Structure

Physi-Chem Properties

Molecular Weight:  425.18
Volume:  426.161
LogP:  2.09
LogD:  2.189
LogS:  -2.407
# Rotatable Bonds:  4
TPSA:  80.21
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.386
Synthetic Accessibility Score:  4.096
Fsp3:  0.417
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.675
MDCK Permeability:  4.262490983819589e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.81
20% Bioavailability (F20%):  0.984
30% Bioavailability (F30%):  0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.66
Plasma Protein Binding (PPB):  73.50129699707031%
Volume Distribution (VD):  1.637
Pgp-substrate:  26.17974853515625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.072
CYP1A2-substrate:  0.973
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.94
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.759
CYP2D6-inhibitor:  0.029
CYP2D6-substrate:  0.82
CYP3A4-inhibitor:  0.027
CYP3A4-substrate:  0.929

ADMET: Excretion

Clearance (CL):  11.246
Half-life (T1/2):  0.916

ADMET: Toxicity

hERG Blockers:  0.042
Human Hepatotoxicity (H-HT):  0.101
Drug-inuced Liver Injury (DILI):  0.074
AMES Toxicity:  0.392
Rat Oral Acute Toxicity:  0.834
Maximum Recommended Daily Dose:  0.946
Skin Sensitization:  0.627
Carcinogencity:  0.045
Eye Corrosion:  0.003
Eye Irritation:  0.025
Respiratory Toxicity:  0.919

Download Data

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

  Natural Product: NPC329911

Natural Product ID:  NPC329911
Common Name*:   14Alpha-Hydroxyisocrebrine N-Oxide
IUPAC Name:   (13aS,14S)-3,4,6,7-tetramethoxy-10-oxido-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-10-ium-14-ol
Synonyms:   14Alpha-Hydroxyisocrebrine N-Oxide
Standard InCHIKey:  MSEYHQHYVWQFRE-ACYOWCCNSA-N
Standard InCHI:  InChI=1S/C24H27NO6/c1-28-18-8-7-13-21-16(12-25(27)9-5-6-17(25)23(21)26)14-10-19(29-2)20(30-3)11-15(14)22(13)24(18)31-4/h7-8,10-11,17,23,26H,5-6,9,12H2,1-4H3/t17-,23+,25?/m0/s1
SMILES:  COC1=C(C2=C(C=C1)C3=C(C[N+]4(CCCC4C3O)[O-])C5=CC(=C(C=C52)OC)OC)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1092162
PubChem CID:   15768065
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000025] Phenanthrenes and derivatives
        • [CHEMONTID:0001906] Phenanthroindolizidines

*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
NPO6257 Ficus septica Species Moraceae Eukaryota Stems Tainan Hsien, Taiwan, Republic of China 2000-JAN PMID[16038551]
NPO6257 Ficus septica Species Moraceae Eukaryota leaves n.a. n.a. PMID[19938815]
NPO6257 Ficus septica Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6257 Ficus septica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6257 Ficus septica Species Moraceae 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
NPT165 Cell Line HeLa Homo sapiens IC50 = 7100.0 nM PMID[557036]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 28000.0 nM PMID[557036]

☑ 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 NPC329911 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
0.9809 High Similarity NPC160570
0.9618 High Similarity NPC76116
0.9437 High Similarity NPC164429
0.9359 High Similarity NPC477132
0.9359 High Similarity NPC477133
0.8854 High Similarity NPC44869
0.8824 High Similarity NPC233718
0.8788 High Similarity NPC150879
0.8606 High Similarity NPC233650
0.8554 High Similarity NPC134858
0.8452 Intermediate Similarity NPC210140
0.8354 Intermediate Similarity NPC244112
0.8344 Intermediate Similarity NPC470924
0.8333 Intermediate Similarity NPC169743
0.8286 Intermediate Similarity NPC248642
0.8276 Intermediate Similarity NPC126284
0.8239 Intermediate Similarity NPC156576
0.8217 Intermediate Similarity NPC210086
0.8204 Intermediate Similarity NPC59028
0.8204 Intermediate Similarity NPC92191
0.8155 Intermediate Similarity NPC205167
0.8155 Intermediate Similarity NPC249274
0.815 Intermediate Similarity NPC2314
0.8144 Intermediate Similarity NPC475326
0.8121 Intermediate Similarity NPC37272
0.8107 Intermediate Similarity NPC60186
0.8092 Intermediate Similarity NPC470739
0.8092 Intermediate Similarity NPC225597
0.8092 Intermediate Similarity NPC477640
0.8084 Intermediate Similarity NPC186063
0.8081 Intermediate Similarity NPC158148
0.8081 Intermediate Similarity NPC266176
0.8081 Intermediate Similarity NPC58766
0.8081 Intermediate Similarity NPC290759
0.8081 Intermediate Similarity NPC82533
0.8081 Intermediate Similarity NPC475686
0.8045 Intermediate Similarity NPC214116
0.8036 Intermediate Similarity NPC65490
0.8036 Intermediate Similarity NPC148014
0.8036 Intermediate Similarity NPC40389
0.8036 Intermediate Similarity NPC315707
0.8036 Intermediate Similarity NPC78359
0.8035 Intermediate Similarity NPC474475
0.8025 Intermediate Similarity NPC475828
0.8023 Intermediate Similarity NPC145832
0.8023 Intermediate Similarity NPC117188
0.8023 Intermediate Similarity NPC205421
0.8023 Intermediate Similarity NPC158376
0.8023 Intermediate Similarity NPC306555
0.8023 Intermediate Similarity NPC81218
0.8023 Intermediate Similarity NPC12053
0.8023 Intermediate Similarity NPC474931
0.8012 Intermediate Similarity NPC13504
0.8012 Intermediate Similarity NPC136508
0.8012 Intermediate Similarity NPC253043
0.8012 Intermediate Similarity NPC26601
0.8012 Intermediate Similarity NPC96603
0.8012 Intermediate Similarity NPC78222
0.8012 Intermediate Similarity NPC196447
0.8012 Intermediate Similarity NPC477563
0.8012 Intermediate Similarity NPC306843
0.8012 Intermediate Similarity NPC212794
0.7988 Intermediate Similarity NPC130941
0.7976 Intermediate Similarity NPC147091
0.7966 Intermediate Similarity NPC244554
0.7953 Intermediate Similarity NPC324144
0.7939 Intermediate Similarity NPC219162
0.7929 Intermediate Similarity NPC476572
0.7919 Intermediate Similarity NPC181653
0.7919 Intermediate Similarity NPC190332
0.7919 Intermediate Similarity NPC100566
0.7917 Intermediate Similarity NPC99659
0.7917 Intermediate Similarity NPC325871
0.791 Intermediate Similarity NPC118633
0.791 Intermediate Similarity NPC320223
0.791 Intermediate Similarity NPC148693
0.791 Intermediate Similarity NPC477560
0.791 Intermediate Similarity NPC294790
0.791 Intermediate Similarity NPC114364
0.7898 Intermediate Similarity NPC199465
0.7898 Intermediate Similarity NPC128560
0.7898 Intermediate Similarity NPC229166
0.7892 Intermediate Similarity NPC274026
0.7877 Intermediate Similarity NPC476575
0.7861 Intermediate Similarity NPC124657
0.7861 Intermediate Similarity NPC476432
0.7861 Intermediate Similarity NPC24264
0.7853 Intermediate Similarity NPC474470
0.7853 Intermediate Similarity NPC241704
0.7849 Intermediate Similarity NPC1229
0.7849 Intermediate Similarity NPC320104
0.7836 Intermediate Similarity NPC166014
0.7836 Intermediate Similarity NPC4304
0.7836 Intermediate Similarity NPC18402
0.7836 Intermediate Similarity NPC27410
0.7824 Intermediate Similarity NPC129603
0.7818 Intermediate Similarity NPC253883
0.7818 Intermediate Similarity NPC90844
0.7818 Intermediate Similarity NPC476151
0.7818 Intermediate Similarity NPC95075
0.7816 Intermediate Similarity NPC247389
0.7816 Intermediate Similarity NPC298979
0.7803 Intermediate Similarity NPC302527
0.7803 Intermediate Similarity NPC225774
0.7803 Intermediate Similarity NPC167546
0.7803 Intermediate Similarity NPC16805
0.7784 Intermediate Similarity NPC10871
0.7784 Intermediate Similarity NPC239775
0.7784 Intermediate Similarity NPC57272
0.7772 Intermediate Similarity NPC117717
0.7765 Intermediate Similarity NPC323443
0.7765 Intermediate Similarity NPC180756
0.7765 Intermediate Similarity NPC32154
0.7759 Intermediate Similarity NPC476002
0.7759 Intermediate Similarity NPC219341
0.7753 Intermediate Similarity NPC237044
0.7746 Intermediate Similarity NPC124433
0.7746 Intermediate Similarity NPC293871
0.774 Intermediate Similarity NPC192135
0.774 Intermediate Similarity NPC66341
0.774 Intermediate Similarity NPC477020
0.7738 Intermediate Similarity NPC81733
0.7738 Intermediate Similarity NPC326316
0.7733 Intermediate Similarity NPC97072
0.7733 Intermediate Similarity NPC215829
0.7727 Intermediate Similarity NPC168753
0.7727 Intermediate Similarity NPC69712
0.7727 Intermediate Similarity NPC118274
0.7727 Intermediate Similarity NPC26240
0.7727 Intermediate Similarity NPC477562
0.7725 Intermediate Similarity NPC103379
0.7725 Intermediate Similarity NPC477565
0.7714 Intermediate Similarity NPC298186
0.7714 Intermediate Similarity NPC252960
0.7714 Intermediate Similarity NPC210918
0.7714 Intermediate Similarity NPC301189
0.7709 Intermediate Similarity NPC474325
0.7706 Intermediate Similarity NPC127674
0.7706 Intermediate Similarity NPC2413
0.7706 Intermediate Similarity NPC5238
0.7706 Intermediate Similarity NPC39701
0.7706 Intermediate Similarity NPC278799
0.7706 Intermediate Similarity NPC189266
0.7706 Intermediate Similarity NPC184026
0.7706 Intermediate Similarity NPC204828
0.7706 Intermediate Similarity NPC249797
0.7706 Intermediate Similarity NPC193949
0.7706 Intermediate Similarity NPC110416
0.7706 Intermediate Similarity NPC207757
0.7706 Intermediate Similarity NPC276588
0.7706 Intermediate Similarity NPC54379
0.7706 Intermediate Similarity NPC469817
0.7706 Intermediate Similarity NPC295691
0.7706 Intermediate Similarity NPC172765
0.7701 Intermediate Similarity NPC247972
0.7697 Intermediate Similarity NPC304675
0.7697 Intermediate Similarity NPC185838
0.7692 Intermediate Similarity NPC82285
0.7692 Intermediate Similarity NPC133011
0.768 Intermediate Similarity NPC116284
0.7667 Intermediate Similarity NPC474745
0.7667 Intermediate Similarity NPC220961
0.7667 Intermediate Similarity NPC267408
0.7667 Intermediate Similarity NPC99179
0.7665 Intermediate Similarity NPC476571
0.7665 Intermediate Similarity NPC428
0.7665 Intermediate Similarity NPC147390
0.7665 Intermediate Similarity NPC135538
0.7665 Intermediate Similarity NPC246587
0.7665 Intermediate Similarity NPC24233
0.7661 Intermediate Similarity NPC160931
0.7661 Intermediate Similarity NPC37205
0.7657 Intermediate Similarity NPC264850
0.7657 Intermediate Similarity NPC13916
0.7644 Intermediate Similarity NPC218614
0.7637 Intermediate Similarity NPC135772
0.763 Intermediate Similarity NPC160298
0.763 Intermediate Similarity NPC271388
0.763 Intermediate Similarity NPC205255
0.763 Intermediate Similarity NPC477559
0.763 Intermediate Similarity NPC266753
0.763 Intermediate Similarity NPC119649
0.763 Intermediate Similarity NPC235143
0.763 Intermediate Similarity NPC230956
0.763 Intermediate Similarity NPC232924
0.763 Intermediate Similarity NPC306902
0.7627 Intermediate Similarity NPC75958
0.7627 Intermediate Similarity NPC311991
0.7624 Intermediate Similarity NPC305847
0.7624 Intermediate Similarity NPC155442
0.7624 Intermediate Similarity NPC477561
0.7624 Intermediate Similarity NPC312918
0.7624 Intermediate Similarity NPC476574
0.7619 Intermediate Similarity NPC92541
0.7619 Intermediate Similarity NPC211296
0.7609 Intermediate Similarity NPC237579
0.7605 Intermediate Similarity NPC16107
0.7605 Intermediate Similarity NPC179825
0.7605 Intermediate Similarity NPC476144
0.7605 Intermediate Similarity NPC191376

  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 NPC329911 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
0.8036 Intermediate Similarity NPD2560 Approved
0.8036 Intermediate Similarity NPD2563 Approved
0.7919 Intermediate Similarity NPD2970 Approved
0.7919 Intermediate Similarity NPD2969 Approved
0.7861 Intermediate Similarity NPD6071 Discontinued
0.7771 Intermediate Similarity NPD2489 Approved
0.7771 Intermediate Similarity NPD27 Approved
0.7765 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD3051 Approved
0.7636 Intermediate Similarity NPD5241 Discontinued
0.7624 Intermediate Similarity NPD7312 Approved
0.7624 Intermediate Similarity NPD7310 Approved
0.7624 Intermediate Similarity NPD7313 Approved
0.7624 Intermediate Similarity NPD7311 Approved
0.7622 Intermediate Similarity NPD4236 Phase 3
0.7622 Intermediate Similarity NPD4237 Approved
0.7605 Intermediate Similarity NPD4584 Approved
0.7582 Intermediate Similarity NPD7309 Approved
0.7561 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD7906 Approved
0.75 Intermediate Similarity NPD4663 Approved
0.7472 Intermediate Similarity NPD4481 Phase 3
0.7472 Intermediate Similarity NPD2898 Approved
0.7471 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD4772 Phase 2
0.7442 Intermediate Similarity NPD4773 Phase 2
0.7432 Intermediate Similarity NPD4577 Approved
0.7432 Intermediate Similarity NPD4578 Approved
0.7429 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD7831 Phase 2
0.7429 Intermediate Similarity NPD7833 Phase 2
0.7305 Intermediate Similarity NPD3060 Approved
0.7257 Intermediate Similarity NPD5772 Approved
0.7257 Intermediate Similarity NPD5773 Approved
0.7204 Intermediate Similarity NPD8053 Approved
0.7204 Intermediate Similarity NPD8054 Approved
0.7193 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD7400 Phase 3
0.7191 Intermediate Similarity NPD5709 Phase 3
0.7179 Intermediate Similarity NPD2972 Approved
0.7179 Intermediate Similarity NPD3533 Approved
0.7159 Intermediate Similarity NPD2978 Approved
0.7159 Intermediate Similarity NPD2977 Approved
0.7158 Intermediate Similarity NPD8156 Discontinued
0.7151 Intermediate Similarity NPD6090 Discontinued
0.7151 Intermediate Similarity NPD4666 Phase 3
0.715 Intermediate Similarity NPD5676 Approved
0.7135 Intermediate Similarity NPD2421 Approved
0.7135 Intermediate Similarity NPD2420 Approved
0.7126 Intermediate Similarity NPD4005 Discontinued
0.7118 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7118 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD5976 Discontinued
0.7104 Intermediate Similarity NPD8099 Discontinued
0.7104 Intermediate Similarity NPD8251 Approved
0.7104 Intermediate Similarity NPD8252 Approved
0.7098 Intermediate Similarity NPD2974 Approved
0.7098 Intermediate Similarity NPD2975 Approved
0.7098 Intermediate Similarity NPD2973 Approved
0.7092 Intermediate Similarity NPD3448 Approved
0.7092 Intermediate Similarity NPD2491 Approved
0.7092 Intermediate Similarity NPD3057 Approved
0.7079 Intermediate Similarity NPD6788 Approved
0.7069 Intermediate Similarity NPD4210 Discontinued
0.7055 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD2493 Approved
0.7041 Intermediate Similarity NPD2494 Approved
0.7041 Intermediate Similarity NPD3452 Approved
0.7041 Intermediate Similarity NPD3450 Approved
0.7029 Intermediate Similarity NPD4017 Approved
0.7016 Intermediate Similarity NPD2488 Approved
0.7016 Intermediate Similarity NPD2490 Approved
0.7011 Intermediate Similarity NPD6031 Approved
0.7011 Intermediate Similarity NPD3641 Approved
0.7011 Intermediate Similarity NPD3640 Phase 3
0.7011 Intermediate Similarity NPD3639 Approved
0.7011 Intermediate Similarity NPD6030 Approved
0.7006 Intermediate Similarity NPD7298 Approved
0.7 Intermediate Similarity NPD5177 Phase 3
0.6994 Remote Similarity NPD4123 Phase 3
0.699 Remote Similarity NPD4580 Approved
0.6978 Remote Similarity NPD4010 Discontinued
0.6977 Remote Similarity NPD6783 Clinical (unspecified phase)
0.6968 Remote Similarity NPD2971 Approved
0.6968 Remote Similarity NPD2968 Approved
0.6964 Remote Similarity NPD6029 Clinical (unspecified phase)
0.6964 Remote Similarity NPD6028 Clinical (unspecified phase)
0.6959 Remote Similarity NPD6331 Phase 2
0.6944 Remote Similarity NPD4055 Discovery
0.6941 Remote Similarity NPD7037 Approved
0.6935 Remote Similarity NPD4583 Approved
0.6935 Remote Similarity NPD4582 Approved
0.6928 Remote Similarity NPD2238 Phase 2
0.6923 Remote Similarity NPD6107 Approved
0.6919 Remote Similarity NPD2677 Approved
0.6901 Remote Similarity NPD4162 Approved
0.6888 Remote Similarity NPD4420 Approved
0.6884 Remote Similarity NPD4002 Approved
0.6884 Remote Similarity NPD4004 Approved
0.6882 Remote Similarity NPD42 Phase 2
0.6882 Remote Similarity NPD6042 Phase 2
0.6879 Remote Similarity NPD6667 Approved
0.6879 Remote Similarity NPD6666 Approved
0.6875 Remote Similarity NPD3687 Approved
0.6875 Remote Similarity NPD3686 Approved
0.6869 Remote Similarity NPD4482 Phase 3
0.6868 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6868 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6857 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6854 Remote Similarity NPD6072 Discontinued
0.6839 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6839 Remote Similarity NPD1774 Approved
0.6836 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6836 Remote Similarity NPD7261 Clinical (unspecified phase)
0.6825 Remote Similarity NPD8453 Clinical (unspecified phase)
0.6825 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6823 Remote Similarity NPD7243 Clinical (unspecified phase)
0.6823 Remote Similarity NPD3398 Discontinued
0.6821 Remote Similarity NPD3692 Discontinued
0.6818 Remote Similarity NPD4107 Approved
0.6809 Remote Similarity NPD6297 Approved
0.6809 Remote Similarity NPD6996 Clinical (unspecified phase)
0.68 Remote Similarity NPD1424 Approved
0.6798 Remote Similarity NPD4675 Approved
0.6798 Remote Similarity NPD4678 Approved
0.6793 Remote Similarity NPD4166 Phase 2
0.6789 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6788 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6786 Remote Similarity NPD5582 Discontinued
0.6782 Remote Similarity NPD3845 Phase 1
0.6774 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6766 Remote Similarity NPD2674 Phase 3
0.6766 Remote Similarity NPD4475 Approved
0.6766 Remote Similarity NPD4474 Approved
0.6765 Remote Similarity NPD1753 Discontinued
0.6763 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6762 Remote Similarity NPD7907 Approved
0.6757 Remote Similarity NPD2388 Discontinued
0.6757 Remote Similarity NPD6688 Approved
0.6757 Remote Similarity NPD6687 Approved
0.6754 Remote Similarity NPD6853 Approved
0.6754 Remote Similarity NPD6851 Approved
0.675 Remote Similarity NPD5006 Approved
0.675 Remote Similarity NPD5005 Approved
0.6746 Remote Similarity NPD4665 Approved
0.6746 Remote Similarity NPD4111 Phase 1
0.6744 Remote Similarity NPD1372 Clinical (unspecified phase)
0.6737 Remote Similarity NPD7132 Clinical (unspecified phase)
0.673 Remote Similarity NPD6997 Phase 2
0.6724 Remote Similarity NPD5160 Discontinued
0.6723 Remote Similarity NPD1914 Approved
0.6707 Remote Similarity NPD5718 Phase 2
0.6706 Remote Similarity NPD6896 Approved
0.6706 Remote Similarity NPD6895 Approved
0.6686 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6686 Remote Similarity NPD7124 Phase 2
0.6686 Remote Similarity NPD1375 Discontinued
0.6685 Remote Similarity NPD2904 Discontinued
0.6684 Remote Similarity NPD7039 Approved
0.6684 Remote Similarity NPD7038 Approved
0.6683 Remote Similarity NPD7047 Phase 3
0.6667 Remote Similarity NPD2154 Approved
0.6667 Remote Similarity NPD2156 Approved
0.6667 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2155 Approved
0.6649 Remote Similarity NPD4157 Discontinued
0.6649 Remote Similarity NPD7802 Discontinued
0.6648 Remote Similarity NPD7213 Phase 3
0.6648 Remote Similarity NPD7212 Phase 2
0.6648 Remote Similarity NPD3124 Discontinued
0.6647 Remote Similarity NPD4579 Clinical (unspecified phase)
0.6629 Remote Similarity NPD2122 Discontinued
0.6628 Remote Similarity NPD2161 Phase 2
0.6627 Remote Similarity NPD3109 Approved
0.6627 Remote Similarity NPD3110 Approved
0.662 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6615 Remote Similarity NPD7280 Phase 3
0.6615 Remote Similarity NPD7281 Phase 3
0.6615 Remote Similarity NPD7235 Clinical (unspecified phase)
0.6614 Remote Similarity NPD5312 Approved
0.6614 Remote Similarity NPD5313 Approved
0.6613 Remote Similarity NPD6747 Phase 1
0.661 Remote Similarity NPD4160 Clinical (unspecified phase)
0.661 Remote Similarity NPD7020 Approved
0.661 Remote Similarity NPD7447 Phase 1
0.661 Remote Similarity NPD7019 Approved
0.6607 Remote Similarity NPD598 Approved
0.6607 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6607 Remote Similarity NPD3144 Approved
0.6607 Remote Similarity NPD601 Approved
0.6607 Remote Similarity NPD3145 Approved
0.6607 Remote Similarity NPD597 Approved
0.6591 Remote Similarity NPD7048 Phase 3
0.6585 Remote Similarity NPD4859 Phase 1
0.6582 Remote Similarity NPD6656 Clinical (unspecified phase)
0.658 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6576 Remote Similarity NPD5604 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
A: chemistry similarity;
B: biological targets similarity;
C: networks similarity;
D: cell-based bioactivity similarity;
E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data