Structure

Physi-Chem Properties

Molecular Weight:  324.18
Volume:  344.006
LogP:  2.337
LogD:  2.172
LogS:  -3.95
# Rotatable Bonds:  2
TPSA:  54.26
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.882
Synthetic Accessibility Score:  3.825
Fsp3:  0.45
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:  -4.632
MDCK Permeability:  2.2285552404355258e-05
Pgp-inhibitor:  0.966
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.047
30% Bioavailability (F30%):  0.818

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.765
Plasma Protein Binding (PPB):  85.9559097290039%
Volume Distribution (VD):  1.135
Pgp-substrate:  11.226287841796875%

ADMET: Metabolism

CYP1A2-inhibitor:  0.516
CYP1A2-substrate:  0.932
CYP2C19-inhibitor:  0.651
CYP2C19-substrate:  0.539
CYP2C9-inhibitor:  0.424
CYP2C9-substrate:  0.213
CYP2D6-inhibitor:  0.694
CYP2D6-substrate:  0.815
CYP3A4-inhibitor:  0.857
CYP3A4-substrate:  0.503

ADMET: Excretion

Clearance (CL):  4.253
Half-life (T1/2):  0.727

ADMET: Toxicity

hERG Blockers:  0.12
Human Hepatotoxicity (H-HT):  0.586
Drug-inuced Liver Injury (DILI):  0.186
AMES Toxicity:  0.599
Rat Oral Acute Toxicity:  0.796
Maximum Recommended Daily Dose:  0.742
Skin Sensitization:  0.074
Carcinogencity:  0.53
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.387

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

  Natural Product: NPC158129

Natural Product ID:  NPC158129
Common Name*:   MFNKGJVBPOITBB-HXUWFJFHSA-N
IUPAC Name:   n.a.
Synonyms:   5-Hydroxymethylrhazinilam
Standard InCHIKey:  MFNKGJVBPOITBB-HXUWFJFHSA-N
Standard InCHI:  InChI=1S/C20H24N2O2/c1-2-20-9-5-11-22-14(13-23)12-16(19(20)22)15-6-3-4-7-17(15)21-18(24)8-10-20/h3-4,6-7,12,23H,2,5,8-11,13H2,1H3,(H,21,24)/t20-/m1/s1
SMILES:  CC[C@@]12CCCn3c2c(cc3CO)c2ccccc2N=C(CC1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL558634
PubChem CID:   25227578
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 = 8210.0 nM PMID[490470]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 8890.0 nM PMID[490470]

☑ 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 NPC158129 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
0.956 High Similarity NPC134586
0.95 High Similarity NPC211997
0.8688 High Similarity NPC129721
0.8412 Intermediate Similarity NPC133261
0.8246 Intermediate Similarity NPC326575
0.8171 Intermediate Similarity NPC141353
0.8161 Intermediate Similarity NPC159125
0.8133 Intermediate Similarity NPC255229
0.8133 Intermediate Similarity NPC81229
0.8092 Intermediate Similarity NPC248462
0.8092 Intermediate Similarity NPC472443
0.8081 Intermediate Similarity NPC24594
0.8081 Intermediate Similarity NPC203754
0.8081 Intermediate Similarity NPC150048
0.8081 Intermediate Similarity NPC472122
0.807 Intermediate Similarity NPC34508
0.8061 Intermediate Similarity NPC285469
0.8038 Intermediate Similarity NPC104483
0.8 Intermediate Similarity NPC314394
0.8 Intermediate Similarity NPC317430
0.7966 Intermediate Similarity NPC62510
0.7955 Intermediate Similarity NPC472444
0.7955 Intermediate Similarity NPC19679
0.7955 Intermediate Similarity NPC48938
0.7943 Intermediate Similarity NPC15840
0.7943 Intermediate Similarity NPC472105
0.7943 Intermediate Similarity NPC187827
0.7912 Intermediate Similarity NPC133366
0.7898 Intermediate Similarity NPC233936
0.7892 Intermediate Similarity NPC207726
0.7892 Intermediate Similarity NPC470507
0.7886 Intermediate Similarity NPC270009
0.7882 Intermediate Similarity NPC470508
0.7877 Intermediate Similarity NPC204565
0.7874 Intermediate Similarity NPC121903
0.787 Intermediate Similarity NPC16667
0.7861 Intermediate Similarity NPC471294
0.7861 Intermediate Similarity NPC472123
0.7857 Intermediate Similarity NPC474177
0.7853 Intermediate Similarity NPC472110
0.7853 Intermediate Similarity NPC472109
0.7833 Intermediate Similarity NPC65215
0.7833 Intermediate Similarity NPC173028
0.7829 Intermediate Similarity NPC293472
0.7829 Intermediate Similarity NPC64436
0.7816 Intermediate Similarity NPC472586
0.7797 Intermediate Similarity NPC113626
0.7797 Intermediate Similarity NPC192270
0.7778 Intermediate Similarity NPC317030
0.7758 Intermediate Similarity NPC37548
0.7751 Intermediate Similarity NPC67056
0.7749 Intermediate Similarity NPC469589
0.7722 Intermediate Similarity NPC474707
0.7719 Intermediate Similarity NPC102423
0.7714 Intermediate Similarity NPC329688
0.7714 Intermediate Similarity NPC189812
0.7701 Intermediate Similarity NPC249040
0.768 Intermediate Similarity NPC472323
0.7657 Intermediate Similarity NPC313791
0.7654 Intermediate Similarity NPC472108
0.7654 Intermediate Similarity NPC139291
0.7651 Intermediate Similarity NPC187951
0.7647 Intermediate Similarity NPC230869
0.7644 Intermediate Similarity NPC280548
0.763 Intermediate Similarity NPC474561
0.763 Intermediate Similarity NPC49954
0.763 Intermediate Similarity NPC54988
0.7622 Intermediate Similarity NPC242556
0.7619 Intermediate Similarity NPC57398
0.7616 Intermediate Similarity NPC476118
0.7607 Intermediate Similarity NPC60553
0.7602 Intermediate Similarity NPC131718
0.7596 Intermediate Similarity NPC95783
0.7594 Intermediate Similarity NPC212213
0.7592 Intermediate Similarity NPC474145
0.7592 Intermediate Similarity NPC472111
0.7592 Intermediate Similarity NPC475841
0.7588 Intermediate Similarity NPC469762
0.7586 Intermediate Similarity NPC44161
0.7586 Intermediate Similarity NPC201700
0.7574 Intermediate Similarity NPC471458
0.7574 Intermediate Similarity NPC38736
0.756 Intermediate Similarity NPC153769
0.7558 Intermediate Similarity NPC282231
0.7552 Intermediate Similarity NPC53344
0.7544 Intermediate Similarity NPC84508
0.7542 Intermediate Similarity NPC478032
0.754 Intermediate Similarity NPC229332
0.7529 Intermediate Similarity NPC469785
0.7529 Intermediate Similarity NPC160105
0.7528 Intermediate Similarity NPC234987
0.7526 Intermediate Similarity NPC5145
0.7514 Intermediate Similarity NPC194640
0.7514 Intermediate Similarity NPC469541
0.7514 Intermediate Similarity NPC311276
0.7514 Intermediate Similarity NPC284678
0.75 Intermediate Similarity NPC279918
0.75 Intermediate Similarity NPC102008
0.7487 Intermediate Similarity NPC475774
0.7486 Intermediate Similarity NPC72980
0.7486 Intermediate Similarity NPC63751
0.7473 Intermediate Similarity NPC473178
0.7472 Intermediate Similarity NPC56618
0.7459 Intermediate Similarity NPC472104
0.7459 Intermediate Similarity NPC143533
0.7459 Intermediate Similarity NPC163055
0.7455 Intermediate Similarity NPC20144
0.7446 Intermediate Similarity NPC46413
0.744 Intermediate Similarity NPC124005
0.7439 Intermediate Similarity NPC2949
0.7433 Intermediate Similarity NPC57994
0.7433 Intermediate Similarity NPC289299
0.7432 Intermediate Similarity NPC171171
0.7432 Intermediate Similarity NPC478077
0.743 Intermediate Similarity NPC151939
0.7425 Intermediate Similarity NPC161292
0.7419 Intermediate Similarity NPC55493
0.7418 Intermediate Similarity NPC207851
0.7418 Intermediate Similarity NPC472119
0.7418 Intermediate Similarity NPC258480
0.7412 Intermediate Similarity NPC25008
0.7412 Intermediate Similarity NPC73952
0.7412 Intermediate Similarity NPC469765
0.7412 Intermediate Similarity NPC469786
0.7412 Intermediate Similarity NPC259644
0.7412 Intermediate Similarity NPC469760
0.7412 Intermediate Similarity NPC469763
0.7411 Intermediate Similarity NPC469592
0.7411 Intermediate Similarity NPC471080
0.7407 Intermediate Similarity NPC239954
0.7405 Intermediate Similarity NPC469501
0.7405 Intermediate Similarity NPC469470
0.7399 Intermediate Similarity NPC473320
0.7389 Intermediate Similarity NPC219336
0.738 Intermediate Similarity NPC198673
0.7377 Intermediate Similarity NPC79062
0.7377 Intermediate Similarity NPC472107
0.7377 Intermediate Similarity NPC314002
0.7375 Intermediate Similarity NPC256893
0.7374 Intermediate Similarity NPC288785
0.7368 Intermediate Similarity NPC211572
0.7368 Intermediate Similarity NPC80597
0.7368 Intermediate Similarity NPC70922
0.7368 Intermediate Similarity NPC241024
0.7368 Intermediate Similarity NPC32200
0.7368 Intermediate Similarity NPC476167
0.7368 Intermediate Similarity NPC75540
0.7368 Intermediate Similarity NPC212376
0.7366 Intermediate Similarity NPC473763
0.7366 Intermediate Similarity NPC117244
0.736 Intermediate Similarity NPC314603
0.736 Intermediate Similarity NPC259545
0.7358 Intermediate Similarity NPC470500
0.7354 Intermediate Similarity NPC232130
0.7351 Intermediate Similarity NPC175474
0.7345 Intermediate Similarity NPC126481
0.7345 Intermediate Similarity NPC314940
0.7345 Intermediate Similarity NPC473764
0.7337 Intermediate Similarity NPC66210
0.7333 Intermediate Similarity NPC283152
0.7333 Intermediate Similarity NPC314957
0.7333 Intermediate Similarity NPC475910
0.7333 Intermediate Similarity NPC248454
0.7333 Intermediate Similarity NPC183662
0.7333 Intermediate Similarity NPC15573
0.7333 Intermediate Similarity NPC217372
0.733 Intermediate Similarity NPC98187
0.7326 Intermediate Similarity NPC99666
0.7322 Intermediate Similarity NPC472294
0.7322 Intermediate Similarity NPC204717
0.7321 Intermediate Similarity NPC129042
0.7316 Intermediate Similarity NPC52557
0.7316 Intermediate Similarity NPC192315
0.7316 Intermediate Similarity NPC168911
0.7314 Intermediate Similarity NPC40779
0.7306 Intermediate Similarity NPC165599
0.7303 Intermediate Similarity NPC470498
0.7302 Intermediate Similarity NPC205403
0.7299 Intermediate Similarity NPC322644
0.7297 Intermediate Similarity NPC46580
0.7294 Intermediate Similarity NPC24678
0.7294 Intermediate Similarity NPC105818
0.7293 Intermediate Similarity NPC232340
0.7288 Intermediate Similarity NPC154293
0.7283 Intermediate Similarity NPC299594
0.7283 Intermediate Similarity NPC188387
0.7283 Intermediate Similarity NPC163421
0.7283 Intermediate Similarity NPC476319
0.7283 Intermediate Similarity NPC241025
0.7277 Intermediate Similarity NPC132642
0.7273 Intermediate Similarity NPC471178
0.7268 Intermediate Similarity NPC133306
0.7268 Intermediate Similarity NPC274291
0.7268 Intermediate Similarity NPC47059
0.7268 Intermediate Similarity NPC264166
0.7268 Intermediate Similarity NPC220765
0.7268 Intermediate Similarity NPC470505
0.7268 Intermediate Similarity NPC475070
0.7268 Intermediate Similarity NPC118832
0.7268 Intermediate Similarity NPC165349

  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 NPC158129 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
0.8286 Intermediate Similarity NPD2383 Phase 1
0.8232 Intermediate Similarity NPD4669 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD4670 Clinical (unspecified phase)
0.8232 Intermediate Similarity NPD4671 Clinical (unspecified phase)
0.815 Intermediate Similarity NPD6452 Discontinued
0.8136 Intermediate Similarity NPD6965 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD6158 Phase 2
0.8098 Intermediate Similarity NPD2882 Phase 1
0.8098 Intermediate Similarity NPD6476 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3525 Discontinued
0.7966 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.7964 Intermediate Similarity NPD5255 Approved
0.7953 Intermediate Similarity NPD1325 Approved
0.7953 Intermediate Similarity NPD1326 Approved
0.7874 Intermediate Similarity NPD5100 Phase 3
0.7874 Intermediate Similarity NPD2380 Approved
0.7874 Intermediate Similarity NPD2381 Approved
0.7874 Intermediate Similarity NPD2382 Approved
0.7853 Intermediate Similarity NPD5596 Phase 2
0.7816 Intermediate Similarity NPD5065 Approved
0.7803 Intermediate Similarity NPD5934 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD2581 Approved
0.7798 Intermediate Similarity NPD2582 Approved
0.7797 Intermediate Similarity NPD4204 Approved
0.7797 Intermediate Similarity NPD4203 Approved
0.7765 Intermediate Similarity NPD6227 Discontinued
0.7737 Intermediate Similarity NPD7222 Phase 2
0.7727 Intermediate Similarity NPD6159 Phase 2
0.7697 Intermediate Similarity NPD4702 Approved
0.7697 Intermediate Similarity NPD4703 Approved
0.768 Intermediate Similarity NPD6141 Clinical (unspecified phase)
0.767 Intermediate Similarity NPD6375 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD5138 Approved
0.7616 Intermediate Similarity NPD5140 Approved
0.761 Intermediate Similarity NPD3385 Approved
0.7596 Intermediate Similarity NPD6281 Approved
0.7588 Intermediate Similarity NPD4326 Phase 2
0.7586 Intermediate Similarity NPD4639 Approved
0.7586 Intermediate Similarity NPD4638 Approved
0.7586 Intermediate Similarity NPD4640 Approved
0.7572 Intermediate Similarity NPD4550 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD7418 Discontinued
0.7556 Intermediate Similarity NPD5522 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD5912 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD5913 Phase 3
0.7553 Intermediate Similarity NPD2177 Approved
0.7553 Intermediate Similarity NPD2176 Approved
0.7553 Intermediate Similarity NPD2175 Phase 3
0.7552 Intermediate Similarity NPD7453 Approved
0.7552 Intermediate Similarity NPD7452 Approved
0.7543 Intermediate Similarity NPD7474 Suspended
0.7515 Intermediate Similarity NPD3813 Approved
0.7514 Intermediate Similarity NPD6492 Phase 2
0.75 Intermediate Similarity NPD5020 Approved
0.75 Intermediate Similarity NPD7777 Approved
0.75 Intermediate Similarity NPD7778 Approved
0.75 Intermediate Similarity NPD7889 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD53 Approved
0.7486 Intermediate Similarity NPD5862 Discovery
0.7486 Intermediate Similarity NPD5021 Discontinued
0.7486 Intermediate Similarity NPD4948 Discontinued
0.7486 Intermediate Similarity NPD5069 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD3654 Approved
0.7444 Intermediate Similarity NPD5898 Approved
0.7444 Intermediate Similarity NPD5897 Approved
0.7444 Intermediate Similarity NPD6595 Phase 3
0.7444 Intermediate Similarity NPD5899 Approved
0.7443 Intermediate Similarity NPD4184 Clinical (unspecified phase)
0.7433 Intermediate Similarity NPD4602 Approved
0.7418 Intermediate Similarity NPD5083 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD3321 Discontinued
0.7405 Intermediate Similarity NPD8063 Discontinued
0.7396 Intermediate Similarity NPD4462 Approved
0.7396 Intermediate Similarity NPD4463 Approved
0.7394 Intermediate Similarity NPD7935 Phase 2
0.7394 Intermediate Similarity NPD1592 Phase 3
0.7377 Intermediate Similarity NPD7424 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD3082 Discontinued
0.7374 Intermediate Similarity NPD5104 Approved
0.7371 Intermediate Similarity NPD926 Approved
0.7371 Intermediate Similarity NPD925 Approved
0.7371 Intermediate Similarity NPD2915 Discontinued
0.7368 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6999 Discontinued
0.736 Intermediate Similarity NPD750 Phase 2
0.7354 Intermediate Similarity NPD5003 Discontinued
0.7326 Intermediate Similarity NPD3404 Approved
0.732 Intermediate Similarity NPD7001 Phase 3
0.732 Intermediate Similarity NPD4901 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD2565 Phase 2
0.7312 Intermediate Similarity NPD2564 Approved
0.7302 Intermediate Similarity NPD6449 Clinical (unspecified phase)
0.7293 Intermediate Similarity NPD8386 Phase 2
0.7288 Intermediate Similarity NPD2844 Phase 3
0.7287 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD6610 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5744 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD4034 Approved
0.7268 Intermediate Similarity NPD32 Approved
0.7268 Intermediate Similarity NPD4035 Approved
0.7268 Intermediate Similarity NPD4122 Approved
0.7268 Intermediate Similarity NPD4039 Approved
0.7268 Intermediate Similarity NPD4038 Approved
0.7268 Intermediate Similarity NPD4036 Approved
0.7268 Intermediate Similarity NPD4037 Approved
0.7268 Intermediate Similarity NPD4033 Approved
0.7268 Intermediate Similarity NPD31 Approved
0.7263 Intermediate Similarity NPD7948 Phase 1
0.7263 Intermediate Similarity NPD2076 Approved
0.7263 Intermediate Similarity NPD2077 Approved
0.7259 Intermediate Similarity NPD4900 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD1684 Approved
0.7257 Intermediate Similarity NPD1685 Approved
0.7249 Intermediate Similarity NPD7944 Discontinued
0.7246 Intermediate Similarity NPD4637 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD3717 Discontinued
0.7238 Intermediate Similarity NPD8123 Approved
0.7238 Intermediate Similarity NPD8122 Approved
0.7238 Intermediate Similarity NPD5751 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD6455 Phase 3
0.7225 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD4736 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD5936 Approved
0.7222 Intermediate Similarity NPD5939 Approved
0.7222 Intermediate Similarity NPD9690 Approved
0.7219 Intermediate Similarity NPD4499 Approved
0.7216 Intermediate Similarity NPD4886 Phase 2
0.7213 Intermediate Similarity NPD4383 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD112 Approved
0.72 Intermediate Similarity NPD9705 Discontinued
0.7198 Intermediate Similarity NPD8037 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD4079 Approved
0.7198 Intermediate Similarity NPD4076 Approved
0.7198 Intermediate Similarity NPD8036 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD6717 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD5352 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD4699 Discontinued
0.7168 Intermediate Similarity NPD5257 Clinical (unspecified phase)
0.7165 Intermediate Similarity NPD5721 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD4418 Discontinued
0.7158 Intermediate Similarity NPD8464 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD3791 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6554 Approved
0.7152 Intermediate Similarity NPD45 Approved
0.7151 Intermediate Similarity NPD5256 Discontinued
0.7143 Intermediate Similarity NPD3506 Approved
0.7143 Intermediate Similarity NPD6732 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2144 Approved
0.7143 Intermediate Similarity NPD6569 Phase 2
0.7143 Intermediate Similarity NPD3505 Approved
0.7143 Intermediate Similarity NPD3003 Approved
0.7143 Intermediate Similarity NPD4909 Approved
0.7136 Intermediate Similarity NPD7470 Discontinued
0.7135 Intermediate Similarity NPD4397 Phase 1
0.7135 Intermediate Similarity NPD4554 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD1649 Discontinued
0.7126 Intermediate Similarity NPD6026 Approved
0.712 Intermediate Similarity NPD7818 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD6307 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD6290 Phase 2
0.7105 Intermediate Similarity NPD1038 Approved
0.7104 Intermediate Similarity NPD3417 Phase 1
0.7102 Intermediate Similarity NPD2511 Approved
0.71 Intermediate Similarity NPD3330 Phase 1
0.7099 Intermediate Similarity NPD3476 Approved
0.7099 Intermediate Similarity NPD3475 Approved
0.7098 Intermediate Similarity NPD4118 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD5075 Discontinued
0.7092 Intermediate Similarity NPD5901 Discontinued
0.7088 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD4547 Phase 3
0.7074 Intermediate Similarity NPD4334 Discontinued
0.7072 Intermediate Similarity NPD3224 Phase 2
0.7071 Intermediate Similarity NPD7665 Phase 2
0.7071 Intermediate Similarity NPD7666 Phase 3
0.7071 Intermediate Similarity NPD2916 Discontinued
0.7071 Intermediate Similarity NPD4612 Discontinued
0.7068 Intermediate Similarity NPD6861 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD4999 Phase 3
0.7068 Intermediate Similarity NPD6590 Discontinued
0.7068 Intermediate Similarity NPD4998 Phase 3
0.7067 Intermediate Similarity NPD6977 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD6978 Phase 2
0.7062 Intermediate Similarity NPD4600 Approved
0.7062 Intermediate Similarity NPD4601 Approved
0.7059 Intermediate Similarity NPD706 Phase 1
0.7056 Intermediate Similarity NPD4862 Clinical (unspecified phase)
0.7053 Intermediate Similarity NPD6976 Clinical (unspecified phase)
0.705 Intermediate Similarity NPD4502 Phase 2
0.705 Intermediate Similarity NPD6220 Phase 3
0.7049 Intermediate Similarity NPD6641 Approved
0.7049 Intermediate Similarity NPD6642 Approved
0.7049 Intermediate Similarity NPD6203 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD9506 Approved
0.7041 Intermediate Similarity NPD6991 Approved
0.7039 Intermediate Similarity NPD425 Approved
0.7039 Intermediate Similarity NPD424 Approved
0.7037 Intermediate Similarity NPD5117 Phase 2
0.7035 Intermediate Similarity NPD2125 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