Structure

Physi-Chem Properties

Molecular Weight:  350.16
Volume:  347.059
LogP:  1.723
LogD:  1.825
LogS:  -3.342
# Rotatable Bonds:  0
TPSA:  53.01
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  7
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.719
Synthetic Accessibility Score:  6.065
Fsp3:  0.571
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.785
MDCK Permeability:  3.4544220397947356e-05
Pgp-inhibitor:  0.505
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.545
20% Bioavailability (F20%):  0.86
30% Bioavailability (F30%):  0.739

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.985
Plasma Protein Binding (PPB):  40.834571838378906%
Volume Distribution (VD):  3.271
Pgp-substrate:  58.704559326171875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.015
CYP1A2-substrate:  0.401
CYP2C19-inhibitor:  0.101
CYP2C19-substrate:  0.934
CYP2C9-inhibitor:  0.187
CYP2C9-substrate:  0.299
CYP2D6-inhibitor:  0.009
CYP2D6-substrate:  0.271
CYP3A4-inhibitor:  0.245
CYP3A4-substrate:  0.939

ADMET: Excretion

Clearance (CL):  12.078
Half-life (T1/2):  0.031

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.141
Drug-inuced Liver Injury (DILI):  0.045
AMES Toxicity:  0.048
Rat Oral Acute Toxicity:  0.989
Maximum Recommended Daily Dose:  0.948
Skin Sensitization:  0.089
Carcinogencity:  0.972
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.888

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

  Natural Product: NPC105055

Natural Product ID:  NPC105055
Common Name*:   5A-Hydroxy-2,4A,5,7,8,13A,15,15A,15B,16-Decahydro4,6-Methanoindolo[3,2,1-Ij]Oxepino[2,3,4-De]Pyrrolo[2,3-H]Quinoline-14-One
IUPAC Name:   5a-hydroxy-2,4a,5,7,8,13a,15,15a,15b,16-decahydro4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one
Synonyms:  
Standard InCHIKey:  HCCFPODVEOBUMM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H22N2O3/c24-17-9-16-18-13-10-21(25)20(6-7-22(21)11-12(13)5-8-26-16)14-3-1-2-4-15(14)23(17)19(18)20/h1-5,13,16,18-19,25H,6-11H2
SMILES:  c1ccc2c(c1)C13CCN4CC5=CCOC6CC(=O)N2C1C6C5CC34O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1970129
PubChem CID:   264627
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002749] Strychnos alkaloids

*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
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[10.1016/j.tet.2012.03.006]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. DOI[10.1016/j.tet.2012.03.006]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10814365]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[16317898]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[17449162]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[19235686]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[19666019]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[22707864]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[23088673]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[2393954]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[25594733]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26476665]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[7912074]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9322358]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21911 Tephrosia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30369 Strychnosn nux-vomica n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21911 Tephrosia purpurea 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 48083.93 nM PMID[471428]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 47533.52 nM PMID[471428]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 97274.72 nM PMID[471428]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[471428]

☑ 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 NPC105055 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 NPC22689
0.9226 High Similarity NPC251212
0.9226 High Similarity NPC139085
0.9226 High Similarity NPC214626
0.8844 High Similarity NPC260075
0.8548 High Similarity NPC138830
0.8548 High Similarity NPC67904
0.852 High Similarity NPC10653
0.852 High Similarity NPC318525
0.8289 Intermediate Similarity NPC162440
0.8177 Intermediate Similarity NPC329833
0.8171 Intermediate Similarity NPC472106
0.8163 Intermediate Similarity NPC159815
0.8161 Intermediate Similarity NPC472101
0.8161 Intermediate Similarity NPC472120
0.8146 Intermediate Similarity NPC96901
0.8142 Intermediate Similarity NPC52262
0.8021 Intermediate Similarity NPC471512
0.7989 Intermediate Similarity NPC221687
0.7933 Intermediate Similarity NPC469915
0.7898 Intermediate Similarity NPC225319
0.7886 Intermediate Similarity NPC113946
0.7876 Intermediate Similarity NPC475489
0.7869 Intermediate Similarity NPC99043
0.7869 Intermediate Similarity NPC218594
0.7857 Intermediate Similarity NPC203202
0.7857 Intermediate Similarity NPC264482
0.7853 Intermediate Similarity NPC97100
0.7853 Intermediate Similarity NPC472117
0.7853 Intermediate Similarity NPC473375
0.7842 Intermediate Similarity NPC470485
0.7829 Intermediate Similarity NPC29285
0.7737 Intermediate Similarity NPC470483
0.7737 Intermediate Similarity NPC25401
0.7697 Intermediate Similarity NPC472102
0.7697 Intermediate Similarity NPC309531
0.7659 Intermediate Similarity NPC288110
0.7656 Intermediate Similarity NPC473458
0.7654 Intermediate Similarity NPC282339
0.7654 Intermediate Similarity NPC99632
0.7647 Intermediate Similarity NPC159963
0.7629 Intermediate Similarity NPC90967
0.7622 Intermediate Similarity NPC186669
0.7606 Intermediate Similarity NPC97584
0.7592 Intermediate Similarity NPC473298
0.7581 Intermediate Similarity NPC6974
0.7568 Intermediate Similarity NPC476441
0.7556 Intermediate Similarity NPC286871
0.7556 Intermediate Similarity NPC176983
0.75 Intermediate Similarity NPC248117
0.7488 Intermediate Similarity NPC471513
0.7487 Intermediate Similarity NPC14994
0.7487 Intermediate Similarity NPC181928
0.7473 Intermediate Similarity NPC471124
0.7459 Intermediate Similarity NPC476425
0.7444 Intermediate Similarity NPC193410
0.7436 Intermediate Similarity NPC34717
0.7427 Intermediate Similarity NPC234772
0.7423 Intermediate Similarity NPC473004
0.7389 Intermediate Similarity NPC61013
0.7384 Intermediate Similarity NPC22082
0.7384 Intermediate Similarity NPC186284
0.738 Intermediate Similarity NPC320147
0.7371 Intermediate Similarity NPC264589
0.7366 Intermediate Similarity NPC276993
0.7366 Intermediate Similarity NPC473743
0.7366 Intermediate Similarity NPC293255
0.7366 Intermediate Similarity NPC181138
0.7366 Intermediate Similarity NPC10732
0.7366 Intermediate Similarity NPC21752
0.7366 Intermediate Similarity NPC210415
0.7366 Intermediate Similarity NPC298851
0.7356 Intermediate Similarity NPC77777
0.7348 Intermediate Similarity NPC471122
0.7348 Intermediate Similarity NPC36495
0.7337 Intermediate Similarity NPC279527
0.7337 Intermediate Similarity NPC214960
0.7321 Intermediate Similarity NPC222046
0.7308 Intermediate Similarity NPC474058
0.7308 Intermediate Similarity NPC315368
0.7306 Intermediate Similarity NPC21425
0.7297 Intermediate Similarity NPC224970
0.7297 Intermediate Similarity NPC167724
0.7297 Intermediate Similarity NPC223595
0.7292 Intermediate Similarity NPC473007
0.7282 Intermediate Similarity NPC127996
0.7277 Intermediate Similarity NPC477159
0.7264 Intermediate Similarity NPC1464
0.7264 Intermediate Similarity NPC473005
0.7256 Intermediate Similarity NPC477397
0.725 Intermediate Similarity NPC127178
0.7246 Intermediate Similarity NPC473006
0.7243 Intermediate Similarity NPC472115
0.7243 Intermediate Similarity NPC472114
0.7238 Intermediate Similarity NPC477156
0.7238 Intermediate Similarity NPC477157
0.7232 Intermediate Similarity NPC212799
0.723 Intermediate Similarity NPC477394
0.7225 Intermediate Similarity NPC476428
0.722 Intermediate Similarity NPC477160
0.7213 Intermediate Similarity NPC143457
0.7213 Intermediate Similarity NPC201424
0.7202 Intermediate Similarity NPC259626
0.7198 Intermediate Similarity NPC123241
0.7194 Intermediate Similarity NPC203628
0.7192 Intermediate Similarity NPC87714
0.7192 Intermediate Similarity NPC470484
0.7175 Intermediate Similarity NPC472100
0.7174 Intermediate Similarity NPC293458
0.7172 Intermediate Similarity NPC230313
0.7172 Intermediate Similarity NPC243626
0.7158 Intermediate Similarity NPC148468
0.7158 Intermediate Similarity NPC243673
0.7158 Intermediate Similarity NPC263709
0.7158 Intermediate Similarity NPC310403
0.7158 Intermediate Similarity NPC97380
0.7158 Intermediate Similarity NPC476326
0.7158 Intermediate Similarity NPC63210
0.7157 Intermediate Similarity NPC246140
0.7157 Intermediate Similarity NPC195787
0.715 Intermediate Similarity NPC100863
0.715 Intermediate Similarity NPC2933
0.7143 Intermediate Similarity NPC470631
0.7143 Intermediate Similarity NPC35390
0.7143 Intermediate Similarity NPC473781
0.7143 Intermediate Similarity NPC473008
0.7143 Intermediate Similarity NPC5630
0.7136 Intermediate Similarity NPC303214
0.7127 Intermediate Similarity NPC478076
0.712 Intermediate Similarity NPC321211
0.7113 Intermediate Similarity NPC322621
0.7112 Intermediate Similarity NPC33507
0.7111 Intermediate Similarity NPC243756
0.7111 Intermediate Similarity NPC475763
0.711 Intermediate Similarity NPC475316
0.711 Intermediate Similarity NPC473486
0.7098 Intermediate Similarity NPC256288
0.7097 Intermediate Similarity NPC470069
0.7097 Intermediate Similarity NPC52059
0.709 Intermediate Similarity NPC307640
0.709 Intermediate Similarity NPC473880
0.7085 Intermediate Similarity NPC477395
0.7083 Intermediate Similarity NPC11149
0.7083 Intermediate Similarity NPC286994
0.7072 Intermediate Similarity NPC469450
0.7048 Intermediate Similarity NPC189661
0.7047 Intermediate Similarity NPC475962
0.7044 Intermediate Similarity NPC232600
0.7041 Intermediate Similarity NPC285841
0.7026 Intermediate Similarity NPC476095
0.7022 Intermediate Similarity NPC477393
0.7017 Intermediate Similarity NPC154602
0.7016 Intermediate Similarity NPC129624
0.7015 Intermediate Similarity NPC475559
0.7014 Intermediate Similarity NPC291173
0.7011 Intermediate Similarity NPC211525
0.7011 Intermediate Similarity NPC153694
0.7009 Intermediate Similarity NPC469452
0.7009 Intermediate Similarity NPC469451
0.7005 Intermediate Similarity NPC284706
0.7005 Intermediate Similarity NPC475420
0.6995 Remote Similarity NPC473297
0.6995 Remote Similarity NPC161827
0.699 Remote Similarity NPC473615
0.6985 Remote Similarity NPC204970
0.6974 Remote Similarity NPC245741
0.697 Remote Similarity NPC474059
0.697 Remote Similarity NPC473569
0.6963 Remote Similarity NPC470548
0.6963 Remote Similarity NPC13367
0.6963 Remote Similarity NPC329338
0.6963 Remote Similarity NPC469726
0.696 Remote Similarity NPC477396
0.6954 Remote Similarity NPC229484
0.6947 Remote Similarity NPC329932
0.6935 Remote Similarity NPC477158
0.6935 Remote Similarity NPC22476
0.6931 Remote Similarity NPC302548
0.693 Remote Similarity NPC128476
0.6919 Remote Similarity NPC292675
0.6911 Remote Similarity NPC285622
0.6908 Remote Similarity NPC477173
0.6906 Remote Similarity NPC131977
0.6904 Remote Similarity NPC282092
0.6898 Remote Similarity NPC472121
0.6898 Remote Similarity NPC85651
0.6897 Remote Similarity NPC218733
0.6897 Remote Similarity NPC138615
0.6897 Remote Similarity NPC132874
0.6897 Remote Similarity NPC265642
0.6895 Remote Similarity NPC472118
0.6893 Remote Similarity NPC477179
0.6885 Remote Similarity NPC122106
0.6878 Remote Similarity NPC278887
0.6875 Remote Similarity NPC470488
0.6875 Remote Similarity NPC301501
0.6875 Remote Similarity NPC478075
0.6864 Remote Similarity NPC223242
0.686 Remote Similarity NPC477181
0.686 Remote Similarity NPC254850

  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 NPC105055 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
0.7222 Intermediate Similarity NPD4120 Approved
0.7222 Intermediate Similarity NPD4121 Phase 3
0.7182 Intermediate Similarity NPD5743 Approved
0.7182 Intermediate Similarity NPD5742 Approved
0.7182 Intermediate Similarity NPD5741 Approved
0.7 Intermediate Similarity NPD5997 Discontinued
0.6784 Remote Similarity NPD8103 Clinical (unspecified phase)
0.675 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6748 Remote Similarity NPD4601 Approved
0.6748 Remote Similarity NPD4600 Approved
0.6738 Remote Similarity NPD5715 Clinical (unspecified phase)
0.6735 Remote Similarity NPD6878 Phase 2
0.6735 Remote Similarity NPD6879 Phase 2
0.6667 Remote Similarity NPD7600 Phase 2
0.6667 Remote Similarity NPD6805 Discontinued
0.6667 Remote Similarity NPD7794 Clinical (unspecified phase)
0.6604 Remote Similarity NPD2916 Discontinued
0.6593 Remote Similarity NPD7487 Discontinued
0.6591 Remote Similarity NPD6995 Phase 1
0.6588 Remote Similarity NPD4775 Clinical (unspecified phase)
0.6584 Remote Similarity NPD5620 Clinical (unspecified phase)
0.6583 Remote Similarity NPD8658 Clinical (unspecified phase)
0.6575 Remote Similarity NPD6566 Discontinued
0.6571 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6548 Remote Similarity NPD5600 Discontinued
0.6538 Remote Similarity NPD4430 Phase 2
0.6538 Remote Similarity NPD2820 Phase 3
0.6531 Remote Similarity NPD3423 Phase 2
0.6531 Remote Similarity NPD3422 Phase 3
0.6526 Remote Similarity NPD7599 Phase 2
0.6524 Remote Similarity NPD8402 Approved
0.6524 Remote Similarity NPD8400 Approved
0.6524 Remote Similarity NPD8401 Approved
0.6517 Remote Similarity NPD6021 Clinical (unspecified phase)
0.6509 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6502 Remote Similarity NPD8025 Phase 2
0.6493 Remote Similarity NPD7205 Discontinued
0.6484 Remote Similarity NPD2365 Approved
0.6478 Remote Similarity NPD8016 Phase 3
0.6478 Remote Similarity NPD8017 Clinical (unspecified phase)
0.6476 Remote Similarity NPD6238 Discontinued
0.6467 Remote Similarity NPD7295 Approved
0.6465 Remote Similarity NPD5312 Approved
0.6465 Remote Similarity NPD5313 Approved
0.6459 Remote Similarity NPD6874 Approved
0.6452 Remote Similarity NPD4682 Phase 2
0.6452 Remote Similarity NPD5881 Clinical (unspecified phase)
0.6447 Remote Similarity NPD7449 Clinical (unspecified phase)
0.6445 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6443 Remote Similarity NPD5823 Approved
0.6432 Remote Similarity NPD3141 Discontinued
0.6425 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6394 Remote Similarity NPD5582 Discontinued
0.6387 Remote Similarity NPD7735 Clinical (unspecified phase)
0.6386 Remote Similarity NPD2968 Approved
0.6386 Remote Similarity NPD2971 Approved
0.6381 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6373 Remote Similarity NPD6484 Approved
0.6373 Remote Similarity NPD6891 Phase 2
0.6373 Remote Similarity NPD6483 Approved
0.6369 Remote Similarity NPD5184 Approved
0.6369 Remote Similarity NPD5182 Approved
0.6369 Remote Similarity NPD5185 Approved
0.6368 Remote Similarity NPD6997 Phase 2
0.6368 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6364 Remote Similarity NPD5919 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6316 Clinical (unspecified phase)
0.6359 Remote Similarity NPD7082 Approved
0.6359 Remote Similarity NPD2490 Approved
0.6359 Remote Similarity NPD2488 Approved
0.6356 Remote Similarity NPD7186 Phase 3
0.6355 Remote Similarity NPD6557 Phase 2
0.6351 Remote Similarity NPD4501 Approved
0.6351 Remote Similarity NPD4500 Approved
0.6351 Remote Similarity NPD3437 Discontinued
0.6341 Remote Similarity NPD4334 Discontinued
0.6335 Remote Similarity NPD1663 Discontinued
0.6333 Remote Similarity NPD2791 Discontinued
0.6324 Remote Similarity NPD5918 Discontinued
0.6324 Remote Similarity NPD7259 Approved
0.6321 Remote Similarity NPD6321 Discontinued
0.6298 Remote Similarity NPD5610 Approved
0.6296 Remote Similarity NPD7666 Phase 3
0.6296 Remote Similarity NPD7665 Phase 2
0.6294 Remote Similarity NPD3376 Clinical (unspecified phase)
0.6294 Remote Similarity NPD5186 Approved
0.6294 Remote Similarity NPD5183 Approved
0.6286 Remote Similarity NPD7238 Clinical (unspecified phase)
0.628 Remote Similarity NPD5504 Discontinued
0.6279 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6279 Remote Similarity NPD7001 Phase 3
0.6279 Remote Similarity NPD4901 Clinical (unspecified phase)
0.6277 Remote Similarity NPD5942 Approved
0.6277 Remote Similarity NPD5941 Approved
0.6269 Remote Similarity NPD5900 Clinical (unspecified phase)
0.6269 Remote Similarity NPD7479 Phase 2
0.6267 Remote Similarity NPD3912 Discontinued
0.6264 Remote Similarity NPD2670 Approved
0.6263 Remote Similarity NPD5727 Clinical (unspecified phase)
0.6256 Remote Similarity NPD5071 Phase 2
0.6256 Remote Similarity NPD7962 Phase 2
0.625 Remote Similarity NPD7569 Approved
0.625 Remote Similarity NPD3625 Discontinued
0.625 Remote Similarity NPD7570 Approved
0.6244 Remote Similarity NPD3983 Phase 3
0.6244 Remote Similarity NPD3984 Clinical (unspecified phase)
0.6244 Remote Similarity NPD6457 Approved
0.6238 Remote Similarity NPD6654 Clinical (unspecified phase)
0.6233 Remote Similarity NPD4040 Phase 1
0.6232 Remote Similarity NPD5896 Clinical (unspecified phase)
0.6232 Remote Similarity NPD5928 Phase 1
0.6231 Remote Similarity NPD3377 Discontinued
0.623 Remote Similarity NPD5086 Approved
0.6229 Remote Similarity NPD7921 Approved
0.6226 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6226 Remote Similarity NPD6999 Discontinued
0.6224 Remote Similarity NPD5430 Discontinued
0.6222 Remote Similarity NPD6740 Clinical (unspecified phase)
0.6221 Remote Similarity NPD8027 Approved
0.6219 Remote Similarity NPD5334 Clinical (unspecified phase)
0.6219 Remote Similarity NPD5521 Clinical (unspecified phase)
0.6219 Remote Similarity NPD3449 Discontinued
0.6218 Remote Similarity NPD8630 Approved
0.6212 Remote Similarity NPD3051 Approved
0.6212 Remote Similarity NPD7795 Phase 2
0.6211 Remote Similarity NPD7606 Phase 3
0.621 Remote Similarity NPD6567 Clinical (unspecified phase)
0.621 Remote Similarity NPD7595 Discontinued
0.6209 Remote Similarity NPD2973 Approved
0.6209 Remote Similarity NPD2975 Approved
0.6209 Remote Similarity NPD2974 Approved
0.6203 Remote Similarity NPD5933 Phase 3
0.6203 Remote Similarity NPD5931 Phase 3
0.6203 Remote Similarity NPD5932 Phase 3
0.6202 Remote Similarity NPD6659 Phase 2
0.6202 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6197 Remote Similarity NPD4580 Approved
0.6195 Remote Similarity NPD7820 Phase 3
0.619 Remote Similarity NPD4602 Approved
0.619 Remote Similarity NPD6723 Discontinued
0.6186 Remote Similarity NPD5294 Clinical (unspecified phase)
0.6183 Remote Similarity NPD5024 Approved
0.6182 Remote Similarity NPD7301 Phase 3
0.6181 Remote Similarity NPD2970 Approved
0.6181 Remote Similarity NPD2969 Approved
0.6181 Remote Similarity NPD3824 Phase 1
0.6179 Remote Similarity NPD4668 Phase 2
0.6178 Remote Similarity NPD7805 Phase 3
0.6176 Remote Similarity NPD8358 Approved
0.6174 Remote Similarity NPD7688 Phase 1
0.6172 Remote Similarity NPD4315 Phase 2
0.617 Remote Similarity NPD6416 Phase 2
0.6168 Remote Similarity NPD3450 Approved
0.6168 Remote Similarity NPD3452 Approved
0.6168 Remote Similarity NPD3416 Discontinued
0.6167 Remote Similarity NPD7821 Clinical (unspecified phase)
0.6166 Remote Similarity NPD6395 Phase 2
0.6166 Remote Similarity NPD6396 Clinical (unspecified phase)
0.6166 Remote Similarity NPD7105 Phase 1
0.6161 Remote Similarity NPD5411 Discontinued
0.6158 Remote Similarity NPD4330 Approved
0.6158 Remote Similarity NPD4329 Approved
0.6157 Remote Similarity NPD6644 Discontinued
0.6157 Remote Similarity NPD8459 Approved
0.6157 Remote Similarity NPD8460 Approved
0.6154 Remote Similarity NPD2506 Approved
0.6154 Remote Similarity NPD4499 Approved
0.615 Remote Similarity NPD6824 Clinical (unspecified phase)
0.615 Remote Similarity NPD2387 Approved
0.6146 Remote Similarity NPD2790 Discontinued
0.6145 Remote Similarity NPD2613 Approved
0.6142 Remote Similarity NPD7035 Approved
0.6142 Remote Similarity NPD7036 Phase 3
0.6142 Remote Similarity NPD4796 Discontinued
0.6141 Remote Similarity NPD6655 Clinical (unspecified phase)
0.6139 Remote Similarity NPD6020 Phase 2
0.6139 Remote Similarity NPD3792 Approved
0.6139 Remote Similarity NPD3793 Phase 3
0.6138 Remote Similarity NPD7478 Approved
0.6134 Remote Similarity NPD7248 Discontinued
0.6134 Remote Similarity NPD8359 Phase 2
0.6132 Remote Similarity NPD3828 Approved
0.613 Remote Similarity NPD7824 Approved
0.6129 Remote Similarity NPD6768 Approved
0.6127 Remote Similarity NPD3470 Approved
0.6127 Remote Similarity NPD3471 Approved
0.6124 Remote Similarity NPD8240 Discontinued
0.6122 Remote Similarity NPD1742 Approved
0.6122 Remote Similarity NPD1743 Approved
0.6122 Remote Similarity NPD19 Approved
0.612 Remote Similarity NPD6102 Clinical (unspecified phase)
0.6119 Remote Similarity NPD5466 Approved
0.6118 Remote Similarity NPD4946 Phase 2
0.6117 Remote Similarity NPD6017 Discontinued
0.6114 Remote Similarity NPD3132 Approved
0.6114 Remote Similarity NPD2610 Approved
0.6114 Remote Similarity NPD2611 Approved
0.6114 Remote Similarity NPD2612 Approved
0.6114 Remote Similarity NPD4218 Approved
0.6114 Remote Similarity NPD2608 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