Structure

Physi-Chem Properties

Molecular Weight:  220.06
Volume:  226.166
LogP:  1.109
LogD:  1.877
LogS:  -4.331
# Rotatable Bonds:  0
TPSA:  39.83
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  4
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.337
Synthetic Accessibility Score:  2.794
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:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.604
MDCK Permeability:  7.174570055212826e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.451
30% Bioavailability (F30%):  0.073

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.871
Plasma Protein Binding (PPB):  85.6621322631836%
Volume Distribution (VD):  1.162
Pgp-substrate:  8.363215446472168%

ADMET: Metabolism

CYP1A2-inhibitor:  0.775
CYP1A2-substrate:  0.535
CYP2C19-inhibitor:  0.071
CYP2C19-substrate:  0.142
CYP2C9-inhibitor:  0.016
CYP2C9-substrate:  0.201
CYP2D6-inhibitor:  0.15
CYP2D6-substrate:  0.189
CYP3A4-inhibitor:  0.078
CYP3A4-substrate:  0.125

ADMET: Excretion

Clearance (CL):  3.617
Half-life (T1/2):  0.321

ADMET: Toxicity

hERG Blockers:  0.081
Human Hepatotoxicity (H-HT):  0.33
Drug-inuced Liver Injury (DILI):  0.853
AMES Toxicity:  0.967
Rat Oral Acute Toxicity:  0.183
Maximum Recommended Daily Dose:  0.193
Skin Sensitization:  0.45
Carcinogencity:  0.424
Eye Corrosion:  0.048
Eye Irritation:  0.974
Respiratory Toxicity:  0.916

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

  Natural Product: NPC138830

Natural Product ID:  NPC138830
Common Name*:   (4Ar,5As,8Ar,13As,15As,15Br)-10-Methoxy-4A,5,5A,7,8,13A,15,15A,15B,16-Decahydro-2H-4,6-Methanoindolo[3,2,1-Ij]Oxepino[2,3,4-De]Pyrrolo[2,3-H]Quinoline-14-One
IUPAC Name:   (4aR,5aS,8aR,13aS,15aS,15bR)-10-methoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one
Synonyms:   Beta-Colubrine
Standard InCHIKey:  ZTHVHELPCLGXHF-JPPAUQSISA-N
Standard InCHI:  InChI=1S/C22H24N2O3/c1-26-13-2-3-16-15(8-13)22-5-6-23-11-12-4-7-27-17-10-19(25)24(16)21(22)20(17)14(12)9-18(22)23/h2-4,8,14,17-18,20-21H,5-7,9-11H2,1H3/t14-,17-,18-,20-,21-,22+/m0/s1
SMILES:  COc1ccc2c(c1)[C@]13CCN4[C@H]1C[C@@H]1[C@@H]5[C@@H]3N2C(=O)C[C@@H]5OCC=C1C4
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1994566
PubChem CID:   251890
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]
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]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[7912074]
NPO570 Semen holarrhenae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO570 Semen holarrhenae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 95719.41 nM PMID[532929]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 18071.74 nM PMID[532929]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 90364.95 nM PMID[532929]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 69183.1 nM PMID[532929]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 18578.04 nM PMID[532929]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 47206.3 nM PMID[532929]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 59156.16 nM PMID[532929]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 27542.29 nM PMID[532929]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 76559.66 nM PMID[532929]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 72276.98 nM PMID[532929]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 44360.86 nM PMID[532929]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 34914.03 nM PMID[532929]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 69984.2 nM PMID[532929]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 33728.73 nM PMID[532929]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 88511.56 nM PMID[532929]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 37239.17 nM PMID[532929]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 177.83 nM PMID[532929]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 80537.84 nM PMID[532929]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[532929]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 84918.05 nM PMID[532929]
NPT660 Cell Line SW480 Homo sapiens IC50 > 40000.0 nM PMID[532930]
NPT83 Cell Line MCF7 Homo sapiens IC50 > 40000.0 nM PMID[532930]
NPT81 Cell Line A549 Homo sapiens IC50 > 40000.0 nM PMID[532930]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 40000.0 nM PMID[532930]
NPT116 Cell Line HL-60 Homo sapiens IC50 > 40000.0 nM PMID[532930]

☑ 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 NPC138830 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
0.9451 High Similarity NPC67904
0.9312 High Similarity NPC159815
0.898 High Similarity NPC318525
0.898 High Similarity NPC10653
0.8757 High Similarity NPC251212
0.8757 High Similarity NPC214626
0.8757 High Similarity NPC139085
0.8641 High Similarity NPC21425
0.8548 High Similarity NPC22689
0.8548 High Similarity NPC105055
0.8434 Intermediate Similarity NPC10732
0.8407 Intermediate Similarity NPC260075
0.8366 Intermediate Similarity NPC288110
0.8263 Intermediate Similarity NPC473004
0.8154 Intermediate Similarity NPC127178
0.8138 Intermediate Similarity NPC473007
0.8086 Intermediate Similarity NPC473458
0.8071 Intermediate Similarity NPC473005
0.803 Intermediate Similarity NPC473006
0.8 Intermediate Similarity NPC162440
0.799 Intermediate Similarity NPC230313
0.799 Intermediate Similarity NPC243626
0.7969 Intermediate Similarity NPC473008
0.7959 Intermediate Similarity NPC100863
0.7951 Intermediate Similarity NPC234772
0.7923 Intermediate Similarity NPC222046
0.7874 Intermediate Similarity NPC77777
0.7849 Intermediate Similarity NPC96901
0.783 Intermediate Similarity NPC471513
0.7822 Intermediate Similarity NPC478075
0.7805 Intermediate Similarity NPC127996
0.7784 Intermediate Similarity NPC473569
0.7756 Intermediate Similarity NPC82541
0.7755 Intermediate Similarity NPC470485
0.7744 Intermediate Similarity NPC22476
0.7723 Intermediate Similarity NPC470484
0.7723 Intermediate Similarity NPC475147
0.7711 Intermediate Similarity NPC52801
0.7692 Intermediate Similarity NPC5630
0.7685 Intermediate Similarity NPC246140
0.7685 Intermediate Similarity NPC195787
0.7659 Intermediate Similarity NPC475133
0.7653 Intermediate Similarity NPC470483
0.7635 Intermediate Similarity NPC329833
0.7609 Intermediate Similarity NPC225319
0.7598 Intermediate Similarity NPC477161
0.7596 Intermediate Similarity NPC113946
0.7593 Intermediate Similarity NPC477397
0.7593 Intermediate Similarity NPC223242
0.7571 Intermediate Similarity NPC195636
0.7571 Intermediate Similarity NPC126556
0.7541 Intermediate Similarity NPC29285
0.7536 Intermediate Similarity NPC269449
0.7525 Intermediate Similarity NPC204970
0.7523 Intermediate Similarity NPC139373
0.7513 Intermediate Similarity NPC474059
0.75 Intermediate Similarity NPC33507
0.75 Intermediate Similarity NPC291173
0.7488 Intermediate Similarity NPC231924
0.7488 Intermediate Similarity NPC477160
0.7487 Intermediate Similarity NPC203972
0.7465 Intermediate Similarity NPC311906
0.7465 Intermediate Similarity NPC476069
0.7464 Intermediate Similarity NPC119722
0.7464 Intermediate Similarity NPC472098
0.7463 Intermediate Similarity NPC161804
0.7463 Intermediate Similarity NPC87714
0.7455 Intermediate Similarity NPC476220
0.7455 Intermediate Similarity NPC160113
0.743 Intermediate Similarity NPC128476
0.7426 Intermediate Similarity NPC71124
0.7411 Intermediate Similarity NPC477395
0.7394 Intermediate Similarity NPC70172
0.7394 Intermediate Similarity NPC472106
0.7387 Intermediate Similarity NPC131977
0.738 Intermediate Similarity NPC282339
0.738 Intermediate Similarity NPC99632
0.7379 Intermediate Similarity NPC14339
0.7379 Intermediate Similarity NPC268077
0.7373 Intermediate Similarity NPC476436
0.7368 Intermediate Similarity NPC469915
0.7366 Intermediate Similarity NPC474077
0.7366 Intermediate Similarity NPC1464
0.7354 Intermediate Similarity NPC301501
0.7345 Intermediate Similarity NPC477393
0.7339 Intermediate Similarity NPC470480
0.733 Intermediate Similarity NPC207971
0.7327 Intermediate Similarity NPC19175
0.7321 Intermediate Similarity NPC304837
0.7321 Intermediate Similarity NPC469450
0.7321 Intermediate Similarity NPC476258
0.7311 Intermediate Similarity NPC189661
0.731 Intermediate Similarity NPC52262
0.7306 Intermediate Similarity NPC203202
0.7306 Intermediate Similarity NPC264482
0.7304 Intermediate Similarity NPC5374
0.73 Intermediate Similarity NPC203628
0.7292 Intermediate Similarity NPC473743
0.729 Intermediate Similarity NPC96321
0.7287 Intermediate Similarity NPC176983
0.7287 Intermediate Similarity NPC286871
0.7287 Intermediate Similarity NPC472120
0.7287 Intermediate Similarity NPC472101
0.7281 Intermediate Similarity NPC477396
0.7277 Intermediate Similarity NPC221687
0.7269 Intermediate Similarity NPC46259
0.7265 Intermediate Similarity NPC154922
0.7263 Intermediate Similarity NPC279527
0.7263 Intermediate Similarity NPC214960
0.7257 Intermediate Similarity NPC469451
0.7257 Intermediate Similarity NPC469452
0.7255 Intermediate Similarity NPC265642
0.7255 Intermediate Similarity NPC132874
0.7255 Intermediate Similarity NPC138615
0.7255 Intermediate Similarity NPC218733
0.7244 Intermediate Similarity NPC475816
0.7234 Intermediate Similarity NPC248117
0.7228 Intermediate Similarity NPC254957
0.7222 Intermediate Similarity NPC102760
0.7214 Intermediate Similarity NPC25401
0.7208 Intermediate Similarity NPC98197
0.7207 Intermediate Similarity NPC476429
0.7204 Intermediate Similarity NPC471304
0.7202 Intermediate Similarity NPC476425
0.7196 Intermediate Similarity NPC230942
0.7196 Intermediate Similarity NPC315498
0.7193 Intermediate Similarity NPC329932
0.7181 Intermediate Similarity NPC193410
0.7171 Intermediate Similarity NPC23080
0.7171 Intermediate Similarity NPC193906
0.7169 Intermediate Similarity NPC477394
0.7167 Intermediate Similarity NPC478080
0.7162 Intermediate Similarity NPC120239
0.7157 Intermediate Similarity NPC303214
0.7157 Intermediate Similarity NPC473375
0.7157 Intermediate Similarity NPC97100
0.715 Intermediate Similarity NPC232600
0.7143 Intermediate Similarity NPC321211
0.7143 Intermediate Similarity NPC472099
0.7143 Intermediate Similarity NPC308943
0.7137 Intermediate Similarity NPC477066
0.7136 Intermediate Similarity NPC322621
0.713 Intermediate Similarity NPC17437
0.7128 Intermediate Similarity NPC61013
0.7121 Intermediate Similarity NPC159963
0.712 Intermediate Similarity NPC471124
0.7114 Intermediate Similarity NPC477186
0.7107 Intermediate Similarity NPC222524
0.7105 Intermediate Similarity NPC478081
0.7105 Intermediate Similarity NPC472117
0.7105 Intermediate Similarity NPC477067
0.7105 Intermediate Similarity NPC113455
0.7105 Intermediate Similarity NPC473540
0.7105 Intermediate Similarity NPC478082
0.7092 Intermediate Similarity NPC186669
0.7092 Intermediate Similarity NPC285941
0.7083 Intermediate Similarity NPC305984
0.7081 Intermediate Similarity NPC41216
0.7079 Intermediate Similarity NPC45389
0.7079 Intermediate Similarity NPC174629
0.707 Intermediate Similarity NPC55470
0.7067 Intermediate Similarity NPC471512
0.7062 Intermediate Similarity NPC85482
0.7056 Intermediate Similarity NPC470482
0.7056 Intermediate Similarity NPC6974
0.7056 Intermediate Similarity NPC99043
0.7056 Intermediate Similarity NPC218594
0.7056 Intermediate Similarity NPC470481
0.7054 Intermediate Similarity NPC475720
0.7054 Intermediate Similarity NPC474192
0.7047 Intermediate Similarity NPC167724
0.7047 Intermediate Similarity NPC223595
0.7047 Intermediate Similarity NPC224970
0.7041 Intermediate Similarity NPC476441
0.7041 Intermediate Similarity NPC320147
0.7039 Intermediate Similarity NPC133609
0.703 Intermediate Similarity NPC169387
0.703 Intermediate Similarity NPC477259
0.703 Intermediate Similarity NPC217294
0.7024 Intermediate Similarity NPC198401
0.702 Intermediate Similarity NPC166169
0.7018 Intermediate Similarity NPC475609
0.7014 Intermediate Similarity NPC122886
0.7014 Intermediate Similarity NPC115588
0.7009 Intermediate Similarity NPC189079
0.7005 Intermediate Similarity NPC17677
0.7 Intermediate Similarity NPC115906
0.7 Intermediate Similarity NPC133817
0.7 Intermediate Similarity NPC471122
0.7 Intermediate Similarity NPC476443
0.6995 Remote Similarity NPC473298
0.6986 Remote Similarity NPC471489
0.6982 Remote Similarity NPC266994
0.698 Remote Similarity NPC14994
0.6977 Remote Similarity NPC264176
0.6976 Remote Similarity NPC302001
0.6965 Remote Similarity NPC259626
0.6965 Remote Similarity NPC249405
0.6963 Remote Similarity NPC472102
0.6963 Remote Similarity NPC93653

  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 NPC138830 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
0.7819 Intermediate Similarity NPD5600 Discontinued
0.7668 Intermediate Similarity NPD6021 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD6533 Clinical (unspecified phase)
0.7462 Intermediate Similarity NPD6608 Clinical (unspecified phase)
0.7448 Intermediate Similarity NPD5312 Approved
0.7448 Intermediate Similarity NPD5313 Approved
0.7423 Intermediate Similarity NPD7149 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD5620 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD5900 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD6238 Discontinued
0.7316 Intermediate Similarity NPD3984 Clinical (unspecified phase)
0.7316 Intermediate Similarity NPD3983 Phase 3
0.7268 Intermediate Similarity NPD5521 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD4796 Discontinued
0.7196 Intermediate Similarity NPD19 Approved
0.7196 Intermediate Similarity NPD1743 Approved
0.7196 Intermediate Similarity NPD1742 Approved
0.7194 Intermediate Similarity NPD6654 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD5186 Approved
0.7188 Intermediate Similarity NPD5183 Approved
0.7181 Intermediate Similarity NPD5294 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD5334 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD5071 Phase 2
0.7164 Intermediate Similarity NPD5896 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD6321 Discontinued
0.7135 Intermediate Similarity NPD6457 Approved
0.713 Intermediate Similarity NPD8358 Approved
0.7128 Intermediate Similarity NPD7248 Discontinued
0.7093 Intermediate Similarity NPD8016 Phase 3
0.7093 Intermediate Similarity NPD8017 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD7064 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD3416 Discontinued
0.7059 Intermediate Similarity NPD7186 Phase 3
0.7045 Intermediate Similarity NPD7820 Phase 3
0.7041 Intermediate Similarity NPD5603 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD5515 Phase 2
0.7028 Intermediate Similarity NPD4154 Approved
0.7026 Intermediate Similarity NPD5997 Discontinued
0.7019 Intermediate Similarity NPD7255 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD7174 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6567 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2968 Approved
0.7 Intermediate Similarity NPD2971 Approved
0.6995 Remote Similarity NPD6037 Discontinued
0.699 Remote Similarity NPD5582 Discontinued
0.6986 Remote Similarity NPD3437 Discontinued
0.6976 Remote Similarity NPD7262 Phase 1
0.6968 Remote Similarity NPD6357 Discontinued
0.6967 Remote Similarity NPD6644 Discontinued
0.6959 Remote Similarity NPD7126 Discontinued
0.6948 Remote Similarity NPD8027 Approved
0.6948 Remote Similarity NPD4859 Phase 1
0.6937 Remote Similarity NPD7821 Clinical (unspecified phase)
0.6935 Remote Similarity NPD6293 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4166 Phase 2
0.6903 Remote Similarity NPD4885 Approved
0.6892 Remote Similarity NPD3912 Discontinued
0.689 Remote Similarity NPD4118 Clinical (unspecified phase)
0.689 Remote Similarity NPD6874 Approved
0.6888 Remote Similarity NPD5680 Clinical (unspecified phase)
0.6884 Remote Similarity NPD7479 Phase 2
0.6862 Remote Similarity NPD3641 Approved
0.6862 Remote Similarity NPD3640 Phase 3
0.6862 Remote Similarity NPD3639 Approved
0.6835 Remote Similarity NPD7559 Phase 2
0.6833 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6825 Remote Similarity NPD814 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7449 Clinical (unspecified phase)
0.6806 Remote Similarity NPD4201 Clinical (unspecified phase)
0.6802 Remote Similarity NPD7805 Phase 3
0.6797 Remote Similarity NPD7560 Approved
0.6796 Remote Similarity NPD2490 Approved
0.6796 Remote Similarity NPD2488 Approved
0.6794 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6771 Remote Similarity NPD1769 Discontinued
0.6768 Remote Similarity NPD6365 Clinical (unspecified phase)
0.675 Remote Similarity NPD3050 Clinical (unspecified phase)
0.6743 Remote Similarity NPD7225 Discontinued
0.6738 Remote Similarity NPD3141 Discontinued
0.6729 Remote Similarity NPD6250 Discontinued
0.6728 Remote Similarity NPD5860 Discontinued
0.672 Remote Similarity NPD5754 Discontinued
0.6715 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6713 Remote Similarity NPD2907 Approved
0.6713 Remote Similarity NPD2906 Approved
0.6701 Remote Similarity NPD4986 Clinical (unspecified phase)
0.6699 Remote Similarity NPD7291 Discontinued
0.6696 Remote Similarity NPD6997 Phase 2
0.6696 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6685 Remote Similarity NPD3110 Approved
0.6685 Remote Similarity NPD3109 Approved
0.6683 Remote Similarity NPD4481 Phase 3
0.6682 Remote Similarity NPD5293 Phase 2
0.6681 Remote Similarity NPD7797 Approved
0.6681 Remote Similarity NPD7796 Approved
0.6667 Remote Similarity NPD5847 Phase 1
0.6667 Remote Similarity NPD3793 Phase 3
0.6667 Remote Similarity NPD5917 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7281 Phase 3
0.6667 Remote Similarity NPD7280 Phase 3
0.6652 Remote Similarity NPD5025 Approved
0.6651 Remote Similarity NPD4997 Clinical (unspecified phase)
0.665 Remote Similarity NPD5938 Phase 3
0.665 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6636 Remote Similarity NPD2916 Discontinued
0.6636 Remote Similarity NPD4082 Approved
0.6633 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6623 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6622 Remote Similarity NPD3940 Clinical (unspecified phase)
0.6621 Remote Similarity NPD4493 Discontinued
0.6618 Remote Similarity NPD6040 Clinical (unspecified phase)
0.6617 Remote Similarity NPD4498 Clinical (unspecified phase)
0.6616 Remote Similarity NPD6107 Approved
0.6614 Remote Similarity NPD3124 Discontinued
0.6607 Remote Similarity NPD3783 Clinical (unspecified phase)
0.6605 Remote Similarity NPD6478 Clinical (unspecified phase)
0.6588 Remote Similarity NPD5548 Clinical (unspecified phase)
0.6585 Remote Similarity NPD4078 Clinical (unspecified phase)
0.6583 Remote Similarity NPD3051 Approved
0.658 Remote Similarity NPD6723 Discontinued
0.6579 Remote Similarity NPD4584 Approved
0.6577 Remote Similarity NPD8149 Discontinued
0.6575 Remote Similarity NPD8460 Approved
0.6575 Remote Similarity NPD8459 Approved
0.6571 Remote Similarity NPD5610 Approved
0.657 Remote Similarity NPD4084 Clinical (unspecified phase)
0.657 Remote Similarity NPD8103 Clinical (unspecified phase)
0.657 Remote Similarity NPD4515 Suspended
0.6566 Remote Similarity NPD5823 Approved
0.656 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6558 Remote Similarity NPD7626 Approved
0.6558 Remote Similarity NPD7627 Approved
0.6557 Remote Similarity NPD2973 Approved
0.6557 Remote Similarity NPD2974 Approved
0.6557 Remote Similarity NPD6284 Clinical (unspecified phase)
0.6557 Remote Similarity NPD2975 Approved
0.6555 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6553 Remote Similarity NPD6618 Phase 2
0.655 Remote Similarity NPD2970 Approved
0.655 Remote Similarity NPD2969 Approved
0.6546 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6546 Remote Similarity NPD7110 Phase 1
0.6542 Remote Similarity NPD4580 Approved
0.6538 Remote Similarity NPD3349 Phase 2
0.6538 Remote Similarity NPD8025 Phase 2
0.6537 Remote Similarity NPD7190 Clinical (unspecified phase)
0.6537 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6535 Remote Similarity NPD6645 Clinical (unspecified phase)
0.6533 Remote Similarity NPD5433 Clinical (unspecified phase)
0.6533 Remote Similarity NPD6379 Discontinued
0.6532 Remote Similarity NPD4897 Phase 2
0.6528 Remote Similarity NPD4120 Approved
0.6528 Remote Similarity NPD4121 Phase 3
0.6526 Remote Similarity NPD4420 Approved
0.6522 Remote Similarity NPD4981 Phase 2
0.6522 Remote Similarity NPD6199 Discontinued
0.6522 Remote Similarity NPD7589 Clinical (unspecified phase)
0.652 Remote Similarity NPD6878 Phase 2
0.652 Remote Similarity NPD6211 Clinical (unspecified phase)
0.652 Remote Similarity NPD6879 Phase 2
0.6518 Remote Similarity NPD6568 Discontinued
0.6517 Remote Similarity NPD27 Approved
0.6517 Remote Similarity NPD2489 Approved
0.6516 Remote Similarity NPD4492 Approved
0.6516 Remote Similarity NPD7956 Approved
0.6516 Remote Similarity NPD4494 Approved
0.6516 Remote Similarity NPD7955 Approved
0.6514 Remote Similarity NPD7222 Phase 2
0.6514 Remote Similarity NPD4596 Phase 1
0.6511 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6507 Remote Similarity NPD5928 Phase 1
0.6505 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6504 Remote Similarity NPD5507 Approved
0.6504 Remote Similarity NPD5506 Approved
0.6502 Remote Similarity NPD5670 Approved
0.6502 Remote Similarity NPD5562 Approved
0.6502 Remote Similarity NPD5561 Approved
0.6498 Remote Similarity NPD4040 Phase 1
0.6498 Remote Similarity NPD3946 Clinical (unspecified phase)
0.6496 Remote Similarity NPD4846 Phase 2
0.6496 Remote Similarity NPD8157 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5742 Approved
0.6495 Remote Similarity NPD1880 Phase 3
0.6495 Remote Similarity NPD5743 Approved
0.6495 Remote Similarity NPD5741 Approved
0.6493 Remote Similarity NPD6526 Approved
0.6488 Remote Similarity NPD8463 Approved
0.6483 Remote Similarity NPD6790 Phase 1
0.6482 Remote Similarity NPD8465 Approved
0.6482 Remote Similarity NPD8466 Approved
0.6482 Remote Similarity NPD8467 Approved
0.6481 Remote Similarity NPD5005 Approved
0.6481 Remote Similarity NPD5006 Approved
0.648 Remote Similarity NPD6737 Phase 2
0.648 Remote Similarity NPD6060 Clinical (unspecified phase)
0.648 Remote Similarity NPD6738 Phase 2
0.6476 Remote Similarity NPD5994 Discontinued
0.6476 Remote Similarity NPD8311 Discontinued
0.6474 Remote Similarity NPD1305 Clinical (unspecified phase)
0.6473 Remote Similarity NPD6853 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