Structure

Physi-Chem Properties

Molecular Weight:  325.13
Volume:  324.737
LogP:  1.535
LogD:  1.969
LogS:  -3.319
# Rotatable Bonds:  1
TPSA:  51.16
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.874
Synthetic Accessibility Score:  3.984
Fsp3:  0.368
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:  -4.871
MDCK Permeability:  3.962402115575969e-05
Pgp-inhibitor:  0.263
Pgp-substrate:  0.915
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.01

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.988
Plasma Protein Binding (PPB):  81.78002166748047%
Volume Distribution (VD):  2.431
Pgp-substrate:  11.830087661743164%

ADMET: Metabolism

CYP1A2-inhibitor:  0.513
CYP1A2-substrate:  0.872
CYP2C19-inhibitor:  0.125
CYP2C19-substrate:  0.917
CYP2C9-inhibitor:  0.093
CYP2C9-substrate:  0.709
CYP2D6-inhibitor:  0.865
CYP2D6-substrate:  0.843
CYP3A4-inhibitor:  0.699
CYP3A4-substrate:  0.91

ADMET: Excretion

Clearance (CL):  12.394
Half-life (T1/2):  0.128

ADMET: Toxicity

hERG Blockers:  0.162
Human Hepatotoxicity (H-HT):  0.39
Drug-inuced Liver Injury (DILI):  0.613
AMES Toxicity:  0.933
Rat Oral Acute Toxicity:  0.654
Maximum Recommended Daily Dose:  0.976
Skin Sensitization:  0.105
Carcinogencity:  0.556
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.945

Download Data

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

  Natural Product: NPC156576

Natural Product ID:  NPC156576
Common Name*:   Pachystaudine
IUPAC Name:   n.a.
Synonyms:   Pachystaudine
Standard InCHIKey:  VRWZVPYPKSHTEU-KKXDTOCCSA-N
Standard InCHI:  InChI=1S/C19H19NO4/c1-20-8-13(21)12-7-14-19(24-9-23-14)16-10-5-3-4-6-11(10)18(22-2)17(20)15(12)16/h3-7,13,17-18,21H,8-9H2,1-2H3/t13-,17-,18-/m0/s1
SMILES:  CO[C@@H]1[C@H]2N(C)C[C@@H](c3c2c(c2c1cccc2)c1c(c3)OCO1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL494453
PubChem CID:   10404031
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0000381] Aporphines

*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
NPO26405 Duguetia staudtii Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26405 Duguetia staudtii Species Annonaceae 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
NPT189 Cell Line Vero Chlorocebus aethiops CC50 = 68000.0 nM PMID[514077]
NPT189 Cell Line Vero Chlorocebus aethiops MTC = 62.0 uM PMID[514077]
NPT1859 Organism Human poliovirus 2 Human poliovirus 2 ED50 = 31.0 uM PMID[514077]
NPT2 Others Unspecified Ratio = 2.2 n.a. PMID[514077]
NPT1859 Organism Human poliovirus 2 Human poliovirus 2 Activity = 0.5 n.a. PMID[514077]
NPT1859 Organism Human poliovirus 2 Human poliovirus 2 Activity = 0.0 n.a. PMID[514077]

☑ 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 NPC156576 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
0.9939 High Similarity NPC248642
0.9818 High Similarity NPC126284
0.9529 High Similarity NPC214116
0.9405 High Similarity NPC114364
0.9405 High Similarity NPC320223
0.9353 High Similarity NPC476575
0.9333 High Similarity NPC247389
0.9286 High Similarity NPC229166
0.9286 High Similarity NPC128560
0.9286 High Similarity NPC199465
0.9273 High Similarity NPC219341
0.9273 High Similarity NPC476432
0.9273 High Similarity NPC24264
0.9235 High Similarity NPC267408
0.9226 High Similarity NPC2314
0.9217 High Similarity NPC298979
0.9212 High Similarity NPC167546
0.9212 High Similarity NPC302527
0.9212 High Similarity NPC16805
0.9212 High Similarity NPC225774
0.92 High Similarity NPC117717
0.9176 High Similarity NPC148693
0.9176 High Similarity NPC118633
0.9176 High Similarity NPC294790
0.9138 High Similarity NPC237579
0.9102 High Similarity NPC210918
0.9075 High Similarity NPC135772
0.903 High Similarity NPC232924
0.903 High Similarity NPC266753
0.903 High Similarity NPC160298
0.903 High Similarity NPC477559
0.903 High Similarity NPC306902
0.9017 High Similarity NPC116284
0.9017 High Similarity NPC233718
0.8988 High Similarity NPC205421
0.8988 High Similarity NPC81218
0.8988 High Similarity NPC158376
0.8988 High Similarity NPC145832
0.8988 High Similarity NPC150879
0.8988 High Similarity NPC117188
0.8988 High Similarity NPC12053
0.8988 High Similarity NPC474931
0.8988 High Similarity NPC306555
0.896 High Similarity NPC312918
0.896 High Similarity NPC155442
0.896 High Similarity NPC477561
0.896 High Similarity NPC476574
0.8947 High Similarity NPC477558
0.8941 High Similarity NPC149090
0.8941 High Similarity NPC19520
0.8909 High Similarity NPC476572
0.8882 High Similarity NPC6152
0.8869 High Similarity NPC196447
0.8869 High Similarity NPC253043
0.8869 High Similarity NPC78222
0.8869 High Similarity NPC477563
0.8869 High Similarity NPC96603
0.8869 High Similarity NPC212794
0.8869 High Similarity NPC306843
0.8869 High Similarity NPC13504
0.8869 High Similarity NPC136508
0.8864 High Similarity NPC57036
0.882 High Similarity NPC475754
0.881 High Similarity NPC1229
0.881 High Similarity NPC233650
0.881 High Similarity NPC324144
0.88 High Similarity NPC275132
0.8793 High Similarity NPC220961
0.8788 High Similarity NPC325871
0.8788 High Similarity NPC99659
0.8772 High Similarity NPC152212
0.8764 High Similarity NPC82763
0.8757 High Similarity NPC134858
0.8743 High Similarity NPC474506
0.8743 High Similarity NPC32413
0.8721 High Similarity NPC470739
0.8721 High Similarity NPC225597
0.8721 High Similarity NPC477640
0.8713 High Similarity NPC241055
0.8708 High Similarity NPC476576
0.8708 High Similarity NPC186546
0.8706 High Similarity NPC86144
0.8706 High Similarity NPC304659
0.869 High Similarity NPC27410
0.869 High Similarity NPC166014
0.8686 High Similarity NPC470879
0.8686 High Similarity NPC258695
0.8671 High Similarity NPC477020
0.8671 High Similarity NPC192135
0.8671 High Similarity NPC66341
0.8663 High Similarity NPC474475
0.8655 High Similarity NPC210140
0.8647 High Similarity NPC168409
0.8647 High Similarity NPC169743
0.8629 High Similarity NPC23219
0.8613 High Similarity NPC239775
0.8606 High Similarity NPC81733
0.8606 High Similarity NPC326316
0.8605 High Similarity NPC58766
0.8605 High Similarity NPC290759
0.8605 High Similarity NPC266176
0.8605 High Similarity NPC475686
0.8605 High Similarity NPC158148
0.8605 High Similarity NPC82533
0.8588 High Similarity NPC189470
0.8571 High Similarity NPC112575
0.8555 High Similarity NPC118274
0.8555 High Similarity NPC477562
0.8555 High Similarity NPC26240
0.8555 High Similarity NPC168753
0.8555 High Similarity NPC69712
0.8547 High Similarity NPC181653
0.8547 High Similarity NPC190332
0.8538 High Similarity NPC276944
0.8538 High Similarity NPC238530
0.8538 High Similarity NPC232514
0.8514 High Similarity NPC187678
0.848 Intermediate Similarity NPC320104
0.8475 Intermediate Similarity NPC244554
0.8452 Intermediate Similarity NPC41178
0.8452 Intermediate Similarity NPC244112
0.8452 Intermediate Similarity NPC138487
0.8452 Intermediate Similarity NPC216459
0.8448 Intermediate Similarity NPC311991
0.8439 Intermediate Similarity NPC100566
0.8424 Intermediate Similarity NPC475959
0.8421 Intermediate Similarity NPC60186
0.8412 Intermediate Similarity NPC92191
0.8412 Intermediate Similarity NPC111485
0.8412 Intermediate Similarity NPC59028
0.8402 Intermediate Similarity NPC146288
0.8398 Intermediate Similarity NPC474904
0.8382 Intermediate Similarity NPC35627
0.8382 Intermediate Similarity NPC81247
0.8382 Intermediate Similarity NPC476573
0.8371 Intermediate Similarity NPC99179
0.8371 Intermediate Similarity NPC474507
0.837 Intermediate Similarity NPC162653
0.8363 Intermediate Similarity NPC4304
0.8362 Intermediate Similarity NPC237044
0.8362 Intermediate Similarity NPC241704
0.8362 Intermediate Similarity NPC474470
0.8333 Intermediate Similarity NPC252960
0.8315 Intermediate Similarity NPC474325
0.8305 Intermediate Similarity NPC304675
0.8304 Intermediate Similarity NPC477080
0.8297 Intermediate Similarity NPC312531
0.8294 Intermediate Similarity NPC31311
0.8294 Intermediate Similarity NPC234392
0.8294 Intermediate Similarity NPC170503
0.8294 Intermediate Similarity NPC126519
0.8294 Intermediate Similarity NPC203784
0.8287 Intermediate Similarity NPC9867
0.8276 Intermediate Similarity NPC124657
0.8276 Intermediate Similarity NPC476002
0.8268 Intermediate Similarity NPC474745
0.8268 Intermediate Similarity NPC32154
0.8266 Intermediate Similarity NPC218614
0.8263 Intermediate Similarity NPC211296
0.8261 Intermediate Similarity NPC78284
0.8258 Intermediate Similarity NPC476577
0.8258 Intermediate Similarity NPC148709
0.8258 Intermediate Similarity NPC173416
0.8256 Intermediate Similarity NPC249274
0.8256 Intermediate Similarity NPC97072
0.8256 Intermediate Similarity NPC205167
0.8256 Intermediate Similarity NPC215829
0.8239 Intermediate Similarity NPC329911
0.8235 Intermediate Similarity NPC76079
0.8229 Intermediate Similarity NPC204947
0.8225 Intermediate Similarity NPC210148
0.8225 Intermediate Similarity NPC26601
0.8225 Intermediate Similarity NPC233029
0.8222 Intermediate Similarity NPC179704
0.8218 Intermediate Similarity NPC247972
0.8212 Intermediate Similarity NPC15919
0.8202 Intermediate Similarity NPC49353
0.8187 Intermediate Similarity NPC180756
0.8187 Intermediate Similarity NPC186063
0.8187 Intermediate Similarity NPC323443
0.8182 Intermediate Similarity NPC160570
0.8156 Intermediate Similarity NPC287588
0.8155 Intermediate Similarity NPC219162
0.8144 Intermediate Similarity NPC476151
0.8136 Intermediate Similarity NPC75958
0.8133 Intermediate Similarity NPC185838
0.8132 Intermediate Similarity NPC474746
0.8132 Intermediate Similarity NPC475981
0.8129 Intermediate Similarity NPC204828
0.8129 Intermediate Similarity NPC249797
0.8129 Intermediate Similarity NPC5238
0.8129 Intermediate Similarity NPC110416
0.8129 Intermediate Similarity NPC295691
0.8129 Intermediate Similarity NPC469817
0.8129 Intermediate Similarity NPC193949
0.8129 Intermediate Similarity NPC54379
0.8129 Intermediate Similarity NPC93593
0.8129 Intermediate Similarity NPC39701
0.8129 Intermediate Similarity NPC207757
0.8129 Intermediate Similarity NPC172765

  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 NPC156576 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
0.8488 Intermediate Similarity NPD3051 Approved
0.8444 Intermediate Similarity NPD7906 Approved
0.8439 Intermediate Similarity NPD2969 Approved
0.8439 Intermediate Similarity NPD2970 Approved
0.8389 Intermediate Similarity NPD4663 Approved
0.8324 Intermediate Similarity NPD4577 Approved
0.8324 Intermediate Similarity NPD4578 Approved
0.8294 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8286 Intermediate Similarity NPD27 Approved
0.8286 Intermediate Similarity NPD2489 Approved
0.8182 Intermediate Similarity NPD5241 Discontinued
0.8079 Intermediate Similarity NPD4481 Phase 3
0.8036 Intermediate Similarity NPD4584 Approved
0.8024 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8022 Intermediate Similarity NPD7312 Approved
0.8022 Intermediate Similarity NPD7313 Approved
0.8022 Intermediate Similarity NPD7311 Approved
0.8022 Intermediate Similarity NPD7310 Approved
0.8 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.7978 Intermediate Similarity NPD7309 Approved
0.7977 Intermediate Similarity NPD2978 Approved
0.7977 Intermediate Similarity NPD2977 Approved
0.7976 Intermediate Similarity NPD2420 Approved
0.7976 Intermediate Similarity NPD2421 Approved
0.7937 Intermediate Similarity NPD2975 Approved
0.7937 Intermediate Similarity NPD2973 Approved
0.7937 Intermediate Similarity NPD2974 Approved
0.7895 Intermediate Similarity NPD4420 Approved
0.7865 Intermediate Similarity NPD6071 Discontinued
0.7865 Intermediate Similarity NPD2494 Approved
0.7865 Intermediate Similarity NPD3452 Approved
0.7865 Intermediate Similarity NPD2493 Approved
0.7865 Intermediate Similarity NPD3450 Approved
0.7853 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD2563 Approved
0.7829 Intermediate Similarity NPD2560 Approved
0.7812 Intermediate Similarity NPD4580 Approved
0.7751 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD4582 Approved
0.7744 Intermediate Similarity NPD4583 Approved
0.7738 Intermediate Similarity NPD4237 Approved
0.7738 Intermediate Similarity NPD4236 Phase 3
0.7732 Intermediate Similarity NPD5005 Approved
0.7732 Intermediate Similarity NPD5006 Approved
0.7692 Intermediate Similarity NPD4002 Approved
0.7692 Intermediate Similarity NPD4004 Approved
0.7688 Intermediate Similarity NPD8053 Approved
0.7688 Intermediate Similarity NPD8054 Approved
0.7672 Intermediate Similarity NPD2490 Approved
0.7672 Intermediate Similarity NPD2488 Approved
0.766 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD4773 Phase 2
0.7657 Intermediate Similarity NPD4772 Phase 2
0.765 Intermediate Similarity NPD8156 Discontinued
0.764 Intermediate Similarity NPD7833 Phase 2
0.764 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD7831 Phase 2
0.7634 Intermediate Similarity NPD2968 Approved
0.7634 Intermediate Similarity NPD2971 Approved
0.7624 Intermediate Similarity NPD7047 Phase 3
0.7605 Intermediate Similarity NPD1753 Discontinued
0.7604 Intermediate Similarity NPD5582 Discontinued
0.7604 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7596 Intermediate Similarity NPD8251 Approved
0.7596 Intermediate Similarity NPD8099 Discontinued
0.7596 Intermediate Similarity NPD8252 Approved
0.7584 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD2898 Approved
0.7573 Intermediate Similarity NPD6997 Phase 2
0.7554 Intermediate Similarity NPD42 Phase 2
0.7554 Intermediate Similarity NPD6042 Phase 2
0.7514 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD6788 Approved
0.7444 Intermediate Similarity NPD5604 Discontinued
0.7443 Intermediate Similarity NPD4017 Approved
0.7442 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD4727 Phase 1
0.7427 Intermediate Similarity NPD3060 Approved
0.7427 Intermediate Similarity NPD5177 Phase 3
0.7416 Intermediate Similarity NPD7298 Approved
0.7403 Intermediate Similarity NPD7400 Phase 3
0.7377 Intermediate Similarity NPD4010 Discontinued
0.7374 Intermediate Similarity NPD5773 Approved
0.7374 Intermediate Similarity NPD5772 Approved
0.7371 Intermediate Similarity NPD6090 Discontinued
0.7348 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD5976 Discontinued
0.733 Intermediate Similarity NPD6030 Approved
0.733 Intermediate Similarity NPD6031 Approved
0.7322 Intermediate Similarity NPD6107 Approved
0.7316 Intermediate Similarity NPD6853 Approved
0.7316 Intermediate Similarity NPD6851 Approved
0.7314 Intermediate Similarity NPD4123 Phase 3
0.731 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD5709 Phase 3
0.7304 Intermediate Similarity NPD7827 Phase 1
0.7302 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD3845 Phase 1
0.7299 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD6297 Approved
0.7286 Intermediate Similarity NPD3057 Approved
0.7268 Intermediate Similarity NPD4666 Phase 3
0.7263 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD3109 Approved
0.7262 Intermediate Similarity NPD3110 Approved
0.7255 Intermediate Similarity NPD5676 Approved
0.7232 Intermediate Similarity NPD3640 Phase 3
0.7232 Intermediate Similarity NPD3641 Approved
0.7232 Intermediate Similarity NPD3639 Approved
0.7225 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD4721 Approved
0.7209 Intermediate Similarity NPD4725 Approved
0.7209 Intermediate Similarity NPD4726 Approved
0.72 Intermediate Similarity NPD3533 Approved
0.72 Intermediate Similarity NPD2972 Approved
0.7173 Intermediate Similarity NPD7280 Phase 3
0.7173 Intermediate Similarity NPD7281 Phase 3
0.7168 Intermediate Similarity NPD7037 Approved
0.7158 Intermediate Similarity NPD4055 Discovery
0.7151 Intermediate Similarity NPD4005 Discontinued
0.7143 Intermediate Similarity NPD5160 Discontinued
0.7143 Intermediate Similarity NPD3692 Discontinued
0.7129 Intermediate Similarity NPD4040 Phase 1
0.7127 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD6674 Discontinued
0.7123 Intermediate Similarity NPD5619 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD2491 Approved
0.7114 Intermediate Similarity NPD3448 Approved
0.7111 Intermediate Similarity NPD4678 Approved
0.7111 Intermediate Similarity NPD4675 Approved
0.711 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD1375 Discontinued
0.7109 Intermediate Similarity NPD7907 Approved
0.7105 Intermediate Similarity NPD7007 Discovery
0.7102 Intermediate Similarity NPD6667 Approved
0.7102 Intermediate Similarity NPD6666 Approved
0.71 Intermediate Similarity NPD4107 Approved
0.7095 Intermediate Similarity NPD4210 Discontinued
0.7095 Intermediate Similarity NPD4111 Phase 1
0.7095 Intermediate Similarity NPD4665 Approved
0.7086 Intermediate Similarity NPD5754 Discontinued
0.7083 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD5677 Discontinued
0.7077 Intermediate Similarity NPD7235 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD5938 Phase 3
0.7062 Intermediate Similarity NPD7213 Phase 3
0.7062 Intermediate Similarity NPD7212 Phase 2
0.7059 Intermediate Similarity NPD2238 Phase 2
0.7059 Intermediate Similarity NPD6687 Approved
0.7059 Intermediate Similarity NPD6688 Approved
0.7056 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD2677 Approved
0.7043 Intermediate Similarity NPD7802 Discontinued
0.7041 Intermediate Similarity NPD5718 Phase 2
0.7041 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7033 Intermediate Similarity NPD37 Approved
0.7029 Intermediate Similarity NPD4162 Approved
0.7022 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7022 Intermediate Similarity NPD7447 Phase 1
0.7 Intermediate Similarity NPD3686 Approved
0.7 Intermediate Similarity NPD4474 Approved
0.7 Intermediate Similarity NPD3687 Approved
0.7 Intermediate Similarity NPD554 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4475 Approved
0.7 Intermediate Similarity NPD7048 Phase 3
0.6994 Remote Similarity NPD4108 Discontinued
0.6991 Remote Similarity NPD8153 Approved
0.6991 Remote Similarity NPD8152 Approved
0.6989 Remote Similarity NPD6037 Discontinued
0.6983 Remote Similarity NPD5261 Clinical (unspecified phase)
0.6982 Remote Similarity NPD5155 Approved
0.6982 Remote Similarity NPD5156 Approved
0.698 Remote Similarity NPD4482 Phase 3
0.6979 Remote Similarity NPD7038 Approved
0.6979 Remote Similarity NPD7039 Approved
0.6978 Remote Similarity NPD6072 Discontinued
0.6977 Remote Similarity NPD4579 Clinical (unspecified phase)
0.697 Remote Similarity NPD7262 Phase 1
0.6963 Remote Similarity NPD3885 Approved
0.6961 Remote Similarity NPD6523 Clinical (unspecified phase)
0.6944 Remote Similarity NPD1914 Approved
0.6943 Remote Similarity NPD7549 Discontinued
0.6942 Remote Similarity NPD7701 Phase 2
0.6942 Remote Similarity NPD4859 Phase 1
0.6941 Remote Similarity NPD6625 Approved
0.6934 Remote Similarity NPD3763 Approved
0.6927 Remote Similarity NPD1424 Approved
0.6923 Remote Similarity NPD3594 Approved
0.6923 Remote Similarity NPD5087 Clinical (unspecified phase)
0.6923 Remote Similarity NPD3595 Approved
0.6923 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2605 Approved
0.6923 Remote Similarity NPD2606 Approved
0.6919 Remote Similarity NPD7296 Approved
0.6919 Remote Similarity NPD4965 Approved
0.6919 Remote Similarity NPD4967 Phase 2
0.6919 Remote Similarity NPD4966 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