Structure

Physi-Chem Properties

Molecular Weight:  680.24
Volume:  712.618
LogP:  7.476
LogD:  3.771
LogS:  -3.843
# Rotatable Bonds:  9
TPSA:  147.68
# H-Bond Aceptor:  8
# H-Bond Donor:  6
# Rings:  7
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.09
Synthetic Accessibility Score:  3.685
Fsp3:  0.14
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.08
MDCK Permeability:  1.7410791770089418e-05
Pgp-inhibitor:  0.227
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.654
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.008
Plasma Protein Binding (PPB):  102.70494842529297%
Volume Distribution (VD):  0.15
Pgp-substrate:  1.1398364305496216%

ADMET: Metabolism

CYP1A2-inhibitor:  0.055
CYP1A2-substrate:  0.105
CYP2C19-inhibitor:  0.909
CYP2C19-substrate:  0.052
CYP2C9-inhibitor:  0.248
CYP2C9-substrate:  0.97
CYP2D6-inhibitor:  0.08
CYP2D6-substrate:  0.762
CYP3A4-inhibitor:  0.125
CYP3A4-substrate:  0.834

ADMET: Excretion

Clearance (CL):  11.07
Half-life (T1/2):  0.703

ADMET: Toxicity

hERG Blockers:  0.022
Human Hepatotoxicity (H-HT):  0.228
Drug-inuced Liver Injury (DILI):  0.978
AMES Toxicity:  0.173
Rat Oral Acute Toxicity:  0.938
Maximum Recommended Daily Dose:  0.064
Skin Sensitization:  0.966
Carcinogencity:  0.103
Eye Corrosion:  0.003
Eye Irritation:  0.931
Respiratory Toxicity:  0.025

Download Data

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

  Natural Product: NPC115601

Natural Product ID:  NPC115601
Common Name*:   Sarmentosumin B
IUPAC Name:   (2S)-5,7-dihydroxy-6-[[2-hydroxy-5-[[2-hydroxy-5-[(2-hydroxyphenyl)methyl]phenyl]methyl]phenyl]methyl]-8-[(2-hydroxyphenyl)methyl]-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:   Sarmentosumin B
Standard InCHIKey:  JORUYFYWUGTBEB-KDXMTYKHSA-N
Standard InCHI:  InChI=1S/C43H36O8/c44-34-12-6-4-10-28(34)18-25-14-16-36(46)30(19-25)20-26-15-17-37(47)31(21-26)23-32-41(49)33(22-29-11-5-7-13-35(29)45)43-40(42(32)50)38(48)24-39(51-43)27-8-2-1-3-9-27/h1-17,19,21,39,44-47,49-50H,18,20,22-24H2/t39-/m0/s1
SMILES:  Oc1ccc(cc1Cc1c(O)c(Cc2ccccc2O)c2c(c1O)C(=O)C[C@H](O2)c1ccccc1)Cc1cc(ccc1O)Cc1ccccc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1835963
PubChem CID:   56600475
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002650] Diarylheptanoids
        • [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO3803 Ardisia japonica Species Primulaceae Eukaryota whole plants Sendai, Miyagi Prefecture, Japan 2000-Sep PMID[17243725]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. whole plant n.a. PMID[17243725]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. whole plant n.a. PMID[17397219]
NPO2846 Piper sarmentosum Species Piperaceae Eukaryota n.a. stem n.a. PMID[21973101]
NPO2846 Piper sarmentosum Species Piperaceae Eukaryota n.a. leaf n.a. PMID[21973101]
NPO2846 Piper sarmentosum Species Piperaceae Eukaryota n.a. inflorescence n.a. PMID[21973101]
NPO2846 Piper sarmentosum Species Piperaceae Eukaryota n.a. Kego Nature Reserve, Hatinh Province, Vietnam 2008-DEC PMID[21973101]
NPO2846 Piper sarmentosum Species Piperaceae Eukaryota n.a. twig n.a. PMID[21973101]
NPO2846 Piper sarmentosum Species Piperaceae Eukaryota aerial parts Kego Nature Reserve, Hatinh Province, Vietnam 2008-DEC PMID[21973101]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[22940450]
NPO4720 Aglaia perviridis Species Meliaceae Eukaryota leaves, twigs, and fruits Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam 2010-Jan PMID[23301897]
NPO4720 Aglaia perviridis Species Meliaceae Eukaryota n.a. n.a. n.a. PMID[31621322]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2846 Piper sarmentosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2846 Piper sarmentosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO992 Betula alnoides Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2846 Piper sarmentosum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5657 Oocystis polymorpha Species Oocystaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4720 Aglaia perviridis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3803 Ardisia japonica Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6614 Rubus pileatus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1912 Acanthosyris paulo-alvinii Species Cervantesiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO61 Phoebe grandis Species Lauraceae 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
NPT139 Cell Line HT-29 Homo sapiens ED50 > 20.0 uM PMID[548218]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 6.8 uM PMID[548218]
NPT2 Others Unspecified ED50 > 20.0 uM PMID[548218]

☑ 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 NPC115601 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 NPC39154
1.0 High Similarity NPC78324
1.0 High Similarity NPC208011
0.9793 High Similarity NPC132345
0.9724 High Similarity NPC122894
0.9662 High Similarity NPC121568
0.9658 High Similarity NPC3642
0.9603 High Similarity NPC98023
0.9603 High Similarity NPC226462
0.9603 High Similarity NPC42965
0.96 High Similarity NPC1796
0.96 High Similarity NPC257166
0.9595 High Similarity NPC174086
0.9536 High Similarity NPC51247
0.9536 High Similarity NPC15815
0.9517 High Similarity NPC470136
0.9517 High Similarity NPC470135
0.9517 High Similarity NPC39045
0.9474 High Similarity NPC195136
0.947 High Similarity NPC318527
0.947 High Similarity NPC208258
0.947 High Similarity NPC324358
0.947 High Similarity NPC323627
0.947 High Similarity NPC322459
0.9467 High Similarity NPC300668
0.9467 High Similarity NPC182555
0.9467 High Similarity NPC66441
0.9467 High Similarity NPC37253
0.9467 High Similarity NPC79375
0.9467 High Similarity NPC134171
0.9452 High Similarity NPC473078
0.9452 High Similarity NPC470132
0.9452 High Similarity NPC109183
0.9452 High Similarity NPC470133
0.9452 High Similarity NPC470131
0.9452 High Similarity NPC228779
0.9452 High Similarity NPC470134
0.9408 High Similarity NPC105584
0.9404 High Similarity NPC32867
0.9404 High Similarity NPC69531
0.9396 High Similarity NPC178484
0.9384 High Similarity NPC282957
0.9384 High Similarity NPC194949
0.9351 High Similarity NPC473012
0.9346 High Similarity NPC121647
0.9342 High Similarity NPC475184
0.9315 High Similarity NPC185276
0.929 High Similarity NPC473009
0.9286 High Similarity NPC301256
0.9286 High Similarity NPC312273
0.9281 High Similarity NPC295090
0.9281 High Similarity NPC51760
0.9281 High Similarity NPC123544
0.9262 High Similarity NPC291746
0.9262 High Similarity NPC288840
0.9257 High Similarity NPC283234
0.9252 High Similarity NPC197252
0.9252 High Similarity NPC235217
0.9252 High Similarity NPC236766
0.9252 High Similarity NPC473014
0.9247 High Similarity NPC194432
0.9247 High Similarity NPC265040
0.9247 High Similarity NPC76372
0.9247 High Similarity NPC306829
0.9247 High Similarity NPC148757
0.9247 High Similarity NPC125855
0.9247 High Similarity NPC296917
0.9247 High Similarity NPC228504
0.9247 High Similarity NPC10937
0.9247 High Similarity NPC182852
0.9247 High Similarity NPC78
0.9247 High Similarity NPC66515
0.9247 High Similarity NPC166482
0.9247 High Similarity NPC220998
0.9247 High Similarity NPC177354
0.9247 High Similarity NPC64915
0.9247 High Similarity NPC107572
0.9247 High Similarity NPC227579
0.9247 High Similarity NPC223500
0.9247 High Similarity NPC76338
0.9247 High Similarity NPC324134
0.9247 High Similarity NPC166934
0.9247 High Similarity NPC1089
0.9247 High Similarity NPC161506
0.9247 High Similarity NPC37496
0.9247 High Similarity NPC324436
0.9247 High Similarity NPC167624
0.9247 High Similarity NPC40833
0.9247 High Similarity NPC32739
0.9247 High Similarity NPC328164
0.9231 High Similarity NPC473010
0.9216 High Similarity NPC287789
0.9216 High Similarity NPC271741
0.9211 High Similarity NPC159707
0.9211 High Similarity NPC14606
0.9211 High Similarity NPC265624
0.9211 High Similarity NPC201227
0.9211 High Similarity NPC258474
0.9211 High Similarity NPC158027
0.9211 High Similarity NPC186227
0.9211 High Similarity NPC205026
0.9211 High Similarity NPC150908
0.9211 High Similarity NPC52611
0.9211 High Similarity NPC121649
0.9211 High Similarity NPC248739
0.9211 High Similarity NPC215203
0.9211 High Similarity NPC100049
0.9205 High Similarity NPC43345
0.9195 High Similarity NPC161191
0.9195 High Similarity NPC132592
0.9195 High Similarity NPC160821
0.9189 High Similarity NPC312973
0.9189 High Similarity NPC88964
0.9189 High Similarity NPC111786
0.9189 High Similarity NPC301276
0.9189 High Similarity NPC285630
0.9189 High Similarity NPC246948
0.9189 High Similarity NPC267375
0.9189 High Similarity NPC54577
0.9189 High Similarity NPC475052
0.9189 High Similarity NPC195621
0.9189 High Similarity NPC470647
0.9189 High Similarity NPC127059
0.9189 High Similarity NPC20488
0.9189 High Similarity NPC67805
0.9189 High Similarity NPC176229
0.9189 High Similarity NPC142405
0.9189 High Similarity NPC83357
0.9189 High Similarity NPC214774
0.9184 High Similarity NPC125894
0.9184 High Similarity NPC310130
0.9184 High Similarity NPC257097
0.9184 High Similarity NPC68104
0.9184 High Similarity NPC77794
0.9184 High Similarity NPC85162
0.9184 High Similarity NPC221432
0.9184 High Similarity NPC164980
0.9184 High Similarity NPC478086
0.9184 High Similarity NPC278249
0.9184 High Similarity NPC175504
0.9184 High Similarity NPC149026
0.9184 High Similarity NPC91560
0.9184 High Similarity NPC150408
0.9184 High Similarity NPC75049
0.9184 High Similarity NPC143896
0.9184 High Similarity NPC81697
0.9184 High Similarity NPC223812
0.9184 High Similarity NPC107177
0.9184 High Similarity NPC316816
0.9184 High Similarity NPC39329
0.9184 High Similarity NPC214166
0.9184 High Similarity NPC169591
0.9178 High Similarity NPC17170
0.9178 High Similarity NPC248372
0.9178 High Similarity NPC110038
0.9178 High Similarity NPC166689
0.9178 High Similarity NPC96408
0.9178 High Similarity NPC4743
0.9178 High Similarity NPC324386
0.9178 High Similarity NPC26238
0.9178 High Similarity NPC213322
0.9178 High Similarity NPC258630
0.9178 High Similarity NPC312391
0.9178 High Similarity NPC14871
0.9178 High Similarity NPC156190
0.9178 High Similarity NPC279650
0.9172 High Similarity NPC251336
0.9156 High Similarity NPC195167
0.915 High Similarity NPC61112
0.915 High Similarity NPC54830
0.915 High Similarity NPC56049
0.915 High Similarity NPC309648
0.915 High Similarity NPC198489
0.9145 High Similarity NPC290830
0.9145 High Similarity NPC324447
0.9145 High Similarity NPC194593
0.9145 High Similarity NPC72425
0.9145 High Similarity NPC71061
0.9145 High Similarity NPC303485
0.9139 High Similarity NPC222713
0.9139 High Similarity NPC309512
0.9139 High Similarity NPC111112
0.9139 High Similarity NPC148945
0.9139 High Similarity NPC476553
0.9139 High Similarity NPC204561
0.9139 High Similarity NPC67322
0.9139 High Similarity NPC317715
0.9139 High Similarity NPC78835
0.9139 High Similarity NPC476551
0.9139 High Similarity NPC316960
0.9139 High Similarity NPC138299
0.9139 High Similarity NPC476552
0.9128 High Similarity NPC296998
0.9128 High Similarity NPC110303
0.9128 High Similarity NPC261271
0.9128 High Similarity NPC473077
0.9128 High Similarity NPC475348
0.9128 High Similarity NPC23728
0.9122 High Similarity NPC319752
0.9122 High Similarity NPC473015

  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 NPC115601 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
0.9338 High Similarity NPD8443 Clinical (unspecified phase)
0.9034 High Similarity NPD1552 Clinical (unspecified phase)
0.9034 High Similarity NPD1550 Clinical (unspecified phase)
0.9013 High Similarity NPD7411 Suspended
0.8993 High Similarity NPD7410 Clinical (unspecified phase)
0.8987 High Similarity NPD7852 Clinical (unspecified phase)
0.8973 High Similarity NPD1549 Phase 2
0.8917 High Similarity NPD6959 Discontinued
0.8824 High Similarity NPD4380 Phase 2
0.8782 High Similarity NPD7768 Phase 2
0.8742 High Similarity NPD4378 Clinical (unspecified phase)
0.8726 High Similarity NPD7075 Discontinued
0.8654 High Similarity NPD2393 Clinical (unspecified phase)
0.8654 High Similarity NPD7819 Suspended
0.8589 High Similarity NPD7804 Clinical (unspecified phase)
0.8535 High Similarity NPD7096 Clinical (unspecified phase)
0.8519 High Similarity NPD6167 Clinical (unspecified phase)
0.8519 High Similarity NPD6168 Clinical (unspecified phase)
0.8519 High Similarity NPD6166 Phase 2
0.8514 High Similarity NPD1510 Phase 2
0.8491 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8456 Intermediate Similarity NPD2796 Approved
0.8367 Intermediate Similarity NPD1240 Approved
0.8354 Intermediate Similarity NPD1934 Approved
0.8354 Intermediate Similarity NPD6801 Discontinued
0.8289 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD3749 Approved
0.8255 Intermediate Similarity NPD1607 Approved
0.8204 Intermediate Similarity NPD7074 Phase 3
0.8199 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8144 Intermediate Similarity NPD7054 Approved
0.8095 Intermediate Similarity NPD7472 Approved
0.8077 Intermediate Similarity NPD7390 Discontinued
0.8077 Intermediate Similarity NPD6799 Approved
0.8077 Intermediate Similarity NPD1511 Approved
0.8059 Intermediate Similarity NPD7808 Phase 3
0.8038 Intermediate Similarity NPD5403 Approved
0.8013 Intermediate Similarity NPD6651 Approved
0.8012 Intermediate Similarity NPD8312 Approved
0.8012 Intermediate Similarity NPD8313 Approved
0.8 Intermediate Similarity NPD7251 Discontinued
0.8 Intermediate Similarity NPD3750 Approved
0.7987 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD1512 Approved
0.7963 Intermediate Similarity NPD2801 Approved
0.7941 Intermediate Similarity NPD6797 Phase 2
0.7939 Intermediate Similarity NPD5494 Approved
0.7917 Intermediate Similarity NPD7473 Discontinued
0.7911 Intermediate Similarity NPD5401 Approved
0.7895 Intermediate Similarity NPD6559 Discontinued
0.7888 Intermediate Similarity NPD6599 Discontinued
0.787 Intermediate Similarity NPD3818 Discontinued
0.7866 Intermediate Similarity NPD3882 Suspended
0.7857 Intermediate Similarity NPD1551 Phase 2
0.7853 Intermediate Similarity NPD8455 Phase 2
0.7852 Intermediate Similarity NPD4908 Phase 1
0.7844 Intermediate Similarity NPD6232 Discontinued
0.7824 Intermediate Similarity NPD5844 Phase 1
0.7821 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD2800 Approved
0.7805 Intermediate Similarity NPD3817 Phase 2
0.7746 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD5953 Discontinued
0.7719 Intermediate Similarity NPD7286 Phase 2
0.7697 Intermediate Similarity NPD5402 Approved
0.7697 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD3748 Approved
0.7673 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD2935 Discontinued
0.7616 Intermediate Similarity NPD6832 Phase 2
0.7607 Intermediate Similarity NPD7458 Discontinued
0.7595 Intermediate Similarity NPD1243 Approved
0.7593 Intermediate Similarity NPD920 Approved
0.758 Intermediate Similarity NPD2344 Approved
0.7578 Intermediate Similarity NPD2534 Approved
0.7578 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD2532 Approved
0.7578 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD2533 Approved
0.7564 Intermediate Similarity NPD2799 Discontinued
0.7533 Intermediate Similarity NPD1203 Approved
0.7516 Intermediate Similarity NPD6099 Approved
0.7516 Intermediate Similarity NPD2313 Discontinued
0.7516 Intermediate Similarity NPD6100 Approved
0.7515 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD4363 Phase 3
0.7514 Intermediate Similarity NPD4360 Phase 2
0.75 Intermediate Similarity NPD3226 Approved
0.75 Intermediate Similarity NPD1610 Phase 2
0.75 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD5124 Phase 1
0.7484 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD1548 Phase 1
0.746 Intermediate Similarity NPD8151 Discontinued
0.7452 Intermediate Similarity NPD7033 Discontinued
0.7452 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD4628 Phase 3
0.7438 Intermediate Similarity NPD7003 Approved
0.7433 Intermediate Similarity NPD7871 Phase 2
0.7433 Intermediate Similarity NPD7870 Phase 2
0.7405 Intermediate Similarity NPD5408 Approved
0.7405 Intermediate Similarity NPD5404 Approved
0.7405 Intermediate Similarity NPD5405 Approved
0.7405 Intermediate Similarity NPD5406 Approved
0.7391 Intermediate Similarity NPD2309 Approved
0.7329 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD3787 Discontinued
0.7321 Intermediate Similarity NPD1465 Phase 2
0.7308 Intermediate Similarity NPD943 Approved
0.7301 Intermediate Similarity NPD7213 Phase 3
0.7301 Intermediate Similarity NPD7212 Phase 2
0.7293 Intermediate Similarity NPD4287 Approved
0.729 Intermediate Similarity NPD6798 Discontinued
0.729 Intermediate Similarity NPD3268 Approved
0.7287 Intermediate Similarity NPD7696 Phase 3
0.7287 Intermediate Similarity NPD7698 Approved
0.7287 Intermediate Similarity NPD7697 Approved
0.7283 Intermediate Similarity NPD3926 Phase 2
0.7273 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7584 Approved
0.7257 Intermediate Similarity NPD3751 Discontinued
0.7256 Intermediate Similarity NPD7447 Phase 1
0.7251 Intermediate Similarity NPD919 Approved
0.725 Intermediate Similarity NPD2346 Discontinued
0.7241 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD3225 Approved
0.7225 Intermediate Similarity NPD7229 Phase 3
0.7219 Intermediate Similarity NPD6777 Approved
0.7219 Intermediate Similarity NPD6780 Approved
0.7219 Intermediate Similarity NPD6776 Approved
0.7219 Intermediate Similarity NPD6778 Approved
0.7219 Intermediate Similarity NPD6779 Approved
0.7219 Intermediate Similarity NPD9717 Approved
0.7219 Intermediate Similarity NPD6782 Approved
0.7219 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6781 Approved
0.7202 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7783 Phase 2
0.7197 Intermediate Similarity NPD1613 Approved
0.7197 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD7435 Discontinued
0.719 Intermediate Similarity NPD2797 Approved
0.7189 Intermediate Similarity NPD4361 Phase 2
0.7189 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD8150 Discontinued
0.7175 Intermediate Similarity NPD1729 Discontinued
0.717 Intermediate Similarity NPD7097 Phase 1
0.7168 Intermediate Similarity NPD1247 Approved
0.716 Intermediate Similarity NPD2654 Approved
0.716 Intermediate Similarity NPD7577 Discontinued
0.7159 Intermediate Similarity NPD7177 Discontinued
0.7159 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD422 Phase 1
0.7143 Intermediate Similarity NPD2798 Approved
0.7135 Intermediate Similarity NPD7701 Phase 2
0.7126 Intermediate Similarity NPD5710 Approved
0.7126 Intermediate Similarity NPD5711 Approved
0.7115 Intermediate Similarity NPD4625 Phase 3
0.7101 Intermediate Similarity NPD5889 Approved
0.7101 Intermediate Similarity NPD5890 Approved
0.7095 Intermediate Similarity NPD6104 Discontinued
0.7083 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD4288 Approved
0.707 Intermediate Similarity NPD3764 Approved
0.7069 Intermediate Similarity NPD7199 Phase 2
0.7062 Intermediate Similarity NPD7874 Approved
0.7062 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD6844 Discontinued
0.7053 Intermediate Similarity NPD6823 Phase 2
0.7051 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD1933 Approved
0.7039 Intermediate Similarity NPD1201 Approved
0.7033 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD7440 Discontinued
0.7026 Intermediate Similarity NPD7801 Approved
0.7025 Intermediate Similarity NPD6233 Phase 2
0.7021 Intermediate Similarity NPD7700 Phase 2
0.7021 Intermediate Similarity NPD7699 Phase 2
0.7019 Intermediate Similarity NPD4308 Phase 3
0.7006 Intermediate Similarity NPD6273 Approved
0.7 Intermediate Similarity NPD9545 Approved
0.6995 Remote Similarity NPD8434 Phase 2
0.6994 Remote Similarity NPD8005 Clinical (unspecified phase)
0.6993 Remote Similarity NPD3972 Approved
0.6989 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6988 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6987 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6987 Remote Similarity NPD2861 Phase 2
0.6968 Remote Similarity NPD3266 Approved
0.6968 Remote Similarity NPD1470 Approved
0.6968 Remote Similarity NPD3267 Approved
0.6966 Remote Similarity NPD7228 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