Structure

Physi-Chem Properties

Molecular Weight:  279.13
Volume:  295.78
LogP:  4.771
LogD:  4.19
LogS:  -3.33
# Rotatable Bonds:  0
TPSA:  45.25
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.635
Synthetic Accessibility Score:  2.863
Fsp3:  0.222
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.1
MDCK Permeability:  1.6232674170169048e-05
Pgp-inhibitor:  0.709
Pgp-substrate:  0.015
Human Intestinal Absorption (HIA):  0.029
20% Bioavailability (F20%):  0.082
30% Bioavailability (F30%):  0.106

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.235
Plasma Protein Binding (PPB):  98.65235900878906%
Volume Distribution (VD):  0.834
Pgp-substrate:  1.1400705575942993%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.846
CYP2C19-inhibitor:  0.775
CYP2C19-substrate:  0.152
CYP2C9-inhibitor:  0.668
CYP2C9-substrate:  0.924
CYP2D6-inhibitor:  0.905
CYP2D6-substrate:  0.914
CYP3A4-inhibitor:  0.67
CYP3A4-substrate:  0.257

ADMET: Excretion

Clearance (CL):  5.061
Half-life (T1/2):  0.281

ADMET: Toxicity

hERG Blockers:  0.302
Human Hepatotoxicity (H-HT):  0.884
Drug-inuced Liver Injury (DILI):  0.786
AMES Toxicity:  0.725
Rat Oral Acute Toxicity:  0.841
Maximum Recommended Daily Dose:  0.949
Skin Sensitization:  0.813
Carcinogencity:  0.909
Eye Corrosion:  0.004
Eye Irritation:  0.904
Respiratory Toxicity:  0.973

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

  Natural Product: NPC291535

Natural Product ID:  NPC291535
Common Name*:   Sid506290
IUPAC Name:   2,2,7-trimethyl-10H-pyrano[2,3-b]carbazol-8-ol
Synonyms:  
Standard InCHIKey:  RUQHCCGMEXXSBD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H17NO2/c1-10-6-12-13-7-11-4-5-18(2,3)21-17(11)9-15(13)19-14(12)8-16(10)20/h4-9,19-20H,1-3H3
SMILES:  Cc1cc2c3cc4C=CC(C)(C)Oc4cc3[nH]c2cc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL495872
PubChem CID:   375149
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000211] Indoles and derivatives
        • [CHEMONTID:0000210] Carbazoles

*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
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota stem bark;fruit n.a. n.a. PMID[10924160]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota root bark Kuantaochi, Nantou Hsien, Taiwan n.a. PMID[10924160]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3118 Murraya euchrestifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3118 Murraya euchrestifolia Species Rutaceae 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
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 = 19952.62 nM PMID[558980]
NPT111 Cell Line K562 Homo sapiens GI50 = 25118.86 nM PMID[558980]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 = 3.236 nM PMID[558980]
NPT385 Cell Line SR Homo sapiens GI50 = 6456.54 nM PMID[558980]
NPT81 Cell Line A549 Homo sapiens GI50 = 6456.54 nM PMID[558980]
NPT379 Cell Line HOP-62 Homo sapiens GI50 = 7943.28 nM PMID[558980]
NPT372 Cell Line HOP-92 Homo sapiens GI50 = 9772.37 nM PMID[558980]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 = 19054.61 nM PMID[558980]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 = 13182.57 nM PMID[558980]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 5370.32 nM PMID[558980]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 = 8317.64 nM PMID[558980]
NPT572 Cell Line DMS-273 Homo sapiens GI50 = 5011.87 nM PMID[558980]
NPT407 Cell Line COLO 205 Homo sapiens GI50 = 25118.86 nM PMID[558980]
NPT579 Cell Line DLD-1 Homo sapiens GI50 = 12882.5 nM PMID[558980]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 = 6760.83 nM PMID[558980]
NPT393 Cell Line HCT-116 Homo sapiens GI50 = 12882.5 nM PMID[558980]
NPT148 Cell Line HCT-15 Homo sapiens GI50 = 8709.64 nM PMID[558980]
NPT139 Cell Line HT-29 Homo sapiens GI50 = 11748.98 nM PMID[558980]
NPT386 Cell Line KM12 Homo sapiens GI50 = 5248.07 nM PMID[558980]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 = 9332.54 nM PMID[558980]
NPT323 Cell Line SW-620 Homo sapiens GI50 = 7585.78 nM PMID[558980]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 6760.83 nM PMID[558980]
NPT374 Cell Line SF-539 Homo sapiens GI50 = 4073.8 nM PMID[558980]
NPT383 Cell Line SNB-19 Homo sapiens GI50 = 25118.86 nM PMID[558980]
NPT392 Cell Line SNB-75 Homo sapiens GI50 = 11220.18 nM PMID[558980]
NPT380 Cell Line U-251 Homo sapiens GI50 = 6025.6 nM PMID[558980]
NPT574 Cell Line XF498 Homo sapiens GI50 = 25118.86 nM PMID[558980]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 = 3981.07 nM PMID[558980]
NPT375 Cell Line Malme-3M Homo sapiens GI50 = 10000.0 nM PMID[558980]
NPT387 Cell Line M14 Homo sapiens GI50 = 6025.6 nM PMID[558980]
NPT573 Cell Line M19-MEL Homo sapiens GI50 = 19498.45 nM PMID[558980]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 = 25118.86 nM PMID[558980]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 = 14454.4 nM PMID[558980]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 = 17378.01 nM PMID[558980]
NPT398 Cell Line UACC-62 Homo sapiens GI50 = 6760.83 nM PMID[558980]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 = 22908.68 nM PMID[558980]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 = 25118.86 nM PMID[558980]
NPT369 Cell Line ACHN Homo sapiens GI50 = 9332.54 nM PMID[558980]
NPT406 Cell Line RXF 393 Homo sapiens GI50 = 4897.79 nM PMID[558980]
NPT368 Cell Line SN12C Homo sapiens GI50 = 6309.57 nM PMID[558980]
NPT384 Cell Line TK-10 Homo sapiens GI50 = 25118.86 nM PMID[558980]
NPT371 Cell Line UO-31 Homo sapiens GI50 = 11481.54 nM PMID[558980]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 6309.57 nM PMID[558981]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 9311.08 nM PMID[558981]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 9862.79 nM PMID[558981]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 11402.5 nM PMID[558981]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 6982.32 nM PMID[558981]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 17498.47 nM PMID[558981]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 4083.19 nM PMID[558981]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 10046.16 nM PMID[558981]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 25003.45 nM PMID[558981]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 3.228 nM PMID[558981]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 7277.8 nM PMID[558981]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 7943.28 nM PMID[558981]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 4549.88 nM PMID[558981]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 6053.41 nM PMID[558981]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 17741.89 nM PMID[558981]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 25003.45 nM PMID[558981]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 5035.01 nM PMID[558981]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 6382.63 nM PMID[558981]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 25003.45 nM PMID[558981]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 19588.45 nM PMID[558981]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 7638.36 nM PMID[558981]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 5260.17 nM PMID[558981]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 8394.6 nM PMID[558981]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 13061.71 nM PMID[558981]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 6067.36 nM PMID[558981]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 25003.45 nM PMID[558981]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 9099.13 nM PMID[558981]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 10471.29 nM PMID[558981]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 3953.67 nM PMID[558981]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 25003.45 nM PMID[558981]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 9354.06 nM PMID[558981]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 6729.77 nM PMID[558981]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 6412.1 nM PMID[558981]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 12793.81 nM PMID[558981]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 8729.71 nM PMID[558981]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 6698.85 nM PMID[558981]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 25003.45 nM PMID[558981]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 9311.08 nM PMID[558981]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 10592.54 nM PMID[558981]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 5357.97 nM PMID[558981]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 6745.28 nM PMID[558981]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 22855.99 nM PMID[558981]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 2500.35 nM PMID[558981]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 11324.0 nM PMID[558981]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 19815.27 nM PMID[558981]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 12764.39 nM PMID[558981]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 11776.06 nM PMID[558981]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 18879.91 nM PMID[558981]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 4931.74 nM PMID[558981]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 14521.12 nM PMID[558981]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 25003.45 nM PMID[558981]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 6918.31 nM PMID[558980]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 9120.11 nM PMID[558980]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 9332.54 nM PMID[558980]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 10715.19 nM PMID[558980]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 7244.36 nM PMID[558980]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 10471.29 nM PMID[558980]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 17782.79 nM PMID[558980]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. GI50 = 4570.88 nM PMID[558980]

☑ 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 NPC291535 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 NPC475085
1.0 High Similarity NPC475112
0.9667 High Similarity NPC72211
0.9665 High Similarity NPC70259
0.962 High Similarity NPC476106
0.9611 High Similarity NPC243834
0.9611 High Similarity NPC70956
0.9609 High Similarity NPC43787
0.9609 High Similarity NPC205934
0.9521 High Similarity NPC48353
0.9405 High Similarity NPC162484
0.9259 High Similarity NPC209769
0.9194 High Similarity NPC476044
0.9194 High Similarity NPC267423
0.9162 High Similarity NPC94943
0.9158 High Similarity NPC201697
0.9153 High Similarity NPC193777
0.9133 High Similarity NPC477532
0.9106 High Similarity NPC190007
0.905 High Similarity NPC212535
0.8973 High Similarity NPC131017
0.8947 High Similarity NPC470930
0.8906 High Similarity NPC470931
0.8861 High Similarity NPC252251
0.8818 High Similarity NPC209174
0.8777 High Similarity NPC153042
0.8775 High Similarity NPC477531
0.8744 High Similarity NPC473179
0.8657 High Similarity NPC198503
0.8607 High Similarity NPC477533
0.8607 High Similarity NPC150239
0.8587 High Similarity NPC84478
0.8556 High Similarity NPC474409
0.8549 High Similarity NPC135887
0.8549 High Similarity NPC199277
0.8542 High Similarity NPC11017
0.8507 High Similarity NPC247803
0.8485 Intermediate Similarity NPC87413
0.8476 Intermediate Similarity NPC6786
0.847 Intermediate Similarity NPC72980
0.8447 Intermediate Similarity NPC473185
0.8446 Intermediate Similarity NPC329747
0.8434 Intermediate Similarity NPC11464
0.8426 Intermediate Similarity NPC475910
0.841 Intermediate Similarity NPC223427
0.8404 Intermediate Similarity NPC246700
0.8394 Intermediate Similarity NPC128823
0.837 Intermediate Similarity NPC88363
0.8333 Intermediate Similarity NPC39679
0.8333 Intermediate Similarity NPC174760
0.8325 Intermediate Similarity NPC475253
0.8294 Intermediate Similarity NPC277351
0.8283 Intermediate Similarity NPC249583
0.8283 Intermediate Similarity NPC4687
0.8274 Intermediate Similarity NPC285558
0.8259 Intermediate Similarity NPC308137
0.8259 Intermediate Similarity NPC310211
0.8246 Intermediate Similarity NPC473182
0.8227 Intermediate Similarity NPC3207
0.8211 Intermediate Similarity NPC128751
0.8211 Intermediate Similarity NPC242928
0.8209 Intermediate Similarity NPC23294
0.8186 Intermediate Similarity NPC169402
0.8177 Intermediate Similarity NPC116238
0.8169 Intermediate Similarity NPC473187
0.8168 Intermediate Similarity NPC106833
0.8168 Intermediate Similarity NPC469497
0.8162 Intermediate Similarity NPC288943
0.8159 Intermediate Similarity NPC303951
0.8137 Intermediate Similarity NPC170114
0.8134 Intermediate Similarity NPC202503
0.8131 Intermediate Similarity NPC473183
0.8128 Intermediate Similarity NPC471080
0.8128 Intermediate Similarity NPC469592
0.8122 Intermediate Similarity NPC473184
0.8116 Intermediate Similarity NPC280799
0.8107 Intermediate Similarity NPC193267
0.8107 Intermediate Similarity NPC213530
0.8088 Intermediate Similarity NPC470549
0.8086 Intermediate Similarity NPC179287
0.806 Intermediate Similarity NPC210828
0.806 Intermediate Similarity NPC86834
0.8058 Intermediate Similarity NPC46561
0.8058 Intermediate Similarity NPC469594
0.8042 Intermediate Similarity NPC176127
0.8021 Intermediate Similarity NPC283152
0.799 Intermediate Similarity NPC141915
0.799 Intermediate Similarity NPC114335
0.799 Intermediate Similarity NPC280964
0.798 Intermediate Similarity NPC199667
0.7969 Intermediate Similarity NPC66083
0.7969 Intermediate Similarity NPC46580
0.7951 Intermediate Similarity NPC478074
0.7949 Intermediate Similarity NPC475190
0.794 Intermediate Similarity NPC232727
0.7931 Intermediate Similarity NPC473181
0.7906 Intermediate Similarity NPC62069
0.7902 Intermediate Similarity NPC316981
0.7902 Intermediate Similarity NPC473180
0.7902 Intermediate Similarity NPC294620
0.7895 Intermediate Similarity NPC132642
0.7895 Intermediate Similarity NPC474798
0.7892 Intermediate Similarity NPC167860
0.7892 Intermediate Similarity NPC123976
0.7885 Intermediate Similarity NPC303658
0.7885 Intermediate Similarity NPC473041
0.7879 Intermediate Similarity NPC306376
0.7874 Intermediate Similarity NPC183407
0.7868 Intermediate Similarity NPC13880
0.7864 Intermediate Similarity NPC266931
0.7857 Intermediate Similarity NPC310118
0.7847 Intermediate Similarity NPC208084
0.7824 Intermediate Similarity NPC61350
0.7816 Intermediate Similarity NPC94157
0.781 Intermediate Similarity NPC86078
0.7806 Intermediate Similarity NPC99666
0.7802 Intermediate Similarity NPC26850
0.78 Intermediate Similarity NPC329793
0.7788 Intermediate Similarity NPC330009
0.7783 Intermediate Similarity NPC300156
0.7783 Intermediate Similarity NPC45190
0.7778 Intermediate Similarity NPC251090
0.7772 Intermediate Similarity NPC473189
0.7772 Intermediate Similarity NPC469440
0.7767 Intermediate Similarity NPC208284
0.7766 Intermediate Similarity NPC307963
0.7763 Intermediate Similarity NPC131486
0.7751 Intermediate Similarity NPC314552
0.775 Intermediate Similarity NPC18487
0.7737 Intermediate Similarity NPC96890
0.7736 Intermediate Similarity NPC280272
0.7721 Intermediate Similarity NPC274640
0.7714 Intermediate Similarity NPC184408
0.7688 Intermediate Similarity NPC242209
0.7681 Intermediate Similarity NPC9894
0.7677 Intermediate Similarity NPC279401
0.7677 Intermediate Similarity NPC79293
0.7674 Intermediate Similarity NPC110151
0.767 Intermediate Similarity NPC469589
0.7667 Intermediate Similarity NPC305984
0.7665 Intermediate Similarity NPC469390
0.7641 Intermediate Similarity NPC204385
0.7637 Intermediate Similarity NPC26872
0.7633 Intermediate Similarity NPC471304
0.7632 Intermediate Similarity NPC312872
0.7628 Intermediate Similarity NPC227908
0.7619 Intermediate Similarity NPC148183
0.7619 Intermediate Similarity NPC152768
0.7617 Intermediate Similarity NPC51388
0.7614 Intermediate Similarity NPC76748
0.7606 Intermediate Similarity NPC60621
0.7589 Intermediate Similarity NPC78609
0.758 Intermediate Similarity NPC473105
0.7576 Intermediate Similarity NPC92111
0.7571 Intermediate Similarity NPC118228
0.757 Intermediate Similarity NPC144452
0.7563 Intermediate Similarity NPC296527
0.7561 Intermediate Similarity NPC164374
0.7561 Intermediate Similarity NPC137929
0.7559 Intermediate Similarity NPC225279
0.7558 Intermediate Similarity NPC194740
0.7549 Intermediate Similarity NPC295898
0.7546 Intermediate Similarity NPC200888
0.7537 Intermediate Similarity NPC121772
0.7537 Intermediate Similarity NPC249040
0.7535 Intermediate Similarity NPC211416
0.7534 Intermediate Similarity NPC475844
0.7524 Intermediate Similarity NPC39500
0.7523 Intermediate Similarity NPC11408
0.7512 Intermediate Similarity NPC134848
0.7512 Intermediate Similarity NPC187501
0.75 Intermediate Similarity NPC314002
0.75 Intermediate Similarity NPC21638
0.75 Intermediate Similarity NPC89549
0.75 Intermediate Similarity NPC106937
0.7489 Intermediate Similarity NPC474688
0.7489 Intermediate Similarity NPC474701
0.7488 Intermediate Similarity NPC32200
0.7488 Intermediate Similarity NPC162748
0.7487 Intermediate Similarity NPC34508
0.7487 Intermediate Similarity NPC16667
0.7478 Intermediate Similarity NPC475666
0.7477 Intermediate Similarity NPC471762
0.7467 Intermediate Similarity NPC189079
0.7465 Intermediate Similarity NPC96321
0.7463 Intermediate Similarity NPC326634
0.7463 Intermediate Similarity NPC276517
0.7462 Intermediate Similarity NPC171171
0.7455 Intermediate Similarity NPC217554
0.7453 Intermediate Similarity NPC74969
0.7451 Intermediate Similarity NPC176538
0.745 Intermediate Similarity NPC324149
0.7449 Intermediate Similarity NPC204717
0.7444 Intermediate Similarity NPC470784
0.7436 Intermediate Similarity NPC206201
0.7434 Intermediate Similarity NPC81939
0.7424 Intermediate Similarity NPC133609
0.7424 Intermediate Similarity NPC473188
0.7423 Intermediate Similarity NPC270009
0.7418 Intermediate Similarity NPC293151

  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 NPC291535 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
0.8513 High Similarity NPD3003 Approved
0.8267 Intermediate Similarity NPD5903 Approved
0.8267 Intermediate Similarity NPD5902 Approved
0.8205 Intermediate Similarity NPD1768 Approved
0.815 Intermediate Similarity NPD5658 Approved
0.7991 Intermediate Similarity NPD7558 Phase 2
0.7971 Intermediate Similarity NPD6985 Discontinued
0.7961 Intermediate Similarity NPD5612 Discontinued
0.7933 Intermediate Similarity NPD7194 Discontinued
0.7929 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7921 Intermediate Similarity NPD7452 Approved
0.7921 Intermediate Similarity NPD7222 Phase 2
0.7921 Intermediate Similarity NPD7453 Approved
0.7921 Intermediate Similarity NPD1392 Approved
0.7908 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.785 Intermediate Similarity NPD4511 Phase 1
0.7817 Intermediate Similarity NPD6491 Clinical (unspecified phase)
0.7817 Intermediate Similarity NPD4418 Discontinued
0.7812 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7767 Intermediate Similarity NPD5067 Phase 2
0.7767 Intermediate Similarity NPD5066 Phase 2
0.7767 Intermediate Similarity NPD6220 Phase 3
0.7766 Intermediate Similarity NPD1038 Approved
0.7754 Intermediate Similarity NPD1326 Approved
0.7754 Intermediate Similarity NPD1325 Approved
0.7751 Intermediate Similarity NPD5164 Discontinued
0.7739 Intermediate Similarity NPD7948 Phase 1
0.7727 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD5632 Approved
0.7696 Intermediate Similarity NPD8403 Phase 1
0.7677 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.766 Intermediate Similarity NPD4724 Clinical (unspecified phase)
0.7638 Intermediate Similarity NPD6590 Discontinued
0.7617 Intermediate Similarity NPD4204 Approved
0.7617 Intermediate Similarity NPD4203 Approved
0.76 Intermediate Similarity NPD5512 Phase 3
0.759 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7574 Intermediate Similarity NPD3825 Phase 3
0.7571 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7524 Intermediate Similarity NPD5530 Phase 1
0.7524 Intermediate Similarity NPD4305 Clinical (unspecified phase)
0.7513 Intermediate Similarity NPD3920 Phase 2
0.75 Intermediate Similarity NPD802 Phase 2
0.75 Intermediate Similarity NPD6494 Phase 2
0.75 Intermediate Similarity NPD6503 Clinical (unspecified phase)
0.7488 Intermediate Similarity NPD6160 Clinical (unspecified phase)
0.7488 Intermediate Similarity NPD3814 Phase 1
0.7487 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7487 Intermediate Similarity NPD5913 Phase 3
0.7477 Intermediate Similarity NPD5930 Phase 3
0.7475 Intermediate Similarity NPD5003 Discontinued
0.7452 Intermediate Similarity NPD2916 Discontinued
0.7434 Intermediate Similarity NPD4349 Approved
0.7434 Intermediate Similarity NPD4350 Approved
0.7429 Intermediate Similarity NPD4502 Phase 2
0.7422 Intermediate Similarity NPD6473 Phase 1
0.7418 Intermediate Similarity NPD7823 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7404 Intermediate Similarity NPD5429 Discontinued
0.7402 Intermediate Similarity NPD8395 Approved
0.7402 Intermediate Similarity NPD8396 Approved
0.7393 Intermediate Similarity NPD7069 Discontinued
0.7363 Intermediate Similarity NPD6569 Phase 2
0.733 Intermediate Similarity NPD6962 Phase 2
0.7327 Intermediate Similarity NPD7221 Approved
0.7327 Intermediate Similarity NPD7219 Approved
0.7311 Intermediate Similarity NPD2794 Discontinued
0.7304 Intermediate Similarity NPD6988 Phase 1
0.7291 Intermediate Similarity NPD6251 Discontinued
0.7291 Intermediate Similarity NPD3810 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD5256 Discontinued
0.728 Intermediate Similarity NPD8363 Approved
0.728 Intermediate Similarity NPD8364 Approved
0.7273 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD6150 Discontinued
0.7269 Intermediate Similarity NPD3875 Discontinued
0.7264 Intermediate Similarity NPD2565 Phase 2
0.7264 Intermediate Similarity NPD2564 Approved
0.726 Intermediate Similarity NPD6246 Approved
0.7257 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD6550 Discontinued
0.724 Intermediate Similarity NPD7555 Discontinued
0.724 Intermediate Similarity NPD5559 Phase 2
0.7238 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD4889 Approved
0.7235 Intermediate Similarity NPD6242 Discontinued
0.723 Intermediate Similarity NPD3330 Phase 1
0.7225 Intermediate Similarity NPD3397 Phase 2
0.7225 Intermediate Similarity NPD4795 Phase 2
0.722 Intermediate Similarity NPD8365 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD7672 Approved
0.7204 Intermediate Similarity NPD7671 Approved
0.7194 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD3402 Phase 1
0.7188 Intermediate Similarity NPD4373 Phase 2
0.7184 Intermediate Similarity NPD2727 Phase 2
0.7183 Intermediate Similarity NPD5416 Discontinued
0.7177 Intermediate Similarity NPD6991 Approved
0.7177 Intermediate Similarity NPD6324 Phase 1
0.7172 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD8466 Approved
0.7172 Intermediate Similarity NPD8465 Approved
0.7172 Intermediate Similarity NPD8427 Approved
0.7172 Intermediate Similarity NPD8429 Approved
0.7172 Intermediate Similarity NPD3037 Phase 1
0.7172 Intermediate Similarity NPD8428 Approved
0.7172 Intermediate Similarity NPD8467 Approved
0.7169 Intermediate Similarity NPD6736 Discontinued
0.7169 Intermediate Similarity NPD1954 Phase 1
0.7157 Intermediate Similarity NPD7479 Phase 2
0.7155 Intermediate Similarity NPD5482 Discontinued
0.715 Intermediate Similarity NPD3815 Phase 1
0.715 Intermediate Similarity NPD1921 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD3816 Phase 1
0.7143 Intermediate Similarity NPD8405 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2334 Discontinued
0.7136 Intermediate Similarity NPD2952 Discontinued
0.7136 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7136 Intermediate Similarity NPD6769 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD4952 Phase 3
0.7129 Intermediate Similarity NPD6975 Discontinued
0.7129 Intermediate Similarity NPD6208 Discontinued
0.7128 Intermediate Similarity NPD5617 Suspended
0.7125 Intermediate Similarity NPD6773 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD2187 Approved
0.7123 Intermediate Similarity NPD4439 Discontinued
0.7123 Intermediate Similarity NPD2189 Approved
0.712 Intermediate Similarity NPD1685 Approved
0.712 Intermediate Similarity NPD1684 Approved
0.7117 Intermediate Similarity NPD7268 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD1739 Approved
0.7115 Intermediate Similarity NPD1740 Approved
0.7112 Intermediate Similarity NPD814 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD3921 Approved
0.7108 Intermediate Similarity NPD3924 Approved
0.7108 Intermediate Similarity NPD3923 Approved
0.7108 Intermediate Similarity NPD3922 Approved
0.7107 Intermediate Similarity NPD6159 Phase 2
0.7103 Intermediate Similarity NPD5939 Approved
0.7103 Intermediate Similarity NPD5936 Approved
0.7092 Intermediate Similarity NPD5065 Approved
0.7089 Intermediate Similarity NPD4437 Phase 3
0.7083 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7074 Intermediate Similarity NPD7417 Discontinued
0.7074 Intermediate Similarity NPD6790 Phase 1
0.7073 Intermediate Similarity NPD6361 Phase 2
0.7071 Intermediate Similarity NPD1503 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD6202 Discontinued
0.7067 Intermediate Similarity NPD4885 Approved
0.7064 Intermediate Similarity NPD7395 Discontinued
0.7062 Intermediate Similarity NPD3946 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD4986 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD5901 Discontinued
0.7059 Intermediate Similarity NPD6530 Approved
0.7059 Intermediate Similarity NPD6531 Approved
0.7056 Intermediate Similarity NPD8426 Approved
0.7056 Intermediate Similarity NPD8425 Approved
0.7056 Intermediate Similarity NPD8460 Approved
0.7056 Intermediate Similarity NPD8459 Approved
0.7054 Intermediate Similarity NPD8512 Phase 3
0.7054 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD4021 Phase 2
0.704 Intermediate Similarity NPD3259 Approved
0.7037 Intermediate Similarity NPD1322 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD7025 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD2882 Phase 1
0.7009 Intermediate Similarity NPD6525 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6243 Phase 3
0.7009 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6244 Phase 3
0.7 Intermediate Similarity NPD7678 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5070 Clinical (unspecified phase)
0.6996 Remote Similarity NPD7676 Clinical (unspecified phase)
0.6996 Remote Similarity NPD7675 Phase 3
0.6996 Remote Similarity NPD7426 Phase 1
0.6996 Remote Similarity NPD7674 Phase 3
0.6995 Remote Similarity NPD2383 Phase 1
0.6995 Remote Similarity NPD6141 Clinical (unspecified phase)
0.6995 Remote Similarity NPD6290 Phase 2
0.6995 Remote Similarity NPD2749 Discontinued
0.699 Remote Similarity NPD4551 Phase 2
0.6986 Remote Similarity NPD2177 Approved
0.6986 Remote Similarity NPD5547 Clinical (unspecified phase)
0.6986 Remote Similarity NPD3837 Clinical (unspecified phase)
0.6986 Remote Similarity NPD2175 Phase 3
0.6986 Remote Similarity NPD2176 Approved
0.6985 Remote Similarity NPD8386 Phase 2
0.6985 Remote Similarity NPD1620 Clinical (unspecified phase)
0.6978 Remote Similarity NPD7589 Clinical (unspecified phase)
0.6974 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6147 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6803 Clinical (unspecified phase)
0.6968 Remote Similarity NPD4462 Approved
0.6968 Remote Similarity NPD4463 Approved
0.6957 Remote Similarity NPD5905 Phase 1
0.6957 Remote Similarity NPD3395 Approved
0.6957 Remote Similarity NPD1592 Phase 3
0.6957 Remote Similarity NPD3396 Approved
0.6955 Remote Similarity NPD3763 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