Structure

Physi-Chem Properties

Molecular Weight:  702.38
Volume:  707.896
LogP:  3.553
LogD:  3.341
LogS:  -4.447
# Rotatable Bonds:  3
TPSA:  76.07
# H-Bond Aceptor:  9
# H-Bond Donor:  0
# Rings:  13
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.411
Synthetic Accessibility Score:  7.267
Fsp3:  0.674
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.484
MDCK Permeability:  1.569303094584029e-05
Pgp-inhibitor:  0.051
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.442
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.873
Plasma Protein Binding (PPB):  70.00603485107422%
Volume Distribution (VD):  5.682
Pgp-substrate:  33.96235656738281%

ADMET: Metabolism

CYP1A2-inhibitor:  0.005
CYP1A2-substrate:  0.674
CYP2C19-inhibitor:  0.01
CYP2C19-substrate:  0.954
CYP2C9-inhibitor:  0.023
CYP2C9-substrate:  0.027
CYP2D6-inhibitor:  0.737
CYP2D6-substrate:  0.868
CYP3A4-inhibitor:  0.926
CYP3A4-substrate:  0.927

ADMET: Excretion

Clearance (CL):  6.39
Half-life (T1/2):  0.015

ADMET: Toxicity

hERG Blockers:  0.995
Human Hepatotoxicity (H-HT):  0.851
Drug-inuced Liver Injury (DILI):  0.129
AMES Toxicity:  0.17
Rat Oral Acute Toxicity:  0.984
Maximum Recommended Daily Dose:  0.964
Skin Sensitization:  0.648
Carcinogencity:  0.814
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.964

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

  Natural Product: NPC223236

Natural Product ID:  NPC223236
Common Name*:   Michellamine F
IUPAC Name:   n.a.
Synonyms:   Michellamine F
Standard InCHIKey:  VSDWMCJBOALEDE-WXFUMESZSA-N
Standard InCHI:  InChI=1S/C47H48N2O8/c1-20-10-26-28(42-32-14-22(3)48-24(5)40(32)34(50)18-35(42)51)16-30(46(53)44(26)37(12-20)55-7)31-17-29(27-11-21(2)13-38(56-8)45(27)47(31)54)43-33-15-23(4)49-25(6)41(33)39(57-9)19-36(43)52/h10-13,16-19,22-24,48,50-54H,14-15H2,1-9H3/t22-,23-,24-/m1/s1
SMILES:  Cc1cc2c(cc(c3cc(c4cc(C)cc(c4c3O)OC)c3c4C[C@@H](C)N=C(C)c4c(cc3O)OC)c(c2c(c1)OC)O)c1c2C[C@@H](C)N[C@H](C)c2c(cc1O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL501944
PubChem CID:   n.a.
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0002195] Naphthylisoquinolines

*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
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. Cameroon n.a. PMID[11430019]
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. PMID[9249970]
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. PMID[9873424]
NPO2073 Ancistrocladus korupensis Species Ancistrocladaceae Eukaryota n.a. n.a. n.a. Database[TCMID]

☑ 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
NPT315 Cell Line CEM-SS Homo sapiens IC50 = 188000.0 nM PMID[474021]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 2000.0 nM PMID[474021]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 9000.0 nM PMID[474021]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 11000.0 nM PMID[474021]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 8000.0 nM PMID[474021]

☑ 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 NPC223236 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 NPC259350
0.9942 High Similarity NPC476565
0.936 High Similarity NPC257269
0.9302 High Similarity NPC40496
0.9302 High Similarity NPC119068
0.9249 High Similarity NPC230276
0.8889 High Similarity NPC223077
0.8889 High Similarity NPC56887
0.8889 High Similarity NPC193853
0.883 High Similarity NPC209377
0.8671 High Similarity NPC195392
0.8605 High Similarity NPC80759
0.8605 High Similarity NPC79402
0.8596 High Similarity NPC7393
0.8595 High Similarity NPC234318
0.8547 High Similarity NPC271388
0.8547 High Similarity NPC235143
0.8547 High Similarity NPC230956
0.8547 High Similarity NPC205255
0.8547 High Similarity NPC119649
0.8538 High Similarity NPC206736
0.8538 High Similarity NPC195766
0.8538 High Similarity NPC79328
0.8488 Intermediate Similarity NPC221864
0.8486 Intermediate Similarity NPC256124
0.848 Intermediate Similarity NPC29647
0.8478 Intermediate Similarity NPC318805
0.8478 Intermediate Similarity NPC41122
0.8387 Intermediate Similarity NPC85381
0.8314 Intermediate Similarity NPC123323
0.8297 Intermediate Similarity NPC195538
0.8261 Intermediate Similarity NPC249996
0.8261 Intermediate Similarity NPC302245
0.8261 Intermediate Similarity NPC16357
0.8261 Intermediate Similarity NPC95426
0.8251 Intermediate Similarity NPC476202
0.8226 Intermediate Similarity NPC175890
0.8226 Intermediate Similarity NPC274661
0.8226 Intermediate Similarity NPC48490
0.8226 Intermediate Similarity NPC82457
0.8226 Intermediate Similarity NPC11296
0.8216 Intermediate Similarity NPC139783
0.8216 Intermediate Similarity NPC65312
0.8187 Intermediate Similarity NPC265473
0.8187 Intermediate Similarity NPC276665
0.8182 Intermediate Similarity NPC191132
0.8182 Intermediate Similarity NPC60295
0.8172 Intermediate Similarity NPC22115
0.8172 Intermediate Similarity NPC275680
0.8142 Intermediate Similarity NPC474507
0.8095 Intermediate Similarity NPC478092
0.8095 Intermediate Similarity NPC30182
0.8095 Intermediate Similarity NPC478091
0.8095 Intermediate Similarity NPC473589
0.8043 Intermediate Similarity NPC243454
0.8043 Intermediate Similarity NPC475479
0.8042 Intermediate Similarity NPC478093
0.8033 Intermediate Similarity NPC148709
0.8033 Intermediate Similarity NPC173416
0.8033 Intermediate Similarity NPC476577
0.8021 Intermediate Similarity NPC57036
0.8 Intermediate Similarity NPC204947
0.8 Intermediate Similarity NPC239584
0.7957 Intermediate Similarity NPC239824
0.7957 Intermediate Similarity NPC15414
0.7957 Intermediate Similarity NPC49075
0.7957 Intermediate Similarity NPC182052
0.7957 Intermediate Similarity NPC258657
0.7957 Intermediate Similarity NPC311973
0.7957 Intermediate Similarity NPC30779
0.7957 Intermediate Similarity NPC290005
0.7957 Intermediate Similarity NPC90998
0.7957 Intermediate Similarity NPC185639
0.7957 Intermediate Similarity NPC285931
0.7957 Intermediate Similarity NPC328155
0.7957 Intermediate Similarity NPC251735
0.7957 Intermediate Similarity NPC181796
0.7957 Intermediate Similarity NPC229373
0.7957 Intermediate Similarity NPC8836
0.7957 Intermediate Similarity NPC271013
0.7957 Intermediate Similarity NPC54654
0.7957 Intermediate Similarity NPC290582
0.7957 Intermediate Similarity NPC217748
0.7957 Intermediate Similarity NPC7715
0.7957 Intermediate Similarity NPC223690
0.7957 Intermediate Similarity NPC279228
0.7957 Intermediate Similarity NPC104196
0.7957 Intermediate Similarity NPC42663
0.7957 Intermediate Similarity NPC222661
0.7937 Intermediate Similarity NPC206900
0.7926 Intermediate Similarity NPC116465
0.7926 Intermediate Similarity NPC212237
0.7926 Intermediate Similarity NPC47077
0.7926 Intermediate Similarity NPC14507
0.7923 Intermediate Similarity NPC66341
0.7923 Intermediate Similarity NPC192135
0.7923 Intermediate Similarity NPC477020
0.7914 Intermediate Similarity NPC302275
0.7914 Intermediate Similarity NPC254441
0.7914 Intermediate Similarity NPC274716
0.7914 Intermediate Similarity NPC167116
0.7912 Intermediate Similarity NPC69712
0.7912 Intermediate Similarity NPC26240
0.7912 Intermediate Similarity NPC477562
0.7903 Intermediate Similarity NPC286119
0.7884 Intermediate Similarity NPC476576
0.7884 Intermediate Similarity NPC186546
0.7869 Intermediate Similarity NPC239775
0.7869 Intermediate Similarity NPC231371
0.7845 Intermediate Similarity NPC68328
0.7772 Intermediate Similarity NPC227060
0.7772 Intermediate Similarity NPC317145
0.7772 Intermediate Similarity NPC276890
0.7772 Intermediate Similarity NPC76682
0.7772 Intermediate Similarity NPC115284
0.7772 Intermediate Similarity NPC317439
0.7772 Intermediate Similarity NPC10908
0.7772 Intermediate Similarity NPC198498
0.7772 Intermediate Similarity NPC63646
0.7754 Intermediate Similarity NPC258695
0.7754 Intermediate Similarity NPC470879
0.7749 Intermediate Similarity NPC281581
0.7742 Intermediate Similarity NPC293093
0.773 Intermediate Similarity NPC12424
0.773 Intermediate Similarity NPC41376
0.773 Intermediate Similarity NPC129518
0.773 Intermediate Similarity NPC251580
0.7717 Intermediate Similarity NPC168753
0.7717 Intermediate Similarity NPC118274
0.7713 Intermediate Similarity NPC474506
0.7713 Intermediate Similarity NPC32413
0.7692 Intermediate Similarity NPC24465
0.768 Intermediate Similarity NPC60186
0.7677 Intermediate Similarity NPC254581
0.7676 Intermediate Similarity NPC108434
0.7676 Intermediate Similarity NPC475215
0.7668 Intermediate Similarity NPC24260
0.7663 Intermediate Similarity NPC66573
0.7661 Intermediate Similarity NPC273623
0.765 Intermediate Similarity NPC81247
0.765 Intermediate Similarity NPC264850
0.765 Intermediate Similarity NPC35627
0.765 Intermediate Similarity NPC476573
0.765 Intermediate Similarity NPC13916
0.7637 Intermediate Similarity NPC1229
0.7632 Intermediate Similarity NPC135772
0.7619 Intermediate Similarity NPC312918
0.7619 Intermediate Similarity NPC476574
0.7619 Intermediate Similarity NPC155442
0.7619 Intermediate Similarity NPC477561
0.7614 Intermediate Similarity NPC469689
0.7614 Intermediate Similarity NPC471031
0.7609 Intermediate Similarity NPC145832
0.7609 Intermediate Similarity NPC474931
0.7609 Intermediate Similarity NPC81218
0.7609 Intermediate Similarity NPC306555
0.7609 Intermediate Similarity NPC12053
0.7609 Intermediate Similarity NPC158376
0.7609 Intermediate Similarity NPC117188
0.7609 Intermediate Similarity NPC205421
0.7606 Intermediate Similarity NPC23219
0.7598 Intermediate Similarity NPC107602
0.7596 Intermediate Similarity NPC196447
0.7596 Intermediate Similarity NPC253043
0.7596 Intermediate Similarity NPC136508
0.7596 Intermediate Similarity NPC306843
0.7596 Intermediate Similarity NPC96603
0.7596 Intermediate Similarity NPC212794
0.7596 Intermediate Similarity NPC13504
0.7596 Intermediate Similarity NPC78222
0.7596 Intermediate Similarity NPC477563
0.7584 Intermediate Similarity NPC114124
0.7577 Intermediate Similarity NPC117717
0.7553 Intermediate Similarity NPC112575
0.755 Intermediate Similarity NPC137929
0.755 Intermediate Similarity NPC164374
0.7544 Intermediate Similarity NPC71465
0.7544 Intermediate Similarity NPC472646
0.7541 Intermediate Similarity NPC324144
0.754 Intermediate Similarity NPC474051
0.7527 Intermediate Similarity NPC109925
0.75 Intermediate Similarity NPC477558
0.7487 Intermediate Similarity NPC73492
0.7487 Intermediate Similarity NPC299990
0.7485 Intermediate Similarity NPC170328
0.7485 Intermediate Similarity NPC206525
0.7485 Intermediate Similarity NPC133463
0.7485 Intermediate Similarity NPC472648
0.7485 Intermediate Similarity NPC191462
0.7485 Intermediate Similarity NPC472647
0.7485 Intermediate Similarity NPC472649
0.7473 Intermediate Similarity NPC83198
0.7473 Intermediate Similarity NPC216816
0.7473 Intermediate Similarity NPC204908
0.7473 Intermediate Similarity NPC329837
0.7462 Intermediate Similarity NPC281629
0.7459 Intermediate Similarity NPC126519
0.7459 Intermediate Similarity NPC170503
0.7459 Intermediate Similarity NPC203784
0.7447 Intermediate Similarity NPC152680

  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 NPC223236 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
0.9302 High Similarity NPD8453 Clinical (unspecified phase)
0.7957 Intermediate Similarity NPD8053 Approved
0.7957 Intermediate Similarity NPD8054 Approved
0.7772 Intermediate Similarity NPD8099 Discontinued
0.7772 Intermediate Similarity NPD8252 Approved
0.7772 Intermediate Similarity NPD8251 Approved
0.773 Intermediate Similarity NPD8156 Discontinued
0.7487 Intermediate Similarity NPD7493 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7598 Phase 2
0.7333 Intermediate Similarity NPD4005 Discontinued
0.7316 Intermediate Similarity NPD7479 Phase 2
0.7213 Intermediate Similarity NPD7298 Approved
0.7207 Intermediate Similarity NPD7447 Phase 1
0.7191 Intermediate Similarity NPD3845 Phase 1
0.7189 Intermediate Similarity NPD6788 Approved
0.7173 Intermediate Similarity NPD42 Phase 2
0.7173 Intermediate Similarity NPD6042 Phase 2
0.7158 Intermediate Similarity NPD7438 Suspended
0.7151 Intermediate Similarity NPD4055 Discovery
0.7143 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD7827 Phase 1
0.7098 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD7654 Discontinued
0.7062 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD7213 Phase 3
0.7056 Intermediate Similarity NPD7212 Phase 2
0.7044 Intermediate Similarity NPD8095 Phase 1
0.7035 Intermediate Similarity NPD6656 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD7906 Approved
0.7017 Intermediate Similarity NPD1424 Approved
0.7017 Intermediate Similarity NPD4584 Approved
0.7005 Intermediate Similarity NPD7773 Phase 2
0.6989 Remote Similarity NPD7046 Clinical (unspecified phase)
0.6984 Remote Similarity NPD6746 Phase 2
0.6979 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6978 Remote Similarity NPD6090 Discontinued
0.6961 Remote Similarity NPD2420 Approved
0.6961 Remote Similarity NPD2421 Approved
0.6961 Remote Similarity NPD6087 Phase 1
0.6943 Remote Similarity NPD5940 Clinical (unspecified phase)
0.6942 Remote Similarity NPD6823 Phase 2
0.6931 Remote Similarity NPD5709 Phase 3
0.6906 Remote Similarity NPD2422 Clinical (unspecified phase)
0.69 Remote Similarity NPD7861 Discontinued
0.6895 Remote Similarity NPD4666 Phase 3
0.6889 Remote Similarity NPD3977 Clinical (unspecified phase)
0.6885 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6882 Remote Similarity NPD6072 Discontinued
0.6875 Remote Similarity NPD2568 Approved
0.6872 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6851 Remote Similarity NPD3692 Discontinued
0.684 Remote Similarity NPD7801 Approved
0.6839 Remote Similarity NPD6607 Clinical (unspecified phase)
0.6839 Remote Similarity NPD8011 Discontinued
0.6836 Remote Similarity NPD3553 Approved
0.6836 Remote Similarity NPD3555 Approved
0.6836 Remote Similarity NPD3554 Approved
0.6836 Remote Similarity NPD7718 Clinical (unspecified phase)
0.6836 Remote Similarity NPD3552 Approved
0.6833 Remote Similarity NPD2458 Approved
0.6833 Remote Similarity NPD2460 Phase 3
0.6833 Remote Similarity NPD2459 Approved
0.6831 Remote Similarity NPD2874 Phase 2
0.6828 Remote Similarity NPD4675 Approved
0.6828 Remote Similarity NPD4678 Approved
0.6825 Remote Similarity NPD8151 Discontinued
0.6823 Remote Similarity NPD6747 Phase 1
0.68 Remote Similarity NPD7477 Discontinued
0.68 Remote Similarity NPD4951 Discontinued
0.6796 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6796 Remote Similarity NPD7066 Clinical (unspecified phase)
0.6789 Remote Similarity NPD7832 Clinical (unspecified phase)
0.6789 Remote Similarity NPD7831 Phase 2
0.6789 Remote Similarity NPD7833 Phase 2
0.6788 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6787 Remote Similarity NPD8059 Phase 3
0.6787 Remote Similarity NPD8058 Clinical (unspecified phase)
0.678 Remote Similarity NPD4605 Approved
0.678 Remote Similarity NPD4604 Approved
0.678 Remote Similarity NPD4097 Suspended
0.6774 Remote Similarity NPD8318 Clinical (unspecified phase)
0.6774 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6767 Remote Similarity NPD8153 Approved
0.6767 Remote Similarity NPD8152 Approved
0.676 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6757 Remote Similarity NPD6030 Approved
0.6757 Remote Similarity NPD6031 Approved
0.6739 Remote Similarity NPD3157 Approved
0.6739 Remote Similarity NPD3158 Phase 1
0.6734 Remote Similarity NPD7313 Approved
0.6734 Remote Similarity NPD7311 Approved
0.6734 Remote Similarity NPD7310 Approved
0.6734 Remote Similarity NPD7312 Approved
0.6732 Remote Similarity NPD7667 Clinical (unspecified phase)
0.673 Remote Similarity NPD6973 Clinical (unspecified phase)
0.6725 Remote Similarity NPD1669 Approved
0.672 Remote Similarity NPD4585 Approved
0.6715 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6713 Remote Similarity NPD8149 Discontinued
0.6705 Remote Similarity NPD4474 Approved
0.6705 Remote Similarity NPD4475 Approved
0.67 Remote Similarity NPD7309 Approved
0.6699 Remote Similarity NPD7034 Discontinued
0.6686 Remote Similarity NPD4625 Phase 3
0.6685 Remote Similarity NPD4257 Approved
0.6685 Remote Similarity NPD4256 Phase 2
0.6683 Remote Similarity NPD6612 Phase 2
0.6683 Remote Similarity NPD7291 Discontinued
0.6682 Remote Similarity NPD4502 Phase 2
0.6667 Remote Similarity NPD2238 Phase 2
0.6667 Remote Similarity NPD4727 Phase 1
0.6667 Remote Similarity NPD6967 Phase 2
0.6667 Remote Similarity NPD8131 Suspended
0.6651 Remote Similarity NPD7134 Clinical (unspecified phase)
0.665 Remote Similarity NPD4578 Approved
0.665 Remote Similarity NPD8249 Clinical (unspecified phase)
0.665 Remote Similarity NPD4577 Approved
0.6649 Remote Similarity NPD2504 Approved
0.6649 Remote Similarity NPD6071 Discontinued
0.6649 Remote Similarity NPD3051 Approved
0.6649 Remote Similarity NPD7019 Approved
0.6649 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6649 Remote Similarity NPD2505 Approved
0.6649 Remote Similarity NPD7020 Approved
0.6648 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6648 Remote Similarity NPD3060 Approved
0.6635 Remote Similarity NPD7871 Phase 2
0.6635 Remote Similarity NPD7870 Phase 2
0.6634 Remote Similarity NPD6361 Phase 2
0.6634 Remote Similarity NPD4663 Approved
0.6632 Remote Similarity NPD5772 Approved
0.6632 Remote Similarity NPD5773 Approved
0.6631 Remote Similarity NPD5267 Discontinued
0.663 Remote Similarity NPD6809 Clinical (unspecified phase)
0.6618 Remote Similarity NPD6284 Clinical (unspecified phase)
0.6615 Remote Similarity NPD2969 Approved
0.6615 Remote Similarity NPD4083 Discontinued
0.6615 Remote Similarity NPD2970 Approved
0.6615 Remote Similarity NPD8070 Approved
0.6614 Remote Similarity NPD5089 Approved
0.6614 Remote Similarity NPD4773 Phase 2
0.6614 Remote Similarity NPD4772 Phase 2
0.6614 Remote Similarity NPD5090 Approved
0.6613 Remote Similarity NPD52 Approved
0.6613 Remote Similarity NPD7526 Approved
0.6613 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6612 Remote Similarity NPD6658 Clinical (unspecified phase)
0.661 Remote Similarity NPD6405 Approved
0.661 Remote Similarity NPD6407 Approved
0.6601 Remote Similarity NPD7693 Approved
0.66 Remote Similarity NPD7883 Discontinued
0.66 Remote Similarity NPD7549 Discontinued
0.6598 Remote Similarity NPD6107 Approved
0.6598 Remote Similarity NPD6959 Discontinued
0.6597 Remote Similarity NPD8461 Discontinued
0.6596 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6595 Remote Similarity NPD3124 Discontinued
0.6592 Remote Similarity NPD1772 Clinical (unspecified phase)
0.6583 Remote Similarity NPD6297 Approved
0.6582 Remote Similarity NPD2898 Approved
0.6582 Remote Similarity NPD27 Approved
0.6582 Remote Similarity NPD2489 Approved
0.6582 Remote Similarity NPD6894 Phase 1
0.6579 Remote Similarity NPD5722 Discontinued
0.6579 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6576 Remote Similarity NPD5307 Clinical (unspecified phase)
0.6576 Remote Similarity NPD2677 Approved
0.6576 Remote Similarity NPD5160 Discontinued
0.6573 Remote Similarity NPD3110 Approved
0.6573 Remote Similarity NPD3109 Approved
0.6564 Remote Similarity NPD6494 Phase 2
0.6564 Remote Similarity NPD7922 Phase 1
0.6564 Remote Similarity NPD4010 Discontinued
0.6564 Remote Similarity NPD4606 Clinical (unspecified phase)
0.6561 Remote Similarity NPD6502 Phase 2
0.6559 Remote Similarity NPD4123 Phase 3
0.6557 Remote Similarity NPD2209 Approved
0.6557 Remote Similarity NPD2211 Approved
0.6555 Remote Similarity NPD4052 Clinical (unspecified phase)
0.6554 Remote Similarity NPD6812 Clinical (unspecified phase)
0.655 Remote Similarity NPD3386 Phase 2
0.655 Remote Similarity NPD7414 Clinical (unspecified phase)
0.6545 Remote Similarity NPD2978 Approved
0.6545 Remote Similarity NPD2977 Approved
0.6541 Remote Similarity NPD6667 Approved
0.6541 Remote Similarity NPD6666 Approved
0.6541 Remote Similarity NPD7124 Phase 2
0.6538 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6538 Remote Similarity NPD2174 Clinical (unspecified phase)
0.6535 Remote Similarity NPD6851 Approved
0.6535 Remote Similarity NPD6853 Approved
0.6534 Remote Similarity NPD4908 Phase 1
0.6533 Remote Similarity NPD5190 Phase 2
0.6528 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6528 Remote Similarity NPD7783 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