Structure

Physi-Chem Properties

Molecular Weight:  338.2
Volume:  361.302
LogP:  2.876
LogD:  2.558
LogS:  -4.19
# Rotatable Bonds:  3
TPSA:  43.26
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.897
Synthetic Accessibility Score:  3.8
Fsp3:  0.476
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:  -4.661
MDCK Permeability:  2.172839049308095e-05
Pgp-inhibitor:  0.997
Pgp-substrate:  0.011
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.113

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.692
Plasma Protein Binding (PPB):  90.2522964477539%
Volume Distribution (VD):  1.413
Pgp-substrate:  5.779438495635986%

ADMET: Metabolism

CYP1A2-inhibitor:  0.473
CYP1A2-substrate:  0.951
CYP2C19-inhibitor:  0.755
CYP2C19-substrate:  0.644
CYP2C9-inhibitor:  0.505
CYP2C9-substrate:  0.195
CYP2D6-inhibitor:  0.672
CYP2D6-substrate:  0.867
CYP3A4-inhibitor:  0.866
CYP3A4-substrate:  0.606

ADMET: Excretion

Clearance (CL):  3.585
Half-life (T1/2):  0.541

ADMET: Toxicity

hERG Blockers:  0.198
Human Hepatotoxicity (H-HT):  0.608
Drug-inuced Liver Injury (DILI):  0.292
AMES Toxicity:  0.848
Rat Oral Acute Toxicity:  0.822
Maximum Recommended Daily Dose:  0.82
Skin Sensitization:  0.069
Carcinogencity:  0.735
Eye Corrosion:  0.003
Eye Irritation:  0.011
Respiratory Toxicity:  0.329

Download Data

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

  Natural Product: NPC134586

Natural Product ID:  NPC134586
Common Name*:   FGHROJSHRIKSBW-OAQYLSRUSA-N
IUPAC Name:   n.a.
Synonyms:   5-Methoxymethylrhazinilam
Standard InCHIKey:  FGHROJSHRIKSBW-OAQYLSRUSA-N
Standard InCHI:  InChI=1S/C21H26N2O2/c1-3-21-10-6-12-23-15(14-25-2)13-17(20(21)23)16-7-4-5-8-18(16)22-19(24)9-11-21/h4-5,7-8,13H,3,6,9-12,14H2,1-2H3,(H,22,24)/t21-/m1/s1
SMILES:  CC[C@@]12CCCn3c(cc(-c4ccccc4N=C(CC1)O)c23)COC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL557810
PubChem CID:   25227568
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000090] Pyrroles
        • [CHEMONTID:0002257] Substituted pyrroles

*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
NPO2700 Kopsia arborea Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[17665953]
NPO2700 Kopsia arborea Species Apocynaceae Eukaryota n.a. Yunnan, China n.a. PMID[19133778]
NPO2700 Kopsia arborea Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[31241923]
NPO2700 Kopsia arborea Species Apocynaceae 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
NPT81 Cell Line A549 Homo sapiens IC50 = 5380.0 nM PMID[536140]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 4670.0 nM PMID[536140]

☑ 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 NPC134586 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
0.9937 High Similarity NPC211997
0.956 High Similarity NPC158129
0.8528 High Similarity NPC129721
0.8161 Intermediate Similarity NPC133261
0.8095 Intermediate Similarity NPC255229
0.8095 Intermediate Similarity NPC81229
0.8023 Intermediate Similarity NPC159125
0.8 Intermediate Similarity NPC104483
0.7955 Intermediate Similarity NPC248462
0.7943 Intermediate Similarity NPC24594
0.7943 Intermediate Similarity NPC472122
0.7917 Intermediate Similarity NPC285469
0.7917 Intermediate Similarity NPC141353
0.7898 Intermediate Similarity NPC326575
0.7877 Intermediate Similarity NPC284678
0.7833 Intermediate Similarity NPC62510
0.7812 Intermediate Similarity NPC469589
0.7809 Intermediate Similarity NPC472105
0.7809 Intermediate Similarity NPC187827
0.7759 Intermediate Similarity NPC317430
0.7754 Intermediate Similarity NPC239954
0.7753 Intermediate Similarity NPC472443
0.7751 Intermediate Similarity NPC207726
0.7749 Intermediate Similarity NPC472111
0.774 Intermediate Similarity NPC56618
0.774 Intermediate Similarity NPC203754
0.774 Intermediate Similarity NPC150048
0.7737 Intermediate Similarity NPC475774
0.7733 Intermediate Similarity NPC16667
0.773 Intermediate Similarity NPC198673
0.773 Intermediate Similarity NPC473178
0.7727 Intermediate Similarity NPC34508
0.7722 Intermediate Similarity NPC472444
0.7722 Intermediate Similarity NPC472109
0.7722 Intermediate Similarity NPC472110
0.7722 Intermediate Similarity NPC19679
0.7709 Intermediate Similarity NPC15840
0.7697 Intermediate Similarity NPC64436
0.7667 Intermediate Similarity NPC314394
0.7667 Intermediate Similarity NPC233936
0.766 Intermediate Similarity NPC168911
0.7656 Intermediate Similarity NPC475841
0.7656 Intermediate Similarity NPC474145
0.765 Intermediate Similarity NPC204565
0.7644 Intermediate Similarity NPC470508
0.764 Intermediate Similarity NPC121903
0.7627 Intermediate Similarity NPC472123
0.7627 Intermediate Similarity NPC471294
0.7624 Intermediate Similarity NPC48938
0.7616 Intermediate Similarity NPC67056
0.7609 Intermediate Similarity NPC65215
0.7609 Intermediate Similarity NPC173028
0.7594 Intermediate Similarity NPC133366
0.7584 Intermediate Similarity NPC472586
0.7581 Intermediate Similarity NPC55493
0.7569 Intermediate Similarity NPC113626
0.7566 Intermediate Similarity NPC212213
0.7556 Intermediate Similarity NPC270009
0.7554 Intermediate Similarity NPC317030
0.7544 Intermediate Similarity NPC470507
0.754 Intermediate Similarity NPC474177
0.7527 Intermediate Similarity NPC472108
0.7527 Intermediate Similarity NPC143533
0.7527 Intermediate Similarity NPC139291
0.7526 Intermediate Similarity NPC241024
0.7526 Intermediate Similarity NPC32200
0.7515 Intermediate Similarity NPC37548
0.7514 Intermediate Similarity NPC280548
0.75 Intermediate Similarity NPC474561
0.75 Intermediate Similarity NPC289299
0.75 Intermediate Similarity NPC57994
0.75 Intermediate Similarity NPC283152
0.75 Intermediate Similarity NPC234987
0.75 Intermediate Similarity NPC474707
0.75 Intermediate Similarity NPC49954
0.75 Intermediate Similarity NPC293472
0.7487 Intermediate Similarity NPC475910
0.7486 Intermediate Similarity NPC469541
0.7486 Intermediate Similarity NPC311276
0.7486 Intermediate Similarity NPC329688
0.7486 Intermediate Similarity NPC189812
0.7475 Intermediate Similarity NPC471080
0.7475 Intermediate Similarity NPC469592
0.7473 Intermediate Similarity NPC192270
0.7459 Intermediate Similarity NPC472323
0.7446 Intermediate Similarity NPC473189
0.7444 Intermediate Similarity NPC84347
0.7442 Intermediate Similarity NPC471458
0.7436 Intermediate Similarity NPC53344
0.7432 Intermediate Similarity NPC472104
0.7429 Intermediate Similarity NPC282231
0.7426 Intermediate Similarity NPC132642
0.7414 Intermediate Similarity NPC230869
0.7412 Intermediate Similarity NPC187951
0.7409 Intermediate Similarity NPC57398
0.7401 Intermediate Similarity NPC54988
0.7401 Intermediate Similarity NPC160105
0.7396 Intermediate Similarity NPC214428
0.7396 Intermediate Similarity NPC249040
0.7391 Intermediate Similarity NPC284559
0.7391 Intermediate Similarity NPC472119
0.7391 Intermediate Similarity NPC258480
0.7386 Intermediate Similarity NPC476118
0.7386 Intermediate Similarity NPC102423
0.7386 Intermediate Similarity NPC118511
0.7386 Intermediate Similarity NPC194640
0.7384 Intermediate Similarity NPC26872
0.7381 Intermediate Similarity NPC242556
0.7381 Intermediate Similarity NPC471323
0.738 Intermediate Similarity NPC95783
0.7371 Intermediate Similarity NPC131718
0.7371 Intermediate Similarity NPC279918
0.7368 Intermediate Similarity NPC245916
0.7368 Intermediate Similarity NPC251090
0.7366 Intermediate Similarity NPC473177
0.7365 Intermediate Similarity NPC60553
0.736 Intermediate Similarity NPC63751
0.736 Intermediate Similarity NPC201700
0.736 Intermediate Similarity NPC44161
0.7356 Intermediate Similarity NPC469762
0.7354 Intermediate Similarity NPC307963
0.7351 Intermediate Similarity NPC42591
0.7351 Intermediate Similarity NPC472107
0.7351 Intermediate Similarity NPC79062
0.7344 Intermediate Similarity NPC128823
0.7341 Intermediate Similarity NPC38736
0.7337 Intermediate Similarity NPC94157
0.7337 Intermediate Similarity NPC176127
0.7333 Intermediate Similarity NPC118832
0.7333 Intermediate Similarity NPC329708
0.7333 Intermediate Similarity NPC47059
0.7333 Intermediate Similarity NPC165349
0.7333 Intermediate Similarity NPC313791
0.7333 Intermediate Similarity NPC264166
0.7333 Intermediate Similarity NPC274291
0.733 Intermediate Similarity NPC177404
0.733 Intermediate Similarity NPC267928
0.733 Intermediate Similarity NPC229332
0.7327 Intermediate Similarity NPC469594
0.7326 Intermediate Similarity NPC46413
0.7322 Intermediate Similarity NPC469896
0.7321 Intermediate Similarity NPC20144
0.7312 Intermediate Similarity NPC478077
0.7312 Intermediate Similarity NPC66210
0.7306 Intermediate Similarity NPC329793
0.7306 Intermediate Similarity NPC329747
0.7305 Intermediate Similarity NPC2949
0.7299 Intermediate Similarity NPC469785
0.7297 Intermediate Similarity NPC320394
0.7297 Intermediate Similarity NPC84478
0.7296 Intermediate Similarity NPC277350
0.7287 Intermediate Similarity NPC469470
0.7287 Intermediate Similarity NPC469501
0.7283 Intermediate Similarity NPC469760
0.7283 Intermediate Similarity NPC469765
0.7283 Intermediate Similarity NPC25008
0.7283 Intermediate Similarity NPC259644
0.7283 Intermediate Similarity NPC469763
0.7283 Intermediate Similarity NPC73952
0.7283 Intermediate Similarity NPC469786
0.7282 Intermediate Similarity NPC476138
0.7282 Intermediate Similarity NPC245816
0.7273 Intermediate Similarity NPC473320
0.7268 Intermediate Similarity NPC72980
0.7268 Intermediate Similarity NPC219336
0.7263 Intermediate Similarity NPC279401
0.7263 Intermediate Similarity NPC79293
0.7258 Intermediate Similarity NPC188387
0.7258 Intermediate Similarity NPC163421
0.7257 Intermediate Similarity NPC26850
0.725 Intermediate Similarity NPC118940
0.725 Intermediate Similarity NPC264176
0.725 Intermediate Similarity NPC472098
0.7249 Intermediate Similarity NPC117244
0.7249 Intermediate Similarity NPC473763
0.7249 Intermediate Similarity NPC92111
0.7243 Intermediate Similarity NPC163055
0.7241 Intermediate Similarity NPC211572
0.7241 Intermediate Similarity NPC70922
0.7241 Intermediate Similarity NPC75540
0.7241 Intermediate Similarity NPC212376
0.7241 Intermediate Similarity NPC80597
0.7238 Intermediate Similarity NPC314603
0.7236 Intermediate Similarity NPC5145
0.7234 Intermediate Similarity NPC175474
0.7234 Intermediate Similarity NPC111602
0.7234 Intermediate Similarity NPC102338
0.7234 Intermediate Similarity NPC196251
0.7234 Intermediate Similarity NPC63199
0.7228 Intermediate Similarity NPC478032
0.7225 Intermediate Similarity NPC153769
0.7219 Intermediate Similarity NPC171171
0.7216 Intermediate Similarity NPC84508
0.7213 Intermediate Similarity NPC151939
0.7213 Intermediate Similarity NPC248454
0.7213 Intermediate Similarity NPC217372
0.7213 Intermediate Similarity NPC183662
0.7213 Intermediate Similarity NPC15573
0.7209 Intermediate Similarity NPC124005
0.7208 Intermediate Similarity NPC317373

  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 NPC134586 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
0.8193 Intermediate Similarity NPD2581 Approved
0.8193 Intermediate Similarity NPD2582 Approved
0.7989 Intermediate Similarity NPD7222 Phase 2
0.7966 Intermediate Similarity NPD4204 Approved
0.7966 Intermediate Similarity NPD4203 Approved
0.7944 Intermediate Similarity NPD2383 Phase 1
0.7912 Intermediate Similarity NPD5913 Phase 3
0.7912 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD6452 Discontinued
0.7901 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.787 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD6281 Approved
0.7844 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD6158 Phase 2
0.7844 Intermediate Similarity NPD2882 Phase 1
0.7801 Intermediate Similarity NPD7452 Approved
0.7801 Intermediate Similarity NPD7453 Approved
0.7735 Intermediate Similarity NPD6227 Discontinued
0.7735 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD5596 Phase 2
0.7719 Intermediate Similarity NPD5255 Approved
0.7714 Intermediate Similarity NPD1326 Approved
0.7714 Intermediate Similarity NPD1325 Approved
0.7701 Intermediate Similarity NPD5003 Discontinued
0.767 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7663 Intermediate Similarity NPD8063 Discontinued
0.7663 Intermediate Similarity NPD2564 Approved
0.7663 Intermediate Similarity NPD2565 Phase 2
0.7644 Intermediate Similarity NPD4550 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD2915 Discontinued
0.764 Intermediate Similarity NPD5104 Approved
0.764 Intermediate Similarity NPD5100 Phase 3
0.7637 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD3525 Discontinued
0.7627 Intermediate Similarity NPD2077 Approved
0.7627 Intermediate Similarity NPD2076 Approved
0.7584 Intermediate Similarity NPD5065 Approved
0.7582 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.756 Intermediate Similarity NPD4702 Approved
0.756 Intermediate Similarity NPD4703 Approved
0.7557 Intermediate Similarity NPD5862 Discovery
0.7542 Intermediate Similarity NPD2381 Approved
0.7542 Intermediate Similarity NPD2382 Approved
0.7542 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7542 Intermediate Similarity NPD2380 Approved
0.75 Intermediate Similarity NPD6159 Phase 2
0.75 Intermediate Similarity NPD5256 Discontinued
0.75 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4602 Approved
0.7487 Intermediate Similarity NPD6569 Phase 2
0.7474 Intermediate Similarity NPD7889 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7469 Intermediate Similarity NPD3385 Approved
0.7459 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD4326 Phase 2
0.7407 Intermediate Similarity NPD6590 Discontinued
0.7407 Intermediate Similarity NPD4418 Discontinued
0.7407 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD5138 Approved
0.7386 Intermediate Similarity NPD5140 Approved
0.7385 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD7470 Discontinued
0.736 Intermediate Similarity NPD4638 Approved
0.736 Intermediate Similarity NPD4639 Approved
0.736 Intermediate Similarity NPD2125 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4640 Approved
0.7354 Intermediate Similarity NPD1038 Approved
0.7351 Intermediate Similarity NPD5075 Discontinued
0.7344 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4122 Approved
0.7333 Intermediate Similarity NPD4033 Approved
0.7333 Intermediate Similarity NPD4034 Approved
0.7333 Intermediate Similarity NPD4038 Approved
0.7333 Intermediate Similarity NPD32 Approved
0.7333 Intermediate Similarity NPD4037 Approved
0.7333 Intermediate Similarity NPD4035 Approved
0.7333 Intermediate Similarity NPD31 Approved
0.7333 Intermediate Similarity NPD4036 Approved
0.7333 Intermediate Similarity NPD4039 Approved
0.7329 Intermediate Similarity NPD3654 Approved
0.7318 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD7001 Phase 3
0.7296 Intermediate Similarity NPD3003 Approved
0.7293 Intermediate Similarity NPD6492 Phase 2
0.7286 Intermediate Similarity NPD6220 Phase 3
0.7282 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD2920 Discontinued
0.7278 Intermediate Similarity NPD3813 Approved
0.7278 Intermediate Similarity NPD1078 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD5512 Phase 3
0.7273 Intermediate Similarity NPD4948 Discontinued
0.7273 Intermediate Similarity NPD1033 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1034 Phase 3
0.7273 Intermediate Similarity NPD3390 Phase 2
0.7263 Intermediate Similarity NPD4526 Approved
0.7263 Intermediate Similarity NPD4528 Approved
0.7263 Intermediate Similarity NPD4529 Approved
0.7263 Intermediate Similarity NPD5021 Discontinued
0.7262 Intermediate Similarity NPD5020 Approved
0.7254 Intermediate Similarity NPD2175 Phase 3
0.7254 Intermediate Similarity NPD2177 Approved
0.7254 Intermediate Similarity NPD2176 Approved
0.7238 Intermediate Similarity NPD750 Phase 2
0.7238 Intermediate Similarity NPD7418 Discontinued
0.7228 Intermediate Similarity NPD6595 Phase 3
0.7222 Intermediate Similarity NPD7474 Suspended
0.7213 Intermediate Similarity NPD2144 Approved
0.7202 Intermediate Similarity NPD53 Approved
0.7202 Intermediate Similarity NPD7778 Approved
0.7202 Intermediate Similarity NPD7777 Approved
0.7196 Intermediate Similarity NPD4499 Approved
0.7194 Intermediate Similarity NPD6991 Approved
0.7188 Intermediate Similarity NPD3478 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD3477 Phase 2
0.7188 Intermediate Similarity NPD7935 Phase 2
0.7178 Intermediate Similarity NPD6140 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD1741 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD8386 Phase 2
0.7174 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.7173 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD4462 Approved
0.7168 Intermediate Similarity NPD4463 Approved
0.7167 Intermediate Similarity NPD6872 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD1768 Approved
0.7165 Intermediate Similarity NPD6999 Discontinued
0.716 Intermediate Similarity NPD1592 Phase 3
0.7151 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD926 Approved
0.7151 Intermediate Similarity NPD925 Approved
0.715 Intermediate Similarity NPD1229 Phase 2
0.7143 Intermediate Similarity NPD4334 Discontinued
0.7136 Intermediate Similarity NPD5658 Approved
0.7135 Intermediate Similarity NPD5899 Approved
0.7135 Intermediate Similarity NPD5898 Approved
0.7135 Intermediate Similarity NPD6251 Discontinued
0.7135 Intermediate Similarity NPD5897 Approved
0.7121 Intermediate Similarity NPD5530 Phase 1
0.712 Intermediate Similarity NPD8123 Approved
0.712 Intermediate Similarity NPD6641 Approved
0.712 Intermediate Similarity NPD6642 Approved
0.712 Intermediate Similarity NPD8122 Approved
0.712 Intermediate Similarity NPD3404 Approved
0.7118 Intermediate Similarity NPD3717 Discontinued
0.7118 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD4502 Phase 2
0.7105 Intermediate Similarity NPD3321 Discontinued
0.7101 Intermediate Similarity NPD6824 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD6449 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD3038 Discontinued
0.7097 Intermediate Similarity NPD4383 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD7414 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD7710 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD5903 Approved
0.7094 Intermediate Similarity NPD5902 Approved
0.7092 Intermediate Similarity NPD6307 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD6717 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD3920 Phase 2
0.7079 Intermediate Similarity NPD112 Approved
0.7079 Intermediate Similarity NPD3330 Phase 1
0.7079 Intermediate Similarity NPD9705 Discontinued
0.7074 Intermediate Similarity NPD3082 Discontinued
0.7072 Intermediate Similarity NPD2844 Phase 3
0.7062 Intermediate Similarity NPD7948 Phase 1
0.7059 Intermediate Similarity NPD5612 Discontinued
0.7056 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD7671 Approved
0.705 Intermediate Similarity NPD7672 Approved
0.7047 Intermediate Similarity NPD7944 Discontinued
0.7047 Intermediate Similarity NPD3324 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD3810 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD5257 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD1684 Approved
0.7039 Intermediate Similarity NPD1685 Approved
0.7039 Intermediate Similarity NPD6455 Phase 3
0.7033 Intermediate Similarity NPD6976 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD3921 Approved
0.7031 Intermediate Similarity NPD3922 Approved
0.7031 Intermediate Similarity NPD3924 Approved
0.7031 Intermediate Similarity NPD3923 Approved
0.7027 Intermediate Similarity NPD1032 Phase 2
0.7026 Intermediate Similarity NPD4397 Phase 1
0.7024 Intermediate Similarity NPD45 Approved
0.7024 Intermediate Similarity NPD6554 Approved
0.702 Intermediate Similarity NPD4886 Phase 2
0.7019 Intermediate Similarity NPD6995 Phase 1
0.7015 Intermediate Similarity NPD4520 Approved
0.7011 Intermediate Similarity NPD4736 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD9690 Approved
0.701 Intermediate Similarity NPD7818 Clinical (unspecified phase)

  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