Structure

Physi-Chem Properties

Molecular Weight:  599.31
Volume:  596.355
LogP:  1.867
LogD:  2.43
LogS:  -4.164
# Rotatable Bonds:  10
TPSA:  112.99
# H-Bond Aceptor:  10
# H-Bond Donor:  1
# Rings:  7
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.447
Synthetic Accessibility Score:  7.085
Fsp3:  0.758
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.254
MDCK Permeability:  6.475980626419187e-05
Pgp-inhibitor:  1.0
Pgp-substrate:  0.112
Human Intestinal Absorption (HIA):  0.722
20% Bioavailability (F20%):  0.069
30% Bioavailability (F30%):  0.41

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.244
Plasma Protein Binding (PPB):  18.897415161132812%
Volume Distribution (VD):  1.774
Pgp-substrate:  59.781288146972656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.423
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.871
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.012
CYP2D6-inhibitor:  0.037
CYP2D6-substrate:  0.283
CYP3A4-inhibitor:  0.353
CYP3A4-substrate:  0.657

ADMET: Excretion

Clearance (CL):  9.874
Half-life (T1/2):  0.015

ADMET: Toxicity

hERG Blockers:  0.26
Human Hepatotoxicity (H-HT):  0.395
Drug-inuced Liver Injury (DILI):  0.035
AMES Toxicity:  0.06
Rat Oral Acute Toxicity:  0.874
Maximum Recommended Daily Dose:  0.957
Skin Sensitization:  0.016
Carcinogencity:  0.011
Eye Corrosion:  0.003
Eye Irritation:  0.003
Respiratory Toxicity:  0.97

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

  Natural Product: NPC40539

Natural Product ID:  NPC40539
Common Name*:   REVYTWNGZDPRKE-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  REVYTWNGZDPRKE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3
SMILES:  CC(=O)OC12CC(C3(CC(C1C3OC(=O)c1ccccc1)C13C(CCC4(CN(C)C3C2C(C14)OC)COC)OC)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1995442
PubChem CID:   97909
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001551] Diterpenoids
          • [CHEMONTID:0003788] Aconitane-type diterpenoid 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
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. tuber n.a. PMID[12913245]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[1293938]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[16181762]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota roots n.a. n.a. PMID[18044843]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[22223386]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota Lateral roots n.a. n.a. PMID[22607495]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[22628040]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[22907155]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[23225552]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[23707213]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[23707213]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. root n.a. PMID[24190290]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. leaf n.a. PMID[24190290]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. PMID[24793215]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. root n.a. PMID[27761113]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota Roots n.a. n.a. PMID[30892884]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7490 Aconitum japonicum Species Ranunculaceae 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[557156]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 83752.93 nM PMID[557156]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 85310.01 nM PMID[557156]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 42953.64 nM PMID[557156]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[557156]

☑ 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 NPC40539 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
0.9941 High Similarity NPC108276
0.9941 High Similarity NPC163578
0.9767 High Similarity NPC172769
0.9767 High Similarity NPC205
0.9767 High Similarity NPC166521
0.9767 High Similarity NPC124690
0.9767 High Similarity NPC281470
0.9767 High Similarity NPC184195
0.9235 High Similarity NPC326895
0.9185 High Similarity NPC106840
0.9185 High Similarity NPC94687
0.9185 High Similarity NPC476495
0.9032 High Similarity NPC476496
0.852 High Similarity NPC223590
0.8477 Intermediate Similarity NPC140311
0.8418 Intermediate Similarity NPC473837
0.8392 Intermediate Similarity NPC106593
0.835 Intermediate Similarity NPC473667
0.8107 Intermediate Similarity NPC470631
0.8107 Intermediate Similarity NPC35390
0.8107 Intermediate Similarity NPC473781
0.8068 Intermediate Similarity NPC475316
0.8068 Intermediate Similarity NPC473486
0.7908 Intermediate Similarity NPC476500
0.774 Intermediate Similarity NPC323001
0.774 Intermediate Similarity NPC326235
0.7722 Intermediate Similarity NPC253738
0.7709 Intermediate Similarity NPC476750
0.7697 Intermediate Similarity NPC318447
0.7697 Intermediate Similarity NPC322048
0.7692 Intermediate Similarity NPC30171
0.7688 Intermediate Similarity NPC478263
0.7654 Intermediate Similarity NPC476784
0.763 Intermediate Similarity NPC478264
0.7627 Intermediate Similarity NPC471135
0.7624 Intermediate Similarity NPC478124
0.7611 Intermediate Similarity NPC323356
0.7611 Intermediate Similarity NPC309991
0.7611 Intermediate Similarity NPC326328
0.7611 Intermediate Similarity NPC471138
0.7602 Intermediate Similarity NPC16912
0.76 Intermediate Similarity NPC76103
0.7596 Intermediate Similarity NPC473468
0.7596 Intermediate Similarity NPC475567
0.7596 Intermediate Similarity NPC473557
0.7586 Intermediate Similarity NPC474935
0.7586 Intermediate Similarity NPC312393
0.7572 Intermediate Similarity NPC95265
0.7572 Intermediate Similarity NPC188865
0.7572 Intermediate Similarity NPC125106
0.7572 Intermediate Similarity NPC25768
0.7572 Intermediate Similarity NPC95810
0.7572 Intermediate Similarity NPC57628
0.7572 Intermediate Similarity NPC472573
0.7572 Intermediate Similarity NPC70716
0.7572 Intermediate Similarity NPC472570
0.7572 Intermediate Similarity NPC11685
0.7572 Intermediate Similarity NPC476974
0.7572 Intermediate Similarity NPC472569
0.7572 Intermediate Similarity NPC163719
0.7557 Intermediate Similarity NPC476173
0.7556 Intermediate Similarity NPC319404
0.7554 Intermediate Similarity NPC475175
0.7554 Intermediate Similarity NPC475531
0.7554 Intermediate Similarity NPC475198
0.7544 Intermediate Similarity NPC171207
0.7544 Intermediate Similarity NPC97667
0.7543 Intermediate Similarity NPC281717
0.7543 Intermediate Similarity NPC327031
0.7542 Intermediate Similarity NPC290683
0.7542 Intermediate Similarity NPC475638
0.7542 Intermediate Similarity NPC475548
0.7542 Intermediate Similarity NPC70344
0.7529 Intermediate Similarity NPC473088
0.7529 Intermediate Similarity NPC469349
0.7529 Intermediate Similarity NPC200471
0.7529 Intermediate Similarity NPC472575
0.7529 Intermediate Similarity NPC174982
0.7529 Intermediate Similarity NPC471104
0.7529 Intermediate Similarity NPC184817
0.7529 Intermediate Similarity NPC158663
0.7529 Intermediate Similarity NPC472568
0.7529 Intermediate Similarity NPC171525
0.7529 Intermediate Similarity NPC96903
0.7529 Intermediate Similarity NPC29704
0.7529 Intermediate Similarity NPC177940
0.7529 Intermediate Similarity NPC472571
0.7529 Intermediate Similarity NPC70403
0.7529 Intermediate Similarity NPC470159
0.7529 Intermediate Similarity NPC472572
0.7529 Intermediate Similarity NPC470157
0.7529 Intermediate Similarity NPC476973
0.7514 Intermediate Similarity NPC96308
0.75 Intermediate Similarity NPC471101
0.75 Intermediate Similarity NPC224491
0.75 Intermediate Similarity NPC118080
0.75 Intermediate Similarity NPC87448
0.75 Intermediate Similarity NPC476749
0.75 Intermediate Similarity NPC301556
0.75 Intermediate Similarity NPC472576
0.75 Intermediate Similarity NPC97947
0.75 Intermediate Similarity NPC27377
0.75 Intermediate Similarity NPC291599
0.75 Intermediate Similarity NPC270590
0.75 Intermediate Similarity NPC92293
0.75 Intermediate Similarity NPC41481
0.75 Intermediate Similarity NPC477491
0.75 Intermediate Similarity NPC266265
0.7486 Intermediate Similarity NPC473611
0.7486 Intermediate Similarity NPC478125
0.7486 Intermediate Similarity NPC473602
0.7472 Intermediate Similarity NPC472548
0.7471 Intermediate Similarity NPC470152
0.7471 Intermediate Similarity NPC475759
0.7471 Intermediate Similarity NPC475122
0.7471 Intermediate Similarity NPC241951
0.7457 Intermediate Similarity NPC34012
0.7447 Intermediate Similarity NPC203005
0.7442 Intermediate Similarity NPC100913
0.7442 Intermediate Similarity NPC472547
0.7442 Intermediate Similarity NPC275592
0.7442 Intermediate Similarity NPC90614
0.7429 Intermediate Similarity NPC472556
0.7414 Intermediate Similarity NPC163087
0.7411 Intermediate Similarity NPC36607
0.7409 Intermediate Similarity NPC327699
0.7401 Intermediate Similarity NPC476975
0.7389 Intermediate Similarity NPC473632
0.7389 Intermediate Similarity NPC132599
0.7389 Intermediate Similarity NPC472549
0.7389 Intermediate Similarity NPC469730
0.7386 Intermediate Similarity NPC240115
0.7386 Intermediate Similarity NPC48599
0.7386 Intermediate Similarity NPC209592
0.738 Intermediate Similarity NPC477488
0.7377 Intermediate Similarity NPC476077
0.7374 Intermediate Similarity NPC477905
0.7371 Intermediate Similarity NPC34943
0.7368 Intermediate Similarity NPC472551
0.7368 Intermediate Similarity NPC472545
0.736 Intermediate Similarity NPC473214
0.736 Intermediate Similarity NPC470245
0.736 Intermediate Similarity NPC31829
0.7356 Intermediate Similarity NPC472546
0.7356 Intermediate Similarity NPC475135
0.7345 Intermediate Similarity NPC473760
0.7341 Intermediate Similarity NPC473613
0.7341 Intermediate Similarity NPC473109
0.7341 Intermediate Similarity NPC147880
0.7341 Intermediate Similarity NPC473758
0.7341 Intermediate Similarity NPC473081
0.7341 Intermediate Similarity NPC211137
0.7341 Intermediate Similarity NPC48017
0.7341 Intermediate Similarity NPC184747
0.7341 Intermediate Similarity NPC43241
0.7341 Intermediate Similarity NPC473085
0.7341 Intermediate Similarity NPC476094
0.7341 Intermediate Similarity NPC473112
0.7341 Intermediate Similarity NPC4341
0.7341 Intermediate Similarity NPC200592
0.7341 Intermediate Similarity NPC473060
0.7337 Intermediate Similarity NPC472574
0.7333 Intermediate Similarity NPC472658
0.7333 Intermediate Similarity NPC472657
0.7326 Intermediate Similarity NPC39549
0.7318 Intermediate Similarity NPC470153
0.7318 Intermediate Similarity NPC62792
0.7318 Intermediate Similarity NPC478123
0.7314 Intermediate Similarity NPC177340
0.7314 Intermediate Similarity NPC473673
0.7314 Intermediate Similarity NPC139067
0.7314 Intermediate Similarity NPC475429
0.7314 Intermediate Similarity NPC147217
0.7314 Intermediate Similarity NPC191082
0.7314 Intermediate Similarity NPC246480
0.7314 Intermediate Similarity NPC270498
0.731 Intermediate Similarity NPC66761
0.731 Intermediate Similarity NPC291638
0.731 Intermediate Similarity NPC195647
0.731 Intermediate Similarity NPC17877
0.731 Intermediate Similarity NPC472577
0.7303 Intermediate Similarity NPC473215
0.7299 Intermediate Similarity NPC266374
0.7293 Intermediate Similarity NPC34066
0.7288 Intermediate Similarity NPC20255
0.7283 Intermediate Similarity NPC214550
0.7283 Intermediate Similarity NPC475652
0.7283 Intermediate Similarity NPC210591
0.7282 Intermediate Similarity NPC471623
0.7273 Intermediate Similarity NPC38696
0.7273 Intermediate Similarity NPC51314
0.7273 Intermediate Similarity NPC67777
0.7263 Intermediate Similarity NPC475561
0.7263 Intermediate Similarity NPC475417
0.7257 Intermediate Similarity NPC192658
0.7257 Intermediate Similarity NPC63737
0.7251 Intermediate Similarity NPC474608
0.7245 Intermediate Similarity NPC306001
0.7245 Intermediate Similarity NPC317882
0.7245 Intermediate Similarity NPC471629

  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 NPC40539 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
0.8865 High Similarity NPD7497 Discontinued
0.7581 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD8360 Approved
0.7282 Intermediate Similarity NPD8435 Approved
0.7282 Intermediate Similarity NPD8361 Approved
0.7254 Intermediate Similarity NPD8407 Phase 2
0.7188 Intermediate Similarity NPD8368 Discontinued
0.7179 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD7799 Discontinued
0.715 Intermediate Similarity NPD8485 Approved
0.7143 Intermediate Similarity NPD7702 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD7236 Approved
0.7033 Intermediate Similarity NPD7239 Suspended
0.7022 Intermediate Similarity NPD7488 Clinical (unspecified phase)
0.6898 Remote Similarity NPD7907 Approved
0.6889 Remote Similarity NPD7274 Clinical (unspecified phase)
0.6884 Remote Similarity NPD7906 Approved
0.6878 Remote Similarity NPD4107 Approved
0.6853 Remote Similarity NPD7313 Approved
0.6853 Remote Similarity NPD7310 Approved
0.6853 Remote Similarity NPD7311 Approved
0.6853 Remote Similarity NPD7312 Approved
0.6822 Remote Similarity NPD7047 Phase 3
0.6818 Remote Similarity NPD7309 Approved
0.6814 Remote Similarity NPD2975 Approved
0.6814 Remote Similarity NPD2973 Approved
0.6814 Remote Similarity NPD2974 Approved
0.6812 Remote Similarity NPD3057 Approved
0.6811 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6796 Remote Similarity NPD4580 Approved
0.6789 Remote Similarity NPD6997 Phase 2
0.6788 Remote Similarity NPD4481 Phase 3
0.678 Remote Similarity NPD2569 Approved
0.678 Remote Similarity NPD2567 Approved
0.6776 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6763 Remote Similarity NPD2493 Approved
0.6763 Remote Similarity NPD2494 Approved
0.6763 Remote Similarity NPD4482 Phase 3
0.6758 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6746 Remote Similarity NPD8319 Approved
0.6746 Remote Similarity NPD4582 Approved
0.6746 Remote Similarity NPD4583 Approved
0.6746 Remote Similarity NPD8320 Phase 1
0.6743 Remote Similarity NPD7713 Phase 3
0.6743 Remote Similarity NPD7714 Approved
0.6743 Remote Similarity NPD7715 Approved
0.6731 Remote Similarity NPD3533 Approved
0.6731 Remote Similarity NPD2972 Approved
0.6728 Remote Similarity NPD4665 Approved
0.6728 Remote Similarity NPD4111 Phase 1
0.6699 Remote Similarity NPD4002 Approved
0.6699 Remote Similarity NPD4004 Approved
0.6684 Remote Similarity NPD3051 Approved
0.6683 Remote Similarity NPD3450 Approved
0.6683 Remote Similarity NPD3452 Approved
0.6682 Remote Similarity NPD8462 Phase 1
0.6667 Remote Similarity NPD4663 Approved
0.6651 Remote Similarity NPD2491 Approved
0.6651 Remote Similarity NPD7701 Phase 2
0.665 Remote Similarity NPD2490 Approved
0.665 Remote Similarity NPD2488 Approved
0.6649 Remote Similarity NPD2970 Approved
0.6649 Remote Similarity NPD2969 Approved
0.6636 Remote Similarity NPD5676 Approved
0.6633 Remote Similarity NPD8658 Clinical (unspecified phase)
0.66 Remote Similarity NPD4577 Approved
0.66 Remote Similarity NPD3534 Clinical (unspecified phase)
0.66 Remote Similarity NPD2968 Approved
0.66 Remote Similarity NPD2971 Approved
0.66 Remote Similarity NPD4578 Approved
0.6597 Remote Similarity NPD7057 Phase 3
0.6597 Remote Similarity NPD7058 Phase 2
0.6571 Remote Similarity NPD3448 Approved
0.656 Remote Similarity NPD8404 Phase 2
0.6557 Remote Similarity NPD2575 Approved
0.6531 Remote Similarity NPD2489 Approved
0.6531 Remote Similarity NPD27 Approved
0.6517 Remote Similarity NPD6310 Approved
0.6517 Remote Similarity NPD6309 Approved
0.6517 Remote Similarity NPD6311 Approved
0.6507 Remote Similarity NPD8285 Discontinued
0.6502 Remote Similarity NPD8150 Discontinued
0.65 Remote Similarity NPD5039 Approved
0.6479 Remote Similarity NPD7999 Approved
0.6462 Remote Similarity NPD8127 Discontinued
0.6459 Remote Similarity NPD7700 Phase 2
0.6459 Remote Similarity NPD7699 Phase 2
0.6453 Remote Similarity NPD5036 Approved
0.6453 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6447 Remote Similarity NPD7997 Clinical (unspecified phase)
0.6437 Remote Similarity NPD5667 Approved
0.6435 Remote Similarity NPD7048 Phase 3
0.6429 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7315 Approved
0.6425 Remote Similarity NPD5120 Approved
0.6425 Remote Similarity NPD5121 Approved
0.6425 Remote Similarity NPD6213 Phase 3
0.6425 Remote Similarity NPD5119 Approved
0.6425 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6425 Remote Similarity NPD6212 Phase 3
0.6422 Remote Similarity NPD5038 Approved
0.6422 Remote Similarity NPD5037 Approved
0.6415 Remote Similarity NPD5005 Approved
0.6415 Remote Similarity NPD5006 Approved
0.6409 Remote Similarity NPD5980 Discovery
0.6402 Remote Similarity NPD7211 Clinical (unspecified phase)
0.64 Remote Similarity NPD4956 Approved
0.6396 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6394 Remote Similarity NPD6535 Approved
0.6394 Remote Similarity NPD6534 Approved
0.6393 Remote Similarity NPD7930 Approved
0.6387 Remote Similarity NPD6385 Approved
0.6387 Remote Similarity NPD6386 Approved
0.6386 Remote Similarity NPD7549 Discontinued
0.6386 Remote Similarity NPD7962 Phase 2
0.6384 Remote Similarity NPD4617 Approved
0.6384 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6384 Remote Similarity NPD5203 Approved
0.6384 Remote Similarity NPD4620 Approved
0.6384 Remote Similarity NPD2613 Approved
0.6384 Remote Similarity NPD5201 Approved
0.6381 Remote Similarity NPD4420 Approved
0.6368 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6364 Remote Similarity NPD2898 Approved
0.6364 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6359 Remote Similarity NPD7874 Approved
0.6359 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6355 Remote Similarity NPD4040 Phase 1
0.6341 Remote Similarity NPD8434 Phase 2
0.6332 Remote Similarity NPD5033 Approved
0.6329 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6324 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6313 Remote Similarity NPD4619 Approved
0.6313 Remote Similarity NPD4621 Approved
0.6307 Remote Similarity NPD2628 Approved
0.6307 Remote Similarity NPD2627 Approved
0.6307 Remote Similarity NPD2159 Approved
0.6307 Remote Similarity NPD2626 Approved
0.6307 Remote Similarity NPD2160 Approved
0.6307 Remote Similarity NPD2625 Approved
0.6298 Remote Similarity NPD7296 Approved
0.6286 Remote Similarity NPD5157 Phase 1
0.6286 Remote Similarity NPD5159 Phase 2
0.6286 Remote Similarity NPD5158 Clinical (unspecified phase)
0.628 Remote Similarity NPD6836 Approved
0.6278 Remote Similarity NPD2571 Approved
0.6278 Remote Similarity NPD3087 Approved
0.6278 Remote Similarity NPD3090 Approved
0.6278 Remote Similarity NPD3614 Approved
0.6278 Remote Similarity NPD4746 Phase 3
0.6278 Remote Similarity NPD2570 Approved
0.6278 Remote Similarity NPD2566 Approved
0.6278 Remote Similarity NPD2572 Clinical (unspecified phase)
0.6278 Remote Similarity NPD3088 Approved
0.6278 Remote Similarity NPD4745 Approved
0.6278 Remote Similarity NPD2574 Discontinued
0.6278 Remote Similarity NPD2573 Approved
0.6278 Remote Similarity NPD3615 Approved
0.6278 Remote Similarity NPD3089 Approved
0.6278 Remote Similarity NPD3616 Approved
0.6271 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6264 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6262 Remote Similarity NPD6823 Phase 2
0.6257 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6257 Remote Similarity NPD7910 Clinical (unspecified phase)
0.6256 Remote Similarity NPD7801 Approved
0.6256 Remote Similarity NPD7039 Approved
0.6256 Remote Similarity NPD5027 Approved
0.6256 Remote Similarity NPD7685 Pre-registration
0.6256 Remote Similarity NPD5031 Approved
0.6256 Remote Similarity NPD7038 Approved
0.6256 Remote Similarity NPD5029 Approved
0.6256 Remote Similarity NPD5030 Phase 2
0.6256 Remote Similarity NPD7783 Phase 2
0.6256 Remote Similarity NPD7782 Clinical (unspecified phase)
0.625 Remote Similarity NPD8161 Suspended
0.625 Remote Similarity NPD7283 Approved
0.6244 Remote Similarity NPD6781 Approved
0.6244 Remote Similarity NPD6776 Approved
0.6244 Remote Similarity NPD6782 Approved
0.6244 Remote Similarity NPD6780 Approved
0.6244 Remote Similarity NPD6779 Approved
0.6244 Remote Similarity NPD6777 Approved
0.6244 Remote Similarity NPD6778 Approved
0.6236 Remote Similarity NPD3662 Phase 3
0.6236 Remote Similarity NPD3663 Approved
0.6236 Remote Similarity NPD3664 Approved
0.6236 Remote Similarity NPD3661 Approved
0.6233 Remote Similarity NPD7697 Approved
0.6233 Remote Similarity NPD7696 Phase 3
0.6233 Remote Similarity NPD7698 Approved
0.6232 Remote Similarity NPD6835 Approved
0.6228 Remote Similarity NPD8058 Clinical (unspecified phase)
0.6228 Remote Similarity NPD8059 Phase 3
0.6227 Remote Similarity NPD7827 Phase 1
0.6225 Remote Similarity NPD36 Approved
0.6225 Remote Similarity NPD5028 Approved
0.6225 Remote Similarity NPD4954 Approved
0.6225 Remote Similarity NPD5026 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