Structure

Physi-Chem Properties

Molecular Weight:  362.25
Volume:  384.73
LogP:  3.999
LogD:  4.118
LogS:  -4.28
# Rotatable Bonds:  2
TPSA:  44.76
# H-Bond Aceptor:  4
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.52
Synthetic Accessibility Score:  6.106
Fsp3:  0.864
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:  -4.656
MDCK Permeability:  5.5645858083153144e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.442

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.313
Plasma Protein Binding (PPB):  91.613037109375%
Volume Distribution (VD):  1.891
Pgp-substrate:  8.037400245666504%

ADMET: Metabolism

CYP1A2-inhibitor:  0.07
CYP1A2-substrate:  0.338
CYP2C19-inhibitor:  0.025
CYP2C19-substrate:  0.898
CYP2C9-inhibitor:  0.063
CYP2C9-substrate:  0.031
CYP2D6-inhibitor:  0.019
CYP2D6-substrate:  0.462
CYP3A4-inhibitor:  0.639
CYP3A4-substrate:  0.529

ADMET: Excretion

Clearance (CL):  9.558
Half-life (T1/2):  0.831

ADMET: Toxicity

hERG Blockers:  0.361
Human Hepatotoxicity (H-HT):  0.918
Drug-inuced Liver Injury (DILI):  0.848
AMES Toxicity:  0.031
Rat Oral Acute Toxicity:  0.197
Maximum Recommended Daily Dose:  0.028
Skin Sensitization:  0.741
Carcinogencity:  0.147
Eye Corrosion:  0.397
Eye Irritation:  0.104
Respiratory Toxicity:  0.973

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

  Natural Product: NPC214315

Natural Product ID:  NPC214315
Common Name*:   MDSDQZGJBVBIFN-DDVYNGAOSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  MDSDQZGJBVBIFN-DDVYNGAOSA-N
Standard InCHI:  InChI=1S/C22H34O4/c1-12-7-6-8-22(5)21-18-16(14(3)11-24-22)10-13(2)20(25-15(4)23)19(18)17(9-12)26-21/h7,13-14,16-21H,6,8-11H2,1-5H3/b12-7-/t13-,14+,16+,17+,18+,19+,20-,21+,22+/m1/s1
SMILES:  C/C/1=C/CC[C@@]2(C)[C@@H]3[C@H]4[C@@H](C[C@@H](C)[C@H]([C@H]4[C@H](C1)O3)OC(=O)C)[C@@H](C)CO2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL524149
PubChem CID:   23427142
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001729] Oxepanes

*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
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. n.a. n.a. PMID[12662092]
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. Caribbean n.a. PMID[1686898]
NPO15275 Briareum asbestinum Species Briareidae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 56234.13 nM PMID[521583]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[521583]
NPT27 Others Unspecified ED50 = 4.82 ug ml-1 PMID[521582]

☑ 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 NPC214315 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
0.9195 High Similarity NPC476716
0.8929 High Similarity NPC476725
0.8876 High Similarity NPC476720
0.869 High Similarity NPC127917
0.8621 High Similarity NPC476724
0.8621 High Similarity NPC476723
0.8391 Intermediate Similarity NPC475684
0.8295 Intermediate Similarity NPC44538
0.8202 Intermediate Similarity NPC75443
0.8202 Intermediate Similarity NPC92370
0.8202 Intermediate Similarity NPC470260
0.8202 Intermediate Similarity NPC309656
0.8152 Intermediate Similarity NPC476722
0.8148 Intermediate Similarity NPC476718
0.8111 Intermediate Similarity NPC291875
0.8111 Intermediate Similarity NPC161560
0.8105 Intermediate Similarity NPC272223
0.8095 Intermediate Similarity NPC264610
0.8068 Intermediate Similarity NPC196911
0.8068 Intermediate Similarity NPC471379
0.8046 Intermediate Similarity NPC5958
0.8043 Intermediate Similarity NPC477615
0.8023 Intermediate Similarity NPC118116
0.8 Intermediate Similarity NPC470067
0.8 Intermediate Similarity NPC470066
0.7935 Intermediate Similarity NPC312805
0.7935 Intermediate Similarity NPC91251
0.7935 Intermediate Similarity NPC165180
0.7927 Intermediate Similarity NPC123122
0.7841 Intermediate Similarity NPC239308
0.7826 Intermediate Similarity NPC471378
0.7826 Intermediate Similarity NPC312471
0.7816 Intermediate Similarity NPC77003
0.7766 Intermediate Similarity NPC96736
0.7766 Intermediate Similarity NPC178949
0.7765 Intermediate Similarity NPC476719
0.7742 Intermediate Similarity NPC122057
0.7742 Intermediate Similarity NPC208839
0.7742 Intermediate Similarity NPC8729
0.7738 Intermediate Similarity NPC93213
0.7738 Intermediate Similarity NPC12696
0.7727 Intermediate Similarity NPC103171
0.7717 Intermediate Similarity NPC246028
0.7708 Intermediate Similarity NPC473244
0.7692 Intermediate Similarity NPC264546
0.7684 Intermediate Similarity NPC471362
0.7684 Intermediate Similarity NPC472189
0.7684 Intermediate Similarity NPC471372
0.7667 Intermediate Similarity NPC290731
0.7653 Intermediate Similarity NPC475767
0.7653 Intermediate Similarity NPC472554
0.7653 Intermediate Similarity NPC119467
0.7629 Intermediate Similarity NPC470068
0.7614 Intermediate Similarity NPC25554
0.7609 Intermediate Similarity NPC106332
0.7604 Intermediate Similarity NPC171598
0.7604 Intermediate Similarity NPC475178
0.7582 Intermediate Similarity NPC102996
0.7579 Intermediate Similarity NPC140277
0.7576 Intermediate Similarity NPC472552
0.7553 Intermediate Similarity NPC210268
0.7551 Intermediate Similarity NPC38855
0.7529 Intermediate Similarity NPC36479
0.7527 Intermediate Similarity NPC170633
0.7526 Intermediate Similarity NPC475033
0.7526 Intermediate Similarity NPC111348
0.7526 Intermediate Similarity NPC475032
0.7526 Intermediate Similarity NPC472188
0.75 Intermediate Similarity NPC475334
0.75 Intermediate Similarity NPC102640
0.75 Intermediate Similarity NPC475623
0.75 Intermediate Similarity NPC86893
0.75 Intermediate Similarity NPC474575
0.75 Intermediate Similarity NPC473694
0.75 Intermediate Similarity NPC189777
0.75 Intermediate Similarity NPC474739
0.75 Intermediate Similarity NPC292178
0.75 Intermediate Similarity NPC166857
0.75 Intermediate Similarity NPC276110
0.75 Intermediate Similarity NPC469802
0.7475 Intermediate Similarity NPC470054
0.7475 Intermediate Similarity NPC475617
0.7474 Intermediate Similarity NPC473678
0.7474 Intermediate Similarity NPC7349
0.7449 Intermediate Similarity NPC477876
0.7449 Intermediate Similarity NPC476800
0.7449 Intermediate Similarity NPC472186
0.7449 Intermediate Similarity NPC471366
0.7449 Intermediate Similarity NPC477875
0.7449 Intermediate Similarity NPC318917
0.7442 Intermediate Similarity NPC293223
0.7442 Intermediate Similarity NPC136424
0.7426 Intermediate Similarity NPC470061
0.7426 Intermediate Similarity NPC470064
0.7426 Intermediate Similarity NPC80809
0.7426 Intermediate Similarity NPC470060
0.7426 Intermediate Similarity NPC31430
0.7426 Intermediate Similarity NPC470058
0.7426 Intermediate Similarity NPC474550
0.7426 Intermediate Similarity NPC475585
0.7426 Intermediate Similarity NPC85593
0.7426 Intermediate Similarity NPC201144
0.7426 Intermediate Similarity NPC103298
0.7426 Intermediate Similarity NPC473543
0.7426 Intermediate Similarity NPC470057
0.7426 Intermediate Similarity NPC470043
0.7426 Intermediate Similarity NPC288502
0.7426 Intermediate Similarity NPC475335
0.7426 Intermediate Similarity NPC121518
0.7426 Intermediate Similarity NPC181104
0.7426 Intermediate Similarity NPC473577
0.7426 Intermediate Similarity NPC475331
0.7426 Intermediate Similarity NPC470062
0.7426 Intermediate Similarity NPC470059
0.7423 Intermediate Similarity NPC284194
0.7423 Intermediate Similarity NPC209297
0.7423 Intermediate Similarity NPC475380
0.7423 Intermediate Similarity NPC211810
0.7423 Intermediate Similarity NPC471765
0.7423 Intermediate Similarity NPC471903
0.7423 Intermediate Similarity NPC475304
0.7423 Intermediate Similarity NPC194132
0.7423 Intermediate Similarity NPC8954
0.7423 Intermediate Similarity NPC221801
0.7423 Intermediate Similarity NPC94905
0.7419 Intermediate Similarity NPC470612
0.7419 Intermediate Similarity NPC93411
0.7419 Intermediate Similarity NPC69713
0.7419 Intermediate Similarity NPC470613
0.74 Intermediate Similarity NPC11956
0.74 Intermediate Similarity NPC470053
0.74 Intermediate Similarity NPC476471
0.74 Intermediate Similarity NPC470972
0.74 Intermediate Similarity NPC475344
0.7396 Intermediate Similarity NPC472360
0.7396 Intermediate Similarity NPC472416
0.7396 Intermediate Similarity NPC161998
0.7396 Intermediate Similarity NPC105490
0.7396 Intermediate Similarity NPC211238
0.7391 Intermediate Similarity NPC476217
0.7391 Intermediate Similarity NPC322922
0.7391 Intermediate Similarity NPC321812
0.7379 Intermediate Similarity NPC38948
0.7374 Intermediate Similarity NPC473204
0.7374 Intermediate Similarity NPC188968
0.7374 Intermediate Similarity NPC472187
0.7374 Intermediate Similarity NPC473545
0.7368 Intermediate Similarity NPC473675
0.7363 Intermediate Similarity NPC471367
0.7363 Intermediate Similarity NPC222634
0.7363 Intermediate Similarity NPC102048
0.7353 Intermediate Similarity NPC60315
0.7353 Intermediate Similarity NPC475290
0.7347 Intermediate Similarity NPC113976
0.7347 Intermediate Similarity NPC254121
0.7347 Intermediate Similarity NPC100912
0.7347 Intermediate Similarity NPC198549
0.7347 Intermediate Similarity NPC311241
0.7347 Intermediate Similarity NPC475446
0.7347 Intermediate Similarity NPC120446
0.734 Intermediate Similarity NPC97103
0.734 Intermediate Similarity NPC471222
0.734 Intermediate Similarity NPC261320
0.734 Intermediate Similarity NPC115607
0.7327 Intermediate Similarity NPC474124
0.7327 Intermediate Similarity NPC23584
0.7327 Intermediate Similarity NPC473523
0.7327 Intermediate Similarity NPC120009
0.732 Intermediate Similarity NPC230347
0.732 Intermediate Similarity NPC286612
0.732 Intermediate Similarity NPC275310
0.7308 Intermediate Similarity NPC206618
0.7303 Intermediate Similarity NPC233332
0.7303 Intermediate Similarity NPC269791
0.73 Intermediate Similarity NPC476132
0.73 Intermediate Similarity NPC11974
0.73 Intermediate Similarity NPC155974
0.7292 Intermediate Similarity NPC12297
0.7283 Intermediate Similarity NPC35933
0.7283 Intermediate Similarity NPC476602
0.7282 Intermediate Similarity NPC475510
0.7282 Intermediate Similarity NPC293512
0.7282 Intermediate Similarity NPC475587
0.7273 Intermediate Similarity NPC43463
0.7273 Intermediate Similarity NPC300179
0.7273 Intermediate Similarity NPC107806
0.7273 Intermediate Similarity NPC102426
0.7273 Intermediate Similarity NPC3852
0.7273 Intermediate Similarity NPC252483
0.7273 Intermediate Similarity NPC191345
0.7273 Intermediate Similarity NPC477928
0.7273 Intermediate Similarity NPC72647
0.7264 Intermediate Similarity NPC474516
0.7263 Intermediate Similarity NPC470832
0.7263 Intermediate Similarity NPC209816
0.7263 Intermediate Similarity NPC48732
0.7263 Intermediate Similarity NPC220216
0.7253 Intermediate Similarity NPC132386
0.7253 Intermediate Similarity NPC49208
0.7253 Intermediate Similarity NPC476721

  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 NPC214315 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
0.72 Intermediate Similarity NPD6648 Approved
0.7129 Intermediate Similarity NPD5344 Discontinued
0.6907 Remote Similarity NPD3168 Discontinued
0.6857 Remote Similarity NPD6008 Approved
0.6765 Remote Similarity NPD7638 Approved
0.6765 Remote Similarity NPD4225 Approved
0.6699 Remote Similarity NPD7640 Approved
0.6699 Remote Similarity NPD7639 Approved
0.66 Remote Similarity NPD6399 Phase 3
0.6571 Remote Similarity NPD3653 Clinical (unspecified phase)
0.6559 Remote Similarity NPD7525 Registered
0.6535 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6535 Remote Similarity NPD7900 Approved
0.6491 Remote Similarity NPD7327 Approved
0.6491 Remote Similarity NPD7328 Approved
0.6481 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6466 Remote Similarity NPD8033 Approved
0.6465 Remote Similarity NPD1695 Approved
0.6465 Remote Similarity NPD6051 Approved
0.6458 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6435 Remote Similarity NPD7516 Approved
0.6429 Remote Similarity NPD7524 Approved
0.64 Remote Similarity NPD7838 Discovery
0.64 Remote Similarity NPD46 Approved
0.64 Remote Similarity NPD6698 Approved
0.6392 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6389 Remote Similarity NPD5739 Approved
0.6389 Remote Similarity NPD6402 Approved
0.6389 Remote Similarity NPD6675 Approved
0.6389 Remote Similarity NPD7128 Approved
0.6386 Remote Similarity NPD1145 Discontinued
0.6379 Remote Similarity NPD8294 Approved
0.6379 Remote Similarity NPD8377 Approved
0.6373 Remote Similarity NPD7748 Approved
0.6364 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6354 Remote Similarity NPD6695 Phase 3
0.6346 Remote Similarity NPD7902 Approved
0.6339 Remote Similarity NPD6053 Discontinued
0.6339 Remote Similarity NPD8297 Approved
0.633 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6327 Remote Similarity NPD7521 Approved
0.6327 Remote Similarity NPD5330 Approved
0.6327 Remote Similarity NPD7334 Approved
0.6327 Remote Similarity NPD7146 Approved
0.6327 Remote Similarity NPD6409 Approved
0.6327 Remote Similarity NPD6684 Approved
0.6325 Remote Similarity NPD8335 Approved
0.6325 Remote Similarity NPD8379 Approved
0.6325 Remote Similarity NPD8378 Approved
0.6325 Remote Similarity NPD8296 Approved
0.6325 Remote Similarity NPD8380 Approved
0.6311 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6306 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6303 Remote Similarity NPD7492 Approved
0.6283 Remote Similarity NPD4632 Approved
0.6277 Remote Similarity NPD7645 Phase 2
0.6275 Remote Similarity NPD5778 Approved
0.6275 Remote Similarity NPD5779 Approved
0.6273 Remote Similarity NPD6899 Approved
0.6273 Remote Similarity NPD7320 Approved
0.6273 Remote Similarity NPD6686 Approved
0.6273 Remote Similarity NPD6881 Approved
0.6263 Remote Similarity NPD4251 Approved
0.6263 Remote Similarity NPD4250 Approved
0.625 Remote Similarity NPD6616 Approved
0.6239 Remote Similarity NPD6059 Approved
0.6239 Remote Similarity NPD6319 Approved
0.6239 Remote Similarity NPD6054 Approved
0.6239 Remote Similarity NPD5357 Phase 1
0.6216 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6216 Remote Similarity NPD6372 Approved
0.6216 Remote Similarity NPD6373 Approved
0.62 Remote Similarity NPD5737 Approved
0.62 Remote Similarity NPD6672 Approved
0.62 Remote Similarity NPD7513 Clinical (unspecified phase)
0.62 Remote Similarity NPD6903 Approved
0.6198 Remote Similarity NPD7078 Approved
0.6198 Remote Similarity NPD8293 Discontinued
0.6186 Remote Similarity NPD7503 Approved
0.6182 Remote Similarity NPD6412 Phase 2
0.6182 Remote Similarity NPD5697 Approved
0.6182 Remote Similarity NPD5701 Approved
0.6176 Remote Similarity NPD7637 Suspended
0.6176 Remote Similarity NPD8034 Phase 2
0.6176 Remote Similarity NPD8035 Phase 2
0.6176 Remote Similarity NPD7983 Approved
0.6176 Remote Similarity NPD7515 Phase 2
0.6162 Remote Similarity NPD4249 Approved
0.6161 Remote Similarity NPD6883 Approved
0.6161 Remote Similarity NPD7290 Approved
0.6161 Remote Similarity NPD7102 Approved
0.6148 Remote Similarity NPD7736 Approved
0.6139 Remote Similarity NPD6101 Approved
0.6139 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6134 Remote Similarity NPD6370 Approved
0.6126 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6121 Remote Similarity NPD6009 Approved
0.6121 Remote Similarity NPD7115 Discovery
0.6116 Remote Similarity NPD7507 Approved
0.6111 Remote Similarity NPD7632 Discontinued
0.6111 Remote Similarity NPD2686 Approved
0.6111 Remote Similarity NPD2687 Approved
0.6111 Remote Similarity NPD2254 Approved
0.6106 Remote Similarity NPD6617 Approved
0.6106 Remote Similarity NPD6649 Approved
0.6106 Remote Similarity NPD6869 Approved
0.6106 Remote Similarity NPD6847 Approved
0.6106 Remote Similarity NPD8130 Phase 1
0.6106 Remote Similarity NPD6650 Approved
0.61 Remote Similarity NPD7750 Discontinued
0.61 Remote Similarity NPD3573 Approved
0.6083 Remote Similarity NPD7604 Phase 2
0.6082 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6071 Remote Similarity NPD6013 Approved
0.6071 Remote Similarity NPD6014 Approved
0.6071 Remote Similarity NPD6012 Approved
0.6061 Remote Similarity NPD1694 Approved
0.6058 Remote Similarity NPD5282 Discontinued
0.6053 Remote Similarity NPD6882 Approved
0.605 Remote Similarity NPD8516 Approved
0.605 Remote Similarity NPD8515 Approved
0.605 Remote Similarity NPD6016 Approved
0.605 Remote Similarity NPD5983 Phase 2
0.605 Remote Similarity NPD8517 Approved
0.605 Remote Similarity NPD6015 Approved
0.605 Remote Similarity NPD8513 Phase 3
0.6042 Remote Similarity NPD4821 Approved
0.6042 Remote Similarity NPD4820 Approved
0.6042 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6042 Remote Similarity NPD6930 Phase 2
0.6042 Remote Similarity NPD4819 Approved
0.6042 Remote Similarity NPD4822 Approved
0.6042 Remote Similarity NPD6931 Approved
0.6038 Remote Similarity NPD6084 Phase 2
0.6038 Remote Similarity NPD6083 Phase 2
0.6022 Remote Similarity NPD7339 Approved
0.6022 Remote Similarity NPD6942 Approved
0.602 Remote Similarity NPD3670 Clinical (unspecified phase)
0.602 Remote Similarity NPD3669 Approved
0.6019 Remote Similarity NPD6411 Approved
0.6018 Remote Similarity NPD6371 Approved
0.6 Remote Similarity NPD8133 Approved
0.6 Remote Similarity NPD5695 Phase 3
0.6 Remote Similarity NPD6098 Approved
0.6 Remote Similarity NPD5988 Approved
0.5984 Remote Similarity NPD6336 Discontinued
0.5983 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5982 Remote Similarity NPD6011 Approved
0.5981 Remote Similarity NPD8029 Clinical (unspecified phase)
0.598 Remote Similarity NPD6904 Approved
0.598 Remote Similarity NPD6080 Approved
0.598 Remote Similarity NPD6673 Approved
0.5979 Remote Similarity NPD1780 Approved
0.5979 Remote Similarity NPD1779 Approved
0.5968 Remote Similarity NPD7319 Approved
0.5965 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5965 Remote Similarity NPD8413 Clinical (unspecified phase)
0.596 Remote Similarity NPD3668 Phase 3
0.596 Remote Similarity NPD4786 Approved
0.5957 Remote Similarity NPD3701 Clinical (unspecified phase)
0.5957 Remote Similarity NPD6933 Approved
0.595 Remote Similarity NPD8328 Phase 3
0.5938 Remote Similarity NPD6929 Approved
0.5918 Remote Similarity NPD6435 Approved
0.5918 Remote Similarity NPD3667 Approved
0.5914 Remote Similarity NPD6926 Approved
0.5914 Remote Similarity NPD6924 Approved
0.5909 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5905 Remote Similarity NPD6001 Approved
0.59 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5895 Remote Similarity NPD6932 Approved
0.5888 Remote Similarity NPD4755 Approved
0.5876 Remote Similarity NPD7509 Discontinued
0.5865 Remote Similarity NPD6050 Approved
0.5865 Remote Similarity NPD7087 Discontinued
0.5859 Remote Similarity NPD7154 Phase 3
0.5842 Remote Similarity NPD3618 Phase 1
0.5833 Remote Similarity NPD5696 Approved
0.5833 Remote Similarity NPD4268 Approved
0.5833 Remote Similarity NPD4271 Approved
0.5825 Remote Similarity NPD5328 Approved
0.582 Remote Similarity NPD6067 Discontinued
0.5816 Remote Similarity NPD5369 Approved
0.581 Remote Similarity NPD4202 Approved
0.5806 Remote Similarity NPD8074 Phase 3
0.5794 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5784 Remote Similarity NPD4751 Clinical (unspecified phase)
0.578 Remote Similarity NPD4696 Approved
0.578 Remote Similarity NPD5285 Approved
0.578 Remote Similarity NPD4700 Approved
0.578 Remote Similarity NPD5286 Approved
0.5773 Remote Similarity NPD6683 Phase 2
0.5769 Remote Similarity NPD5692 Phase 3
0.5769 Remote Similarity NPD5207 Approved
0.5763 Remote Similarity NPD6274 Approved
0.5761 Remote Similarity NPD7532 Clinical (unspecified phase)
0.576 Remote Similarity NPD6033 Approved
0.575 Remote Similarity NPD7101 Approved
0.575 Remote Similarity NPD7100 Approved
0.5745 Remote Similarity NPD1811 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