Structure

Physi-Chem Properties

Molecular Weight:  852.23
Volume:  784.769
LogP:  -0.084
LogD:  -0.318
LogS:  -1.674
# Rotatable Bonds:  15
TPSA:  377.42
# H-Bond Aceptor:  22
# H-Bond Donor:  13
# Rings:  5
# Heavy Atoms:  22

MedChem Properties

QED Drug-Likeness Score:  0.043
Synthetic Accessibility Score:  5.687
Fsp3:  0.474
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  2
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -7.02
MDCK Permeability:  8.718458411749452e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  1.0
Human Intestinal Absorption (HIA):  0.935
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.161
Plasma Protein Binding (PPB):  86.57328796386719%
Volume Distribution (VD):  0.429
Pgp-substrate:  11.155319213867188%

ADMET: Metabolism

CYP1A2-inhibitor:  0.091
CYP1A2-substrate:  0.003
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.039
CYP2C9-inhibitor:  0.007
CYP2C9-substrate:  0.653
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.083
CYP3A4-inhibitor:  0.333
CYP3A4-substrate:  0.001

ADMET: Excretion

Clearance (CL):  1.067
Half-life (T1/2):  0.739

ADMET: Toxicity

hERG Blockers:  0.134
Human Hepatotoxicity (H-HT):  0.182
Drug-inuced Liver Injury (DILI):  0.641
AMES Toxicity:  0.082
Rat Oral Acute Toxicity:  0.009
Maximum Recommended Daily Dose:  0.293
Skin Sensitization:  0.035
Carcinogencity:  0.065
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.007

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

  Natural Product: NPC227297

Natural Product ID:  NPC227297
Common Name*:   Viarumacids A
IUPAC Name:   (1S,3R,4R,5R)-3-[(E)-3-[4-[(2S,3R,4S,5S,6R)-6-[[(1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexanecarbonyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxyphenyl]prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
Synonyms:   viarumacids A
Standard InCHIKey:  MEGCMHCHWAMJBV-QCNSHTHNSA-N
Standard InCHI:  InChI=1S/C38H44O22/c39-18-5-1-16(9-19(18)40)3-7-28(45)58-25-14-38(55,12-22(43)30(25)47)36(53)56-15-26-31(48)32(49)33(50)34(60-26)59-23-6-2-17(10-20(23)41)4-8-27(44)57-24-13-37(54,35(51)52)11-21(42)29(24)46/h1-10,21-22,24-26,29-34,39-43,46-50,54-55H,11-15H2,(H,51,52)/b7-3+,8-4+/t21-,22-,24-,25-,26-,29-,30-,31-,32+,33-,34-,37+,38+/m1/s1
SMILES:  O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)O)C(=O)OC[C@H]1O[C@@H](Oc2ccc(cc2O)/C=C/C(=O)O[C@@H]2C[C@@](O)(C[C@H]([C@H]2O)O)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2208390
PubChem CID:   71456110
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000238] Tannins
        • [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO7768 Solanum viarum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[23237411]
NPO7768 Solanum viarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7768 Solanum viarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7768 Solanum viarum Species Solanaceae 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
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.73 n.a. PMID[456082]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.72 n.a. PMID[456082]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.71 n.a. PMID[456082]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.65 n.a. PMID[456082]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.6 n.a. PMID[456082]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.68 n.a. PMID[456082]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.67 n.a. PMID[456082]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1.44 n.a. PMID[456082]

☑ 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 NPC227297 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
0.9809 High Similarity NPC128403
0.9146 High Similarity NPC102851
0.9146 High Similarity NPC5786
0.9141 High Similarity NPC658
0.9141 High Similarity NPC198125
0.9141 High Similarity NPC197708
0.9141 High Similarity NPC95421
0.9114 High Similarity NPC473275
0.9114 High Similarity NPC470896
0.9057 High Similarity NPC133984
0.9024 High Similarity NPC149300
0.8987 High Similarity NPC327032
0.8987 High Similarity NPC194095
0.8987 High Similarity NPC191046
0.8976 High Similarity NPC470438
0.8951 High Similarity NPC90905
0.8951 High Similarity NPC285108
0.8951 High Similarity NPC33298
0.8951 High Similarity NPC4013
0.8944 High Similarity NPC44507
0.8944 High Similarity NPC289346
0.8924 High Similarity NPC146277
0.8924 High Similarity NPC19380
0.8922 High Similarity NPC473630
0.8889 High Similarity NPC472859
0.8889 High Similarity NPC25389
0.8889 High Similarity NPC311803
0.8882 High Similarity NPC74319
0.8882 High Similarity NPC469654
0.8882 High Similarity NPC289811
0.8882 High Similarity NPC287872
0.8882 High Similarity NPC160780
0.8875 High Similarity NPC471405
0.8862 High Similarity NPC163165
0.8861 High Similarity NPC134905
0.8861 High Similarity NPC36130
0.8861 High Similarity NPC163883
0.8861 High Similarity NPC93498
0.8854 High Similarity NPC476871
0.8839 High Similarity NPC98356
0.8827 High Similarity NPC119125
0.8827 High Similarity NPC203020
0.8827 High Similarity NPC166277
0.8827 High Similarity NPC239966
0.882 High Similarity NPC40920
0.882 High Similarity NPC226759
0.882 High Similarity NPC1913
0.882 High Similarity NPC223335
0.8812 High Similarity NPC10205
0.881 High Similarity NPC84482
0.881 High Similarity NPC169645
0.8805 High Similarity NPC44730
0.8797 High Similarity NPC477334
0.879 High Similarity NPC478242
0.8779 High Similarity NPC104910
0.8779 High Similarity NPC474093
0.8774 High Similarity NPC476866
0.8774 High Similarity NPC476864
0.8774 High Similarity NPC476869
0.8774 High Similarity NPC477333
0.8774 High Similarity NPC476868
0.8772 High Similarity NPC135831
0.8772 High Similarity NPC297503
0.8772 High Similarity NPC470718
0.8772 High Similarity NPC97119
0.8758 High Similarity NPC163635
0.8742 High Similarity NPC106818
0.8728 High Similarity NPC475179
0.8721 High Similarity NPC470713
0.8721 High Similarity NPC470451
0.8721 High Similarity NPC470717
0.8721 High Similarity NPC470416
0.8721 High Similarity NPC25946
0.8721 High Similarity NPC470720
0.8721 High Similarity NPC21359
0.8721 High Similarity NPC460984
0.8721 High Similarity NPC470455
0.872 High Similarity NPC246024
0.8718 High Similarity NPC476865
0.871 High Similarity NPC476867
0.8706 High Similarity NPC253521
0.8706 High Similarity NPC113836
0.8706 High Similarity NPC37668
0.8704 High Similarity NPC238419
0.8704 High Similarity NPC472860
0.8704 High Similarity NPC172419
0.8701 High Similarity NPC35702
0.8701 High Similarity NPC471027
0.8701 High Similarity NPC13818
0.8701 High Similarity NPC206095
0.8701 High Similarity NPC224389
0.8701 High Similarity NPC477335
0.8701 High Similarity NPC297517
0.8696 High Similarity NPC131532
0.8696 High Similarity NPC145425
0.8688 High Similarity NPC87403
0.8688 High Similarity NPC157898
0.8688 High Similarity NPC137813
0.8679 High Similarity NPC7145
0.8679 High Similarity NPC85192
0.8679 High Similarity NPC125823
0.8679 High Similarity NPC143480
0.8678 High Similarity NPC7839
0.8678 High Similarity NPC142291
0.8675 High Similarity NPC471823
0.8671 High Similarity NPC94871
0.8671 High Similarity NPC111785
0.8671 High Similarity NPC470933
0.8671 High Similarity NPC471062
0.8671 High Similarity NPC476398
0.8671 High Similarity NPC306890
0.8671 High Similarity NPC295625
0.8671 High Similarity NPC473427
0.8671 High Similarity NPC470719
0.8671 High Similarity NPC259347
0.8671 High Similarity NPC476386
0.8671 High Similarity NPC473554
0.8663 High Similarity NPC162394
0.8663 High Similarity NPC470445
0.8663 High Similarity NPC35924
0.8663 High Similarity NPC156785
0.8663 High Similarity NPC241781
0.8663 High Similarity NPC470447
0.8663 High Similarity NPC199172
0.8663 High Similarity NPC470446
0.8663 High Similarity NPC470449
0.8663 High Similarity NPC36138
0.8655 High Similarity NPC471030
0.8655 High Similarity NPC80956
0.865 High Similarity NPC141331
0.865 High Similarity NPC104222
0.865 High Similarity NPC210501
0.865 High Similarity NPC318826
0.865 High Similarity NPC114791
0.8647 High Similarity NPC472992
0.8647 High Similarity NPC472991
0.8647 High Similarity NPC61904
0.8647 High Similarity NPC144097
0.8647 High Similarity NPC79736
0.8647 High Similarity NPC67629
0.8645 High Similarity NPC37331
0.8645 High Similarity NPC284948
0.8645 High Similarity NPC220664
0.8645 High Similarity NPC192831
0.8645 High Similarity NPC303090
0.8645 High Similarity NPC258469
0.8645 High Similarity NPC478239
0.8645 High Similarity NPC319628
0.8645 High Similarity NPC472016
0.8645 High Similarity NPC43158
0.8645 High Similarity NPC277315
0.8642 High Similarity NPC239019
0.8642 High Similarity NPC247629
0.8639 High Similarity NPC88560
0.8639 High Similarity NPC175230
0.8639 High Similarity NPC316539
0.8639 High Similarity NPC172033
0.8636 High Similarity NPC186406
0.8634 High Similarity NPC469888
0.8634 High Similarity NPC160882
0.8631 High Similarity NPC204937
0.8631 High Similarity NPC149011
0.8623 High Similarity NPC473818
0.8621 High Similarity NPC30011
0.8621 High Similarity NPC97817
0.8621 High Similarity NPC72554
0.8616 High Similarity NPC259576
0.8616 High Similarity NPC221091
0.8616 High Similarity NPC470927
0.8616 High Similarity NPC257970
0.8616 High Similarity NPC188393
0.8616 High Similarity NPC470934
0.8613 High Similarity NPC275977
0.8613 High Similarity NPC249560
0.8613 High Similarity NPC223860
0.8608 High Similarity NPC3460
0.8608 High Similarity NPC28651
0.8608 High Similarity NPC199311
0.8608 High Similarity NPC201148
0.8608 High Similarity NPC192763
0.8608 High Similarity NPC215095
0.8608 High Similarity NPC300262
0.8608 High Similarity NPC261122
0.8608 High Similarity NPC116229
0.8608 High Similarity NPC210611
0.8608 High Similarity NPC80732
0.8606 High Similarity NPC148273
0.8605 High Similarity NPC8940
0.8605 High Similarity NPC469371
0.8598 High Similarity NPC476373
0.8596 High Similarity NPC139571
0.8596 High Similarity NPC267680
0.8596 High Similarity NPC196127
0.8596 High Similarity NPC476619
0.8596 High Similarity NPC476618
0.8596 High Similarity NPC476622
0.8596 High Similarity NPC217520
0.8596 High Similarity NPC476620
0.8596 High Similarity NPC217387
0.8596 High Similarity NPC476623

  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 NPC227297 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
0.8645 High Similarity NPD6190 Approved
0.8588 High Similarity NPD4338 Clinical (unspecified phase)
0.848 Intermediate Similarity NPD7808 Phase 3
0.8471 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8439 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD7685 Pre-registration
0.8421 Intermediate Similarity NPD7251 Discontinued
0.8412 Intermediate Similarity NPD7472 Approved
0.8363 Intermediate Similarity NPD6797 Phase 2
0.8353 Intermediate Similarity NPD7054 Approved
0.8304 Intermediate Similarity NPD7074 Phase 3
0.8303 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD1653 Approved
0.8187 Intermediate Similarity NPD3818 Discontinued
0.8153 Intermediate Similarity NPD7266 Discontinued
0.8101 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8081 Intermediate Similarity NPD7228 Approved
0.8072 Intermediate Similarity NPD8455 Phase 2
0.807 Intermediate Similarity NPD6166 Phase 2
0.807 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.807 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7977 Intermediate Similarity NPD3751 Discontinued
0.7953 Intermediate Similarity NPD3787 Discontinued
0.7931 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD8312 Approved
0.791 Intermediate Similarity NPD8313 Approved
0.7853 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.779 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD6234 Discontinued
0.7727 Intermediate Similarity NPD5844 Phase 1
0.7706 Intermediate Similarity NPD3817 Phase 2
0.7701 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD7240 Approved
0.7692 Intermediate Similarity NPD1934 Approved
0.7692 Intermediate Similarity NPD37 Approved
0.7688 Intermediate Similarity NPD7199 Phase 2
0.7661 Intermediate Similarity NPD4966 Approved
0.7661 Intermediate Similarity NPD4967 Phase 2
0.7661 Intermediate Similarity NPD4965 Approved
0.7661 Intermediate Similarity NPD3882 Suspended
0.7647 Intermediate Similarity NPD2801 Approved
0.7647 Intermediate Similarity NPD1465 Phase 2
0.7616 Intermediate Similarity NPD7075 Discontinued
0.7605 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD5402 Approved
0.7579 Intermediate Similarity NPD7435 Discontinued
0.7544 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7486 Intermediate Similarity NPD8127 Discontinued
0.7484 Intermediate Similarity NPD6233 Phase 2
0.7455 Intermediate Similarity NPD4628 Phase 3
0.7442 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD1512 Approved
0.7436 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7874 Approved
0.7421 Intermediate Similarity NPD6781 Approved
0.7421 Intermediate Similarity NPD6777 Approved
0.7421 Intermediate Similarity NPD6776 Approved
0.7421 Intermediate Similarity NPD6778 Approved
0.7421 Intermediate Similarity NPD6779 Approved
0.7421 Intermediate Similarity NPD6780 Approved
0.7421 Intermediate Similarity NPD6782 Approved
0.7407 Intermediate Similarity NPD7097 Phase 1
0.7403 Intermediate Similarity NPD6559 Discontinued
0.7396 Intermediate Similarity NPD7698 Approved
0.7396 Intermediate Similarity NPD7696 Phase 3
0.7396 Intermediate Similarity NPD7697 Approved
0.7391 Intermediate Similarity NPD230 Phase 1
0.7391 Intermediate Similarity NPD8434 Phase 2
0.7368 Intermediate Similarity NPD4380 Phase 2
0.7358 Intermediate Similarity NPD7870 Phase 2
0.7358 Intermediate Similarity NPD7871 Phase 2
0.7333 Intermediate Similarity NPD7701 Phase 2
0.7329 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD1613 Approved
0.7321 Intermediate Similarity NPD1511 Approved
0.7306 Intermediate Similarity NPD7680 Approved
0.7296 Intermediate Similarity NPD8151 Discontinued
0.7294 Intermediate Similarity NPD5403 Approved
0.7283 Intermediate Similarity NPD6801 Discontinued
0.7277 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD3027 Phase 3
0.7247 Intermediate Similarity NPD6232 Discontinued
0.7246 Intermediate Similarity NPD8166 Discontinued
0.7241 Intermediate Similarity NPD7819 Suspended
0.7232 Intermediate Similarity NPD5494 Approved
0.7225 Intermediate Similarity NPD7700 Phase 2
0.7225 Intermediate Similarity NPD7699 Phase 2
0.7222 Intermediate Similarity NPD7801 Approved
0.7222 Intermediate Similarity NPD7473 Discontinued
0.7222 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7783 Phase 2
0.7219 Intermediate Similarity NPD6799 Approved
0.7209 Intermediate Similarity NPD7458 Discontinued
0.7205 Intermediate Similarity NPD6798 Discontinued
0.7205 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD8150 Discontinued
0.7197 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD6674 Discontinued
0.7179 Intermediate Similarity NPD8320 Phase 1
0.7179 Intermediate Similarity NPD8319 Approved
0.7176 Intermediate Similarity NPD5401 Approved
0.7176 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD6535 Approved
0.7158 Intermediate Similarity NPD6534 Approved
0.7143 Intermediate Similarity NPD7095 Approved
0.7126 Intermediate Similarity NPD7411 Suspended
0.7125 Intermediate Similarity NPD9494 Approved
0.7102 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7077 Intermediate Similarity NPD6823 Phase 2
0.7073 Intermediate Similarity NPD6355 Discontinued
0.7073 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD1933 Approved
0.707 Intermediate Similarity NPD1091 Approved
0.7062 Intermediate Similarity NPD7768 Phase 2
0.7029 Intermediate Similarity NPD6386 Approved
0.7029 Intermediate Similarity NPD6385 Approved
0.7024 Intermediate Similarity NPD1549 Phase 2
0.7019 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD5353 Approved
0.7005 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6959 Discontinued
0.6977 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6971 Remote Similarity NPD6599 Discontinued
0.697 Remote Similarity NPD447 Suspended
0.6964 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6964 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6951 Remote Similarity NPD4062 Phase 3
0.6946 Remote Similarity NPD7033 Discontinued
0.6941 Remote Similarity NPD3750 Approved
0.6941 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6935 Remote Similarity NPD7038 Approved
0.6935 Remote Similarity NPD7039 Approved
0.6927 Remote Similarity NPD3749 Approved
0.69 Remote Similarity NPD7585 Approved
0.6898 Remote Similarity NPD7549 Discontinued
0.6879 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6867 Remote Similarity NPD4340 Discontinued
0.685 Remote Similarity NPD7583 Approved
0.6842 Remote Similarity NPD4110 Phase 3
0.6842 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6839 Remote Similarity NPD6273 Approved
0.6832 Remote Similarity NPD3225 Approved
0.6821 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6813 Remote Similarity NPD1608 Approved
0.6813 Remote Similarity NPD9269 Phase 2
0.6807 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6807 Remote Similarity NPD4060 Phase 1
0.6805 Remote Similarity NPD1551 Phase 2
0.6805 Remote Similarity NPD2935 Discontinued
0.6796 Remote Similarity NPD919 Approved
0.6788 Remote Similarity NPD3764 Approved
0.6782 Remote Similarity NPD3688 Clinical (unspecified phase)
0.6782 Remote Similarity NPD3146 Approved
0.6768 Remote Similarity NPD2493 Approved
0.6768 Remote Similarity NPD3452 Approved
0.6768 Remote Similarity NPD3450 Approved
0.6768 Remote Similarity NPD2494 Approved
0.6766 Remote Similarity NPD7584 Approved
0.6762 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6752 Remote Similarity NPD5536 Phase 2
0.675 Remote Similarity NPD1535 Discovery
0.6746 Remote Similarity NPD1510 Phase 2
0.6744 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6742 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6739 Remote Similarity NPD3926 Phase 2
0.6739 Remote Similarity NPD5242 Approved
0.6726 Remote Similarity NPD6653 Approved
0.6723 Remote Similarity NPD3226 Approved
0.6721 Remote Similarity NPD1247 Approved
0.6709 Remote Similarity NPD9545 Approved
0.6708 Remote Similarity NPD1481 Phase 2
0.6707 Remote Similarity NPD2861 Phase 2
0.6706 Remote Similarity NPD6100 Approved
0.6706 Remote Similarity NPD6099 Approved
0.6706 Remote Similarity NPD2796 Approved
0.6705 Remote Similarity NPD3887 Approved
0.6705 Remote Similarity NPD2354 Approved
0.67 Remote Similarity NPD4004 Approved
0.67 Remote Similarity NPD4002 Approved
0.6686 Remote Similarity NPD1652 Phase 2
0.6685 Remote Similarity NPD7229 Phase 3
0.6685 Remote Similarity NPD7028 Phase 2
0.6684 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6213 Phase 3
0.6667 Remote Similarity NPD4582 Approved
0.6667 Remote Similarity NPD4908 Phase 1
0.6667 Remote Similarity NPD1357 Approved
0.6667 Remote Similarity NPD6212 Phase 3
0.6667 Remote Similarity NPD5058 Phase 3
0.6667 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4583 Approved
0.6667 Remote Similarity NPD5124 Phase 1
0.6667 Remote Similarity NPD7440 Discontinued
0.6648 Remote Similarity NPD7314 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