Structure

Physi-Chem Properties

Molecular Weight:  273.14
Volume:  277.888
LogP:  1.08
LogD:  0.819
LogS:  -1.076
# Rotatable Bonds:  1
TPSA:  50.72
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.762
Synthetic Accessibility Score:  4.37
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.695
MDCK Permeability:  1.114902534027351e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.307
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.974
Plasma Protein Binding (PPB):  11.295099258422852%
Volume Distribution (VD):  2.976
Pgp-substrate:  79.23280334472656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.359
CYP1A2-substrate:  0.504
CYP2C19-inhibitor:  0.048
CYP2C19-substrate:  0.862
CYP2C9-inhibitor:  0.011
CYP2C9-substrate:  0.324
CYP2D6-inhibitor:  0.654
CYP2D6-substrate:  0.878
CYP3A4-inhibitor:  0.249
CYP3A4-substrate:  0.431

ADMET: Excretion

Clearance (CL):  5.214
Half-life (T1/2):  0.522

ADMET: Toxicity

hERG Blockers:  0.46
Human Hepatotoxicity (H-HT):  0.541
Drug-inuced Liver Injury (DILI):  0.049
AMES Toxicity:  0.013
Rat Oral Acute Toxicity:  0.881
Maximum Recommended Daily Dose:  0.957
Skin Sensitization:  0.783
Carcinogencity:  0.576
Eye Corrosion:  0.004
Eye Irritation:  0.011
Respiratory Toxicity:  0.957

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

  Natural Product: NPC124433

Natural Product ID:  NPC124433
Common Name*:   AIXQQSTVOSFSMO-FFSVYQOJSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  AIXQQSTVOSFSMO-FFSVYQOJSA-N
Standard InCHI:  InChI=1S/C16H19NO3/c1-19-12-3-2-10-9-17-7-6-16-5-4-11(18)8-13(16)20-15(12)14(10)16/h2-5,11,13,17-18H,6-9H2,1H3/t11-,13+,16+/m1/s1
SMILES:  COc1ccc2c3c1O[C@@H]1[C@@]3(CCNC2)C=C[C@H](C1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3604339
PubChem CID:   443721
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0001775] Amaryllidaceae alkaloids
        • [CHEMONTID:0004128] Galanthamine-type amaryllidaceae alkaloids

*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
NPO3630 Crotalaria crispata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3630 Crotalaria crispata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9485 Haplopappus deserticola Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9144 Atriplex parvifolia Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3630 Crotalaria crispata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9927 Crinum asiaticum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1412 Artemisia juncea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19776 Hesperocyparis arizonica Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11000 Eupatorium laevigatum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11473 Viburnum lantana Species Adoxaceae 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
NPT2668 Individual Protein Acetylcholinesterase Torpedo californica IC50 = 15000.0 nM PMID[553285]

☑ 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 NPC124433 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 NPC293871
0.9605 High Similarity NPC315707
0.9605 High Similarity NPC78359
0.9605 High Similarity NPC40389
0.9605 High Similarity NPC65490
0.9605 High Similarity NPC148014
0.9355 High Similarity NPC18402
0.9351 High Similarity NPC129603
0.8485 Intermediate Similarity NPC284842
0.8313 Intermediate Similarity NPC124657
0.8221 Intermediate Similarity NPC160931
0.8221 Intermediate Similarity NPC37205
0.8221 Intermediate Similarity NPC147091
0.8221 Intermediate Similarity NPC323443
0.8221 Intermediate Similarity NPC180756
0.821 Intermediate Similarity NPC2295
0.821 Intermediate Similarity NPC477564
0.8204 Intermediate Similarity NPC476002
0.8187 Intermediate Similarity NPC207824
0.8187 Intermediate Similarity NPC60538
0.8137 Intermediate Similarity NPC274026
0.8121 Intermediate Similarity NPC59028
0.8121 Intermediate Similarity NPC92191
0.8107 Intermediate Similarity NPC83198
0.8107 Intermediate Similarity NPC204908
0.8086 Intermediate Similarity NPC76213
0.8086 Intermediate Similarity NPC277669
0.8072 Intermediate Similarity NPC249274
0.8039 Intermediate Similarity NPC160692
0.8023 Intermediate Similarity NPC329969
0.8012 Intermediate Similarity NPC470739
0.8012 Intermediate Similarity NPC225597
0.8012 Intermediate Similarity NPC477640
0.8 Intermediate Similarity NPC475686
0.8 Intermediate Similarity NPC58766
0.8 Intermediate Similarity NPC266176
0.8 Intermediate Similarity NPC290759
0.8 Intermediate Similarity NPC82533
0.8 Intermediate Similarity NPC158148
0.7989 Intermediate Similarity NPC244554
0.7987 Intermediate Similarity NPC294249
0.7965 Intermediate Similarity NPC232386
0.7965 Intermediate Similarity NPC152680
0.7965 Intermediate Similarity NPC190783
0.7964 Intermediate Similarity NPC215829
0.7964 Intermediate Similarity NPC205167
0.7964 Intermediate Similarity NPC97072
0.7953 Intermediate Similarity NPC474475
0.795 Intermediate Similarity NPC476151
0.7949 Intermediate Similarity NPC253429
0.7933 Intermediate Similarity NPC475754
0.7927 Intermediate Similarity NPC82285
0.7927 Intermediate Similarity NPC133011
0.7919 Intermediate Similarity NPC49353
0.7898 Intermediate Similarity NPC275132
0.7898 Intermediate Similarity NPC476575
0.7874 Intermediate Similarity NPC474470
0.7861 Intermediate Similarity NPC2314
0.7861 Intermediate Similarity NPC66341
0.7861 Intermediate Similarity NPC192135
0.7861 Intermediate Similarity NPC477020
0.7853 Intermediate Similarity NPC477565
0.7853 Intermediate Similarity NPC103379
0.7849 Intermediate Similarity NPC69712
0.7849 Intermediate Similarity NPC75958
0.7849 Intermediate Similarity NPC26240
0.7849 Intermediate Similarity NPC477562
0.7836 Intermediate Similarity NPC100566
0.7836 Intermediate Similarity NPC150879
0.7826 Intermediate Similarity NPC185838
0.7826 Intermediate Similarity NPC130926
0.7824 Intermediate Similarity NPC39103
0.7824 Intermediate Similarity NPC2770
0.7816 Intermediate Similarity NPC477558
0.779 Intermediate Similarity NPC117717
0.7784 Intermediate Similarity NPC474507
0.7778 Intermediate Similarity NPC476573
0.7778 Intermediate Similarity NPC35627
0.7778 Intermediate Similarity NPC81247
0.7778 Intermediate Similarity NPC175890
0.7778 Intermediate Similarity NPC48490
0.7778 Intermediate Similarity NPC11296
0.7778 Intermediate Similarity NPC82457
0.7778 Intermediate Similarity NPC274661
0.7771 Intermediate Similarity NPC475557
0.7771 Intermediate Similarity NPC131204
0.7771 Intermediate Similarity NPC301050
0.7771 Intermediate Similarity NPC476577
0.7771 Intermediate Similarity NPC148709
0.7771 Intermediate Similarity NPC173416
0.7765 Intermediate Similarity NPC320104
0.7753 Intermediate Similarity NPC135772
0.7751 Intermediate Similarity NPC4304
0.7746 Intermediate Similarity NPC329911
0.7746 Intermediate Similarity NPC311991
0.774 Intermediate Similarity NPC477561
0.774 Intermediate Similarity NPC305847
0.774 Intermediate Similarity NPC312918
0.774 Intermediate Similarity NPC155442
0.774 Intermediate Similarity NPC476574
0.7735 Intermediate Similarity NPC60295
0.7735 Intermediate Similarity NPC191132
0.7733 Intermediate Similarity NPC181653
0.7733 Intermediate Similarity NPC190332
0.7733 Intermediate Similarity NPC252960
0.773 Intermediate Similarity NPC191376
0.773 Intermediate Similarity NPC321505
0.773 Intermediate Similarity NPC179825
0.7727 Intermediate Similarity NPC160193
0.7727 Intermediate Similarity NPC15919
0.7725 Intermediate Similarity NPC78733
0.7714 Intermediate Similarity NPC187678
0.7711 Intermediate Similarity NPC114124
0.7709 Intermediate Similarity NPC9867
0.7706 Intermediate Similarity NPC60186
0.7701 Intermediate Similarity NPC476331
0.7701 Intermediate Similarity NPC108434
0.7701 Intermediate Similarity NPC475215
0.7697 Intermediate Similarity NPC302449
0.7688 Intermediate Similarity NPC160570
0.7684 Intermediate Similarity NPC126284
0.7684 Intermediate Similarity NPC267408
0.7684 Intermediate Similarity NPC243454
0.7684 Intermediate Similarity NPC475479
0.7683 Intermediate Similarity NPC428
0.7683 Intermediate Similarity NPC476571
0.7683 Intermediate Similarity NPC246587
0.7683 Intermediate Similarity NPC59907
0.7683 Intermediate Similarity NPC135538
0.7683 Intermediate Similarity NPC37144
0.7683 Intermediate Similarity NPC147390
0.7683 Intermediate Similarity NPC24233
0.7679 Intermediate Similarity NPC170503
0.7679 Intermediate Similarity NPC126519
0.7679 Intermediate Similarity NPC203784
0.7674 Intermediate Similarity NPC13916
0.7674 Intermediate Similarity NPC264850
0.767 Intermediate Similarity NPC237044
0.7669 Intermediate Similarity NPC473934
0.7667 Intermediate Similarity NPC57036
0.7661 Intermediate Similarity NPC218614
0.7661 Intermediate Similarity NPC233650
0.765 Intermediate Similarity NPC256124
0.7644 Intermediate Similarity NPC152212
0.7644 Intermediate Similarity NPC6152
0.764 Intermediate Similarity NPC239584
0.763 Intermediate Similarity NPC204947
0.7627 Intermediate Similarity NPC118633
0.7627 Intermediate Similarity NPC148693
0.7627 Intermediate Similarity NPC474325
0.7627 Intermediate Similarity NPC294790
0.7625 Intermediate Similarity NPC314682
0.7624 Intermediate Similarity NPC476576
0.7624 Intermediate Similarity NPC186546
0.7619 Intermediate Similarity NPC278799
0.7619 Intermediate Similarity NPC207757
0.7619 Intermediate Similarity NPC276588
0.7619 Intermediate Similarity NPC54379
0.7619 Intermediate Similarity NPC184026
0.7619 Intermediate Similarity NPC172765
0.7619 Intermediate Similarity NPC127674
0.7619 Intermediate Similarity NPC110416
0.7619 Intermediate Similarity NPC2413
0.7619 Intermediate Similarity NPC39701
0.7619 Intermediate Similarity NPC189266
0.7619 Intermediate Similarity NPC193949
0.7619 Intermediate Similarity NPC469817
0.7619 Intermediate Similarity NPC5238
0.7619 Intermediate Similarity NPC204828
0.7619 Intermediate Similarity NPC249797
0.7619 Intermediate Similarity NPC295691
0.7616 Intermediate Similarity NPC247972
0.7616 Intermediate Similarity NPC298486
0.7616 Intermediate Similarity NPC24465
0.7616 Intermediate Similarity NPC134858
0.7614 Intermediate Similarity NPC304675
0.7613 Intermediate Similarity NPC262641
0.7605 Intermediate Similarity NPC148898
0.76 Intermediate Similarity NPC65403
0.7598 Intermediate Similarity NPC248642
0.7597 Intermediate Similarity NPC172403
0.7586 Intermediate Similarity NPC470324
0.7584 Intermediate Similarity NPC99179
0.7584 Intermediate Similarity NPC474745
0.7582 Intermediate Similarity NPC281581
0.7582 Intermediate Similarity NPC206900
0.758 Intermediate Similarity NPC18842
0.7578 Intermediate Similarity NPC474915
0.7578 Intermediate Similarity NPC328750
0.7578 Intermediate Similarity NPC323204
0.7578 Intermediate Similarity NPC188163
0.7578 Intermediate Similarity NPC213206
0.7572 Intermediate Similarity NPC195392
0.7572 Intermediate Similarity NPC86144
0.7572 Intermediate Similarity NPC304659
0.7571 Intermediate Similarity NPC241704
0.7571 Intermediate Similarity NPC112575
0.7564 Intermediate Similarity NPC329595
0.7564 Intermediate Similarity NPC326599
0.7558 Intermediate Similarity NPC475393

  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 NPC124433 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
0.9605 High Similarity NPD2563 Approved
0.9605 High Similarity NPD2560 Approved
0.9241 High Similarity NPD6071 Discontinued
0.8263 Intermediate Similarity NPD2970 Approved
0.8263 Intermediate Similarity NPD2969 Approved
0.8107 Intermediate Similarity NPD2489 Approved
0.8107 Intermediate Similarity NPD27 Approved
0.8095 Intermediate Similarity NPD3051 Approved
0.8089 Intermediate Similarity NPD3060 Approved
0.8075 Intermediate Similarity NPD6030 Approved
0.8075 Intermediate Similarity NPD6031 Approved
0.8075 Intermediate Similarity NPD5976 Discontinued
0.8025 Intermediate Similarity NPD3686 Approved
0.8025 Intermediate Similarity NPD3687 Approved
0.7975 Intermediate Similarity NPD4162 Approved
0.7964 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7964 Intermediate Similarity NPD7831 Phase 2
0.7964 Intermediate Similarity NPD7833 Phase 2
0.7904 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD4773 Phase 2
0.7879 Intermediate Similarity NPD4772 Phase 2
0.7875 Intermediate Similarity NPD2677 Approved
0.784 Intermediate Similarity NPD1424 Approved
0.7799 Intermediate Similarity NPD1372 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD7312 Approved
0.774 Intermediate Similarity NPD7311 Approved
0.774 Intermediate Similarity NPD7310 Approved
0.774 Intermediate Similarity NPD7313 Approved
0.7697 Intermediate Similarity NPD7309 Approved
0.7688 Intermediate Similarity NPD4481 Phase 3
0.7688 Intermediate Similarity NPD7153 Discontinued
0.7679 Intermediate Similarity NPD2978 Approved
0.7679 Intermediate Similarity NPD2977 Approved
0.7667 Intermediate Similarity NPD7906 Approved
0.764 Intermediate Similarity NPD4578 Approved
0.764 Intermediate Similarity NPD4577 Approved
0.7619 Intermediate Similarity NPD5720 Discontinued
0.7611 Intermediate Similarity NPD4663 Approved
0.7602 Intermediate Similarity NPD5709 Phase 3
0.7586 Intermediate Similarity NPD2898 Approved
0.7578 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD4666 Phase 3
0.7548 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7546 Intermediate Similarity NPD5241 Discontinued
0.7546 Intermediate Similarity NPD5160 Discontinued
0.7531 Intermediate Similarity NPD4236 Phase 3
0.7531 Intermediate Similarity NPD4237 Approved
0.7516 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD4584 Approved
0.75 Intermediate Similarity NPD8054 Approved
0.75 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD8053 Approved
0.75 Intermediate Similarity NPD2154 Approved
0.75 Intermediate Similarity NPD2156 Approved
0.75 Intermediate Similarity NPD2155 Approved
0.7484 Intermediate Similarity NPD3054 Approved
0.7484 Intermediate Similarity NPD3052 Approved
0.7471 Intermediate Similarity NPD5772 Approved
0.7471 Intermediate Similarity NPD5773 Approved
0.747 Intermediate Similarity NPD7526 Approved
0.747 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD52 Approved
0.7468 Intermediate Similarity NPD2238 Phase 2
0.7458 Intermediate Similarity NPD8156 Discontinued
0.7455 Intermediate Similarity NPD1774 Approved
0.7453 Intermediate Similarity NPD2161 Phase 2
0.7452 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD5177 Phase 3
0.7412 Intermediate Similarity NPD7298 Approved
0.741 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD4123 Phase 3
0.741 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7401 Intermediate Similarity NPD8252 Approved
0.7401 Intermediate Similarity NPD8099 Discontinued
0.7401 Intermediate Similarity NPD8251 Approved
0.7381 Intermediate Similarity NPD4210 Discontinued
0.7375 Intermediate Similarity NPD2653 Approved
0.7368 Intermediate Similarity NPD4585 Approved
0.736 Intermediate Similarity NPD4873 Discontinued
0.7353 Intermediate Similarity NPD6072 Discontinued
0.7346 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD3056 Clinical (unspecified phase)
0.7342 Intermediate Similarity NPD1336 Approved
0.7333 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD6107 Approved
0.7305 Intermediate Similarity NPD1771 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD7019 Approved
0.7305 Intermediate Similarity NPD2874 Phase 2
0.7305 Intermediate Similarity NPD7020 Approved
0.7301 Intermediate Similarity NPD1375 Discontinued
0.7297 Intermediate Similarity NPD2488 Approved
0.7297 Intermediate Similarity NPD2490 Approved
0.7296 Intermediate Similarity NPD3163 Approved
0.7296 Intermediate Similarity NPD3162 Approved
0.7296 Intermediate Similarity NPD2674 Phase 3
0.7296 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD4678 Approved
0.7294 Intermediate Similarity NPD4675 Approved
0.7289 Intermediate Similarity NPD7124 Phase 2
0.7278 Intermediate Similarity NPD3180 Approved
0.7278 Intermediate Similarity NPD3179 Approved
0.7278 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6331 Phase 2
0.7263 Intermediate Similarity NPD42 Phase 2
0.7263 Intermediate Similarity NPD6042 Phase 2
0.7257 Intermediate Similarity NPD3365 Discontinued
0.7253 Intermediate Similarity NPD2971 Approved
0.7253 Intermediate Similarity NPD2968 Approved
0.725 Intermediate Similarity NPD3061 Approved
0.725 Intermediate Similarity NPD3059 Approved
0.725 Intermediate Similarity NPD3062 Approved
0.725 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD6087 Phase 1
0.7241 Intermediate Similarity NPD4055 Discovery
0.7238 Intermediate Similarity NPD7039 Approved
0.7238 Intermediate Similarity NPD7038 Approved
0.7235 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD601 Approved
0.7233 Intermediate Similarity NPD598 Approved
0.7233 Intermediate Similarity NPD597 Approved
0.7229 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6895 Approved
0.7222 Intermediate Similarity NPD6896 Approved
0.7212 Intermediate Similarity NPD2460 Phase 3
0.7212 Intermediate Similarity NPD2459 Approved
0.7212 Intermediate Similarity NPD2458 Approved
0.7209 Intermediate Similarity NPD5722 Discontinued
0.7202 Intermediate Similarity NPD3536 Discontinued
0.7197 Intermediate Similarity NPD558 Phase 2
0.7197 Intermediate Similarity NPD9620 Approved
0.7197 Intermediate Similarity NPD9621 Approved
0.7197 Intermediate Similarity NPD9619 Approved
0.7196 Intermediate Similarity NPD2974 Approved
0.7196 Intermediate Similarity NPD2973 Approved
0.7196 Intermediate Similarity NPD2975 Approved
0.7188 Intermediate Similarity NPD3531 Approved
0.7188 Intermediate Similarity NPD3530 Approved
0.7188 Intermediate Similarity NPD1132 Approved
0.7188 Intermediate Similarity NPD3532 Approved
0.7188 Intermediate Similarity NPD1136 Approved
0.7188 Intermediate Similarity NPD1130 Approved
0.7186 Intermediate Similarity NPD6667 Approved
0.7186 Intermediate Similarity NPD3122 Phase 3
0.7186 Intermediate Similarity NPD6666 Approved
0.7184 Intermediate Similarity NPD6788 Approved
0.7175 Intermediate Similarity NPD4166 Phase 2
0.7161 Intermediate Similarity NPD2231 Phase 2
0.7161 Intermediate Similarity NPD2235 Phase 2
0.716 Intermediate Similarity NPD823 Approved
0.716 Intermediate Similarity NPD5314 Approved
0.716 Intermediate Similarity NPD6090 Discontinued
0.716 Intermediate Similarity NPD817 Approved
0.7151 Intermediate Similarity NPD2845 Phase 2
0.7151 Intermediate Similarity NPD2843 Phase 2
0.7151 Intermediate Similarity NPD3489 Phase 3
0.7143 Intermediate Similarity NPD2688 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD4017 Approved
0.7135 Intermediate Similarity NPD3452 Approved
0.7135 Intermediate Similarity NPD2494 Approved
0.7135 Intermediate Similarity NPD2493 Approved
0.7135 Intermediate Similarity NPD3450 Approved
0.7134 Intermediate Similarity NPD1794 Approved
0.7134 Intermediate Similarity NPD1818 Approved
0.7134 Intermediate Similarity NPD1819 Approved
0.7134 Intermediate Similarity NPD3156 Discontinued
0.7134 Intermediate Similarity NPD1820 Approved
0.7134 Intermediate Similarity NPD1817 Approved
0.7126 Intermediate Similarity NPD3692 Discontinued
0.7125 Intermediate Similarity NPD3145 Approved
0.7125 Intermediate Similarity NPD3144 Approved
0.7124 Intermediate Similarity NPD3049 Approved
0.712 Intermediate Similarity NPD6853 Approved
0.712 Intermediate Similarity NPD6851 Approved
0.7118 Intermediate Similarity NPD3640 Phase 3
0.7118 Intermediate Similarity NPD3641 Approved
0.7118 Intermediate Similarity NPD3639 Approved
0.7117 Intermediate Similarity NPD6111 Discontinued
0.7112 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD3384 Approved
0.711 Intermediate Similarity NPD3382 Approved
0.711 Intermediate Similarity NPD3383 Approved
0.7108 Intermediate Similarity NPD5061 Approved
0.7108 Intermediate Similarity NPD5062 Approved
0.7107 Intermediate Similarity NPD600 Approved
0.7107 Intermediate Similarity NPD596 Approved
0.7099 Intermediate Similarity NPD1341 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD3057 Approved
0.7088 Intermediate Similarity NPD6297 Approved
0.7083 Intermediate Similarity NPD4580 Approved
0.7083 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD3845 Phase 1
0.7081 Intermediate Similarity NPD6405 Approved
0.7081 Intermediate Similarity NPD4474 Approved
0.7081 Intermediate Similarity NPD4475 Approved
0.7081 Intermediate Similarity NPD6407 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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