Structure

Physi-Chem Properties

Molecular Weight:  379.18
Volume:  391.284
LogP:  3.724
LogD:  3.22
LogS:  -4.791
# Rotatable Bonds:  3
TPSA:  51.16
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.697
Synthetic Accessibility Score:  3.264
Fsp3:  0.391
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -5.112
MDCK Permeability:  3.434860991546884e-05
Pgp-inhibitor:  0.932
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.254

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.981
Plasma Protein Binding (PPB):  79.23069763183594%
Volume Distribution (VD):  1.946
Pgp-substrate:  8.139331817626953%

ADMET: Metabolism

CYP1A2-inhibitor:  0.405
CYP1A2-substrate:  0.97
CYP2C19-inhibitor:  0.061
CYP2C19-substrate:  0.941
CYP2C9-inhibitor:  0.007
CYP2C9-substrate:  0.737
CYP2D6-inhibitor:  0.961
CYP2D6-substrate:  0.918
CYP3A4-inhibitor:  0.019
CYP3A4-substrate:  0.801

ADMET: Excretion

Clearance (CL):  8.167
Half-life (T1/2):  0.277

ADMET: Toxicity

hERG Blockers:  0.439
Human Hepatotoxicity (H-HT):  0.461
Drug-inuced Liver Injury (DILI):  0.945
AMES Toxicity:  0.812
Rat Oral Acute Toxicity:  0.445
Maximum Recommended Daily Dose:  0.889
Skin Sensitization:  0.825
Carcinogencity:  0.068
Eye Corrosion:  0.003
Eye Irritation:  0.018
Respiratory Toxicity:  0.942

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

  Natural Product: NPC150879

Natural Product ID:  NPC150879
Common Name*:   (13Ar,14R)-2,3,6-Trimethoxy-9,11,12,13,13A,14-Hexahydrophenanthro[9,10-F]Indolizin-14-Ol
IUPAC Name:   (13aR,14R)-2,3,6-trimethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-14-ol
Synonyms:  
Standard InCHIKey:  VEPWWLXWVFFRLY-XXBNENTESA-N
Standard InCHI:  InChI=1S/C23H25NO4/c1-26-13-6-7-14-15(9-13)16-10-20(27-2)21(28-3)11-17(16)22-18(14)12-24-8-4-5-19(24)23(22)25/h6-7,9-11,19,23,25H,4-5,8,12H2,1-3H3/t19-,23+/m1/s1
SMILES:  COc1ccc2c(c1)c1cc(OC)c(cc1c1c2CN2CCC[C@@H]2[C@@H]1O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1958058
PubChem CID:   46183346
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
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[22029392]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. fruit n.a. PMID[24897106]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24981 Dimetia capitellata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28410 Nandina domestica Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18056 Silene rubicunda Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18788 Isertia hypoleuca Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18515 Uncaria pilosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14290 Bryonia cretica Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17803 Parmelia omphalodes Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24981 Dimetia capitellata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28410 Nandina domestica Species Berberidaceae 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
NPT81 Cell Line A549 Homo sapiens GI50 > 10000.0 nM PMID[530806]
NPT116 Cell Line HL-60 Homo sapiens GI50 > 10000.0 nM PMID[530806]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 7.3 % PMID[530807]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 39.6 % PMID[530807]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 10.2 % PMID[530807]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 34.9 % PMID[530807]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 14.2 % PMID[530807]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Activity = 38.5 % PMID[530807]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 21.6 % PMID[530807]
NPT786 Organism Tobacco mosaic virus Tobacco mosaic virus Inhibition = 43.5 % PMID[530807]

☑ 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 NPC150879 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
0.9805 High Similarity NPC233650
0.9742 High Similarity NPC134858
0.9618 High Similarity NPC210140
0.949 High Similarity NPC169743
0.9167 High Similarity NPC244112
0.9161 High Similarity NPC26601
0.9108 High Similarity NPC186063
0.9091 High Similarity NPC219162
0.9042 High Similarity NPC248642
0.9036 High Similarity NPC126284
0.9026 High Similarity NPC130941
0.9 High Similarity NPC60186
0.8988 High Similarity NPC156576
0.8961 High Similarity NPC90844
0.8961 High Similarity NPC95075
0.8961 High Similarity NPC253883
0.8957 High Similarity NPC160570
0.8795 High Similarity NPC2314
0.8788 High Similarity NPC329911
0.878 High Similarity NPC474931
0.878 High Similarity NPC117188
0.878 High Similarity NPC81218
0.878 High Similarity NPC205421
0.878 High Similarity NPC158376
0.878 High Similarity NPC12053
0.878 High Similarity NPC145832
0.878 High Similarity NPC306555
0.8773 High Similarity NPC78222
0.8773 High Similarity NPC136508
0.8773 High Similarity NPC96603
0.8773 High Similarity NPC196447
0.8773 High Similarity NPC212794
0.8773 High Similarity NPC306843
0.8773 High Similarity NPC13504
0.8773 High Similarity NPC477563
0.8773 High Similarity NPC76116
0.8773 High Similarity NPC253043
0.8772 High Similarity NPC214116
0.8758 High Similarity NPC59028
0.8758 High Similarity NPC92191
0.8726 High Similarity NPC92541
0.8712 High Similarity NPC324144
0.8704 High Similarity NPC205167
0.8704 High Similarity NPC249274
0.8696 High Similarity NPC476572
0.8688 High Similarity NPC99659
0.8688 High Similarity NPC325871
0.8639 High Similarity NPC320223
0.8639 High Similarity NPC148693
0.8639 High Similarity NPC118633
0.8639 High Similarity NPC294790
0.8639 High Similarity NPC114364
0.8631 High Similarity NPC199465
0.8631 High Similarity NPC229166
0.8631 High Similarity NPC128560
0.8623 High Similarity NPC477640
0.8623 High Similarity NPC225597
0.8623 High Similarity NPC470739
0.8614 High Similarity NPC475686
0.8614 High Similarity NPC158148
0.8614 High Similarity NPC266176
0.8614 High Similarity NPC164429
0.8614 High Similarity NPC82533
0.8614 High Similarity NPC58766
0.8614 High Similarity NPC290759
0.8606 High Similarity NPC476432
0.8606 High Similarity NPC24264
0.8599 High Similarity NPC144863
0.8598 High Similarity NPC1229
0.8596 High Similarity NPC476575
0.859 High Similarity NPC185838
0.8589 High Similarity NPC27410
0.8589 High Similarity NPC166014
0.8571 High Similarity NPC76079
0.8563 High Similarity NPC474475
0.8554 High Similarity NPC298979
0.8554 High Similarity NPC247389
0.8545 High Similarity NPC225774
0.8545 High Similarity NPC16805
0.8545 High Similarity NPC167546
0.8545 High Similarity NPC302527
0.8544 High Similarity NPC147390
0.8544 High Similarity NPC246587
0.8544 High Similarity NPC135538
0.8544 High Similarity NPC476571
0.8544 High Similarity NPC428
0.8544 High Similarity NPC24233
0.8519 High Similarity NPC147091
0.8512 High Similarity NPC239775
0.85 High Similarity NPC81733
0.85 High Similarity NPC326316
0.8494 Intermediate Similarity NPC219341
0.8481 Intermediate Similarity NPC321505
0.8481 Intermediate Similarity NPC191376
0.8481 Intermediate Similarity NPC179825
0.8481 Intermediate Similarity NPC476151
0.8476 Intermediate Similarity NPC119649
0.8476 Intermediate Similarity NPC230956
0.8476 Intermediate Similarity NPC205255
0.8476 Intermediate Similarity NPC271388
0.8476 Intermediate Similarity NPC235143
0.8471 Intermediate Similarity NPC241704
0.8466 Intermediate Similarity NPC117717
0.8462 Intermediate Similarity NPC192135
0.8462 Intermediate Similarity NPC477020
0.8462 Intermediate Similarity NPC66341
0.8452 Intermediate Similarity NPC477562
0.8452 Intermediate Similarity NPC168753
0.8452 Intermediate Similarity NPC474915
0.8452 Intermediate Similarity NPC213206
0.8452 Intermediate Similarity NPC328750
0.8452 Intermediate Similarity NPC188163
0.8452 Intermediate Similarity NPC118274
0.8452 Intermediate Similarity NPC69712
0.8452 Intermediate Similarity NPC26240
0.8443 Intermediate Similarity NPC100566
0.8443 Intermediate Similarity NPC190332
0.8443 Intermediate Similarity NPC210918
0.8443 Intermediate Similarity NPC181653
0.8438 Intermediate Similarity NPC220858
0.8438 Intermediate Similarity NPC151895
0.8438 Intermediate Similarity NPC192768
0.8438 Intermediate Similarity NPC274026
0.8438 Intermediate Similarity NPC97221
0.8438 Intermediate Similarity NPC88249
0.8424 Intermediate Similarity NPC80759
0.8424 Intermediate Similarity NPC79402
0.8415 Intermediate Similarity NPC221864
0.8387 Intermediate Similarity NPC314682
0.8382 Intermediate Similarity NPC116284
0.8375 Intermediate Similarity NPC103379
0.8375 Intermediate Similarity NPC477565
0.8373 Intermediate Similarity NPC320104
0.8372 Intermediate Similarity NPC32154
0.8372 Intermediate Similarity NPC220961
0.8372 Intermediate Similarity NPC267408
0.8364 Intermediate Similarity NPC266753
0.8364 Intermediate Similarity NPC160298
0.8364 Intermediate Similarity NPC232924
0.8364 Intermediate Similarity NPC477559
0.8364 Intermediate Similarity NPC306902
0.8363 Intermediate Similarity NPC474470
0.8344 Intermediate Similarity NPC207757
0.8344 Intermediate Similarity NPC278799
0.8344 Intermediate Similarity NPC193949
0.8344 Intermediate Similarity NPC476567
0.8344 Intermediate Similarity NPC469817
0.8344 Intermediate Similarity NPC110416
0.8344 Intermediate Similarity NPC5238
0.8344 Intermediate Similarity NPC39701
0.8344 Intermediate Similarity NPC172765
0.8344 Intermediate Similarity NPC54379
0.8344 Intermediate Similarity NPC128019
0.8344 Intermediate Similarity NPC276588
0.8344 Intermediate Similarity NPC189266
0.8344 Intermediate Similarity NPC127674
0.8344 Intermediate Similarity NPC2413
0.8344 Intermediate Similarity NPC249797
0.8344 Intermediate Similarity NPC184026
0.8344 Intermediate Similarity NPC295691
0.8344 Intermediate Similarity NPC204828
0.8344 Intermediate Similarity NPC136860
0.8333 Intermediate Similarity NPC135772
0.8324 Intermediate Similarity NPC477561
0.8324 Intermediate Similarity NPC476574
0.8324 Intermediate Similarity NPC155442
0.8324 Intermediate Similarity NPC312918
0.8313 Intermediate Similarity NPC475959
0.8304 Intermediate Similarity NPC477558
0.8303 Intermediate Similarity NPC477080
0.8303 Intermediate Similarity NPC111485
0.8295 Intermediate Similarity NPC237579
0.8294 Intermediate Similarity NPC149090
0.8294 Intermediate Similarity NPC19520
0.8276 Intermediate Similarity NPC275132
0.8276 Intermediate Similarity NPC233718
0.8274 Intermediate Similarity NPC264850
0.8274 Intermediate Similarity NPC81247
0.8274 Intermediate Similarity NPC124657
0.8274 Intermediate Similarity NPC476573
0.8274 Intermediate Similarity NPC35627
0.8274 Intermediate Similarity NPC13916
0.8274 Intermediate Similarity NPC195392
0.8266 Intermediate Similarity NPC474507
0.8266 Intermediate Similarity NPC244554
0.8261 Intermediate Similarity NPC207824
0.8261 Intermediate Similarity NPC60538
0.8261 Intermediate Similarity NPC211296
0.8256 Intermediate Similarity NPC237044
0.8253 Intermediate Similarity NPC4304
0.8253 Intermediate Similarity NPC97072
0.8253 Intermediate Similarity NPC215829
0.825 Intermediate Similarity NPC51957
0.825 Intermediate Similarity NPC16107
0.825 Intermediate Similarity NPC210437
0.825 Intermediate Similarity NPC106295
0.825 Intermediate Similarity NPC476144
0.8235 Intermediate Similarity NPC6152
0.8235 Intermediate Similarity NPC311991
0.8232 Intermediate Similarity NPC123323

  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 NPC150879 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
0.8868 High Similarity NPD6818 Clinical (unspecified phase)
0.8485 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8452 Intermediate Similarity NPD4664 Clinical (unspecified phase)
0.8408 Intermediate Similarity NPD5241 Discontinued
0.8383 Intermediate Similarity NPD3051 Approved
0.8333 Intermediate Similarity NPD2970 Approved
0.8333 Intermediate Similarity NPD2969 Approved
0.825 Intermediate Similarity NPD4584 Approved
0.8176 Intermediate Similarity NPD2489 Approved
0.8176 Intermediate Similarity NPD27 Approved
0.8166 Intermediate Similarity NPD6071 Discontinued
0.8165 Intermediate Similarity NPD4237 Approved
0.8165 Intermediate Similarity NPD4236 Phase 3
0.8144 Intermediate Similarity NPD7833 Phase 2
0.8144 Intermediate Similarity NPD7831 Phase 2
0.8144 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.8136 Intermediate Similarity NPD7906 Approved
0.8133 Intermediate Similarity NPD2560 Approved
0.8133 Intermediate Similarity NPD2563 Approved
0.8084 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD4663 Approved
0.8061 Intermediate Similarity NPD4773 Phase 2
0.8061 Intermediate Similarity NPD4772 Phase 2
0.8012 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.8011 Intermediate Similarity NPD4577 Approved
0.8011 Intermediate Similarity NPD4578 Approved
0.7966 Intermediate Similarity NPD8053 Approved
0.7966 Intermediate Similarity NPD8054 Approved
0.7937 Intermediate Similarity NPD3060 Approved
0.7931 Intermediate Similarity NPD8156 Discontinued
0.7874 Intermediate Similarity NPD8252 Approved
0.7874 Intermediate Similarity NPD8251 Approved
0.7874 Intermediate Similarity NPD8099 Discontinued
0.787 Intermediate Similarity NPD6788 Approved
0.7861 Intermediate Similarity NPD4481 Phase 3
0.7853 Intermediate Similarity NPD2420 Approved
0.7853 Intermediate Similarity NPD2421 Approved
0.7831 Intermediate Similarity NPD4017 Approved
0.7818 Intermediate Similarity NPD6030 Approved
0.7818 Intermediate Similarity NPD6031 Approved
0.7809 Intermediate Similarity NPD7311 Approved
0.7809 Intermediate Similarity NPD7312 Approved
0.7809 Intermediate Similarity NPD7313 Approved
0.7809 Intermediate Similarity NPD7310 Approved
0.7798 Intermediate Similarity NPD7298 Approved
0.7791 Intermediate Similarity NPD3845 Phase 1
0.7778 Intermediate Similarity NPD7400 Phase 3
0.7772 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD7309 Approved
0.7764 Intermediate Similarity NPD7037 Approved
0.7759 Intermediate Similarity NPD2898 Approved
0.7751 Intermediate Similarity NPD5773 Approved
0.7751 Intermediate Similarity NPD2977 Approved
0.7751 Intermediate Similarity NPD2978 Approved
0.7751 Intermediate Similarity NPD5772 Approved
0.7746 Intermediate Similarity NPD4010 Discontinued
0.773 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7634 Intermediate Similarity NPD2973 Approved
0.7634 Intermediate Similarity NPD2975 Approved
0.7634 Intermediate Similarity NPD2974 Approved
0.7622 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD5177 Phase 3
0.7605 Intermediate Similarity NPD3641 Approved
0.7605 Intermediate Similarity NPD3640 Phase 3
0.7605 Intermediate Similarity NPD3639 Approved
0.759 Intermediate Similarity NPD4123 Phase 3
0.759 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD7802 Discontinued
0.7578 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD5709 Phase 3
0.7566 Intermediate Similarity NPD3450 Approved
0.7566 Intermediate Similarity NPD2493 Approved
0.7566 Intermediate Similarity NPD2494 Approved
0.7566 Intermediate Similarity NPD3452 Approved
0.7556 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD2488 Approved
0.7554 Intermediate Similarity NPD2490 Approved
0.7545 Intermediate Similarity NPD6090 Discontinued
0.7542 Intermediate Similarity NPD6297 Approved
0.7532 Intermediate Similarity NPD5718 Phase 2
0.7529 Intermediate Similarity NPD4666 Phase 3
0.7515 Intermediate Similarity NPD4005 Discontinued
0.7514 Intermediate Similarity NPD2971 Approved
0.7514 Intermediate Similarity NPD2968 Approved
0.7513 Intermediate Similarity NPD4580 Approved
0.75 Intermediate Similarity NPD4162 Approved
0.75 Intermediate Similarity NPD5976 Discontinued
0.7487 Intermediate Similarity NPD5582 Discontinued
0.7486 Intermediate Similarity NPD6107 Approved
0.7473 Intermediate Similarity NPD6853 Approved
0.7473 Intermediate Similarity NPD6851 Approved
0.7468 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7456 Intermediate Similarity NPD4210 Discontinued
0.7448 Intermediate Similarity NPD4583 Approved
0.7448 Intermediate Similarity NPD4582 Approved
0.7446 Intermediate Similarity NPD7243 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD3110 Approved
0.7438 Intermediate Similarity NPD3109 Approved
0.7421 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD4420 Approved
0.7405 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD7039 Approved
0.7403 Intermediate Similarity NPD7038 Approved
0.7401 Intermediate Similarity NPD6687 Approved
0.7401 Intermediate Similarity NPD6688 Approved
0.7396 Intermediate Similarity NPD4004 Approved
0.7396 Intermediate Similarity NPD4002 Approved
0.7375 Intermediate Similarity NPD4475 Approved
0.7375 Intermediate Similarity NPD4474 Approved
0.7368 Intermediate Similarity NPD4678 Approved
0.7368 Intermediate Similarity NPD4675 Approved
0.7365 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD1753 Discontinued
0.7349 Intermediate Similarity NPD6331 Phase 2
0.7348 Intermediate Similarity NPD6996 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD4579 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD4166 Phase 2
0.7333 Intermediate Similarity NPD42 Phase 2
0.7333 Intermediate Similarity NPD6042 Phase 2
0.7329 Intermediate Similarity NPD2238 Phase 2
0.7325 Intermediate Similarity NPD4104 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD4103 Phase 2
0.7321 Intermediate Similarity NPD7213 Phase 3
0.7321 Intermediate Similarity NPD7212 Phase 2
0.7318 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD4055 Discovery
0.7314 Intermediate Similarity NPD5604 Discontinued
0.7308 Intermediate Similarity NPD4659 Approved
0.7301 Intermediate Similarity NPD6895 Approved
0.7301 Intermediate Similarity NPD6896 Approved
0.7291 Intermediate Similarity NPD6997 Phase 2
0.7283 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD7447 Phase 1
0.7273 Intermediate Similarity NPD3808 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD6607 Clinical (unspecified phase)
0.7262 Intermediate Similarity NPD7124 Phase 2
0.7262 Intermediate Similarity NPD6666 Approved
0.7262 Intermediate Similarity NPD6667 Approved
0.7261 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD5006 Approved
0.7254 Intermediate Similarity NPD5005 Approved
0.7251 Intermediate Similarity NPD3687 Approved
0.7251 Intermediate Similarity NPD3686 Approved
0.725 Intermediate Similarity NPD7047 Phase 3
0.7232 Intermediate Similarity NPD5677 Discontinued
0.7225 Intermediate Similarity NPD7438 Suspended
0.7225 Intermediate Similarity NPD6072 Discontinued
0.7222 Intermediate Similarity NPD5938 Phase 3
0.7219 Intermediate Similarity NPD3124 Discontinued
0.7205 Intermediate Similarity NPD7294 Phase 1
0.7202 Intermediate Similarity NPD2677 Approved
0.7202 Intermediate Similarity NPD5160 Discontinued
0.72 Intermediate Similarity NPD5978 Approved
0.72 Intermediate Similarity NPD5977 Approved
0.7193 Intermediate Similarity NPD2122 Discontinued
0.7189 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD7019 Approved
0.7176 Intermediate Similarity NPD1424 Approved
0.7176 Intermediate Similarity NPD7020 Approved
0.7174 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD6584 Phase 3
0.7169 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD4726 Approved
0.7169 Intermediate Similarity NPD7030 Discontinued
0.7169 Intermediate Similarity NPD4725 Approved
0.7169 Intermediate Similarity NPD4721 Approved
0.7165 Intermediate Similarity NPD3057 Approved
0.716 Intermediate Similarity NPD2674 Phase 3
0.7151 Intermediate Similarity NPD6747 Phase 1
0.7143 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5312 Approved
0.7143 Intermediate Similarity NPD7466 Approved
0.7143 Intermediate Similarity NPD5155 Approved
0.7143 Intermediate Similarity NPD5156 Approved
0.7143 Intermediate Similarity NPD6748 Discontinued
0.7143 Intermediate Similarity NPD5313 Approved
0.7135 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7280 Phase 3
0.7135 Intermediate Similarity NPD2041 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD2042 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7281 Phase 3
0.7134 Intermediate Similarity NPD823 Approved
0.7134 Intermediate Similarity NPD3052 Approved
0.7134 Intermediate Similarity NPD817 Approved
0.7134 Intermediate Similarity NPD3054 Approved
0.7118 Intermediate Similarity NPD7598 Phase 2
0.7117 Intermediate Similarity NPD3062 Approved
0.7117 Intermediate Similarity NPD3059 Approved
0.7117 Intermediate Similarity NPD3061 Approved
0.7108 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD7262 Phase 1
0.7104 Intermediate Similarity NPD7479 Phase 2
0.7102 Intermediate Similarity NPD6063 Approved
0.7101 Intermediate Similarity NPD3692 Discontinued
0.7098 Intermediate Similarity NPD8095 Phase 1

  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