Structure

Physi-Chem Properties

Molecular Weight:  510.13
Volume:  509.509
LogP:  6.802
LogD:  2.988
LogS:  -4.871
# Rotatable Bonds:  1
TPSA:  161.84
# H-Bond Aceptor:  8
# H-Bond Donor:  8
# Rings:  6
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.121
Synthetic Accessibility Score:  2.901
Fsp3:  0.067
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.187
MDCK Permeability:  5.146925104781985e-06
Pgp-inhibitor:  0.076
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.999
20% Bioavailability (F20%):  0.723
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.0
Plasma Protein Binding (PPB):  90.0632095336914%
Volume Distribution (VD):  0.379
Pgp-substrate:  10.961952209472656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.944
CYP1A2-substrate:  0.177
CYP2C19-inhibitor:  0.113
CYP2C19-substrate:  0.04
CYP2C9-inhibitor:  0.607
CYP2C9-substrate:  0.806
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.246
CYP3A4-inhibitor:  0.031
CYP3A4-substrate:  0.021

ADMET: Excretion

Clearance (CL):  6.31
Half-life (T1/2):  0.535

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.039
Drug-inuced Liver Injury (DILI):  0.982
AMES Toxicity:  0.184
Rat Oral Acute Toxicity:  0.035
Maximum Recommended Daily Dose:  0.988
Skin Sensitization:  0.964
Carcinogencity:  0.021
Eye Corrosion:  0.004
Eye Irritation:  0.944
Respiratory Toxicity:  0.07

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

  Natural Product: NPC293545

Natural Product ID:  NPC293545
Common Name*:   (9S,9's)-2,2',4,4',5,5'-Hexahydroxy-7,7'-Dimethyl-9,9'-Bianthracene-10,10'(9H,9'h)-Dione
IUPAC Name:   (10S)-1,3,8-trihydroxy-6-methyl-10-[(9S)-2,4,5-trihydroxy-7-methyl-10-oxo-9H-anthracen-9-yl]-10H-anthracen-9-one
Synonyms:  
Standard InCHIKey:  UUXPVUHOWQPCSC-ZEQRLZLVSA-N
Standard InCHI:  InChI=1S/C30H22O8/c1-11-3-15-23(17-7-13(31)9-21(35)27(17)29(37)25(15)19(33)5-11)24-16-4-12(2)6-20(34)26(16)30(38)28-18(24)8-14(32)10-22(28)36/h3-10,23-24,31-36H,1-2H3/t23-,24-/m0/s1
SMILES:  Cc1cc2[C@@H](c3cc(cc(c3C(=O)c2c(c1)O)O)O)[C@H]1c2cc(C)cc(c2C(=O)c2c1cc(cc2O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464711
PubChem CID:   12096290
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes

*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
NPO27239 Maclura tinctoria Species Moraceae Eukaryota n.a. n.a. n.a. PMID[11087602]
NPO32935 rhamnus nepalensis Species Rhamnaceae Eukaryota Leaves Pa Co, Mai Chau, Hoa Binh Province, 150 km west of Hanoi, Vietnam 1995-Nov PMID[11575949]
NPO27239 Maclura tinctoria Species Moraceae Eukaryota n.a. stem n.a. PMID[12932124]
NPO27239 Maclura tinctoria Species Moraceae Eukaryota n.a. n.a. n.a. PMID[12932124]
NPO27164 Aspergillus alliaceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[29517220]
NPO27164 Aspergillus alliaceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[3417561]
NPO3980 Frangula purshiana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19050 Garcinia polyantha Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27140 Amanita phalloides Species Amanitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24629 Achromobacter denitrificans Species Alcaligenaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO3980 Frangula purshiana Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27790 Delia arenicola Species Anthomyiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19050 Garcinia polyantha Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4132 Cranfillia fluviatilis Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27454 Turbo cornutus Species Turbinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27239 Maclura tinctoria Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27164 Aspergillus alliaceus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26972 Baccharis potosina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27873 Ravenia spectabilis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17822 Fridericia triplinervia Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27564 Stevia berlandieri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10239 Magnolia figo Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27140 Amanita phalloides Species Amanitaceae 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
NPT91 Cell Line KB Homo sapiens IC50 = 2500.0 nM PMID[554504]

☑ 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 NPC293545 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 NPC174905
0.9854 High Similarity NPC295712
0.9854 High Similarity NPC474203
0.9854 High Similarity NPC451542
0.9854 High Similarity NPC313047
0.9783 High Similarity NPC227841
0.9577 High Similarity NPC477221
0.9574 High Similarity NPC37709
0.9574 High Similarity NPC290194
0.9568 High Similarity NPC296752
0.9433 High Similarity NPC12402
0.9366 High Similarity NPC110882
0.9366 High Similarity NPC85393
0.9366 High Similarity NPC271944
0.9343 High Similarity NPC191976
0.9286 High Similarity NPC246638
0.9265 High Similarity NPC267205
0.9225 High Similarity NPC10764
0.922 High Similarity NPC19631
0.922 High Similarity NPC239136
0.9214 High Similarity NPC169452
0.9214 High Similarity NPC181560
0.9197 High Similarity NPC472262
0.9197 High Similarity NPC287604
0.9197 High Similarity NPC161964
0.9155 High Similarity NPC471682
0.9143 High Similarity NPC138099
0.9143 High Similarity NPC242994
0.9137 High Similarity NPC471905
0.9085 High Similarity NPC193555
0.9085 High Similarity NPC257644
0.9065 High Similarity NPC254847
0.9048 High Similarity NPC35
0.9028 High Similarity NPC471683
0.9 High Similarity NPC53414
0.9 High Similarity NPC474110
0.9 High Similarity NPC53206
0.9 High Similarity NPC44960
0.8951 High Similarity NPC474961
0.8951 High Similarity NPC135524
0.8929 High Similarity NPC118919
0.8921 High Similarity NPC282780
0.8921 High Similarity NPC166480
0.8913 High Similarity NPC175738
0.8882 High Similarity NPC472052
0.8882 High Similarity NPC470342
0.8882 High Similarity NPC472060
0.8881 High Similarity NPC204045
0.8881 High Similarity NPC305845
0.8873 High Similarity NPC143438
0.8865 High Similarity NPC53001
0.8857 High Similarity NPC290803
0.8841 High Similarity NPC474517
0.8841 High Similarity NPC72669
0.8832 High Similarity NPC92624
0.8816 High Similarity NPC177650
0.8811 High Similarity NPC225243
0.8803 High Similarity NPC87723
0.8803 High Similarity NPC20210
0.8786 High Similarity NPC44437
0.8786 High Similarity NPC12070
0.8768 High Similarity NPC259942
0.8767 High Similarity NPC34482
0.8758 High Similarity NPC312993
0.8758 High Similarity NPC186325
0.8742 High Similarity NPC226656
0.8742 High Similarity NPC66508
0.8741 High Similarity NPC190457
0.8732 High Similarity NPC62272
0.8723 High Similarity NPC249272
0.8714 High Similarity NPC114183
0.8714 High Similarity NPC180261
0.8714 High Similarity NPC37299
0.8707 High Similarity NPC470570
0.8701 High Similarity NPC189552
0.8701 High Similarity NPC273467
0.8699 High Similarity NPC193703
0.8699 High Similarity NPC471906
0.8699 High Similarity NPC48762
0.8699 High Similarity NPC244691
0.8699 High Similarity NPC21599
0.8696 High Similarity NPC109123
0.869 High Similarity NPC85310
0.8676 High Similarity NPC477454
0.8671 High Similarity NPC13715
0.8671 High Similarity NPC473622
0.8658 High Similarity NPC329933
0.8652 High Similarity NPC270899
0.8649 High Similarity NPC34802
0.8645 High Similarity NPC15374
0.8623 High Similarity NPC473017
0.8621 High Similarity NPC110810
0.8621 High Similarity NPC91019
0.8621 High Similarity NPC106519
0.8621 High Similarity NPC290550
0.8618 High Similarity NPC254351
0.8613 High Similarity NPC473691
0.8613 High Similarity NPC267846
0.8611 High Similarity NPC162939
0.86 High Similarity NPC205766
0.8599 High Similarity NPC477835
0.8592 High Similarity NPC283088
0.8582 High Similarity NPC225051
0.8582 High Similarity NPC48036
0.8581 High Similarity NPC143685
0.8581 High Similarity NPC18380
0.8571 High Similarity NPC324736
0.8571 High Similarity NPC55443
0.8571 High Similarity NPC18699
0.8571 High Similarity NPC195167
0.8562 High Similarity NPC73061
0.8562 High Similarity NPC137649
0.8561 High Similarity NPC474998
0.8551 High Similarity NPC72158
0.8551 High Similarity NPC266689
0.8551 High Similarity NPC116513
0.8551 High Similarity NPC169250
0.8551 High Similarity NPC103356
0.8551 High Similarity NPC23126
0.8551 High Similarity NPC162612
0.8551 High Similarity NPC100067
0.8551 High Similarity NPC105157
0.8551 High Similarity NPC190043
0.8551 High Similarity NPC98254
0.8551 High Similarity NPC30501
0.854 High Similarity NPC475733
0.8535 High Similarity NPC469664
0.8529 High Similarity NPC472029
0.8529 High Similarity NPC65761
0.8526 High Similarity NPC315772
0.8523 High Similarity NPC56433
0.8523 High Similarity NPC245584
0.8523 High Similarity NPC126767
0.8523 High Similarity NPC475348
0.8523 High Similarity NPC190648
0.8523 High Similarity NPC289042
0.8523 High Similarity NPC261271
0.8523 High Similarity NPC312929
0.8523 High Similarity NPC118027
0.8521 High Similarity NPC474519
0.8521 High Similarity NPC475088
0.8516 High Similarity NPC184326
0.8516 High Similarity NPC292863
0.8506 High Similarity NPC317580
0.8503 High Similarity NPC84266
0.85 High Similarity NPC62219
0.8497 Intermediate Similarity NPC66029
0.8497 Intermediate Similarity NPC318270
0.8493 Intermediate Similarity NPC477275
0.8493 Intermediate Similarity NPC187843
0.8489 Intermediate Similarity NPC21305
0.8489 Intermediate Similarity NPC221777
0.8478 Intermediate Similarity NPC62952
0.8478 Intermediate Similarity NPC160499
0.8477 Intermediate Similarity NPC470568
0.8472 Intermediate Similarity NPC290030
0.8472 Intermediate Similarity NPC245923
0.8467 Intermediate Similarity NPC199273
0.8467 Intermediate Similarity NPC152233
0.8467 Intermediate Similarity NPC173978
0.8462 Intermediate Similarity NPC137232
0.8462 Intermediate Similarity NPC80035
0.8462 Intermediate Similarity NPC219686
0.8456 Intermediate Similarity NPC91105
0.8456 Intermediate Similarity NPC314437
0.8452 Intermediate Similarity NPC326084
0.8452 Intermediate Similarity NPC228654
0.8451 Intermediate Similarity NPC115458
0.8442 Intermediate Similarity NPC56049
0.8442 Intermediate Similarity NPC54830
0.844 Intermediate Similarity NPC41847
0.8435 Intermediate Similarity NPC182255
0.8435 Intermediate Similarity NPC469520
0.8435 Intermediate Similarity NPC26238
0.8435 Intermediate Similarity NPC94076
0.8431 Intermediate Similarity NPC474824
0.8431 Intermediate Similarity NPC218870
0.8431 Intermediate Similarity NPC324447
0.8431 Intermediate Similarity NPC182921
0.8431 Intermediate Similarity NPC470408
0.8431 Intermediate Similarity NPC329844
0.8431 Intermediate Similarity NPC472211
0.8429 Intermediate Similarity NPC303910
0.8429 Intermediate Similarity NPC276238
0.8429 Intermediate Similarity NPC99731
0.8425 Intermediate Similarity NPC168471
0.8425 Intermediate Similarity NPC203063
0.8421 Intermediate Similarity NPC149526
0.8421 Intermediate Similarity NPC478148
0.8421 Intermediate Similarity NPC474417
0.8421 Intermediate Similarity NPC470569
0.8417 Intermediate Similarity NPC78364
0.8417 Intermediate Similarity NPC69424
0.8417 Intermediate Similarity NPC84672
0.8417 Intermediate Similarity NPC176130
0.8414 Intermediate Similarity NPC4214
0.8411 Intermediate Similarity NPC288036
0.8411 Intermediate Similarity NPC97028
0.8411 Intermediate Similarity NPC65589
0.8411 Intermediate Similarity NPC97029

  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 NPC293545 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
0.9783 High Similarity NPD7390 Discontinued
0.9065 High Similarity NPD1509 Clinical (unspecified phase)
0.8732 High Similarity NPD5405 Approved
0.8732 High Similarity NPD5404 Approved
0.8732 High Similarity NPD5406 Approved
0.8732 High Similarity NPD5408 Approved
0.8581 High Similarity NPD6959 Discontinued
0.8389 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.8248 Intermediate Similarity NPD1201 Approved
0.8143 Intermediate Similarity NPD1470 Approved
0.8137 Intermediate Similarity NPD7473 Discontinued
0.8063 Intermediate Similarity NPD6232 Discontinued
0.8026 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD943 Approved
0.7853 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD7819 Suspended
0.7792 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1607 Approved
0.7748 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD7411 Suspended
0.7677 Intermediate Similarity NPD2533 Approved
0.7677 Intermediate Similarity NPD2534 Approved
0.7677 Intermediate Similarity NPD2532 Approved
0.7667 Intermediate Similarity NPD1510 Phase 2
0.7667 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD4380 Phase 2
0.7647 Intermediate Similarity NPD7003 Approved
0.764 Intermediate Similarity NPD7768 Phase 2
0.7635 Intermediate Similarity NPD1240 Approved
0.7625 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD3749 Approved
0.753 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD6166 Phase 2
0.753 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3226 Approved
0.7465 Intermediate Similarity NPD3019 Approved
0.7451 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD3300 Phase 2
0.7419 Intermediate Similarity NPD3750 Approved
0.7417 Intermediate Similarity NPD6651 Approved
0.7403 Intermediate Similarity NPD1549 Phase 2
0.7397 Intermediate Similarity NPD1164 Approved
0.7396 Intermediate Similarity NPD5844 Phase 1
0.7389 Intermediate Similarity NPD1511 Approved
0.7386 Intermediate Similarity NPD2935 Discontinued
0.7386 Intermediate Similarity NPD6099 Approved
0.7386 Intermediate Similarity NPD6100 Approved
0.7384 Intermediate Similarity NPD8313 Approved
0.7384 Intermediate Similarity NPD8312 Approved
0.7378 Intermediate Similarity NPD7075 Discontinued
0.7375 Intermediate Similarity NPD7458 Discontinued
0.7371 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD1934 Approved
0.7343 Intermediate Similarity NPD2932 Approved
0.732 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD2801 Approved
0.7299 Intermediate Similarity NPD4750 Phase 3
0.7296 Intermediate Similarity NPD1512 Approved
0.7294 Intermediate Similarity NPD6020 Phase 2
0.7288 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2796 Approved
0.7273 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD8150 Discontinued
0.7256 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD2800 Approved
0.7226 Intermediate Similarity NPD2346 Discontinued
0.7212 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD5494 Approved
0.7169 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD6559 Discontinued
0.7166 Intermediate Similarity NPD8151 Discontinued
0.716 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD3764 Approved
0.7151 Intermediate Similarity NPD7074 Phase 3
0.7134 Intermediate Similarity NPD6801 Discontinued
0.7134 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD6599 Discontinued
0.7111 Intermediate Similarity NPD6534 Approved
0.7111 Intermediate Similarity NPD6535 Approved
0.711 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD3882 Suspended
0.7101 Intermediate Similarity NPD5710 Approved
0.7101 Intermediate Similarity NPD5711 Approved
0.7097 Intermediate Similarity NPD2799 Discontinued
0.7097 Intermediate Similarity NPD3748 Approved
0.7093 Intermediate Similarity NPD7054 Approved
0.7089 Intermediate Similarity NPD8166 Discontinued
0.7089 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD3026 Approved
0.7055 Intermediate Similarity NPD3023 Approved
0.7052 Intermediate Similarity NPD7472 Approved
0.7048 Intermediate Similarity NPD3817 Phase 2
0.7043 Intermediate Similarity NPD7871 Phase 2
0.7043 Intermediate Similarity NPD7870 Phase 2
0.7039 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7034 Intermediate Similarity NPD3024 Approved
0.7034 Intermediate Similarity NPD3025 Approved
0.7029 Intermediate Similarity NPD2342 Discontinued
0.7011 Intermediate Similarity NPD6778 Approved
0.7011 Intermediate Similarity NPD6782 Approved
0.7011 Intermediate Similarity NPD6780 Approved
0.7011 Intermediate Similarity NPD6776 Approved
0.7011 Intermediate Similarity NPD6777 Approved
0.7011 Intermediate Similarity NPD6797 Phase 2
0.7011 Intermediate Similarity NPD6779 Approved
0.7011 Intermediate Similarity NPD6781 Approved
0.7006 Intermediate Similarity NPD2344 Approved
0.7 Intermediate Similarity NPD2798 Approved
0.6995 Remote Similarity NPD7699 Phase 2
0.6995 Remote Similarity NPD7700 Phase 2
0.6988 Remote Similarity NPD1465 Phase 2
0.6974 Remote Similarity NPD4625 Phase 3
0.6971 Remote Similarity NPD7251 Discontinued
0.6959 Remote Similarity NPD9269 Phase 2
0.6957 Remote Similarity NPD6799 Approved
0.6952 Remote Similarity NPD8320 Phase 1
0.6952 Remote Similarity NPD8319 Approved
0.6943 Remote Similarity NPD1551 Phase 2
0.6936 Remote Similarity NPD3818 Discontinued
0.6936 Remote Similarity NPD7177 Discontinued
0.6933 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6932 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6932 Remote Similarity NPD7808 Phase 3
0.6928 Remote Similarity NPD37 Approved
0.6923 Remote Similarity NPD5951 Approved
0.6918 Remote Similarity NPD9268 Approved
0.6918 Remote Similarity NPD1243 Approved
0.6914 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6908 Remote Similarity NPD4908 Phase 1
0.6901 Remote Similarity NPD7635 Approved
0.6898 Remote Similarity NPD7696 Phase 3
0.6898 Remote Similarity NPD7698 Approved
0.6898 Remote Similarity NPD7435 Discontinued
0.6898 Remote Similarity NPD7697 Approved
0.6871 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6868 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6868 Remote Similarity NPD6212 Phase 3
0.6868 Remote Similarity NPD6213 Phase 3
0.6867 Remote Similarity NPD1283 Approved
0.6832 Remote Similarity NPD2309 Approved
0.6824 Remote Similarity NPD6234 Discontinued
0.6818 Remote Similarity NPD5953 Discontinued
0.6805 Remote Similarity NPD4967 Phase 2
0.6805 Remote Similarity NPD4966 Approved
0.6805 Remote Similarity NPD4965 Approved
0.6803 Remote Similarity NPD1651 Approved
0.6802 Remote Similarity NPD7229 Phase 3
0.6795 Remote Similarity NPD230 Phase 1
0.6788 Remote Similarity NPD940 Approved
0.6788 Remote Similarity NPD846 Approved
0.6774 Remote Similarity NPD6663 Approved
0.677 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6768 Remote Similarity NPD6273 Approved
0.6763 Remote Similarity NPD3926 Phase 2
0.6755 Remote Similarity NPD6823 Phase 2
0.6754 Remote Similarity NPD7701 Phase 2
0.6746 Remote Similarity NPD5402 Approved
0.6744 Remote Similarity NPD7199 Phase 2
0.6743 Remote Similarity NPD7228 Approved
0.6742 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6738 Remote Similarity NPD9266 Approved
0.6738 Remote Similarity NPD74 Approved
0.6738 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6737 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6736 Remote Similarity NPD7801 Approved
0.6733 Remote Similarity NPD3972 Approved
0.6732 Remote Similarity NPD5736 Approved
0.6727 Remote Similarity NPD5403 Approved
0.6715 Remote Similarity NPD1242 Phase 1
0.6712 Remote Similarity NPD9493 Approved
0.671 Remote Similarity NPD2313 Discontinued
0.671 Remote Similarity NPD3268 Approved
0.671 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6703 Remote Similarity NPD4287 Approved
0.6689 Remote Similarity NPD4749 Approved
0.6685 Remote Similarity NPD5027 Approved
0.6685 Remote Similarity NPD5029 Approved
0.6685 Remote Similarity NPD5031 Approved
0.6684 Remote Similarity NPD7874 Approved
0.6684 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9264 Approved
0.6667 Remote Similarity NPD9267 Approved
0.6667 Remote Similarity NPD9263 Approved
0.6667 Remote Similarity NPD4628 Phase 3
0.6667 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1281 Approved
0.665 Remote Similarity NPD7654 Discontinued
0.6649 Remote Similarity NPD4363 Phase 3
0.6649 Remote Similarity NPD4360 Phase 2
0.6649 Remote Similarity NPD7783 Phase 2
0.6649 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6648 Remote Similarity NPD5026 Approved
0.6648 Remote Similarity NPD5034 Approved
0.6648 Remote Similarity NPD4954 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