Structure

Physi-Chem Properties

Molecular Weight:  366.16
Volume:  361.769
LogP:  1.969
LogD:  2.138
LogS:  -3.97
# Rotatable Bonds:  3
TPSA:  67.87
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  6
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.373
Synthetic Accessibility Score:  6.517
Fsp3:  0.524
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.315
MDCK Permeability:  2.23509796342114e-05
Pgp-inhibitor:  0.023
Pgp-substrate:  0.254
Human Intestinal Absorption (HIA):  0.586
20% Bioavailability (F20%):  0.311
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.928
Plasma Protein Binding (PPB):  68.22686004638672%
Volume Distribution (VD):  1.676
Pgp-substrate:  38.62141418457031%

ADMET: Metabolism

CYP1A2-inhibitor:  0.043
CYP1A2-substrate:  0.335
CYP2C19-inhibitor:  0.049
CYP2C19-substrate:  0.791
CYP2C9-inhibitor:  0.029
CYP2C9-substrate:  0.069
CYP2D6-inhibitor:  0.029
CYP2D6-substrate:  0.233
CYP3A4-inhibitor:  0.723
CYP3A4-substrate:  0.893

ADMET: Excretion

Clearance (CL):  11.375
Half-life (T1/2):  0.222

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.853
Drug-inuced Liver Injury (DILI):  0.612
AMES Toxicity:  0.98
Rat Oral Acute Toxicity:  0.976
Maximum Recommended Daily Dose:  0.995
Skin Sensitization:  0.925
Carcinogencity:  0.961
Eye Corrosion:  0.005
Eye Irritation:  0.024
Respiratory Toxicity:  0.971

Download Data

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

  Natural Product: NPC34717

Natural Product ID:  NPC34717
Common Name*:   Picralinal
IUPAC Name:   n.a.
Synonyms:   Picralinal
Standard InCHIKey:  RHBAENOZUZWALZ-GGZNVOGHSA-N
Standard InCHI:  InChI=1S/C21H22N2O4/c1-3-12-10-23-16-8-14(12)19(11-24,18(25)26-2)20-9-17(23)27-21(16,20)22-15-7-5-4-6-13(15)20/h3-7,11,14,16-17,22H,8-10H2,1-2H3/b12-3-/t14-,16-,17-,19-,20-,21-/m0/s1
SMILES:  C/C=C1/CN2[C@H]3C[C@@H]1[C@@](C=O)(C(=O)OC)[C@]14C[C@@H]2O[C@@]34Nc2ccccc12
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL590273
PubChem CID:   46229103
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids and derivatives
      • [CHEMONTID:0002750] Corynanthean-type 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
NPO19678 Alstonia macrophylla Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[19191551]
NPO19678 Alstonia macrophylla Species Apocynaceae Eukaryota leaves Purwodadi Botanical Garden, Indonesia n.a. PMID[20189404]
NPO19678 Alstonia macrophylla Species Apocynaceae Eukaryota n.a. stem n.a. PMID[22148233]
NPO19678 Alstonia macrophylla Species Apocynaceae Eukaryota Barks n.a. n.a. PMID[23806072]
NPO19678 Alstonia macrophylla Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19678 Alstonia macrophylla Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19678 Alstonia macrophylla Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19678 Alstonia macrophylla 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
NPT640 Individual Protein Sodium/glucose cotransporter 1 Homo sapiens Inhibition = 16.5 % PMID[466341]
NPT641 Individual Protein Sodium/glucose cotransporter 2 Homo sapiens Inhibition = 36.3 % PMID[466341]

☑ 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 NPC34717 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
0.9651 High Similarity NPC181928
0.9548 High Similarity NPC90967
0.9429 High Similarity NPC473298
0.8241 Intermediate Similarity NPC234772
0.8098 Intermediate Similarity NPC231924
0.8042 Intermediate Similarity NPC25401
0.8009 Intermediate Similarity NPC154922
0.7824 Intermediate Similarity NPC113455
0.7789 Intermediate Similarity NPC14994
0.7778 Intermediate Similarity NPC99632
0.7778 Intermediate Similarity NPC282339
0.7778 Intermediate Similarity NPC52262
0.7766 Intermediate Similarity NPC159963
0.7717 Intermediate Similarity NPC120239
0.7716 Intermediate Similarity NPC475489
0.7688 Intermediate Similarity NPC264482
0.7688 Intermediate Similarity NPC203202
0.7628 Intermediate Similarity NPC476220
0.7628 Intermediate Similarity NPC160113
0.7588 Intermediate Similarity NPC471512
0.7553 Intermediate Similarity NPC186669
0.7527 Intermediate Similarity NPC248117
0.7527 Intermediate Similarity NPC225319
0.7513 Intermediate Similarity NPC6974
0.7489 Intermediate Similarity NPC304837
0.7489 Intermediate Similarity NPC476258
0.7487 Intermediate Similarity NPC476425
0.7473 Intermediate Similarity NPC193410
0.7462 Intermediate Similarity NPC221687
0.7436 Intermediate Similarity NPC105055
0.7436 Intermediate Similarity NPC22689
0.7421 Intermediate Similarity NPC218594
0.7421 Intermediate Similarity NPC99043
0.7419 Intermediate Similarity NPC167724
0.7419 Intermediate Similarity NPC223595
0.7419 Intermediate Similarity NPC224970
0.7418 Intermediate Similarity NPC61013
0.7391 Intermediate Similarity NPC286871
0.7337 Intermediate Similarity NPC201424
0.7337 Intermediate Similarity NPC97100
0.7337 Intermediate Similarity NPC473375
0.7322 Intermediate Similarity NPC113946
0.7302 Intermediate Similarity NPC285622
0.7297 Intermediate Similarity NPC176983
0.7283 Intermediate Similarity NPC36495
0.7273 Intermediate Similarity NPC279527
0.7273 Intermediate Similarity NPC214960
0.7268 Intermediate Similarity NPC97584
0.7245 Intermediate Similarity NPC21425
0.724 Intermediate Similarity NPC321211
0.7228 Intermediate Similarity NPC123241
0.7225 Intermediate Similarity NPC476441
0.7216 Intermediate Similarity NPC477159
0.7211 Intermediate Similarity NPC251212
0.7211 Intermediate Similarity NPC214626
0.7211 Intermediate Similarity NPC139085
0.7204 Intermediate Similarity NPC293458
0.7188 Intermediate Similarity NPC476326
0.7174 Intermediate Similarity NPC29285
0.7173 Intermediate Similarity NPC329338
0.7173 Intermediate Similarity NPC469726
0.7158 Intermediate Similarity NPC478076
0.7136 Intermediate Similarity NPC77777
0.7136 Intermediate Similarity NPC139373
0.7122 Intermediate Similarity NPC1464
0.712 Intermediate Similarity NPC473297
0.7101 Intermediate Similarity NPC246140
0.7101 Intermediate Similarity NPC195787
0.709 Intermediate Similarity NPC472114
0.709 Intermediate Similarity NPC472115
0.7085 Intermediate Similarity NPC131977
0.7062 Intermediate Similarity NPC475778
0.7059 Intermediate Similarity NPC309531
0.7059 Intermediate Similarity NPC472102
0.7059 Intermediate Similarity NPC474058
0.7056 Intermediate Similarity NPC322621
0.7048 Intermediate Similarity NPC234999
0.7045 Intermediate Similarity NPC223242
0.7035 Intermediate Similarity NPC284706
0.7031 Intermediate Similarity NPC96901
0.7021 Intermediate Similarity NPC85651
0.7021 Intermediate Similarity NPC472101
0.7021 Intermediate Similarity NPC472120
0.7017 Intermediate Similarity NPC264589
0.701 Intermediate Similarity NPC132874
0.701 Intermediate Similarity NPC138615
0.701 Intermediate Similarity NPC265642
0.701 Intermediate Similarity NPC218733
0.6995 Remote Similarity NPC13367
0.699 Remote Similarity NPC476428
0.6978 Remote Similarity NPC301501
0.697 Remote Similarity NPC476095
0.696 Remote Similarity NPC469451
0.6957 Remote Similarity NPC162730
0.6955 Remote Similarity NPC473458
0.6947 Remote Similarity NPC469450
0.6947 Remote Similarity NPC472106
0.6943 Remote Similarity NPC276993
0.6943 Remote Similarity NPC293255
0.6943 Remote Similarity NPC177261
0.6943 Remote Similarity NPC21752
0.6943 Remote Similarity NPC181138
0.6943 Remote Similarity NPC210415
0.6943 Remote Similarity NPC298851
0.6938 Remote Similarity NPC277350
0.6935 Remote Similarity NPC161827
0.6931 Remote Similarity NPC472121
0.693 Remote Similarity NPC195636
0.6923 Remote Similarity NPC260075
0.6915 Remote Similarity NPC5630
0.69 Remote Similarity NPC285841
0.69 Remote Similarity NPC329932
0.6886 Remote Similarity NPC469452
0.6884 Remote Similarity NPC259626
0.6878 Remote Similarity NPC471513
0.6875 Remote Similarity NPC474116
0.6866 Remote Similarity NPC288110
0.6862 Remote Similarity NPC153694
0.6862 Remote Similarity NPC211525
0.686 Remote Similarity NPC79129
0.686 Remote Similarity NPC313985
0.686 Remote Similarity NPC214428
0.686 Remote Similarity NPC81654
0.686 Remote Similarity NPC138830
0.686 Remote Similarity NPC49196
0.686 Remote Similarity NPC195461
0.686 Remote Similarity NPC249150
0.6853 Remote Similarity NPC11149
0.6839 Remote Similarity NPC472118
0.6835 Remote Similarity NPC476069
0.6834 Remote Similarity NPC2933
0.6825 Remote Similarity NPC310403
0.6825 Remote Similarity NPC263709
0.6825 Remote Similarity NPC97380
0.6825 Remote Similarity NPC243673
0.6825 Remote Similarity NPC63210
0.6825 Remote Similarity NPC148468
0.6822 Remote Similarity NPC127996
0.681 Remote Similarity NPC477181
0.681 Remote Similarity NPC87714
0.681 Remote Similarity NPC477180
0.681 Remote Similarity NPC477178
0.681 Remote Similarity NPC254850
0.6798 Remote Similarity NPC203628
0.6798 Remote Similarity NPC22476
0.6796 Remote Similarity NPC162440
0.6796 Remote Similarity NPC302548
0.6796 Remote Similarity NPC475559
0.6794 Remote Similarity NPC471436
0.6792 Remote Similarity NPC471945
0.6792 Remote Similarity NPC471950
0.6787 Remote Similarity NPC477394
0.6784 Remote Similarity NPC256288
0.6779 Remote Similarity NPC67904
0.6777 Remote Similarity NPC477174
0.6777 Remote Similarity NPC477173
0.6777 Remote Similarity NPC470490
0.6774 Remote Similarity NPC475763
0.6772 Remote Similarity NPC222029
0.6771 Remote Similarity NPC52059
0.6771 Remote Similarity NPC470069
0.6766 Remote Similarity NPC282092
0.6763 Remote Similarity NPC50503
0.6763 Remote Similarity NPC100863
0.6762 Remote Similarity NPC477179
0.6761 Remote Similarity NPC471951
0.6761 Remote Similarity NPC469743
0.6761 Remote Similarity NPC471946
0.6754 Remote Similarity NPC472117
0.6754 Remote Similarity NPC469741
0.675 Remote Similarity NPC472119
0.6749 Remote Similarity NPC474059
0.6748 Remote Similarity NPC303214
0.6746 Remote Similarity NPC232600
0.6745 Remote Similarity NPC470488
0.6732 Remote Similarity NPC470485
0.6729 Remote Similarity NPC475359
0.6729 Remote Similarity NPC191817
0.6727 Remote Similarity NPC128476
0.6719 Remote Similarity NPC313757
0.6716 Remote Similarity NPC472209
0.6714 Remote Similarity NPC470491
0.6714 Remote Similarity NPC475259
0.6712 Remote Similarity NPC19175
0.6702 Remote Similarity NPC143457
0.67 Remote Similarity NPC292675
0.6699 Remote Similarity NPC243626
0.6683 Remote Similarity NPC473615
0.6682 Remote Similarity NPC189661
0.6667 Remote Similarity NPC469915
0.6667 Remote Similarity NPC477397
0.6667 Remote Similarity NPC469722
0.6651 Remote Similarity NPC475147
0.665 Remote Similarity NPC229484
0.665 Remote Similarity NPC475962
0.6649 Remote Similarity NPC278887
0.6637 Remote Similarity NPC470631
0.6637 Remote Similarity NPC473781
0.6637 Remote Similarity NPC35390
0.6636 Remote Similarity NPC222046

  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 NPC34717 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
0.6971 Remote Similarity NPD5185 Approved
0.6971 Remote Similarity NPD5182 Approved
0.6971 Remote Similarity NPD5184 Approved
0.686 Remote Similarity NPD4600 Approved
0.686 Remote Similarity NPD4601 Approved
0.6757 Remote Similarity NPD5942 Approved
0.6757 Remote Similarity NPD5941 Approved
0.6702 Remote Similarity NPD7600 Phase 2
0.6667 Remote Similarity NPD6238 Discontinued
0.665 Remote Similarity NPD8103 Clinical (unspecified phase)
0.6649 Remote Similarity NPD7599 Phase 2
0.6598 Remote Similarity NPD7035 Approved
0.6598 Remote Similarity NPD7036 Phase 3
0.6553 Remote Similarity NPD5504 Discontinued
0.6535 Remote Similarity NPD8658 Clinical (unspecified phase)
0.6535 Remote Similarity NPD8281 Discontinued
0.6533 Remote Similarity NPD8022 Clinical (unspecified phase)
0.6526 Remote Similarity NPD4120 Approved
0.6526 Remote Similarity NPD4121 Phase 3
0.6524 Remote Similarity NPD1801 Approved
0.6524 Remote Similarity NPD1802 Approved
0.651 Remote Similarity NPD8630 Approved
0.6492 Remote Similarity NPD5742 Approved
0.6492 Remote Similarity NPD5741 Approved
0.6492 Remote Similarity NPD5743 Approved
0.6482 Remote Similarity NPD7940 Phase 3
0.6476 Remote Similarity NPD3828 Approved
0.6458 Remote Similarity NPD6570 Approved
0.6458 Remote Similarity NPD6571 Approved
0.6425 Remote Similarity NPD4499 Approved
0.6425 Remote Similarity NPD5715 Clinical (unspecified phase)
0.6406 Remote Similarity NPD4082 Approved
0.6404 Remote Similarity NPD3471 Approved
0.6404 Remote Similarity NPD3470 Approved
0.64 Remote Similarity NPD5466 Approved
0.6398 Remote Similarity NPD5024 Approved
0.6396 Remote Similarity NPD3940 Clinical (unspecified phase)
0.6392 Remote Similarity NPD7114 Clinical (unspecified phase)
0.6385 Remote Similarity NPD6805 Discontinued
0.6385 Remote Similarity NPD4500 Approved
0.6385 Remote Similarity NPD4501 Approved
0.6384 Remote Similarity NPD5433 Clinical (unspecified phase)
0.6378 Remote Similarity NPD3625 Discontinued
0.6373 Remote Similarity NPD7105 Phase 1
0.6373 Remote Similarity NPD1663 Discontinued
0.6364 Remote Similarity NPD7487 Discontinued
0.6364 Remote Similarity NPD4492 Approved
0.6364 Remote Similarity NPD4494 Approved
0.6355 Remote Similarity NPD6878 Phase 2
0.6355 Remote Similarity NPD4330 Approved
0.6355 Remote Similarity NPD6879 Phase 2
0.6355 Remote Similarity NPD6833 Clinical (unspecified phase)
0.6355 Remote Similarity NPD4329 Approved
0.635 Remote Similarity NPD7854 Phase 2
0.635 Remote Similarity NPD5997 Discontinued
0.6346 Remote Similarity NPD5758 Clinical (unspecified phase)
0.6345 Remote Similarity NPD5430 Discontinued
0.6339 Remote Similarity NPD6073 Approved
0.6338 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6337 Remote Similarity NPD7587 Clinical (unspecified phase)
0.6335 Remote Similarity NPD7606 Phase 3
0.6321 Remote Similarity NPD5003 Discontinued
0.6318 Remote Similarity NPD6316 Clinical (unspecified phase)
0.6318 Remote Similarity NPD5919 Clinical (unspecified phase)
0.6311 Remote Similarity NPD3437 Discontinued
0.6305 Remote Similarity NPD2869 Clinical (unspecified phase)
0.6304 Remote Similarity NPD6295 Approved
0.6304 Remote Similarity NPD6294 Approved
0.6303 Remote Similarity NPD4602 Approved
0.6296 Remote Similarity NPD6416 Phase 2
0.6291 Remote Similarity NPD5197 Approved
0.6291 Remote Similarity NPD5196 Approved
0.6291 Remote Similarity NPD5194 Approved
0.6281 Remote Similarity NPD2037 Approved
0.6267 Remote Similarity NPD1294 Discontinued
0.6264 Remote Similarity NPD7634 Clinical (unspecified phase)
0.6263 Remote Similarity NPD7478 Approved
0.6256 Remote Similarity NPD3792 Approved
0.625 Remote Similarity NPD3376 Clinical (unspecified phase)
0.6244 Remote Similarity NPD4493 Discontinued
0.6238 Remote Similarity NPD8240 Discontinued
0.6234 Remote Similarity NPD7824 Approved
0.6231 Remote Similarity NPD8002 Clinical (unspecified phase)
0.6231 Remote Similarity NPD8003 Clinical (unspecified phase)
0.623 Remote Similarity NPD7528 Approved
0.6228 Remote Similarity NPD3912 Discontinued
0.6223 Remote Similarity NPD2820 Phase 3
0.6219 Remote Similarity NPD2432 Approved
0.6219 Remote Similarity NPD5727 Clinical (unspecified phase)
0.6219 Remote Similarity NPD2431 Approved
0.6214 Remote Similarity NPD7252 Clinical (unspecified phase)
0.6214 Remote Similarity NPD7962 Phase 2
0.6212 Remote Similarity NPD3790 Phase 2
0.6212 Remote Similarity NPD8008 Approved
0.6212 Remote Similarity NPD8007 Approved
0.6211 Remote Similarity NPD4041 Approved
0.6207 Remote Similarity NPD7688 Phase 1
0.6204 Remote Similarity NPD6321 Discontinued
0.62 Remote Similarity NPD2454 Approved
0.62 Remote Similarity NPD2455 Approved
0.6195 Remote Similarity NPD6770 Approved
0.6193 Remote Similarity NPD7244 Discontinued
0.619 Remote Similarity NPD5918 Discontinued
0.6188 Remote Similarity NPD4455 Discontinued
0.6188 Remote Similarity NPD2613 Approved
0.6183 Remote Similarity NPD1109 Approved
0.6183 Remote Similarity NPD1110 Approved
0.6182 Remote Similarity NPD3472 Approved
0.6182 Remote Similarity NPD4022 Approved
0.6176 Remote Similarity NPD5600 Discontinued
0.6175 Remote Similarity NPD2566 Approved
0.6175 Remote Similarity NPD3090 Approved
0.6175 Remote Similarity NPD2572 Clinical (unspecified phase)
0.6175 Remote Similarity NPD3089 Approved
0.6175 Remote Similarity NPD3088 Approved
0.6175 Remote Similarity NPD4746 Phase 3
0.6175 Remote Similarity NPD2574 Discontinued
0.6175 Remote Similarity NPD4745 Approved
0.6175 Remote Similarity NPD3616 Approved
0.6175 Remote Similarity NPD2571 Approved
0.6175 Remote Similarity NPD3087 Approved
0.6175 Remote Similarity NPD2570 Approved
0.6175 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6175 Remote Similarity NPD2573 Approved
0.6175 Remote Similarity NPD3615 Approved
0.6175 Remote Similarity NPD3614 Approved
0.6171 Remote Similarity NPD1945 Phase 1
0.617 Remote Similarity NPD2365 Approved
0.6167 Remote Similarity NPD5993 Phase 1
0.6162 Remote Similarity NPD5725 Approved
0.6161 Remote Similarity NPD6630 Clinical (unspecified phase)
0.6158 Remote Similarity NPD5933 Phase 3
0.6158 Remote Similarity NPD5932 Phase 3
0.6158 Remote Similarity NPD5931 Phase 3
0.6157 Remote Similarity NPD8466 Approved
0.6157 Remote Similarity NPD8465 Approved
0.6157 Remote Similarity NPD8467 Approved
0.6154 Remote Similarity NPD7708 Approved
0.6154 Remote Similarity NPD7952 Approved
0.6154 Remote Similarity NPD7790 Approved
0.6154 Remote Similarity NPD7789 Approved
0.6154 Remote Similarity NPD7791 Approved
0.6154 Remote Similarity NPD7953 Approved
0.6154 Remote Similarity NPD7950 Approved
0.6154 Remote Similarity NPD7951 Approved
0.6154 Remote Similarity NPD6625 Approved
0.6147 Remote Similarity NPD7731 Approved
0.6147 Remote Similarity NPD7730 Approved
0.6146 Remote Similarity NPD3782 Discontinued
0.6146 Remote Similarity NPD7775 Approved
0.6146 Remote Similarity NPD7881 Approved
0.6143 Remote Similarity NPD7301 Phase 3
0.6143 Remote Similarity NPD3888 Discontinued
0.614 Remote Similarity NPD4420 Approved
0.6136 Remote Similarity NPD4596 Phase 1
0.6134 Remote Similarity NPD3399 Approved
0.613 Remote Similarity NPD7271 Approved
0.6129 Remote Similarity NPD2670 Approved
0.6126 Remote Similarity NPD3372 Discontinued
0.6126 Remote Similarity NPD5860 Discontinued
0.6124 Remote Similarity NPD8459 Approved
0.6124 Remote Similarity NPD8460 Approved
0.6119 Remote Similarity NPD5426 Phase 3
0.6117 Remote Similarity NPD6293 Clinical (unspecified phase)
0.6114 Remote Similarity NPD5928 Phase 1
0.6114 Remote Similarity NPD2565 Phase 2
0.6114 Remote Similarity NPD2737 Clinical (unspecified phase)
0.6114 Remote Similarity NPD2564 Approved
0.6113 Remote Similarity NPD7956 Approved
0.6113 Remote Similarity NPD7955 Approved
0.6111 Remote Similarity NPD2506 Approved
0.6109 Remote Similarity NPD7302 Phase 3
0.6109 Remote Similarity NPD7300 Phase 3
0.6108 Remote Similarity NPD4685 Phase 3
0.6108 Remote Similarity NPD4684 Phase 3
0.6108 Remote Similarity NPD4686 Approved
0.6105 Remote Similarity NPD2435 Approved
0.6103 Remote Similarity NPD5610 Approved
0.6099 Remote Similarity NPD5263 Approved
0.6099 Remote Similarity NPD7470 Discontinued
0.6098 Remote Similarity NPD5334 Clinical (unspecified phase)
0.6096 Remote Similarity NPD3170 Approved
0.6096 Remote Similarity NPD3783 Clinical (unspecified phase)
0.6089 Remote Similarity NPD5183 Approved
0.6089 Remote Similarity NPD5186 Approved
0.6087 Remote Similarity NPD7149 Clinical (unspecified phase)
0.6085 Remote Similarity NPD6723 Discontinued
0.6082 Remote Similarity NPD5982 Phase 2
0.6077 Remote Similarity NPD6557 Phase 2
0.6073 Remote Similarity NPD4711 Clinical (unspecified phase)
0.6073 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6073 Remote Similarity NPD7205 Discontinued
0.6073 Remote Similarity NPD7295 Approved
0.6065 Remote Similarity NPD5071 Phase 2
0.6062 Remote Similarity NPD8426 Approved
0.6062 Remote Similarity NPD8425 Approved
0.6062 Remote Similarity NPD4682 Phase 2
0.6056 Remote Similarity NPD7569 Approved
0.6056 Remote Similarity NPD7803 Approved
0.6056 Remote Similarity NPD7570 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