Structure

Physi-Chem Properties

Molecular Weight:  565.19
Volume:  548.632
LogP:  2.855
LogD:  1.198
LogS:  -2.785
# Rotatable Bonds:  2
TPSA:  204.68
# H-Bond Aceptor:  11
# H-Bond Donor:  7
# Rings:  6
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.226
Synthetic Accessibility Score:  5.74
Fsp3:  0.467
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.138
MDCK Permeability:  3.0587984838348348e-06
Pgp-inhibitor:  0.388
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.822
20% Bioavailability (F20%):  0.958
30% Bioavailability (F30%):  0.202

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.066
Plasma Protein Binding (PPB):  93.0040054321289%
Volume Distribution (VD):  1.609
Pgp-substrate:  4.22813606262207%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.912
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.363
CYP2C9-inhibitor:  0.028
CYP2C9-substrate:  0.192
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.109
CYP3A4-inhibitor:  0.361
CYP3A4-substrate:  0.431

ADMET: Excretion

Clearance (CL):  2.511
Half-life (T1/2):  0.031

ADMET: Toxicity

hERG Blockers:  0.003
Human Hepatotoxicity (H-HT):  0.116
Drug-inuced Liver Injury (DILI):  0.912
AMES Toxicity:  0.318
Rat Oral Acute Toxicity:  0.338
Maximum Recommended Daily Dose:  0.213
Skin Sensitization:  0.105
Carcinogencity:  0.045
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.961

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC289223

Natural Product ID:  NPC289223
Common Name*:   SUWQGLGDFGHZNH-WBWZXODPSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  SUWQGLGDFGHZNH-WBWZXODPSA-N
Standard InCHI:  InChI=1S/C30H31NO10/c1-11-6-5-7-27(2,3)28(11)9-12-16-18(13(32)8-15(41-4)21(16)28)22(34)20-17(12)23(35)29(39)10-14(33)19(26(31)38)24(36)30(29,40)25(20)37/h6,8,23,32-35,39-40H,5,7,9-10H2,1-4H3,(H2,31,38)/t23-,28-,29-,30+/m0/s1
SMILES:  COc1cc(O)c2c3c1[C@]1(Cc3c3c(c2O)C(=O)[C@]2([C@]([C@H]3O)(O)CC(=C(C2=O)C(=N)O)O)O)C(=CCCC1(C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1984811
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000181] Tetracyclines

*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
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[19769341]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota Suberites domuncula n.a. n.a. PMID[19778087]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21348461]
NPO10052 Penicillium aethiopicum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[22590971]
NPO22483 Penicillium brasilianum Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[23168407]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[24033077]
NPO33267 eupenicillium sp. lg41 Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25356913]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[25706180]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[29286660]
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10052 Penicillium aethiopicum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22483 Penicillium brasilianum Species Aspergillaceae 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. 53.09 nM PMID[495242]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 333.43 nM PMID[495242]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 164.44 nM PMID[495242]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 339.63 nM PMID[495242]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 209.41 nM PMID[495242]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 164.44 nM PMID[495242]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 362.24 nM PMID[495242]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 166.34 nM PMID[495242]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 358.92 nM PMID[495242]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 158.49 nM PMID[495242]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 174.58 nM PMID[495242]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 122.74 nM PMID[495242]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 227.51 nM PMID[495242]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 163.31 nM PMID[495242]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 159.59 nM PMID[495242]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 332.66 nM PMID[495242]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 345.14 nM PMID[495242]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 45.29 nM PMID[495242]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 112.72 nM PMID[495242]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 323.59 nM PMID[495242]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 419.76 nM PMID[495242]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 269.15 nM PMID[495242]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 259.42 nM PMID[495242]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 61.94 nM PMID[495242]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 188.8 nM PMID[495242]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 70.96 nM PMID[495242]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 126.47 nM PMID[495242]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 345.94 nM PMID[495242]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 61.24 nM PMID[495242]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 443.61 nM PMID[495242]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 244.91 nM PMID[495242]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 318.42 nM PMID[495242]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 304.79 nM PMID[495242]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 236.05 nM PMID[495242]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 49.89 nM PMID[495242]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 108.39 nM PMID[495242]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 163.68 nM PMID[495242]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 269.15 nM PMID[495242]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 209.41 nM PMID[495242]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 164.44 nM PMID[495242]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 180.3 nM PMID[495242]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 119.12 nM PMID[495242]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 364.75 nM PMID[495242]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 348.34 nM PMID[495242]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 43.55 nM PMID[495242]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 572.8 nM PMID[495242]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 66.68 nM PMID[495242]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 293.76 nM PMID[495242]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 322.11 nM PMID[495242]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 642.69 nM PMID[495242]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 146.55 nM PMID[495242]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 247.17 nM PMID[495242]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 231.21 nM PMID[495242]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 32.58 nM PMID[495242]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 238.78 nM PMID[495242]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 872.97 nM PMID[495242]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 61.52 nM PMID[495242]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 459.2 nM PMID[495242]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 107.65 nM PMID[495242]

☑ 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 NPC289223 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
0.8708 High Similarity NPC470333
0.8588 High Similarity NPC472058
0.8588 High Similarity NPC470341
0.8588 High Similarity NPC105414
0.8588 High Similarity NPC234497
0.8588 High Similarity NPC324522
0.8516 High Similarity NPC70318
0.8483 Intermediate Similarity NPC473094
0.8475 Intermediate Similarity NPC472057
0.8475 Intermediate Similarity NPC472051
0.8466 Intermediate Similarity NPC472059
0.8462 Intermediate Similarity NPC470334
0.8439 Intermediate Similarity NPC68727
0.8436 Intermediate Similarity NPC473096
0.8436 Intermediate Similarity NPC473095
0.8418 Intermediate Similarity NPC472053
0.8352 Intermediate Similarity NPC477992
0.8352 Intermediate Similarity NPC477991
0.8343 Intermediate Similarity NPC473113
0.8324 Intermediate Similarity NPC113608
0.8324 Intermediate Similarity NPC470338
0.8324 Intermediate Similarity NPC268992
0.8324 Intermediate Similarity NPC51824
0.8324 Intermediate Similarity NPC178173
0.8324 Intermediate Similarity NPC470337
0.8324 Intermediate Similarity NPC470332
0.8305 Intermediate Similarity NPC219686
0.8297 Intermediate Similarity NPC469393
0.8297 Intermediate Similarity NPC154986
0.8295 Intermediate Similarity NPC228654
0.8276 Intermediate Similarity NPC155686
0.8268 Intermediate Similarity NPC472049
0.8261 Intermediate Similarity NPC477683
0.8261 Intermediate Similarity NPC477682
0.8249 Intermediate Similarity NPC470810
0.8249 Intermediate Similarity NPC284495
0.8232 Intermediate Similarity NPC264063
0.8232 Intermediate Similarity NPC469486
0.8222 Intermediate Similarity NPC469394
0.8218 Intermediate Similarity NPC180944
0.8218 Intermediate Similarity NPC470340
0.8202 Intermediate Similarity NPC117985
0.8197 Intermediate Similarity NPC470336
0.8197 Intermediate Similarity NPC470335
0.8192 Intermediate Similarity NPC324736
0.8187 Intermediate Similarity NPC313717
0.8187 Intermediate Similarity NPC315306
0.8172 Intermediate Similarity NPC208069
0.8172 Intermediate Similarity NPC315221
0.8161 Intermediate Similarity NPC132990
0.8161 Intermediate Similarity NPC470569
0.8161 Intermediate Similarity NPC46882
0.8156 Intermediate Similarity NPC478229
0.8146 Intermediate Similarity NPC472055
0.814 Intermediate Similarity NPC34802
0.8138 Intermediate Similarity NPC197972
0.8132 Intermediate Similarity NPC54903
0.8132 Intermediate Similarity NPC286074
0.8128 Intermediate Similarity NPC313452
0.8128 Intermediate Similarity NPC228209
0.8128 Intermediate Similarity NPC8927
0.8105 Intermediate Similarity NPC314672
0.8103 Intermediate Similarity NPC470568
0.8103 Intermediate Similarity NPC147735
0.8103 Intermediate Similarity NPC225854
0.8101 Intermediate Similarity NPC96031
0.8101 Intermediate Similarity NPC472261
0.8101 Intermediate Similarity NPC478222
0.8101 Intermediate Similarity NPC87431
0.8098 Intermediate Similarity NPC229051
0.809 Intermediate Similarity NPC470339
0.8079 Intermediate Similarity NPC474360
0.8079 Intermediate Similarity NPC478223
0.8077 Intermediate Similarity NPC474024
0.8068 Intermediate Similarity NPC472211
0.8066 Intermediate Similarity NPC469664
0.8066 Intermediate Similarity NPC473286
0.8066 Intermediate Similarity NPC314653
0.8066 Intermediate Similarity NPC316262
0.8057 Intermediate Similarity NPC474417
0.8057 Intermediate Similarity NPC149526
0.8056 Intermediate Similarity NPC473961
0.8054 Intermediate Similarity NPC294149
0.8046 Intermediate Similarity NPC329933
0.8045 Intermediate Similarity NPC313368
0.8045 Intermediate Similarity NPC470342
0.8045 Intermediate Similarity NPC472052
0.8045 Intermediate Similarity NPC472618
0.8045 Intermediate Similarity NPC155302
0.8045 Intermediate Similarity NPC161947
0.8045 Intermediate Similarity NPC472060
0.8043 Intermediate Similarity NPC118128
0.8043 Intermediate Similarity NPC472620
0.8034 Intermediate Similarity NPC474637
0.8033 Intermediate Similarity NPC326877
0.8032 Intermediate Similarity NPC475656
0.8032 Intermediate Similarity NPC475148
0.8032 Intermediate Similarity NPC182693
0.8023 Intermediate Similarity NPC226656
0.8023 Intermediate Similarity NPC66508
0.8022 Intermediate Similarity NPC85047
0.8022 Intermediate Similarity NPC17274
0.8022 Intermediate Similarity NPC120857
0.8021 Intermediate Similarity NPC120102
0.8011 Intermediate Similarity NPC197168
0.8011 Intermediate Similarity NPC476295
0.8011 Intermediate Similarity NPC290160
0.8011 Intermediate Similarity NPC469395
0.8011 Intermediate Similarity NPC475233
0.8011 Intermediate Similarity NPC312630
0.8011 Intermediate Similarity NPC324220
0.8011 Intermediate Similarity NPC100849
0.8 Intermediate Similarity NPC187354
0.8 Intermediate Similarity NPC294646
0.8 Intermediate Similarity NPC131862
0.8 Intermediate Similarity NPC478134
0.8 Intermediate Similarity NPC240808
0.8 Intermediate Similarity NPC98776
0.8 Intermediate Similarity NPC255641
0.8 Intermediate Similarity NPC290954
0.7989 Intermediate Similarity NPC472617
0.7989 Intermediate Similarity NPC85121
0.7978 Intermediate Similarity NPC164427
0.7978 Intermediate Similarity NPC477154
0.7978 Intermediate Similarity NPC150131
0.7978 Intermediate Similarity NPC472622
0.7978 Intermediate Similarity NPC117854
0.7978 Intermediate Similarity NPC6588
0.7978 Intermediate Similarity NPC225419
0.7968 Intermediate Similarity NPC77179
0.7968 Intermediate Similarity NPC23553
0.7968 Intermediate Similarity NPC221820
0.7967 Intermediate Similarity NPC25361
0.7967 Intermediate Similarity NPC146584
0.7967 Intermediate Similarity NPC21016
0.7967 Intermediate Similarity NPC26386
0.7966 Intermediate Similarity NPC303950
0.7966 Intermediate Similarity NPC107109
0.7966 Intermediate Similarity NPC477048
0.7966 Intermediate Similarity NPC93552
0.7966 Intermediate Similarity NPC477047
0.7966 Intermediate Similarity NPC329844
0.7957 Intermediate Similarity NPC98667
0.7957 Intermediate Similarity NPC86809
0.7957 Intermediate Similarity NPC232412
0.7956 Intermediate Similarity NPC211107
0.7956 Intermediate Similarity NPC472402
0.7956 Intermediate Similarity NPC15374
0.7956 Intermediate Similarity NPC470694
0.7955 Intermediate Similarity NPC478148
0.7955 Intermediate Similarity NPC72958
0.7955 Intermediate Similarity NPC232645
0.7946 Intermediate Similarity NPC30432
0.7946 Intermediate Similarity NPC111536
0.7946 Intermediate Similarity NPC121333
0.7946 Intermediate Similarity NPC76128
0.7946 Intermediate Similarity NPC477836
0.7946 Intermediate Similarity NPC5029
0.7946 Intermediate Similarity NPC271385
0.7944 Intermediate Similarity NPC84571
0.7944 Intermediate Similarity NPC186325
0.7935 Intermediate Similarity NPC259905
0.7935 Intermediate Similarity NPC188079
0.7935 Intermediate Similarity NPC20734
0.7935 Intermediate Similarity NPC472619
0.7935 Intermediate Similarity NPC177480
0.7935 Intermediate Similarity NPC165456
0.7935 Intermediate Similarity NPC300307
0.7933 Intermediate Similarity NPC272196
0.7933 Intermediate Similarity NPC246466
0.7933 Intermediate Similarity NPC281137
0.7933 Intermediate Similarity NPC199463
0.7933 Intermediate Similarity NPC37543
0.7933 Intermediate Similarity NPC282390
0.7933 Intermediate Similarity NPC196448
0.7931 Intermediate Similarity NPC245584
0.7931 Intermediate Similarity NPC56433
0.7931 Intermediate Similarity NPC126767
0.7931 Intermediate Similarity NPC312929
0.7931 Intermediate Similarity NPC190648
0.7931 Intermediate Similarity NPC118027
0.7931 Intermediate Similarity NPC289042
0.7926 Intermediate Similarity NPC277710
0.7926 Intermediate Similarity NPC299149
0.7926 Intermediate Similarity NPC244903
0.7926 Intermediate Similarity NPC114257
0.7926 Intermediate Similarity NPC153578
0.7923 Intermediate Similarity NPC477835
0.7923 Intermediate Similarity NPC30027
0.7923 Intermediate Similarity NPC178851
0.7923 Intermediate Similarity NPC272502
0.7923 Intermediate Similarity NPC170245
0.7923 Intermediate Similarity NPC20237
0.7923 Intermediate Similarity NPC165460
0.7923 Intermediate Similarity NPC43319
0.7923 Intermediate Similarity NPC472621
0.7921 Intermediate Similarity NPC326910
0.7921 Intermediate Similarity NPC471116
0.7921 Intermediate Similarity NPC175192
0.7914 Intermediate Similarity NPC475246

  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 NPC289223 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
0.847 Intermediate Similarity NPD8150 Discontinued
0.8 Intermediate Similarity NPD6959 Discontinued
0.7897 Intermediate Similarity NPD6776 Approved
0.7897 Intermediate Similarity NPD6777 Approved
0.7897 Intermediate Similarity NPD6779 Approved
0.7897 Intermediate Similarity NPD6782 Approved
0.7897 Intermediate Similarity NPD6781 Approved
0.7897 Intermediate Similarity NPD6778 Approved
0.7897 Intermediate Similarity NPD6780 Approved
0.7857 Intermediate Similarity NPD6232 Discontinued
0.785 Intermediate Similarity NPD8151 Discontinued
0.7826 Intermediate Similarity NPD7473 Discontinued
0.7817 Intermediate Similarity NPD6823 Phase 2
0.7778 Intermediate Similarity NPD7435 Discontinued
0.7772 Intermediate Similarity NPD7801 Approved
0.7772 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7772 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7772 Intermediate Similarity NPD6166 Phase 2
0.772 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD3300 Phase 2
0.7697 Intermediate Similarity NPD4380 Phase 2
0.7688 Intermediate Similarity NPD7697 Approved
0.7688 Intermediate Similarity NPD7696 Phase 3
0.7688 Intermediate Similarity NPD7698 Approved
0.7667 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.765 Intermediate Similarity NPD7870 Phase 2
0.765 Intermediate Similarity NPD7871 Phase 2
0.7641 Intermediate Similarity NPD6535 Approved
0.7641 Intermediate Similarity NPD6534 Approved
0.7557 Intermediate Similarity NPD7390 Discontinued
0.7553 Intermediate Similarity NPD5844 Phase 1
0.7549 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7549 Intermediate Similarity NPD7874 Approved
0.7526 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7525 Intermediate Similarity NPD7699 Phase 2
0.7525 Intermediate Similarity NPD7700 Phase 2
0.7514 Intermediate Similarity NPD2532 Approved
0.7514 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD2534 Approved
0.7514 Intermediate Similarity NPD2533 Approved
0.746 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD7701 Phase 2
0.7446 Intermediate Similarity NPD7075 Discontinued
0.7432 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD7783 Phase 2
0.7427 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7418 Intermediate Similarity NPD1934 Approved
0.7407 Intermediate Similarity NPD3751 Discontinued
0.7396 Intermediate Similarity NPD5026 Approved
0.7396 Intermediate Similarity NPD36 Approved
0.7396 Intermediate Similarity NPD4954 Approved
0.7396 Intermediate Similarity NPD5034 Approved
0.7396 Intermediate Similarity NPD4955 Approved
0.7396 Intermediate Similarity NPD5028 Approved
0.7391 Intermediate Similarity NPD3882 Suspended
0.7382 Intermediate Similarity NPD6797 Phase 2
0.7377 Intermediate Similarity NPD7819 Suspended
0.7377 Intermediate Similarity NPD2801 Approved
0.7366 Intermediate Similarity NPD5494 Approved
0.7344 Intermediate Similarity NPD5030 Phase 2
0.7344 Intermediate Similarity NPD7251 Discontinued
0.7344 Intermediate Similarity NPD6559 Discontinued
0.7333 Intermediate Similarity NPD5037 Approved
0.7333 Intermediate Similarity NPD5038 Approved
0.733 Intermediate Similarity NPD7074 Phase 3
0.733 Intermediate Similarity NPD2800 Approved
0.7322 Intermediate Similarity NPD6801 Discontinued
0.7318 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD3818 Discontinued
0.7308 Intermediate Similarity NPD6599 Discontinued
0.7306 Intermediate Similarity NPD7808 Phase 3
0.7306 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD3787 Discontinued
0.7287 Intermediate Similarity NPD5710 Approved
0.7287 Intermediate Similarity NPD5711 Approved
0.7283 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD5036 Approved
0.7278 Intermediate Similarity NPD1512 Approved
0.7277 Intermediate Similarity NPD7054 Approved
0.7268 Intermediate Similarity NPD5035 Approved
0.7258 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7245 Intermediate Similarity NPD8434 Phase 2
0.7243 Intermediate Similarity NPD5402 Approved
0.7243 Intermediate Similarity NPD3817 Phase 2
0.724 Intermediate Similarity NPD7472 Approved
0.7211 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1510 Phase 2
0.7196 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD8058 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD8059 Phase 3
0.7184 Intermediate Similarity NPD1607 Approved
0.7184 Intermediate Similarity NPD6651 Approved
0.7174 Intermediate Similarity NPD7411 Suspended
0.7167 Intermediate Similarity NPD1511 Approved
0.7166 Intermediate Similarity NPD3749 Approved
0.715 Intermediate Similarity NPD6213 Phase 3
0.715 Intermediate Similarity NPD6212 Phase 3
0.715 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD8319 Approved
0.7136 Intermediate Similarity NPD8320 Phase 1
0.7135 Intermediate Similarity NPD37 Approved
0.7127 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD8312 Approved
0.7092 Intermediate Similarity NPD8313 Approved
0.7079 Intermediate Similarity NPD1549 Phase 2
0.7079 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD5031 Approved
0.7077 Intermediate Similarity NPD5027 Approved
0.7077 Intermediate Similarity NPD5029 Approved
0.7069 Intermediate Similarity NPD1240 Approved
0.7065 Intermediate Similarity NPD3226 Approved
0.7047 Intermediate Similarity NPD7228 Approved
0.7037 Intermediate Similarity NPD6234 Discontinued
0.7033 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD7768 Phase 2
0.7021 Intermediate Similarity NPD4965 Approved
0.7021 Intermediate Similarity NPD4966 Approved
0.7021 Intermediate Similarity NPD4967 Phase 2
0.7005 Intermediate Similarity NPD1465 Phase 2
0.6989 Remote Similarity NPD4097 Suspended
0.6979 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6979 Remote Similarity NPD3926 Phase 2
0.6978 Remote Similarity NPD6799 Approved
0.6966 Remote Similarity NPD2796 Approved
0.6966 Remote Similarity NPD6099 Approved
0.6966 Remote Similarity NPD6100 Approved
0.6966 Remote Similarity NPD2935 Discontinued
0.6963 Remote Similarity NPD7199 Phase 2
0.6963 Remote Similarity NPD1247 Approved
0.6959 Remote Similarity NPD7907 Approved
0.6959 Remote Similarity NPD8366 Approved
0.6957 Remote Similarity NPD5403 Approved
0.6954 Remote Similarity NPD5032 Approved
0.6954 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6944 Remote Similarity NPD4111 Phase 1
0.6944 Remote Similarity NPD4665 Approved
0.6938 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6937 Remote Similarity NPD8067 Phase 3
0.6931 Remote Similarity NPD5968 Phase 3
0.6915 Remote Similarity NPD5760 Phase 2
0.6915 Remote Similarity NPD5761 Phase 2
0.6909 Remote Similarity NPD8491 Approved
0.6906 Remote Similarity NPD7003 Approved
0.6906 Remote Similarity NPD4628 Phase 3
0.6906 Remote Similarity NPD3750 Approved
0.6905 Remote Similarity NPD7584 Approved
0.6904 Remote Similarity NPD3658 Clinical (unspecified phase)
0.6882 Remote Similarity NPD7458 Discontinued
0.6878 Remote Similarity NPD8485 Approved
0.686 Remote Similarity NPD7501 Clinical (unspecified phase)
0.686 Remote Similarity NPD4914 Approved
0.6848 Remote Similarity NPD5401 Approved
0.6847 Remote Similarity NPD7654 Discontinued
0.6837 Remote Similarity NPD7930 Approved
0.6816 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6816 Remote Similarity NPD651 Clinical (unspecified phase)
0.6813 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6812 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6811 Remote Similarity NPD6273 Approved
0.6809 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6791 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6788 Remote Similarity NPD8127 Discontinued
0.678 Remote Similarity NPD4363 Phase 3
0.678 Remote Similarity NPD4360 Phase 2
0.678 Remote Similarity NPD943 Approved
0.6779 Remote Similarity NPD8486 Clinical (unspecified phase)
0.6778 Remote Similarity NPD5408 Approved
0.6778 Remote Similarity NPD5406 Approved
0.6778 Remote Similarity NPD5404 Approved
0.6778 Remote Similarity NPD5405 Approved
0.6776 Remote Similarity NPD6190 Approved
0.6771 Remote Similarity NPD5537 Clinical (unspecified phase)
0.6771 Remote Similarity NPD919 Approved
0.6762 Remote Similarity NPD7497 Discontinued
0.6749 Remote Similarity NPD6836 Approved
0.6749 Remote Similarity NPD8360 Approved
0.6749 Remote Similarity NPD8361 Approved
0.6746 Remote Similarity NPD2493 Approved
0.6746 Remote Similarity NPD2494 Approved
0.674 Remote Similarity NPD2346 Discontinued
0.6738 Remote Similarity NPD7239 Suspended
0.6736 Remote Similarity NPD6746 Phase 2
0.6734 Remote Similarity NPD7685 Pre-registration
0.6734 Remote Similarity NPD7240 Approved
0.6726 Remote Similarity NPD8469 Approved
0.6715 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6714 Remote Similarity NPD4386 Approved
0.6714 Remote Similarity NPD4387 Approved
0.6701 Remote Similarity NPD7799 Discontinued
0.6701 Remote Similarity NPD7177 Discontinued
0.6697 Remote Similarity NPD8404 Phase 2
0.6684 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6684 Remote Similarity NPD920 Approved
0.6667 Remote Similarity NPD3452 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