Structure

Physi-Chem Properties

Molecular Weight:  610.3
Volume:  640.267
LogP:  5.451
LogD:  4.068
LogS:  -3.494
# Rotatable Bonds:  9
TPSA:  83.86
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  6
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.224
Synthetic Accessibility Score:  3.663
Fsp3:  0.351
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.715
MDCK Permeability:  2.002360633923672e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.029
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.86
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.626
Plasma Protein Binding (PPB):  95.31669616699219%
Volume Distribution (VD):  1.29
Pgp-substrate:  4.2303972244262695%

ADMET: Metabolism

CYP1A2-inhibitor:  0.091
CYP1A2-substrate:  0.973
CYP2C19-inhibitor:  0.096
CYP2C19-substrate:  0.946
CYP2C9-inhibitor:  0.036
CYP2C9-substrate:  0.608
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.965
CYP3A4-inhibitor:  0.089
CYP3A4-substrate:  0.947

ADMET: Excretion

Clearance (CL):  10.451
Half-life (T1/2):  0.582

ADMET: Toxicity

hERG Blockers:  0.952
Human Hepatotoxicity (H-HT):  0.129
Drug-inuced Liver Injury (DILI):  0.547
AMES Toxicity:  0.176
Rat Oral Acute Toxicity:  0.307
Maximum Recommended Daily Dose:  0.99
Skin Sensitization:  0.827
Carcinogencity:  0.034
Eye Corrosion:  0.003
Eye Irritation:  0.005
Respiratory Toxicity:  0.514

Download Data

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

  Natural Product: NPC42549

Natural Product ID:  NPC42549
Common Name*:   Isoliensinine
IUPAC Name:   (1R)-1-[[4-hydroxy-3-[[(1R)-6-methoxy-1-[(4-methoxyphenyl)methyl]-2-methyl-3,4-dihydro-1H-isoquinolin-7-yl]oxy]phenyl]methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol
Synonyms:   Isoliensinine
Standard InCHIKey:  AJPXZTKPPINUKN-FIRIVFDPSA-N
Standard InCHI:  InChI=1S/C37H42N2O6/c1-38-15-13-26-20-36(44-5)37(22-29(26)30(38)16-23-6-9-27(42-3)10-7-23)45-35-18-24(8-11-32(35)40)17-31-28-21-33(41)34(43-4)19-25(28)12-14-39(31)2/h6-11,18-22,30-31,40-41H,12-17H2,1-5H3/p+2/t30-,31-/m1/s1
SMILES:  C[NH+]1CCc2cc(c(cc2[C@H]1Cc1ccc(cc1)OC)Oc1cc(ccc1O)C[C@@H]1c2cc(c(cc2CC[NH+]1C)OC)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL502370
PubChem CID:   5274591
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0002566] Isoquinolines and derivatives
        • [CHEMONTID:0000054] Benzylisoquinolines

*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
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. PMID[19919095]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota flower buds and leaves Khon Kaen province, Thailand 2010 PMID[23270663]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Leaves n.a. n.a. PMID[23642481]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Flowers n.a. n.a. PMID[26462418]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3478 Nelumbo nucifera Species Nelumbonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3478 Nelumbo nucifera Species Nelumbonaceae 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
NPT2 Others Unspecified Inhibition = 59.6 % PMID[535655]

☑ 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 NPC42549 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 NPC240841
1.0 High Similarity NPC250846
1.0 High Similarity NPC268503
1.0 High Similarity NPC317272
1.0 High Similarity NPC256012
0.962 High Similarity NPC108434
0.962 High Similarity NPC475215
0.9542 High Similarity NPC25084
0.9542 High Similarity NPC247639
0.9387 High Similarity NPC286119
0.9329 High Similarity NPC229373
0.9329 High Similarity NPC251735
0.9329 High Similarity NPC223690
0.9329 High Similarity NPC328155
0.9329 High Similarity NPC42663
0.9329 High Similarity NPC222661
0.9329 High Similarity NPC49075
0.9329 High Similarity NPC311973
0.9329 High Similarity NPC30779
0.9329 High Similarity NPC258657
0.9329 High Similarity NPC90998
0.9329 High Similarity NPC7715
0.9329 High Similarity NPC15414
0.9329 High Similarity NPC104196
0.9329 High Similarity NPC54654
0.9329 High Similarity NPC285931
0.9329 High Similarity NPC290005
0.9329 High Similarity NPC239824
0.9329 High Similarity NPC290582
0.9329 High Similarity NPC185639
0.9329 High Similarity NPC181796
0.9329 High Similarity NPC279228
0.9329 High Similarity NPC217748
0.9329 High Similarity NPC271013
0.9329 High Similarity NPC8836
0.9329 High Similarity NPC182052
0.9273 High Similarity NPC274716
0.9273 High Similarity NPC254441
0.9273 High Similarity NPC167116
0.9241 High Similarity NPC475393
0.9216 High Similarity NPC220858
0.9216 High Similarity NPC88249
0.9216 High Similarity NPC192768
0.9216 High Similarity NPC97221
0.9216 High Similarity NPC151895
0.9162 High Similarity NPC212237
0.9162 High Similarity NPC116465
0.9107 High Similarity NPC275680
0.9107 High Similarity NPC22115
0.9103 High Similarity NPC207757
0.9103 High Similarity NPC295691
0.9103 High Similarity NPC39701
0.9103 High Similarity NPC469817
0.9103 High Similarity NPC172765
0.9103 High Similarity NPC193949
0.9103 High Similarity NPC189266
0.9103 High Similarity NPC2413
0.9103 High Similarity NPC278799
0.9103 High Similarity NPC184026
0.9103 High Similarity NPC204828
0.9103 High Similarity NPC110416
0.9103 High Similarity NPC249797
0.9103 High Similarity NPC54379
0.9103 High Similarity NPC5238
0.9103 High Similarity NPC276588
0.9103 High Similarity NPC127674
0.9085 High Similarity NPC147390
0.9085 High Similarity NPC246587
0.9085 High Similarity NPC428
0.9085 High Similarity NPC24233
0.9085 High Similarity NPC476571
0.9085 High Similarity NPC135538
0.9053 High Similarity NPC274661
0.9053 High Similarity NPC206900
0.9053 High Similarity NPC175890
0.9053 High Similarity NPC48490
0.9053 High Similarity NPC11296
0.9053 High Similarity NPC82457
0.902 High Similarity NPC191376
0.902 High Similarity NPC179825
0.902 High Similarity NPC321505
0.9 High Similarity NPC191132
0.9 High Similarity NPC60295
0.8988 High Similarity NPC95426
0.8988 High Similarity NPC16357
0.8988 High Similarity NPC302245
0.8947 High Similarity NPC24260
0.8947 High Similarity NPC478093
0.8944 High Similarity NPC4138
0.8944 High Similarity NPC284183
0.8944 High Similarity NPC121275
0.8935 High Similarity NPC139783
0.8935 High Similarity NPC65312
0.8902 High Similarity NPC76682
0.8902 High Similarity NPC317145
0.8902 High Similarity NPC317439
0.8902 High Similarity NPC10908
0.8902 High Similarity NPC63646
0.8902 High Similarity NPC276890
0.8902 High Similarity NPC115284
0.8902 High Similarity NPC198498
0.8902 High Similarity NPC227060
0.8895 High Similarity NPC473589
0.8895 High Similarity NPC30182
0.8895 High Similarity NPC478092
0.8895 High Similarity NPC478091
0.8889 High Similarity NPC185838
0.8848 High Similarity NPC41376
0.8848 High Similarity NPC12424
0.8848 High Similarity NPC129518
0.8848 High Similarity NPC251580
0.8812 High Similarity NPC111485
0.8782 High Similarity NPC103379
0.8782 High Similarity NPC477565
0.878 High Similarity NPC66573
0.8779 High Similarity NPC318805
0.8779 High Similarity NPC41122
0.8758 High Similarity NPC136860
0.8758 High Similarity NPC476567
0.8758 High Similarity NPC128019
0.8743 High Similarity NPC293093
0.8727 High Similarity NPC109925
0.8712 High Similarity NPC238530
0.8712 High Similarity NPC232514
0.8712 High Similarity NPC276944
0.8678 High Similarity NPC256124
0.8678 High Similarity NPC85381
0.8671 High Similarity NPC277669
0.8671 High Similarity NPC76213
0.8659 High Similarity NPC13916
0.8659 High Similarity NPC264850
0.8654 High Similarity NPC16107
0.8654 High Similarity NPC51957
0.8654 High Similarity NPC210437
0.8654 High Similarity NPC106295
0.8654 High Similarity NPC476144
0.8654 High Similarity NPC476151
0.8644 High Similarity NPC475654
0.8642 High Similarity NPC27410
0.8642 High Similarity NPC166014
0.8639 High Similarity NPC243454
0.8639 High Similarity NPC475479
0.8627 High Similarity NPC328750
0.8627 High Similarity NPC213206
0.8627 High Similarity NPC188163
0.8627 High Similarity NPC474915
0.8616 High Similarity NPC37272
0.8599 High Similarity NPC7467
0.8598 High Similarity NPC24465
0.8588 High Similarity NPC239584
0.858 High Similarity NPC234318
0.8571 High Similarity NPC186063
0.8562 High Similarity NPC314682
0.8554 High Similarity NPC83198
0.8554 High Similarity NPC204908
0.8544 High Similarity NPC60538
0.8544 High Similarity NPC92541
0.8544 High Similarity NPC207824
0.8538 High Similarity NPC299990
0.8538 High Similarity NPC73492
0.8537 High Similarity NPC324144
0.8509 High Similarity NPC187022
0.8509 High Similarity NPC80129
0.8494 Intermediate Similarity NPC474931
0.8494 Intermediate Similarity NPC145832
0.8494 Intermediate Similarity NPC210140
0.8494 Intermediate Similarity NPC158376
0.8494 Intermediate Similarity NPC12053
0.8494 Intermediate Similarity NPC81218
0.8494 Intermediate Similarity NPC117188
0.8494 Intermediate Similarity NPC205421
0.8494 Intermediate Similarity NPC306555
0.8488 Intermediate Similarity NPC302275
0.8485 Intermediate Similarity NPC13504
0.8485 Intermediate Similarity NPC306843
0.8485 Intermediate Similarity NPC136508
0.8485 Intermediate Similarity NPC196447
0.8485 Intermediate Similarity NPC253043
0.8485 Intermediate Similarity NPC96603
0.8485 Intermediate Similarity NPC477563
0.8485 Intermediate Similarity NPC78222
0.8485 Intermediate Similarity NPC212794
0.8476 Intermediate Similarity NPC60186
0.8447 Intermediate Similarity NPC2295
0.8447 Intermediate Similarity NPC477564
0.8418 Intermediate Similarity NPC144863
0.8402 Intermediate Similarity NPC232386
0.8402 Intermediate Similarity NPC152680
0.8402 Intermediate Similarity NPC190783
0.8385 Intermediate Similarity NPC26601
0.8385 Intermediate Similarity NPC82285
0.8385 Intermediate Similarity NPC133011
0.8373 Intermediate Similarity NPC134858
0.8373 Intermediate Similarity NPC169743
0.8372 Intermediate Similarity NPC195538
0.8366 Intermediate Similarity NPC131204
0.8366 Intermediate Similarity NPC301050
0.8354 Intermediate Similarity NPC216816
0.8344 Intermediate Similarity NPC147091
0.8333 Intermediate Similarity NPC249996

  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 NPC42549 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
0.9329 High Similarity NPD8054 Approved
0.9329 High Similarity NPD8053 Approved
0.8902 High Similarity NPD8251 Approved
0.8902 High Similarity NPD8252 Approved
0.8902 High Similarity NPD8099 Discontinued
0.8848 High Similarity NPD8156 Discontinued
0.8654 High Similarity NPD4584 Approved
0.8627 High Similarity NPD4664 Clinical (unspecified phase)
0.8562 High Similarity NPD4772 Phase 2
0.8562 High Similarity NPD4773 Phase 2
0.8528 High Similarity NPD7832 Clinical (unspecified phase)
0.8528 High Similarity NPD7831 Phase 2
0.8528 High Similarity NPD7833 Phase 2
0.8509 High Similarity NPD7298 Approved
0.8313 Intermediate Similarity NPD7201 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.8214 Intermediate Similarity NPD4010 Discontinued
0.8187 Intermediate Similarity NPD1754 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD6030 Approved
0.8086 Intermediate Similarity NPD6031 Approved
0.8012 Intermediate Similarity NPD2489 Approved
0.8012 Intermediate Similarity NPD27 Approved
0.8011 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD5241 Discontinued
0.7988 Intermediate Similarity NPD4017 Approved
0.7978 Intermediate Similarity NPD7906 Approved
0.7978 Intermediate Similarity NPD8095 Phase 1
0.7975 Intermediate Similarity NPD3641 Approved
0.7975 Intermediate Similarity NPD3639 Approved
0.7975 Intermediate Similarity NPD3640 Phase 3
0.7962 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD3845 Phase 1
0.7941 Intermediate Similarity NPD7802 Discontinued
0.7907 Intermediate Similarity NPD2898 Approved
0.7901 Intermediate Similarity NPD2421 Approved
0.7901 Intermediate Similarity NPD2420 Approved
0.7898 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD6071 Discontinued
0.7895 Intermediate Similarity NPD3051 Approved
0.7853 Intermediate Similarity NPD7310 Approved
0.7853 Intermediate Similarity NPD7313 Approved
0.7853 Intermediate Similarity NPD7312 Approved
0.7853 Intermediate Similarity NPD7311 Approved
0.7849 Intermediate Similarity NPD2969 Approved
0.7849 Intermediate Similarity NPD2970 Approved
0.7836 Intermediate Similarity NPD6107 Approved
0.7809 Intermediate Similarity NPD7309 Approved
0.7806 Intermediate Similarity NPD5718 Phase 2
0.7792 Intermediate Similarity NPD5752 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD2422 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD6788 Approved
0.7683 Intermediate Similarity NPD3124 Discontinued
0.7654 Intermediate Similarity NPD4578 Approved
0.7654 Intermediate Similarity NPD4577 Approved
0.7647 Intermediate Similarity NPD2563 Approved
0.7647 Intermediate Similarity NPD2560 Approved
0.7624 Intermediate Similarity NPD4663 Approved
0.7611 Intermediate Similarity NPD6851 Approved
0.7611 Intermediate Similarity NPD6853 Approved
0.7602 Intermediate Similarity NPD4581 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD7132 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD6297 Approved
0.7571 Intermediate Similarity NPD5313 Approved
0.7571 Intermediate Similarity NPD5312 Approved
0.7562 Intermediate Similarity NPD6896 Approved
0.7562 Intermediate Similarity NPD6895 Approved
0.756 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD5602 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD4475 Approved
0.7532 Intermediate Similarity NPD2674 Phase 3
0.7532 Intermediate Similarity NPD4474 Approved
0.7529 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD2669 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6783 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2488 Approved
0.75 Intermediate Similarity NPD2490 Approved
0.75 Intermediate Similarity NPD6748 Discontinued
0.7486 Intermediate Similarity NPD4166 Phase 2
0.7485 Intermediate Similarity NPD7037 Approved
0.747 Intermediate Similarity NPD7598 Phase 2
0.7469 Intermediate Similarity NPD1632 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD2122 Discontinued
0.7439 Intermediate Similarity NPD4162 Approved
0.7425 Intermediate Similarity NPD4123 Phase 3
0.7401 Intermediate Similarity NPD4481 Phase 3
0.7394 Intermediate Similarity NPD6658 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD7291 Discontinued
0.7384 Intermediate Similarity NPD5773 Approved
0.7384 Intermediate Similarity NPD5772 Approved
0.7381 Intermediate Similarity NPD6090 Discontinued
0.7378 Intermediate Similarity NPD7045 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD3145 Approved
0.7358 Intermediate Similarity NPD3144 Approved
0.7358 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD3692 Discontinued
0.7333 Intermediate Similarity NPD5177 Phase 3
0.7333 Intermediate Similarity NPD3060 Approved
0.7333 Intermediate Similarity NPD7479 Phase 2
0.7325 Intermediate Similarity NPD6584 Phase 3
0.7321 Intermediate Similarity NPD7447 Phase 1
0.7308 Intermediate Similarity NPD7258 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD1753 Discontinued
0.7283 Intermediate Similarity NPD2978 Approved
0.7283 Intermediate Similarity NPD2977 Approved
0.7273 Intermediate Similarity NPD7153 Discontinued
0.7267 Intermediate Similarity NPD7110 Phase 1
0.7267 Intermediate Similarity NPD3109 Approved
0.7267 Intermediate Similarity NPD7109 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD3110 Approved
0.7257 Intermediate Similarity NPD8005 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD6523 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD5084 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.724 Intermediate Similarity NPD3452 Approved
0.724 Intermediate Similarity NPD2493 Approved
0.724 Intermediate Similarity NPD2494 Approved
0.724 Intermediate Similarity NPD3450 Approved
0.7229 Intermediate Similarity NPD44 Approved
0.7229 Intermediate Similarity NPD6364 Approved
0.7228 Intermediate Similarity NPD6618 Phase 2
0.7225 Intermediate Similarity NPD5720 Discontinued
0.7219 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD3656 Approved
0.7209 Intermediate Similarity NPD4675 Approved
0.7209 Intermediate Similarity NPD4678 Approved
0.7202 Intermediate Similarity NPD7124 Phase 2
0.7186 Intermediate Similarity NPD6331 Phase 2
0.7182 Intermediate Similarity NPD4873 Discontinued
0.7182 Intermediate Similarity NPD6042 Phase 2
0.7182 Intermediate Similarity NPD42 Phase 2
0.7176 Intermediate Similarity NPD3647 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD5677 Discontinued
0.7174 Intermediate Similarity NPD7280 Phase 3
0.7174 Intermediate Similarity NPD7281 Phase 3
0.7168 Intermediate Similarity NPD7438 Suspended
0.7167 Intermediate Similarity NPD5938 Phase 3
0.7166 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD7212 Phase 2
0.716 Intermediate Similarity NPD7213 Phase 3
0.7157 Intermediate Similarity NPD6997 Phase 2
0.7152 Intermediate Similarity NPD3055 Approved
0.7152 Intermediate Similarity NPD3053 Approved
0.7151 Intermediate Similarity NPD6688 Approved
0.7151 Intermediate Similarity NPD6687 Approved
0.7143 Intermediate Similarity NPD5160 Discontinued
0.7143 Intermediate Similarity NPD5977 Approved
0.7143 Intermediate Similarity NPD5978 Approved
0.7135 Intermediate Similarity NPD6662 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD6582 Phase 2
0.7134 Intermediate Similarity NPD6583 Phase 3
0.7134 Intermediate Similarity NPD7718 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD4582 Approved
0.7128 Intermediate Similarity NPD4583 Approved
0.7126 Intermediate Similarity NPD4237 Approved
0.7126 Intermediate Similarity NPD4236 Phase 3
0.712 Intermediate Similarity NPD7549 Discontinued
0.7119 Intermediate Similarity NPD8245 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD7047 Phase 3
0.7107 Intermediate Similarity NPD7905 Discontinued
0.7099 Intermediate Similarity NPD7477 Discontinued
0.7089 Intermediate Similarity NPD5311 Approved
0.7089 Intermediate Similarity NPD5310 Approved
0.7081 Intermediate Similarity NPD2968 Approved
0.7081 Intermediate Similarity NPD5156 Approved
0.7081 Intermediate Similarity NPD5155 Approved
0.7081 Intermediate Similarity NPD2971 Approved
0.7077 Intermediate Similarity NPD4002 Approved
0.7077 Intermediate Similarity NPD4004 Approved
0.7076 Intermediate Similarity NPD7527 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD52 Approved
0.7076 Intermediate Similarity NPD7526 Approved
0.7069 Intermediate Similarity NPD6072 Discontinued
0.7062 Intermediate Similarity NPD4055 Discovery
0.7052 Intermediate Similarity NPD824 Approved
0.7052 Intermediate Similarity NPD4005 Discontinued
0.7048 Intermediate Similarity NPD2161 Phase 2
0.7047 Intermediate Similarity NPD3837 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD6063 Approved
0.7044 Intermediate Similarity NPD4098 Discontinued
0.7043 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD4040 Phase 1
0.7037 Intermediate Similarity NPD2028 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD7427 Discontinued
0.7033 Intermediate Similarity NPD4498 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD4093 Discontinued
0.7031 Intermediate Similarity NPD2975 Approved
0.7031 Intermediate Similarity NPD7034 Discontinued
0.7031 Intermediate Similarity NPD2974 Approved
0.7031 Intermediate Similarity NPD2973 Approved
0.703 Intermediate Similarity NPD8149 Discontinued
0.7024 Intermediate Similarity NPD2458 Approved
0.7024 Intermediate Similarity NPD2460 Phase 3
0.7024 Intermediate Similarity NPD2459 Approved
0.7019 Intermediate Similarity NPD3594 Approved
0.7019 Intermediate Similarity NPD3595 Approved
0.7019 Intermediate Similarity NPD2606 Approved
0.7019 Intermediate Similarity NPD2605 Approved
0.7018 Intermediate Similarity NPD7019 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