Structure

Physi-Chem Properties

Molecular Weight:  518.3
Volume:  540.801
LogP:  3.466
LogD:  3.094
LogS:  -3.765
# Rotatable Bonds:  4
TPSA:  140.34
# H-Bond Aceptor:  9
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.351
Synthetic Accessibility Score:  5.972
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.809
MDCK Permeability:  1.5176826309470925e-05
Pgp-inhibitor:  0.977
Pgp-substrate:  0.993
Human Intestinal Absorption (HIA):  0.898
20% Bioavailability (F20%):  0.016
30% Bioavailability (F30%):  0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.406
Plasma Protein Binding (PPB):  97.47340393066406%
Volume Distribution (VD):  0.691
Pgp-substrate:  2.6927883625030518%

ADMET: Metabolism

CYP1A2-inhibitor:  0.023
CYP1A2-substrate:  0.179
CYP2C19-inhibitor:  0.021
CYP2C19-substrate:  0.517
CYP2C9-inhibitor:  0.044
CYP2C9-substrate:  0.106
CYP2D6-inhibitor:  0.097
CYP2D6-substrate:  0.192
CYP3A4-inhibitor:  0.572
CYP3A4-substrate:  0.229

ADMET: Excretion

Clearance (CL):  12.865
Half-life (T1/2):  0.121

ADMET: Toxicity

hERG Blockers:  0.122
Human Hepatotoxicity (H-HT):  0.949
Drug-inuced Liver Injury (DILI):  0.912
AMES Toxicity:  0.578
Rat Oral Acute Toxicity:  0.244
Maximum Recommended Daily Dose:  0.901
Skin Sensitization:  0.597
Carcinogencity:  0.363
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.161

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

  Natural Product: NPC139506

Natural Product ID:  NPC139506
Common Name*:   [(3R,5S,6R,7S,8E,10S,11S,14E)-6,21-Dihydroxy-5,11-Dimethoxy-3,7,9,15-Tetramethyl-16-Oxo-17-Azabicyclo[16.3.1]Docosa-1(21),8,14,18(22),19-Pentaen-10-Yl] Carbamate
IUPAC Name:   [(3R,5S,6R,7S,8E,10S,11S,14E)-6,21-dihydroxy-5,11-dimethoxy-3,7,9,15-tetramethyl-16-oxo-17-azabicyclo[16.3.1]docosa-1(21),8,14,18(22),19-pentaen-10-yl] carbamate
Synonyms:  
Standard InCHIKey:  SIXVFZKPBRDLQR-LRFOCFGISA-N
Standard InCHI:  InChI=1S/C28H42N2O7/c1-16-12-20-15-21(10-11-22(20)31)30-27(33)17(2)8-7-9-23(35-5)26(37-28(29)34)19(4)14-18(3)25(32)24(13-16)36-6/h8,10-11,14-16,18,23-26,31-32H,7,9,12-13H2,1-6H3,(H2,29,34)(H,30,33)/b17-8+,19-14+/t16-,18+,23+,24+,25-,26+/m1/s1
SMILES:  C[C@@H]1Cc2cc(ccc2O)NC(=O)/C(=C/CC[C@@H]([C@H](/C(=C/[C@H](C)[C@H]([C@H](C1)OC)O)/C)OC(=N)O)OC)/C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL512489
PubChem CID:   24984995
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000064] Macrolactams

*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
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[14563159]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[15844961]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16378365]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16453790]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[16724461]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[17632514]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[19231864]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21486005]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[21504214]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[24224794]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[3170341]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[3819734]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[5549382]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[TCMID]
NPO13391 Streptomyces hygroscopicus Species Streptomycetaceae Bacteria 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
NPT134 Cell Line SK-BR-3 Homo sapiens IC50 = 835.0 nM PMID[493014]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 840.0 nM PMID[493014]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 1050.0 nM PMID[493014]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 610.0 nM PMID[493014]
NPT2335 Cell Line NCI-H596 IC50 = 1200.0 nM PMID[493014]
NPT918 Individual Protein Heat shock protein HSP 90-alpha Homo sapiens Kd = 0.8 nM PMID[493014]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 420.0 nM PMID[493014]

☑ 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 NPC139506 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 NPC292143
0.7892 Intermediate Similarity NPC72291
0.7647 Intermediate Similarity NPC238430
0.7616 Intermediate Similarity NPC310894
0.7582 Intermediate Similarity NPC101372
0.7514 Intermediate Similarity NPC469671
0.7514 Intermediate Similarity NPC126676
0.7273 Intermediate Similarity NPC225381
0.7181 Intermediate Similarity NPC222982
0.7169 Intermediate Similarity NPC146370
0.7081 Intermediate Similarity NPC295287
0.7062 Intermediate Similarity NPC471778
0.6971 Remote Similarity NPC199737
0.6946 Remote Similarity NPC323798
0.6914 Remote Similarity NPC320064
0.6909 Remote Similarity NPC204156
0.689 Remote Similarity NPC316574
0.6862 Remote Similarity NPC474059
0.6862 Remote Similarity NPC5630
0.6851 Remote Similarity NPC95412
0.6833 Remote Similarity NPC112336
0.6833 Remote Similarity NPC474814
0.6833 Remote Similarity NPC83241
0.6823 Remote Similarity NPC472191
0.6823 Remote Similarity NPC314948
0.6807 Remote Similarity NPC47986
0.6766 Remote Similarity NPC314113
0.6738 Remote Similarity NPC477391
0.6736 Remote Similarity NPC478049
0.6736 Remote Similarity NPC316282
0.6722 Remote Similarity NPC470971
0.6705 Remote Similarity NPC470082
0.6704 Remote Similarity NPC70172
0.6703 Remote Similarity NPC283810
0.6702 Remote Similarity NPC262725
0.67 Remote Similarity NPC298449
0.6687 Remote Similarity NPC313466
0.6667 Remote Similarity NPC25961
0.6651 Remote Similarity NPC314702
0.6634 Remote Similarity NPC126556
0.661 Remote Similarity NPC469428
0.6607 Remote Similarity NPC242933
0.6605 Remote Similarity NPC17374
0.6599 Remote Similarity NPC232600
0.6598 Remote Similarity NPC303214
0.6596 Remote Similarity NPC315934
0.6596 Remote Similarity NPC477392
0.6592 Remote Similarity NPC35510
0.6592 Remote Similarity NPC315498
0.6592 Remote Similarity NPC230942
0.6592 Remote Similarity NPC253667
0.6584 Remote Similarity NPC250476
0.6582 Remote Similarity NPC317727
0.6575 Remote Similarity NPC471652
0.6571 Remote Similarity NPC184161
0.6569 Remote Similarity NPC316181
0.6569 Remote Similarity NPC74562
0.6569 Remote Similarity NPC151781
0.6567 Remote Similarity NPC90185
0.6567 Remote Similarity NPC257728
0.6562 Remote Similarity NPC203628
0.6562 Remote Similarity NPC475411
0.6548 Remote Similarity NPC127178
0.6543 Remote Similarity NPC471785
0.6536 Remote Similarity NPC93653
0.6535 Remote Similarity NPC477160
0.6529 Remote Similarity NPC472241
0.6528 Remote Similarity NPC17160
0.6528 Remote Similarity NPC313720
0.6526 Remote Similarity NPC291759
0.6524 Remote Similarity NPC70092
0.6522 Remote Similarity NPC73280
0.6522 Remote Similarity NPC474479
0.652 Remote Similarity NPC119722
0.6517 Remote Similarity NPC257266
0.6517 Remote Similarity NPC478075
0.6512 Remote Similarity NPC472242
0.6509 Remote Similarity NPC181526
0.6508 Remote Similarity NPC320394
0.65 Remote Similarity NPC57105
0.65 Remote Similarity NPC14339
0.6488 Remote Similarity NPC287358
0.6485 Remote Similarity NPC207873
0.6485 Remote Similarity NPC100573
0.6484 Remote Similarity NPC19555
0.6484 Remote Similarity NPC182131
0.648 Remote Similarity NPC291359
0.648 Remote Similarity NPC301163
0.6476 Remote Similarity NPC148124
0.6474 Remote Similarity NPC133591
0.6471 Remote Similarity NPC474815
0.6467 Remote Similarity NPC470441
0.6467 Remote Similarity NPC85482
0.6462 Remote Similarity NPC243626
0.6462 Remote Similarity NPC230313
0.6461 Remote Similarity NPC10730
0.6461 Remote Similarity NPC10875
0.6458 Remote Similarity NPC316405
0.6457 Remote Similarity NPC144691
0.6453 Remote Similarity NPC153365
0.6444 Remote Similarity NPC231862
0.6441 Remote Similarity NPC256689
0.6441 Remote Similarity NPC123011
0.644 Remote Similarity NPC276674
0.644 Remote Similarity NPC33902
0.6436 Remote Similarity NPC222561
0.6436 Remote Similarity NPC85613
0.6433 Remote Similarity NPC204546
0.6432 Remote Similarity NPC472329
0.6432 Remote Similarity NPC248903
0.6432 Remote Similarity NPC472330
0.6429 Remote Similarity NPC99724
0.6424 Remote Similarity NPC231382
0.6422 Remote Similarity NPC269449
0.6417 Remote Similarity NPC220560
0.6413 Remote Similarity NPC469915
0.6413 Remote Similarity NPC257354
0.6412 Remote Similarity NPC197921
0.6412 Remote Similarity NPC472243
0.6412 Remote Similarity NPC314252
0.641 Remote Similarity NPC470485
0.6409 Remote Similarity NPC289776
0.6409 Remote Similarity NPC191863
0.6409 Remote Similarity NPC133470
0.6409 Remote Similarity NPC475983
0.6407 Remote Similarity NPC253476
0.6404 Remote Similarity NPC270811
0.6404 Remote Similarity NPC471073
0.6402 Remote Similarity NPC116096
0.64 Remote Similarity NPC311357
0.64 Remote Similarity NPC1464
0.64 Remote Similarity NPC475223
0.64 Remote Similarity NPC242000
0.6398 Remote Similarity NPC327070
0.6393 Remote Similarity NPC314861
0.6392 Remote Similarity NPC470483
0.639 Remote Similarity NPC9894
0.6387 Remote Similarity NPC313886
0.6385 Remote Similarity NPC26928
0.6383 Remote Similarity NPC472331
0.6383 Remote Similarity NPC126515
0.6383 Remote Similarity NPC274002
0.6374 Remote Similarity NPC158900
0.6374 Remote Similarity NPC204867
0.6374 Remote Similarity NPC91953
0.6373 Remote Similarity NPC477998
0.6373 Remote Similarity NPC320088
0.6369 Remote Similarity NPC173295
0.6368 Remote Similarity NPC475448
0.6368 Remote Similarity NPC246983
0.6364 Remote Similarity NPC311054
0.6364 Remote Similarity NPC71124
0.6364 Remote Similarity NPC100863
0.6364 Remote Similarity NPC290069
0.6364 Remote Similarity NPC168153
0.6364 Remote Similarity NPC129624
0.6364 Remote Similarity NPC112752
0.6354 Remote Similarity NPC156348
0.6354 Remote Similarity NPC38823
0.6354 Remote Similarity NPC207033
0.6353 Remote Similarity NPC471201
0.635 Remote Similarity NPC214368
0.6347 Remote Similarity NPC208757
0.6341 Remote Similarity NPC218323
0.634 Remote Similarity NPC474904
0.634 Remote Similarity NPC106833
0.634 Remote Similarity NPC469497
0.6337 Remote Similarity NPC87714
0.6332 Remote Similarity NPC90358
0.6332 Remote Similarity NPC107828
0.6331 Remote Similarity NPC6570
0.6329 Remote Similarity NPC217903
0.6327 Remote Similarity NPC45850
0.6327 Remote Similarity NPC471825
0.6324 Remote Similarity NPC126481
0.6319 Remote Similarity NPC85651
0.6316 Remote Similarity NPC231572
0.6316 Remote Similarity NPC150712
0.6316 Remote Similarity NPC472163
0.6316 Remote Similarity NPC76327
0.6308 Remote Similarity NPC28510
0.6305 Remote Similarity NPC477161
0.6301 Remote Similarity NPC308197
0.6301 Remote Similarity NPC272549
0.6301 Remote Similarity NPC266741
0.6298 Remote Similarity NPC160931
0.6298 Remote Similarity NPC37205
0.6298 Remote Similarity NPC471203
0.6296 Remote Similarity NPC325301
0.6294 Remote Similarity NPC198205
0.6294 Remote Similarity NPC166667
0.6294 Remote Similarity NPC21483
0.6292 Remote Similarity NPC219383
0.6292 Remote Similarity NPC39431
0.6289 Remote Similarity NPC128751
0.6289 Remote Similarity NPC229353
0.6289 Remote Similarity NPC246700
0.6287 Remote Similarity NPC207971
0.6284 Remote Similarity NPC313757
0.6283 Remote Similarity NPC314659

  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 NPC139506 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
0.7987 Intermediate Similarity NPD6636 Phase 3
0.7647 Intermediate Similarity NPD7129 Suspended
0.7611 Intermediate Similarity NPD7628 Phase 3
0.7611 Intermediate Similarity NPD7629 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD7630 Phase 3
0.7389 Intermediate Similarity NPD8167 Discontinued
0.7378 Intermediate Similarity NPD3141 Discontinued
0.7348 Intermediate Similarity NPD3153 Approved
0.7348 Intermediate Similarity NPD3154 Approved
0.7345 Intermediate Similarity NPD5334 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD822 Approved
0.7235 Intermediate Similarity NPD2672 Discontinued
0.7234 Intermediate Similarity NPD4668 Phase 2
0.7232 Intermediate Similarity NPD7324 Discontinued
0.7228 Intermediate Similarity NPD4258 Approved
0.7228 Intermediate Similarity NPD4259 Approved
0.7219 Intermediate Similarity NPD7880 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD1913 Phase 1
0.7052 Intermediate Similarity NPD6283 Phase 2
0.7048 Intermediate Similarity NPD2241 Approved
0.7029 Intermediate Similarity NPD3453 Discontinued
0.7022 Intermediate Similarity NPD4083 Discontinued
0.7011 Intermediate Similarity NPD3560 Approved
0.7011 Intermediate Similarity NPD3556 Approved
0.7011 Intermediate Similarity NPD3557 Approved
0.7011 Intermediate Similarity NPD3559 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD3558 Approved
0.7 Intermediate Similarity NPD2361 Approved
0.6978 Remote Similarity NPD6184 Discontinued
0.6964 Remote Similarity NPD1305 Clinical (unspecified phase)
0.6944 Remote Similarity NPD2359 Approved
0.6943 Remote Similarity NPD7476 Discontinued
0.694 Remote Similarity NPD5637 Discontinued
0.6931 Remote Similarity NPD5150 Phase 2
0.6909 Remote Similarity NPD3391 Approved
0.689 Remote Similarity NPD9279 Approved
0.6872 Remote Similarity NPD1839 Phase 1
0.6872 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6868 Remote Similarity NPD5560 Clinical (unspecified phase)
0.6866 Remote Similarity NPD4679 Discontinued
0.6862 Remote Similarity NPD5928 Phase 1
0.6857 Remote Similarity NPD2842 Clinical (unspecified phase)
0.6845 Remote Similarity NPD6793 Clinical (unspecified phase)
0.6839 Remote Similarity NPD2836 Approved
0.6828 Remote Similarity NPD6021 Clinical (unspecified phase)
0.6821 Remote Similarity NPD5086 Approved
0.6806 Remote Similarity NPD7256 Discontinued
0.6793 Remote Similarity NPD5445 Approved
0.6778 Remote Similarity NPD5183 Approved
0.6778 Remote Similarity NPD5186 Approved
0.6758 Remote Similarity NPD7449 Clinical (unspecified phase)
0.6754 Remote Similarity NPD7262 Phase 1
0.6746 Remote Similarity NPD1196 Approved
0.6746 Remote Similarity NPD2387 Approved
0.6744 Remote Similarity NPD9509 Clinical (unspecified phase)
0.6743 Remote Similarity NPD4255 Phase 1
0.6736 Remote Similarity NPD6162 Approved
0.6736 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6736 Remote Similarity NPD6161 Approved
0.6735 Remote Similarity NPD7316 Discontinued
0.6725 Remote Similarity NPD1543 Discontinued
0.6724 Remote Similarity NPD3229 Phase 2
0.672 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6704 Remote Similarity NPD1168 Approved
0.6704 Remote Similarity NPD4796 Discontinued
0.6703 Remote Similarity NPD6496 Clinical (unspecified phase)
0.6686 Remote Similarity NPD4430 Phase 2
0.6686 Remote Similarity NPD7528 Approved
0.6686 Remote Similarity NPD1195 Approved
0.6686 Remote Similarity NPD3684 Discontinued
0.6685 Remote Similarity NPD3793 Phase 3
0.6685 Remote Similarity NPD4871 Phase 2
0.6684 Remote Similarity NPD5582 Discontinued
0.6683 Remote Similarity NPD7584 Approved
0.6667 Remote Similarity NPD2162 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2791 Discontinued
0.6667 Remote Similarity NPD4003 Phase 3
0.6667 Remote Similarity NPD5823 Approved
0.6667 Remote Similarity NPD5506 Approved
0.6667 Remote Similarity NPD9694 Discovery
0.6667 Remote Similarity NPD7083 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5507 Approved
0.6667 Remote Similarity NPD4539 Phase 1
0.6667 Remote Similarity NPD1294 Discontinued
0.6649 Remote Similarity NPD5871 Discontinued
0.6649 Remote Similarity NPD4604 Approved
0.6649 Remote Similarity NPD4605 Approved
0.6648 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6648 Remote Similarity NPD2216 Approved
0.6648 Remote Similarity NPD2215 Approved
0.663 Remote Similarity NPD1544 Phase 1
0.6627 Remote Similarity NPD4597 Approved
0.6627 Remote Similarity NPD4598 Approved
0.6627 Remote Similarity NPD4168 Approved
0.6615 Remote Similarity NPD7570 Approved
0.6615 Remote Similarity NPD7569 Approved
0.6607 Remote Similarity NPD1422 Approved
0.6597 Remote Similarity NPD5896 Clinical (unspecified phase)
0.6592 Remote Similarity NPD1743 Approved
0.6592 Remote Similarity NPD19 Approved
0.6592 Remote Similarity NPD1742 Approved
0.6582 Remote Similarity NPD5609 Approved
0.6582 Remote Similarity NPD6874 Approved
0.6582 Remote Similarity NPD5608 Approved
0.6578 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6567 Remote Similarity NPD7585 Approved
0.6564 Remote Similarity NPD2952 Discontinued
0.6559 Remote Similarity NPD7479 Phase 2
0.6557 Remote Similarity NPD2388 Discontinued
0.6545 Remote Similarity NPD1594 Phase 3
0.6545 Remote Similarity NPD1595 Approved
0.6543 Remote Similarity NPD9723 Approved
0.6538 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6538 Remote Similarity NPD3983 Phase 3
0.6537 Remote Similarity NPD4897 Phase 2
0.6536 Remote Similarity NPD1012 Discontinued
0.6531 Remote Similarity NPD5071 Phase 2
0.6529 Remote Similarity NPD1908 Phase 2
0.6529 Remote Similarity NPD5719 Approved
0.6524 Remote Similarity NPD4274 Approved
0.6524 Remote Similarity NPD3720 Discontinued
0.6524 Remote Similarity NPD4275 Approved
0.6519 Remote Similarity NPD5430 Discontinued
0.6517 Remote Similarity NPD1861 Discovery
0.6517 Remote Similarity NPD7583 Approved
0.6517 Remote Similarity NPD3812 Clinical (unspecified phase)
0.6515 Remote Similarity NPD6604 Discontinued
0.6513 Remote Similarity NPD9376 Approved
0.6509 Remote Similarity NPD3605 Approved
0.6509 Remote Similarity NPD3068 Approved
0.6508 Remote Similarity NPD5895 Clinical (unspecified phase)
0.6505 Remote Similarity NPD5810 Discontinued
0.6503 Remote Similarity NPD1161 Approved
0.65 Remote Similarity NPD4465 Phase 2
0.65 Remote Similarity NPD4467 Phase 2
0.6495 Remote Similarity NPD5610 Approved
0.6494 Remote Similarity NPD4161 Discontinued
0.6492 Remote Similarity NPD4951 Discontinued
0.6491 Remote Similarity NPD1625 Approved
0.6486 Remote Similarity NPD5938 Phase 3
0.6486 Remote Similarity NPD5919 Clinical (unspecified phase)
0.6485 Remote Similarity NPD7302 Phase 3
0.6485 Remote Similarity NPD7300 Phase 3
0.648 Remote Similarity NPD6060 Clinical (unspecified phase)
0.648 Remote Similarity NPD6527 Approved
0.648 Remote Similarity NPD4514 Approved
0.6477 Remote Similarity NPD5641 Discontinued
0.6477 Remote Similarity NPD1678 Clinical (unspecified phase)
0.6474 Remote Similarity NPD4607 Approved
0.6474 Remote Similarity NPD6045 Phase 3
0.6467 Remote Similarity NPD2470 Clinical (unspecified phase)
0.6461 Remote Similarity NPD2366 Approved
0.6459 Remote Similarity NPD3437 Discontinued
0.6455 Remote Similarity NPD7883 Discontinued
0.6453 Remote Similarity NPD6506 Clinical (unspecified phase)
0.6447 Remote Similarity NPD5194 Approved
0.6447 Remote Similarity NPD5196 Approved
0.6447 Remote Similarity NPD5197 Approved
0.6443 Remote Similarity NPD3479 Discontinued
0.644 Remote Similarity NPD6339 Approved
0.644 Remote Similarity NPD6340 Approved
0.6437 Remote Similarity NPD2114 Discontinued
0.6436 Remote Similarity NPD6211 Clinical (unspecified phase)
0.6433 Remote Similarity NPD2578 Phase 3
0.6432 Remote Similarity NPD6238 Discontinued
0.6425 Remote Similarity NPD1769 Discontinued
0.6425 Remote Similarity NPD8149 Discontinued
0.642 Remote Similarity NPD8330 Clinical (unspecified phase)
0.6418 Remote Similarity NPD7891 Discontinued
0.6418 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6417 Remote Similarity NPD1170 Approved
0.6417 Remote Similarity NPD5498 Phase 2
0.6417 Remote Similarity NPD5521 Clinical (unspecified phase)
0.6413 Remote Similarity NPD5847 Phase 1
0.6406 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6406 Remote Similarity NPD4084 Clinical (unspecified phase)
0.6404 Remote Similarity NPD3296 Phase 1
0.6402 Remote Similarity NPD995 Clinical (unspecified phase)
0.6396 Remote Similarity NPD7491 Clinical (unspecified phase)
0.6383 Remote Similarity NPD5900 Clinical (unspecified phase)
0.6379 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6378 Remote Similarity NPD5680 Clinical (unspecified phase)
0.6378 Remote Similarity NPD3824 Phase 1
0.6374 Remote Similarity NPD3069 Approved
0.6369 Remote Similarity NPD7105 Phase 1
0.6368 Remote Similarity NPD6289 Clinical (unspecified phase)
0.6368 Remote Similarity NPD3912 Discontinued
0.6364 Remote Similarity NPD6877 Discontinued
0.6364 Remote Similarity NPD2737 Clinical (unspecified phase)
0.6364 Remote Similarity NPD4513 Discontinued
0.6359 Remote Similarity NPD2247 Approved
0.6359 Remote Similarity NPD6457 Approved
0.6359 Remote Similarity NPD3511 Discontinued
0.6359 Remote Similarity NPD5937 Approved
0.6359 Remote Similarity NPD2249 Approved
0.6359 Remote Similarity NPD2821 Approved
0.6355 Remote Similarity NPD7043 Discontinued
0.6355 Remote Similarity NPD7263 Phase 2
0.6349 Remote Similarity NPD6654 Clinical (unspecified phase)
0.6347 Remote 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