13)24-14-6-12(10-35)7-20(43-3)22(14)32(41)26-16(37)9-18(39)30(34)28(24)26/h4-9,23-24,35-39H,10H2,1-3H3/t23-,24-/m1/s1
SMILES:  OCc1cc(OC)c2c(c1)[C@@H](c1c(C2=O)c(O)cc(c1Cl)O)[C@H]1c2cc(C)cc(c2C(=O)c2c1c(Cl)c(O)cc2O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1643636
PubChem CID:   53317590
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes

*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
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[10479323]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[12350167]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[14640527]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota Axinella verrucosa Mediterranean n.a. PMID[14738391]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15043411]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Sussex Inlet, New South Wales, Australia n.a. PMID[15104517]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[15332862]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Berkeley Pit lake n.a. PMID[17970594]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. New Zealand n.a. PMID[19323568]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19326880]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[20452770]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. North Sea n.a. PMID[21126094]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. Limonium tubiflorum n.a. PMID[21146414]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21916432]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22148349]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22458669]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23360521]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23477451]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23603293]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23972215]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24437979]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31433188]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[9392888]
NPO30770 Penicillium sp. Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[Article]

☑ 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
NPT15 Cell Line Jurkat Homo sapiens IC50 > 100000.0 nM PMID[448234]
NPT466 Cell Line U-937 Homo sapiens IC50 > 100000.0 nM PMID[448234]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei MIC > 100000.0 nM PMID[448234]
NPT2 Others Unspecified IC50 > 100000.0 nM PMID[448234]

☑ 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 NPC191606 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
0.9822 High Similarity NPC151292
0.924 High Similarity NPC474857
0.9133 High Similarity NPC264922
0.896 High Similarity NPC277865
0.8693 High Similarity NPC470560
0.8652 High Similarity NPC45072
0.8644 High Similarity NPC470422
0.8636 High Similarity NPC470565
0.8636 High Similarity NPC470562
0.8579 High Similarity NPC316091
0.8525 High Similarity NPC474499
0.8497 Intermediate Similarity NPC470342
0.8497 Intermediate Similarity NPC472052
0.8497 Intermediate Similarity NPC472060
0.8453 Intermediate Similarity NPC306240
0.8409 Intermediate Similarity NPC469664
0.8404 Intermediate Similarity NPC313541
0.84 Intermediate Similarity NPC470561
0.8378 Intermediate Similarity NPC313386
0.8352 Intermediate Similarity NPC470563
0.8343 Intermediate Similarity NPC273467
0.8343 Intermediate Similarity NPC189552
0.8333 Intermediate Similarity NPC324736
0.8305 Intermediate Similarity NPC68850
0.8295 Intermediate Similarity NPC15374
0.8294 Intermediate Similarity NPC477221
0.8286 Intermediate Similarity NPC312993
0.8286 Intermediate Similarity NPC186325
0.8239 Intermediate Similarity NPC18380
0.8229 Intermediate Similarity NPC177650
0.8229 Intermediate Similarity NPC470559
0.8218 Intermediate Similarity NPC280497
0.8212 Intermediate Similarity NPC472032
0.8212 Intermediate Similarity NPC105414
0.8212 Intermediate Similarity NPC234497
0.8212 Intermediate Similarity NPC470341
0.8212 Intermediate Similarity NPC324522
0.8212 Intermediate Similarity NPC472058
0.8201 Intermediate Similarity NPC214901
0.8187 Intermediate Similarity NPC477992
0.8187 Intermediate Similarity NPC477568
0.8187 Intermediate Similarity NPC477991
0.8182 Intermediate Similarity NPC292863
0.8182 Intermediate Similarity NPC184326
0.8177 Intermediate Similarity NPC477836
0.8176 Intermediate Similarity NPC290194
0.8171 Intermediate Similarity NPC208258
0.8161 Intermediate Similarity NPC226656
0.8161 Intermediate Similarity NPC66508
0.8156 Intermediate Similarity NPC477835
0.815 Intermediate Similarity NPC43345
0.8148 Intermediate Similarity NPC220369
0.8146 Intermediate Similarity NPC290160
0.8146 Intermediate Similarity NPC470081
0.814 Intermediate Similarity NPC147735
0.8138 Intermediate Similarity NPC470099
0.8138 Intermediate Similarity NPC470100
0.8136 Intermediate Similarity NPC312273
0.8136 Intermediate Similarity NPC137232
0.8136 Intermediate Similarity NPC301256
0.8125 Intermediate Similarity NPC18699
0.8125 Intermediate Similarity NPC55443
0.8125 Intermediate Similarity NPC195167
0.8125 Intermediate Similarity NPC154720
0.8118 Intermediate Similarity NPC99937
0.8114 Intermediate Similarity NPC470564
0.8103 Intermediate Similarity NPC324447
0.8092 Intermediate Similarity NPC476552
0.8092 Intermediate Similarity NPC476553
0.8092 Intermediate Similarity NPC476551
0.8092 Intermediate Similarity NPC470569
0.809 Intermediate Similarity NPC473012
0.809 Intermediate Similarity NPC473696
0.809 Intermediate Similarity NPC474096
0.8081 Intermediate Similarity NPC329933
0.8079 Intermediate Similarity NPC476506
0.807 Intermediate Similarity NPC475348
0.807 Intermediate Similarity NPC34802
0.807 Intermediate Similarity NPC261271
0.8068 Intermediate Similarity NPC475184
0.8068 Intermediate Similarity NPC257166
0.8065 Intermediate Similarity NPC473631
0.8065 Intermediate Similarity NPC475662
0.8065 Intermediate Similarity NPC473717
0.8065 Intermediate Similarity NPC293227
0.8063 Intermediate Similarity NPC48822
0.8057 Intermediate Similarity NPC79375
0.8057 Intermediate Similarity NPC37253
0.8056 Intermediate Similarity NPC28669
0.8056 Intermediate Similarity NPC251336
0.8056 Intermediate Similarity NPC474061
0.8047 Intermediate Similarity NPC174905
0.8047 Intermediate Similarity NPC293545
0.8045 Intermediate Similarity NPC473009
0.8035 Intermediate Similarity NPC255641
0.8035 Intermediate Similarity NPC290954
0.8035 Intermediate Similarity NPC470568
0.8034 Intermediate Similarity NPC298401
0.8034 Intermediate Similarity NPC219686
0.8034 Intermediate Similarity NPC472261
0.8023 Intermediate Similarity NPC51760
0.8023 Intermediate Similarity NPC105584
0.8023 Intermediate Similarity NPC15815
0.8023 Intermediate Similarity NPC51247
0.8023 Intermediate Similarity NPC152233
0.8023 Intermediate Similarity NPC228654
0.8023 Intermediate Similarity NPC90497
0.8022 Intermediate Similarity NPC474004
0.8021 Intermediate Similarity NPC198163
0.8 Intermediate Similarity NPC227841
0.8 Intermediate Similarity NPC173352
0.8 Intermediate Similarity NPC473010
0.8 Intermediate Similarity NPC58653
0.7989 Intermediate Similarity NPC149526
0.7989 Intermediate Similarity NPC474417
0.7989 Intermediate Similarity NPC245122
0.7989 Intermediate Similarity NPC478148
0.7979 Intermediate Similarity NPC473686
0.7979 Intermediate Similarity NPC221140
0.7979 Intermediate Similarity NPC229817
0.7979 Intermediate Similarity NPC475352
0.7979 Intermediate Similarity NPC475220
0.7978 Intermediate Similarity NPC226462
0.7978 Intermediate Similarity NPC42965
0.7978 Intermediate Similarity NPC195136
0.7978 Intermediate Similarity NPC98023
0.7967 Intermediate Similarity NPC300307
0.7966 Intermediate Similarity NPC472404
0.7966 Intermediate Similarity NPC1796
0.7965 Intermediate Similarity NPC190648
0.7965 Intermediate Similarity NPC118027
0.7965 Intermediate Similarity NPC126767
0.7965 Intermediate Similarity NPC312929
0.7965 Intermediate Similarity NPC289042
0.7965 Intermediate Similarity NPC56433
0.7965 Intermediate Similarity NPC245584
0.7965 Intermediate Similarity NPC477569
0.7958 Intermediate Similarity NPC221185
0.7957 Intermediate Similarity NPC471801
0.7956 Intermediate Similarity NPC30027
0.7955 Intermediate Similarity NPC14606
0.7955 Intermediate Similarity NPC186227
0.7955 Intermediate Similarity NPC121649
0.7955 Intermediate Similarity NPC100049
0.7955 Intermediate Similarity NPC150908
0.7955 Intermediate Similarity NPC159707
0.7955 Intermediate Similarity NPC52611
0.7955 Intermediate Similarity NPC265624
0.7955 Intermediate Similarity NPC158027
0.7955 Intermediate Similarity NPC248739
0.7955 Intermediate Similarity NPC215203
0.7955 Intermediate Similarity NPC254351
0.7955 Intermediate Similarity NPC68727
0.7955 Intermediate Similarity NPC205026
0.7953 Intermediate Similarity NPC282957
0.7953 Intermediate Similarity NPC194949
0.7944 Intermediate Similarity NPC476505
0.7943 Intermediate Similarity NPC154683
0.7943 Intermediate Similarity NPC470338
0.7943 Intermediate Similarity NPC87708
0.7943 Intermediate Similarity NPC113608
0.7943 Intermediate Similarity NPC51824
0.7943 Intermediate Similarity NPC470337
0.7943 Intermediate Similarity NPC268992
0.7943 Intermediate Similarity NPC40356
0.7941 Intermediate Similarity NPC84266
0.7941 Intermediate Similarity NPC295712
0.7941 Intermediate Similarity NPC451542
0.7941 Intermediate Similarity NPC313047
0.7941 Intermediate Similarity NPC474203
0.7935 Intermediate Similarity NPC470333
0.7931 Intermediate Similarity NPC202595
0.7931 Intermediate Similarity NPC294646
0.7921 Intermediate Similarity NPC472617
0.7917 Intermediate Similarity NPC247104
0.7912 Intermediate Similarity NPC286230
0.7912 Intermediate Similarity NPC253730
0.791 Intermediate Similarity NPC56049
0.791 Intermediate Similarity NPC69531
0.791 Intermediate Similarity NPC54830
0.791 Intermediate Similarity NPC146211
0.791 Intermediate Similarity NPC32867
0.7901 Intermediate Similarity NPC169471
0.7901 Intermediate Similarity NPC472051
0.7901 Intermediate Similarity NPC472057
0.7898 Intermediate Similarity NPC329844
0.7898 Intermediate Similarity NPC290830
0.7898 Intermediate Similarity NPC71061
0.7898 Intermediate Similarity NPC121568
0.7898 Intermediate Similarity NPC303485
0.7898 Intermediate Similarity NPC72425
0.7898 Intermediate Similarity NPC194593
0.7897 Intermediate Similarity NPC108744
0.7892 Intermediate Similarity NPC300657
0.7889 Intermediate Similarity NPC472059
0.7889 Intermediate Similarity NPC473011
0.7886 Intermediate Similarity NPC72958
0.7886 Intermediate Similarity NPC232645
0.7884 Intermediate Similarity NPC470103
0.7882 Intermediate Similarity NPC94076

  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 NPC191606 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
0.8239 Intermediate Similarity NPD6959 Discontinued
0.8 Intermediate Similarity NPD7390 Discontinued
0.776 Intermediate Similarity NPD7473 Discontinued
0.7753 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6232 Discontinued
0.7609 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD7819 Suspended
0.7528 Intermediate Similarity NPD4380 Phase 2
0.7487 Intermediate Similarity NPD4363 Phase 3
0.7487 Intermediate Similarity NPD4360 Phase 2
0.7459 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD2534 Approved
0.7443 Intermediate Similarity NPD2533 Approved
0.7443 Intermediate Similarity NPD2532 Approved
0.7443 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD6166 Phase 2
0.7419 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD2403 Approved
0.7418 Intermediate Similarity NPD7768 Phase 2
0.7403 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD7411 Suspended
0.7382 Intermediate Similarity NPD8313 Approved
0.7382 Intermediate Similarity NPD8312 Approved
0.7326 Intermediate Similarity NPD1510 Phase 2
0.7326 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD1607 Approved
0.7302 Intermediate Similarity NPD5844 Phase 1
0.7299 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4361 Phase 2
0.7273 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD1240 Approved
0.7184 Intermediate Similarity NPD8151 Discontinued
0.7158 Intermediate Similarity NPD1934 Approved
0.7151 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD7003 Approved
0.7102 Intermediate Similarity NPD1549 Phase 2
0.7098 Intermediate Similarity NPD6559 Discontinued
0.7097 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD3749 Approved
0.7097 Intermediate Similarity NPD7075 Discontinued
0.7088 Intermediate Similarity NPD3226 Approved
0.7086 Intermediate Similarity NPD5405 Approved
0.7086 Intermediate Similarity NPD5404 Approved
0.7086 Intermediate Similarity NPD5408 Approved
0.7086 Intermediate Similarity NPD5406 Approved
0.7083 Intermediate Similarity NPD7074 Phase 3
0.7073 Intermediate Similarity NPD7871 Phase 2
0.7073 Intermediate Similarity NPD7870 Phase 2
0.7043 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD2370 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD7054 Approved
0.7027 Intermediate Similarity NPD2801 Approved
0.7021 Intermediate Similarity NPD5494 Approved
0.7011 Intermediate Similarity NPD6651 Approved
0.7 Intermediate Similarity NPD1511 Approved
0.6995 Remote Similarity NPD7458 Discontinued
0.6995 Remote Similarity NPD7472 Approved
0.6989 Remote Similarity NPD2796 Approved
0.6989 Remote Similarity NPD2935 Discontinued
0.6974 Remote Similarity NPD7808 Phase 3
0.6973 Remote Similarity NPD6801 Discontinued
0.6961 Remote Similarity NPD6777 Approved
0.6961 Remote Similarity NPD6776 Approved
0.6961 Remote Similarity NPD6779 Approved
0.6961 Remote Similarity NPD6781 Approved
0.6961 Remote Similarity NPD6778 Approved
0.6961 Remote Similarity NPD6782 Approved
0.6961 Remote Similarity NPD6780 Approved
0.6959 Remote Similarity NPD6797 Phase 2
0.6947 Remote Similarity NPD5711 Approved
0.6947 Remote Similarity NPD5710 Approved
0.6942 Remote Similarity NPD7698 Approved
0.6942 Remote Similarity NPD7697 Approved
0.6942 Remote Similarity NPD7696 Phase 3
0.6935 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6927 Remote Similarity NPD3750 Approved
0.6923 Remote Similarity NPD1512 Approved
0.6923 Remote Similarity NPD7251 Discontinued
0.6919 Remote Similarity NPD8150 Discontinued
0.6906 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6906 Remote Similarity NPD7041 Phase 2
0.6902 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6898 Remote Similarity NPD3817 Phase 2
0.6893 Remote Similarity NPD6099 Approved
0.6893 Remote Similarity NPD6100 Approved
0.6891 Remote Similarity NPD3818 Discontinued
0.6882 Remote Similarity NPD37 Approved
0.6872 Remote Similarity NPD2800 Approved
0.6872 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6865 Remote Similarity NPD6599 Discontinued
0.6862 Remote Similarity NPD3882 Suspended
0.686 Remote Similarity NPD7435 Discontinued
0.681 Remote Similarity NPD7701 Phase 2
0.6802 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6792 Remote Similarity NPD7801 Approved
0.6782 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6776 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6772 Remote Similarity NPD4966 Approved
0.6772 Remote Similarity NPD4967 Phase 2
0.6772 Remote Similarity NPD4965 Approved
0.676 Remote Similarity NPD2346 Discontinued
0.6745 Remote Similarity NPD7874 Approved
0.6745 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6823 Phase 2
0.6721 Remote Similarity NPD6799 Approved
0.672 Remote Similarity NPD5402 Approved
0.6718 Remote Similarity NPD7177 Discontinued
0.6718 Remote Similarity NPD7228 Approved
0.6717 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6716 Remote Similarity NPD6534 Approved
0.6716 Remote Similarity NPD6535 Approved
0.6714 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6714 Remote Similarity NPD7783 Phase 2
0.6704 Remote Similarity NPD1551 Phase 2
0.6702 Remote Similarity NPD6234 Discontinued
0.6699 Remote Similarity NPD7699 Phase 2
0.6699 Remote Similarity NPD7700 Phase 2
0.6684 Remote Similarity NPD7229 Phase 3
0.6667 Remote Similarity NPD8319 Approved
0.6667 Remote Similarity NPD4908 Phase 1
0.6667 Remote Similarity NPD1465 Phase 2
0.6667 Remote Similarity NPD8320 Phase 1
0.6648 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6648 Remote Similarity NPD3748 Approved
0.6648 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6647 Remote Similarity NPD1201 Approved
0.6632 Remote Similarity NPD7199 Phase 2
0.6632 Remote Similarity NPD2379 Clinical (unspecified phase)
0.6616 Remote Similarity NPD5953 Discontinued
0.6615 Remote Similarity NPD5822 Clinical (unspecified phase)
0.6613 Remote Similarity NPD5403 Approved
0.6613 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6598 Remote Similarity NPD3787 Discontinued
0.6595 Remote Similarity NPD1578 Phase 2
0.6591 Remote Similarity NPD8155 Clinical (unspecified phase)
0.659 Remote Similarity NPD1470 Approved
0.6579 Remote Similarity NPD8455 Phase 2
0.657 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7654 Discontinued
0.6559 Remote Similarity NPD6273 Approved
0.6557 Remote Similarity NPD4628 Phase 3
0.6556 Remote Similarity NPD2799 Discontinued
0.6555 Remote Similarity NPD4914 Approved
0.6548 Remote Similarity NPD3751 Discontinued
0.6535 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6534 Remote Similarity NPD4625 Phase 3
0.6524 Remote Similarity NPD920 Approved
0.6517 Remote Similarity NPD943 Approved
0.6515 Remote Similarity NPD7286 Phase 2
0.6505 Remote Similarity NPD5401 Approved
0.6505 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6505 Remote Similarity NPD6213 Phase 3
0.6505 Remote Similarity NPD6212 Phase 3
0.6503 Remote Similarity NPD1243 Approved
0.6497 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6484 Remote Similarity NPD2344 Approved
0.648 Remote Similarity NPD7184 Clinical (unspecified phase)
0.648 Remote Similarity NPD3926 Phase 2
0.6476 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6457 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6457 Remote Similarity NPD2798 Approved
0.6437 Remote Similarity NPD1283 Approved
0.6429 Remote Similarity NPD5544 Approved
0.6422 Remote Similarity NPD8434 Phase 2
0.6418 Remote Similarity NPD7240 Approved
0.6417 Remote Similarity NPD642 Clinical (unspecified phase)
0.6415 Remote Similarity NPD4387 Approved
0.6415 Remote Similarity NPD4386 Approved
0.6411 Remote Similarity NPD4915 Approved
0.6409 Remote Similarity NPD4536 Approved
0.6409 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6409 Remote Similarity NPD4538 Approved
0.6404 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6398 Remote Similarity NPD643 Clinical (unspecified phase)
0.6387 Remote Similarity NPD958 Approved
0.6378 Remote Similarity NPD1247 Approved
0.6378 Remote Similarity NPD8166 Discontinued
0.6374 Remote Similarity NPD1651 Approved
0.6374 Remote Similarity NPD651 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6785 Approved
0.6373 Remote Similarity NPD6784 Approved
0.6359 Remote Similarity NPD4287 Approved
0.6359 Remote Similarity NPD919 Approved
0.6344 Remote Similarity NPD2309 Approved
0.6337 Remote Similarity NPD3303 Discontinued
0.6333 Remote Similarity NPD4388 Approved
0.6333 Remote Similarity NPD2979 Phase 3
0.6326 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6324 Remote Similarity NPD2654 Approved
0.6322 Remote Similarity NPD3972 Approved
0.6321 Remote Similarity NPD5760 Phase 2
0.6321 Remote Similarity NPD5761 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