Structure

Physi-Chem Properties

Molecular Weight:  240.04
Volume:  239.1
LogP:  2.904
LogD:  2.631
LogS:  -4.681
# Rotatable Bonds:  0
TPSA:  74.6
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.629
Synthetic Accessibility Score:  2.08
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.692
MDCK Permeability:  1.406133196724113e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.015
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.237
Plasma Protein Binding (PPB):  97.15377044677734%
Volume Distribution (VD):  0.547
Pgp-substrate:  2.3835771083831787%

ADMET: Metabolism

CYP1A2-inhibitor:  0.957
CYP1A2-substrate:  0.112
CYP2C19-inhibitor:  0.276
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.469
CYP2C9-substrate:  0.795
CYP2D6-inhibitor:  0.564
CYP2D6-substrate:  0.27
CYP3A4-inhibitor:  0.939
CYP3A4-substrate:  0.145

ADMET: Excretion

Clearance (CL):  9.131
Half-life (T1/2):  0.569

ADMET: Toxicity

hERG Blockers:  0.06
Human Hepatotoxicity (H-HT):  0.055
Drug-inuced Liver Injury (DILI):  0.753
AMES Toxicity:  0.809
Rat Oral Acute Toxicity:  0.177
Maximum Recommended Daily Dose:  0.497
Skin Sensitization:  0.141
Carcinogencity:  0.892
Eye Corrosion:  0.004
Eye Irritation:  0.962
Respiratory Toxicity:  0.041

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

  Natural Product: NPC91478

Natural Product ID:  NPC91478
Common Name*:   Anthraflavicacid
IUPAC Name:   2,6-dihydroxyanthracene-9,10-dione
Synonyms:   2,6-Dihydroxy-Anthraquinone; Anthraflavic Acid; Anthraflavicacid
Standard InCHIKey:  APAJFZPFBHMFQR-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C14H8O4/c15-7-1-3-9-11(5-7)14(18)10-4-2-8(16)6-12(10)13(9)17/h1-6,15-16H
SMILES:  Oc1ccc2c(c1)C(=O)c1c(C2=O)cc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL298398
PubChem CID:   6776
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones
          • [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[11076555]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota Roots n.a. n.a. PMID[11459643]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[1517743]
NPO8921 Senna obtusifolia Species Fabaceae Eukaryota Seeds n.a. n.a. PMID[2213033]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[8277318]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8921 Senna obtusifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8921 Senna obtusifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11391 Polygonum cuspidatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8921 Senna obtusifolia Species Fabaceae 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
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens IC50 = 1100.0 nM PMID[502788]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Ki = 310.0 nM PMID[502788]
NPT248 Individual Protein Estrogen receptor beta Homo sapiens IC50 = 2400.0 nM PMID[502788]
NPT248 Individual Protein Estrogen receptor beta Homo sapiens Ki = 690.0 nM PMID[502788]
NPT80 Cell Line Raji Homo sapiens Activity > 80.0 % PMID[502794]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 73451.39 nM PMID[502798]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 59156.16 nM PMID[502798]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 24266.1 nM PMID[502798]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 36897.76 nM PMID[502798]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 63095.73 nM PMID[502798]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 70469.31 nM PMID[502798]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 40926.07 nM PMID[502798]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 57411.65 nM PMID[502798]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 50118.72 nM PMID[502798]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 78523.56 nM PMID[502798]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 38547.84 nM PMID[502798]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 30619.63 nM PMID[502798]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 31622.78 nM PMID[502798]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 49431.07 nM PMID[502798]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 78886.01 nM PMID[502798]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 49203.95 nM PMID[502798]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 61801.64 nM PMID[502798]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 92469.82 nM PMID[502798]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 32583.67 nM PMID[502798]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 58884.37 nM PMID[502798]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 88715.6 nM PMID[502798]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 41975.9 nM PMID[502798]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 42756.29 nM PMID[502798]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 58076.44 nM PMID[502798]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 45708.82 nM PMID[502798]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 54575.79 nM PMID[502798]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 29648.31 nM PMID[502798]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 46344.69 nM PMID[502798]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 52480.75 nM PMID[502798]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 39355.01 nM PMID[502798]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 55335.01 nM PMID[502798]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 67297.67 nM PMID[502798]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 87297.14 nM PMID[502798]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 95940.06 nM PMID[502798]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 33189.45 nM PMID[502798]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 53210.83 nM PMID[502798]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 56754.46 nM PMID[502798]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 32885.16 nM PMID[502798]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 48305.88 nM PMID[502798]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 74989.42 nM PMID[502798]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 42657.95 nM PMID[502798]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 38636.7 nM PMID[502798]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 59292.53 nM PMID[502798]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 78523.56 nM PMID[502798]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[502798]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 29853.83 nM PMID[502798]
NPT544 Protein Family Estrogen receptor Homo sapiens Control < 170.0 % PMID[502788]
NPT544 Protein Family Estrogen receptor Homo sapiens Control < 164.0 % PMID[502788]
NPT544 Protein Family Estrogen receptor Homo sapiens Control = 167.4 % PMID[502788]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 1000.0 nM PMID[502789]
NPT878 Organism Streptococcus mutans Streptococcus mutans MIC = 250.0 ug.mL-1 PMID[502790]
NPT878 Organism Streptococcus mutans Streptococcus mutans Inhibition = 98.2 % PMID[502790]
NPT32 Organism Mus musculus Mus musculus Activity = 22.0 % PMID[502791]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity > 0.25 mg/ml PMID[502792]
NPT2 Others Unspecified Activity < 50.0 % PMID[502793]
NPT2 Others Unspecified Inhibition = 100.0 % PMID[502794]
NPT2 Others Unspecified Inhibition = 89.9 % PMID[502794]
NPT2 Others Unspecified Inhibition = 78.6 % PMID[502794]
NPT2 Others Unspecified Inhibition = 28.5 % PMID[502794]
NPT2 Others Unspecified logIC50 = 2.88 n.a. PMID[502795]
NPT901 Individual Protein UDP-glucuronosyltransferase 1-1 Homo sapiens Activity = 1720.0 pm/min/mg PMID[502796]
NPT901 Individual Protein UDP-glucuronosyltransferase 1-1 Homo sapiens Activity = 206.0 pm/min/mg PMID[502797]
NPT699 Individual Protein UDP-glucuronosyltransferase 1-10 Homo sapiens Activity = 79.0 pm/min/mg PMID[502797]
NPT694 Individual Protein UDP-glucuronosyltransferase 1-3 Homo sapiens Activity = 149.0 pm/min/mg PMID[502797]
NPT902 Individual Protein UDP-glucuronosyltransferase 1A4 Homo sapiens Activity = 0.0 pm/min/mg PMID[502797]
NPT702 Individual Protein UDP-glucuronosyltransferase 1-6 Homo sapiens Activity = 0.0 pm/min/mg PMID[502797]
NPT695 Individual Protein UDP-glucuronosyltransferase 1-8 Homo sapiens Activity = 806.0 pm/min/mg PMID[502797]
NPT703 Individual Protein UDP-glucuronosyltransferase 1-9 Homo sapiens Activity = 1600.0 pm/min/mg PMID[502797]
NPT696 Individual Protein UDP-glucuronosyltransferase 2A1 Homo sapiens Activity = 210.0 pm/min/mg PMID[502797]
NPT704 Individual Protein UDP-glucuronosyltransferase 2B15 Homo sapiens Activity = 19.0 pm/min/mg PMID[502797]
NPT901 Individual Protein UDP-glucuronosyltransferase 1-1 Homo sapiens IC50 = 4000.0 nM PMID[502799]
NPT901 Individual Protein UDP-glucuronosyltransferase 1-1 Homo sapiens IC50 = 3600.0 nM PMID[502799]

☑ 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 NPC91478 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
0.9913 High Similarity NPC120545
0.9504 High Similarity NPC234175
0.9274 High Similarity NPC93015
0.925 High Similarity NPC375356
0.9167 High Similarity NPC300274
0.9127 High Similarity NPC52407
0.9127 High Similarity NPC294226
0.9113 High Similarity NPC99731
0.9098 High Similarity NPC103540
0.9055 High Similarity NPC44437
0.9024 High Similarity NPC96915
0.8906 High Similarity NPC50924
0.8889 High Similarity NPC27659
0.8889 High Similarity NPC136588
0.8889 High Similarity NPC199253
0.888 High Similarity NPC282923
0.888 High Similarity NPC96024
0.8879 High Similarity NPC231717
0.8871 High Similarity NPC15837
0.8862 High Similarity NPC142956
0.8846 High Similarity NPC53414
0.8846 High Similarity NPC53206
0.8837 High Similarity NPC258502
0.8837 High Similarity NPC80035
0.8828 High Similarity NPC225051
0.8819 High Similarity NPC244699
0.8814 High Similarity NPC322197
0.881 High Similarity NPC276238
0.88 High Similarity NPC176130
0.88 High Similarity NPC78364
0.88 High Similarity NPC69424
0.88 High Similarity NPC84672
0.8779 High Similarity NPC4214
0.8779 High Similarity NPC61398
0.8779 High Similarity NPC13715
0.8779 High Similarity NPC416
0.8769 High Similarity NPC254847
0.875 High Similarity NPC70622
0.874 High Similarity NPC108129
0.874 High Similarity NPC31799
0.873 High Similarity NPC48248
0.872 High Similarity NPC254492
0.872 High Similarity NPC177925
0.872 High Similarity NPC3224
0.8712 High Similarity NPC138099
0.8712 High Similarity NPC242994
0.871 High Similarity NPC199273
0.871 High Similarity NPC164014
0.8702 High Similarity NPC471905
0.8702 High Similarity NPC147418
0.8699 High Similarity NPC282577
0.8696 High Similarity NPC17525
0.8692 High Similarity NPC283088
0.8689 High Similarity NPC248363
0.8689 High Similarity NPC190971
0.8682 High Similarity NPC53896
0.8672 High Similarity NPC205992
0.8661 High Similarity NPC34414
0.8661 High Similarity NPC146647
0.8651 High Similarity NPC72667
0.8647 High Similarity NPC169452
0.8647 High Similarity NPC181560
0.8647 High Similarity NPC203063
0.8626 High Similarity NPC155211
0.8615 High Similarity NPC202225
0.8615 High Similarity NPC288089
0.8607 High Similarity NPC206778
0.8607 High Similarity NPC285829
0.8594 High Similarity NPC117609
0.8583 High Similarity NPC95537
0.8571 High Similarity NPC190457
0.8571 High Similarity NPC143438
0.8571 High Similarity NPC231774
0.8561 High Similarity NPC264022
0.856 High Similarity NPC173978
0.856 High Similarity NPC310540
0.8548 High Similarity NPC68167
0.8548 High Similarity NPC164947
0.8548 High Similarity NPC307174
0.8547 High Similarity NPC116842
0.8538 High Similarity NPC115458
0.8538 High Similarity NPC267205
0.8527 High Similarity NPC471851
0.8519 High Similarity NPC193555
0.8519 High Similarity NPC73061
0.8519 High Similarity NPC239136
0.8519 High Similarity NPC19631
0.8516 High Similarity NPC303910
0.8516 High Similarity NPC171460
0.8504 High Similarity NPC324209
0.8492 Intermediate Similarity NPC123506
0.8475 Intermediate Similarity NPC268388
0.8473 Intermediate Similarity NPC166480
0.8473 Intermediate Similarity NPC282780
0.8462 Intermediate Similarity NPC95172
0.8456 Intermediate Similarity NPC66593
0.8456 Intermediate Similarity NPC238629
0.845 Intermediate Similarity NPC55949
0.8448 Intermediate Similarity NPC34715
0.8448 Intermediate Similarity NPC226699
0.8444 Intermediate Similarity NPC305845
0.8444 Intermediate Similarity NPC204045
0.8444 Intermediate Similarity NPC290550
0.8444 Intermediate Similarity NPC246638
0.8433 Intermediate Similarity NPC26924
0.843 Intermediate Similarity NPC108288
0.8425 Intermediate Similarity NPC8745
0.8425 Intermediate Similarity NPC160499
0.8425 Intermediate Similarity NPC306765
0.8421 Intermediate Similarity NPC475957
0.8421 Intermediate Similarity NPC36868
0.8409 Intermediate Similarity NPC153088
0.84 Intermediate Similarity NPC176208
0.84 Intermediate Similarity NPC283514
0.8397 Intermediate Similarity NPC111845
0.8397 Intermediate Similarity NPC4170
0.8397 Intermediate Similarity NPC314048
0.8397 Intermediate Similarity NPC78307
0.8397 Intermediate Similarity NPC171968
0.8397 Intermediate Similarity NPC477139
0.8394 Intermediate Similarity NPC21599
0.8394 Intermediate Similarity NPC193703
0.8387 Intermediate Similarity NPC216216
0.8385 Intermediate Similarity NPC72669
0.8385 Intermediate Similarity NPC474517
0.8382 Intermediate Similarity NPC229218
0.8382 Intermediate Similarity NPC176030
0.8382 Intermediate Similarity NPC135524
0.8382 Intermediate Similarity NPC169214
0.8382 Intermediate Similarity NPC192597
0.8382 Intermediate Similarity NPC141817
0.8372 Intermediate Similarity NPC25736
0.837 Intermediate Similarity NPC96421
0.837 Intermediate Similarity NPC315578
0.8362 Intermediate Similarity NPC6984
0.8361 Intermediate Similarity NPC150919
0.8359 Intermediate Similarity NPC107672
0.8358 Intermediate Similarity NPC469681
0.8358 Intermediate Similarity NPC469680
0.8358 Intermediate Similarity NPC471974
0.8346 Intermediate Similarity NPC141934
0.8346 Intermediate Similarity NPC474813
0.8346 Intermediate Similarity NPC193358
0.8346 Intermediate Similarity NPC272268
0.8346 Intermediate Similarity NPC191976
0.8346 Intermediate Similarity NPC38158
0.8346 Intermediate Similarity NPC10926
0.8346 Intermediate Similarity NPC7464
0.8333 Intermediate Similarity NPC135062
0.8333 Intermediate Similarity NPC196673
0.8333 Intermediate Similarity NPC478019
0.8333 Intermediate Similarity NPC160777
0.8333 Intermediate Similarity NPC73416
0.8333 Intermediate Similarity NPC242136
0.8321 Intermediate Similarity NPC58685
0.8321 Intermediate Similarity NPC477407
0.832 Intermediate Similarity NPC295034
0.832 Intermediate Similarity NPC198336
0.8309 Intermediate Similarity NPC477275
0.8306 Intermediate Similarity NPC159525
0.8306 Intermediate Similarity NPC190501
0.8306 Intermediate Similarity NPC318552
0.8305 Intermediate Similarity NPC88141
0.8295 Intermediate Similarity NPC3009
0.8295 Intermediate Similarity NPC237225
0.8293 Intermediate Similarity NPC328694
0.8293 Intermediate Similarity NPC249435
0.8291 Intermediate Similarity NPC141523
0.8284 Intermediate Similarity NPC245923
0.8279 Intermediate Similarity NPC158157
0.8273 Intermediate Similarity NPC314437
0.8271 Intermediate Similarity NPC72918
0.8268 Intermediate Similarity NPC474766
0.8268 Intermediate Similarity NPC74507
0.8268 Intermediate Similarity NPC234890
0.8268 Intermediate Similarity NPC13238
0.8261 Intermediate Similarity NPC471906
0.8261 Intermediate Similarity NPC48762
0.8261 Intermediate Similarity NPC244691
0.8261 Intermediate Similarity NPC19896
0.8261 Intermediate Similarity NPC79627
0.8258 Intermediate Similarity NPC59459
0.8258 Intermediate Similarity NPC138472
0.8248 Intermediate Similarity NPC69755
0.8248 Intermediate Similarity NPC257644
0.8248 Intermediate Similarity NPC469520
0.824 Intermediate Similarity NPC236520
0.824 Intermediate Similarity NPC294361
0.8235 Intermediate Similarity NPC21162
0.8231 Intermediate Similarity NPC92624
0.8226 Intermediate Similarity NPC158222
0.8226 Intermediate Similarity NPC232178
0.8226 Intermediate Similarity NPC42657
0.8222 Intermediate Similarity NPC477849
0.8222 Intermediate Similarity NPC289358
0.8222 Intermediate Similarity NPC28592
0.8222 Intermediate Similarity NPC473479
0.8222 Intermediate Similarity NPC42384
0.8222 Intermediate Similarity NPC23667
0.8222 Intermediate Similarity NPC165191

  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 NPC91478 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
0.9098 High Similarity NPD1470 Approved
0.877 High Similarity NPD1201 Approved
0.8769 High Similarity NPD1509 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.8306 Intermediate Similarity NPD3019 Approved
0.8168 Intermediate Similarity NPD3764 Approved
0.816 Intermediate Similarity NPD2932 Approved
0.8045 Intermediate Similarity NPD943 Approved
0.8015 Intermediate Similarity NPD5405 Approved
0.8015 Intermediate Similarity NPD5404 Approved
0.8015 Intermediate Similarity NPD5408 Approved
0.8015 Intermediate Similarity NPD5406 Approved
0.7872 Intermediate Similarity NPD7390 Discontinued
0.7833 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7812 Intermediate Similarity NPD3026 Approved
0.7812 Intermediate Similarity NPD3023 Approved
0.7795 Intermediate Similarity NPD3024 Approved
0.7795 Intermediate Similarity NPD3025 Approved
0.7795 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD1164 Approved
0.7681 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7681 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD5951 Approved
0.7603 Intermediate Similarity NPD3226 Approved
0.7576 Intermediate Similarity NPD1283 Approved
0.7576 Intermediate Similarity NPD1876 Approved
0.7571 Intermediate Similarity NPD2346 Discontinued
0.7571 Intermediate Similarity NPD2344 Approved
0.7557 Intermediate Similarity NPD3972 Approved
0.7557 Intermediate Similarity NPD4878 Approved
0.7554 Intermediate Similarity NPD1510 Phase 2
0.7541 Intermediate Similarity NPD2342 Discontinued
0.7519 Intermediate Similarity NPD1651 Approved
0.7448 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD1471 Phase 3
0.7445 Intermediate Similarity NPD6663 Approved
0.7442 Intermediate Similarity NPD9545 Approved
0.744 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD1237 Approved
0.7431 Intermediate Similarity NPD3300 Phase 2
0.7424 Intermediate Similarity NPD9269 Phase 2
0.7413 Intermediate Similarity NPD8166 Discontinued
0.7413 Intermediate Similarity NPD3750 Approved
0.7413 Intermediate Similarity NPD7003 Approved
0.741 Intermediate Similarity NPD1607 Approved
0.7407 Intermediate Similarity NPD5736 Approved
0.7395 Intermediate Similarity NPD3020 Approved
0.7391 Intermediate Similarity NPD1240 Approved
0.7385 Intermediate Similarity NPD9268 Approved
0.7376 Intermediate Similarity NPD2935 Discontinued
0.7361 Intermediate Similarity NPD2309 Approved
0.7348 Intermediate Similarity NPD1281 Approved
0.7343 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7328 Intermediate Similarity NPD2286 Discontinued
0.7308 Intermediate Similarity NPD3091 Approved
0.7305 Intermediate Similarity NPD2799 Discontinued
0.729 Intermediate Similarity NPD6232 Discontinued
0.7288 Intermediate Similarity NPD2859 Approved
0.7288 Intermediate Similarity NPD2860 Approved
0.728 Intermediate Similarity NPD3022 Approved
0.728 Intermediate Similarity NPD3021 Approved
0.7279 Intermediate Similarity NPD6273 Approved
0.7279 Intermediate Similarity NPD9494 Approved
0.7273 Intermediate Similarity NPD1549 Phase 2
0.7273 Intermediate Similarity NPD1932 Approved
0.7261 Intermediate Similarity NPD7473 Discontinued
0.7248 Intermediate Similarity NPD7458 Discontinued
0.7246 Intermediate Similarity NPD2313 Discontinued
0.7239 Intermediate Similarity NPD1755 Approved
0.7213 Intermediate Similarity NPD1930 Approved
0.7213 Intermediate Similarity NPD1929 Approved
0.7213 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7206 Intermediate Similarity NPD2798 Approved
0.7203 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD2934 Approved
0.7203 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD2933 Approved
0.72 Intermediate Similarity NPD9266 Approved
0.72 Intermediate Similarity NPD74 Approved
0.7197 Intermediate Similarity NPD4059 Approved
0.7172 Intermediate Similarity NPD4628 Phase 3
0.7171 Intermediate Similarity NPD7819 Suspended
0.7164 Intermediate Similarity NPD1608 Approved
0.7153 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3749 Approved
0.7143 Intermediate Similarity NPD4879 Approved
0.7143 Intermediate Similarity NPD1511 Approved
0.7133 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD4093 Discontinued
0.712 Intermediate Similarity NPD9263 Approved
0.712 Intermediate Similarity NPD9264 Approved
0.712 Intermediate Similarity NPD9267 Approved
0.7109 Intermediate Similarity NPD7635 Approved
0.7095 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD230 Phase 1
0.709 Intermediate Similarity NPD3092 Approved
0.7083 Intermediate Similarity NPD288 Approved
0.7068 Intermediate Similarity NPD3095 Discontinued
0.7063 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD3748 Approved
0.7059 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD1242 Phase 1
0.7047 Intermediate Similarity NPD1512 Approved
0.7023 Intermediate Similarity NPD9493 Approved
0.7007 Intermediate Similarity NPD3094 Phase 2
0.7007 Intermediate Similarity NPD1203 Approved
0.7007 Intermediate Similarity NPD6190 Approved
0.7006 Intermediate Similarity NPD6959 Discontinued
0.7 Intermediate Similarity NPD844 Approved
0.6985 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1202 Approved
0.6974 Remote Similarity NPD4380 Phase 2
0.6963 Remote Similarity NPD1547 Clinical (unspecified phase)
0.695 Remote Similarity NPD8032 Phase 2
0.6948 Remote Similarity NPD1465 Phase 2
0.6948 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6944 Remote Similarity NPD4308 Phase 3
0.694 Remote Similarity NPD17 Approved
0.694 Remote Similarity NPD3412 Clinical (unspecified phase)
0.694 Remote Similarity NPD4626 Approved
0.6929 Remote Similarity NPD2329 Discontinued
0.6929 Remote Similarity NPD7008 Discontinued
0.6923 Remote Similarity NPD1241 Discontinued
0.6917 Remote Similarity NPD688 Clinical (unspecified phase)
0.6913 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6912 Remote Similarity NPD1481 Phase 2
0.6911 Remote Similarity NPD289 Clinical (unspecified phase)
0.6903 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6901 Remote Similarity NPD2979 Phase 3
0.6892 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6884 Remote Similarity NPD4339 Clinical (unspecified phase)
0.6883 Remote Similarity NPD1934 Approved
0.688 Remote Similarity NPD164 Approved
0.6879 Remote Similarity NPD3268 Approved
0.687 Remote Similarity NPD9281 Approved
0.6867 Remote Similarity NPD2533 Approved
0.6867 Remote Similarity NPD2534 Approved
0.6867 Remote Similarity NPD2532 Approved
0.6864 Remote Similarity NPD9256 Approved
0.6864 Remote Similarity NPD9258 Approved
0.6861 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6859 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5844 Phase 1
0.6849 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6846 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7610 Discontinued
0.6839 Remote Similarity NPD2801 Approved
0.6838 Remote Similarity NPD1535 Discovery
0.6829 Remote Similarity NPD2066 Phase 3
0.6822 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7411 Suspended
0.6818 Remote Similarity NPD255 Approved
0.6818 Remote Similarity NPD256 Approved
0.6815 Remote Similarity NPD1751 Approved
0.68 Remote Similarity NPD9261 Approved
0.6795 Remote Similarity NPD2296 Approved
0.6781 Remote Similarity NPD2796 Approved
0.6781 Remote Similarity NPD6099 Approved
0.6781 Remote Similarity NPD6100 Approved
0.6779 Remote Similarity NPD2354 Approved
0.6776 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6763 Remote Similarity NPD2797 Approved
0.6752 Remote Similarity NPD3882 Suspended
0.6752 Remote Similarity NPD650 Approved
0.6744 Remote Similarity NPD1792 Phase 2
0.6742 Remote Similarity NPD497 Approved
0.6724 Remote Similarity NPD111 Approved
0.6721 Remote Similarity NPD1809 Phase 2
0.6716 Remote Similarity NPD5536 Phase 2
0.6714 Remote Similarity NPD258 Approved
0.6714 Remote Similarity NPD257 Approved
0.6709 Remote Similarity NPD7075 Discontinued
0.6694 Remote Similarity NPD845 Approved
0.669 Remote Similarity NPD5156 Approved
0.669 Remote Similarity NPD7095 Approved
0.669 Remote Similarity NPD5155 Approved
0.6688 Remote Similarity NPD5978 Approved
0.6688 Remote Similarity NPD5977 Approved
0.6687 Remote Similarity NPD7177 Discontinued
0.6667 Remote Similarity NPD9717 Approved
0.6667 Remote Similarity NPD498 Approved
0.6667 Remote Similarity NPD4060 Phase 1
0.6667 Remote Similarity NPD2438 Suspended
0.6667 Remote Similarity NPD2182 Approved
0.6667 Remote Similarity NPD496 Approved
0.6667 Remote Similarity NPD4307 Phase 2
0.6667 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6667 Remote Similarity NPD495 Approved
0.6667 Remote Similarity NPD1551 Phase 2
0.6667 Remote Similarity NPD1239 Approved
0.6667 Remote Similarity NPD7577 Discontinued
0.6667 Remote Similarity NPD7609 Phase 3
0.6667 Remote Similarity NPD2531 Phase 2
0.6647 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6646 Remote Similarity NPD7768 Phase 2
0.6645 Remote Similarity NPD7004 Clinical (unspecified phase)

  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