Structure

Physi-Chem Properties

Molecular Weight:  536.2
Volume:  537.401
LogP:  4.137
LogD:  3.589
LogS:  -5.109
# Rotatable Bonds:  7
TPSA:  101.91
# H-Bond Aceptor:  9
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.438
Synthetic Accessibility Score:  3.867
Fsp3:  0.367
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.775
MDCK Permeability:  3.626684338087216e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.018
Plasma Protein Binding (PPB):  88.51663970947266%
Volume Distribution (VD):  0.493
Pgp-substrate:  4.321821689605713%

ADMET: Metabolism

CYP1A2-inhibitor:  0.085
CYP1A2-substrate:  0.976
CYP2C19-inhibitor:  0.959
CYP2C19-substrate:  0.853
CYP2C9-inhibitor:  0.863
CYP2C9-substrate:  0.908
CYP2D6-inhibitor:  0.063
CYP2D6-substrate:  0.822
CYP3A4-inhibitor:  0.913
CYP3A4-substrate:  0.891

ADMET: Excretion

Clearance (CL):  7.886
Half-life (T1/2):  0.089

ADMET: Toxicity

hERG Blockers:  0.099
Human Hepatotoxicity (H-HT):  0.072
Drug-inuced Liver Injury (DILI):  0.849
AMES Toxicity:  0.063
Rat Oral Acute Toxicity:  0.022
Maximum Recommended Daily Dose:  0.128
Skin Sensitization:  0.055
Carcinogencity:  0.138
Eye Corrosion:  0.003
Eye Irritation:  0.198
Respiratory Toxicity:  0.126

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Similar NPs/Drugs  

  Natural Product: NPC320471

Natural Product ID:  NPC320471
Common Name*:   UFCGDBKFOKKVAC-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  UFCGDBKFOKKVAC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C30H32O9/c1-16-12-18-13-21-25(38-15-37-21)26(35-5)22(18)23-19(14-20(33-3)24(34-4)27(23)36-6)28(30(16,2)32)39-29(31)17-10-8-7-9-11-17/h7-11,13-14,16,28,32H,12,15H2,1-6H3
SMILES:  COc1cc2c(c(c1OC)OC)c1c(cc3c(c1OC)OCO3)CC(C(C2OC(=O)c1ccccc1)(C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1704343
PubChem CID:   332607
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
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[16562834]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[24155209]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[24959987]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[25302569]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8187 Schisandra chinensis Species Schisandraceae 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
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 39810.7 nM PMID[543720]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 60673.63 nM PMID[543721]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 40457.59 nM PMID[543721]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 31988.95 nM PMID[543721]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 45394.16 nM PMID[543721]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 21086.28 nM PMID[543721]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 12218.0 nM PMID[543721]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 69823.24 nM PMID[543721]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 19453.6 nM PMID[543721]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 31117.16 nM PMID[543721]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[543721]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 45498.81 nM PMID[543721]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 46344.69 nM PMID[543721]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 39810.72 nM PMID[543721]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 29853.83 nM PMID[543721]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 5584.7 nM PMID[543721]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[543721]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 39902.49 nM PMID[543721]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 40644.33 nM PMID[543721]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[543721]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 20183.66 nM PMID[543721]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 37757.22 nM PMID[543721]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 17701.09 nM PMID[543721]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 96161.23 nM PMID[543721]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 71779.43 nM PMID[543721]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 41114.97 nM PMID[543721]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 24603.68 nM PMID[543721]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 34355.79 nM PMID[543721]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 99540.54 nM PMID[543721]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 22029.26 nM PMID[543721]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 35318.32 nM PMID[543721]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 31188.9 nM PMID[543721]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 56104.8 nM PMID[543721]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 25003.45 nM PMID[543721]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 22855.99 nM PMID[543721]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 42072.66 nM PMID[543721]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 41020.41 nM PMID[543721]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 31405.09 nM PMID[543721]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 33189.45 nM PMID[543721]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 35974.93 nM PMID[543721]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 53456.44 nM PMID[543721]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 26607.25 nM PMID[543721]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 44874.54 nM PMID[543721]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 60394.86 nM PMID[543721]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 33342.64 nM PMID[543721]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 42266.86 nM PMID[543721]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 32960.97 nM PMID[543721]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 55975.76 nM PMID[543721]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 39355.01 nM PMID[543721]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 54954.09 nM PMID[543721]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 38282.47 nM PMID[543721]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 55080.77 nM PMID[543721]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 32508.73 nM PMID[543721]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 44874.54 nM PMID[543721]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 25882.13 nM PMID[543721]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 25822.6 nM PMID[543721]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 29376.5 nM PMID[543721]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 63679.55 nM PMID[543721]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 27861.21 nM PMID[543721]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 22490.55 nM PMID[543721]

☑ 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 NPC320471 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 NPC83049
1.0 High Similarity NPC118162
0.981 High Similarity NPC79322
0.9748 High Similarity NPC88557
0.9686 High Similarity NPC311912
0.9618 High Similarity NPC319749
0.9568 High Similarity NPC477881
0.9557 High Similarity NPC280778
0.9494 High Similarity NPC191352
0.9494 High Similarity NPC258322
0.9444 High Similarity NPC477883
0.9437 High Similarity NPC477884
0.9434 High Similarity NPC42797
0.9394 High Similarity NPC477880
0.9394 High Similarity NPC477882
0.9375 High Similarity NPC291977
0.9313 High Similarity NPC473445
0.9295 High Similarity NPC217708
0.9295 High Similarity NPC16791
0.9295 High Similarity NPC126405
0.9295 High Similarity NPC297271
0.9295 High Similarity NPC53669
0.9295 High Similarity NPC77237
0.9295 High Similarity NPC308739
0.9245 High Similarity NPC230531
0.9245 High Similarity NPC215400
0.9245 High Similarity NPC328122
0.9193 High Similarity NPC249070
0.9172 High Similarity NPC477377
0.9167 High Similarity NPC224472
0.9152 High Similarity NPC469506
0.9125 High Similarity NPC325122
0.9119 High Similarity NPC477380
0.9114 High Similarity NPC198461
0.9108 High Similarity NPC475229
0.9108 High Similarity NPC477378
0.9062 High Similarity NPC477885
0.9062 High Similarity NPC475592
0.9057 High Similarity NPC238834
0.9057 High Similarity NPC476065
0.9051 High Similarity NPC24562
0.8994 High Similarity NPC348849
0.8994 High Similarity NPC178195
0.8981 High Similarity NPC316989
0.8974 High Similarity NPC198129
0.8974 High Similarity NPC477375
0.8974 High Similarity NPC327352
0.8974 High Similarity NPC252281
0.8931 High Similarity NPC474606
0.8917 High Similarity NPC477376
0.8917 High Similarity NPC477374
0.8917 High Similarity NPC322426
0.8916 High Similarity NPC117911
0.891 High Similarity NPC295297
0.8909 High Similarity NPC474042
0.8909 High Similarity NPC174734
0.8902 High Similarity NPC475865
0.8882 High Similarity NPC473323
0.8882 High Similarity NPC29727
0.8875 High Similarity NPC312763
0.8875 High Similarity NPC473736
0.8868 High Similarity NPC471154
0.8855 High Similarity NPC471180
0.8846 High Similarity NPC321696
0.8846 High Similarity NPC321958
0.8841 High Similarity NPC469512
0.8834 High Similarity NPC474770
0.8812 High Similarity NPC475141
0.881 High Similarity NPC471181
0.881 High Similarity NPC178737
0.8805 High Similarity NPC303519
0.8805 High Similarity NPC475756
0.8797 High Similarity NPC85141
0.8788 High Similarity NPC469475
0.8788 High Similarity NPC469518
0.8782 High Similarity NPC318286
0.8782 High Similarity NPC327651
0.8773 High Similarity NPC474043
0.8773 High Similarity NPC125713
0.8765 High Similarity NPC196771
0.8758 High Similarity NPC473425
0.8757 High Similarity NPC184624
0.875 High Similarity NPC476434
0.875 High Similarity NPC220577
0.8742 High Similarity NPC470916
0.8734 High Similarity NPC325720
0.8734 High Similarity NPC316676
0.8727 High Similarity NPC22130
0.8727 High Similarity NPC116838
0.8727 High Similarity NPC61141
0.872 High Similarity NPC96593
0.8718 High Similarity NPC326144
0.8713 High Similarity NPC35266
0.8712 High Similarity NPC19947
0.8712 High Similarity NPC207584
0.8698 High Similarity NPC129930
0.8698 High Similarity NPC471920
0.8698 High Similarity NPC20114
0.8698 High Similarity NPC114550
0.8698 High Similarity NPC471921
0.8698 High Similarity NPC292712
0.8698 High Similarity NPC38438
0.8698 High Similarity NPC474075
0.8698 High Similarity NPC471922
0.8698 High Similarity NPC312006
0.8696 High Similarity NPC245948
0.8679 High Similarity NPC474347
0.8679 High Similarity NPC474393
0.8667 High Similarity NPC100465
0.8667 High Similarity NPC288149
0.8667 High Similarity NPC152424
0.8655 High Similarity NPC79736
0.8655 High Similarity NPC67629
0.8655 High Similarity NPC473713
0.8655 High Similarity NPC472723
0.8654 High Similarity NPC218510
0.8654 High Similarity NPC76415
0.865 High Similarity NPC239113
0.865 High Similarity NPC237946
0.865 High Similarity NPC301897
0.865 High Similarity NPC32373
0.865 High Similarity NPC115123
0.8639 High Similarity NPC180768
0.8634 High Similarity NPC267091
0.8634 High Similarity NPC104353
0.8625 High Similarity NPC473989
0.8623 High Similarity NPC222531
0.8616 High Similarity NPC304821
0.8613 High Similarity NPC208797
0.8613 High Similarity NPC53680
0.8606 High Similarity NPC150943
0.8606 High Similarity NPC91634
0.8606 High Similarity NPC63061
0.8606 High Similarity NPC268718
0.8605 High Similarity NPC267549
0.8598 High Similarity NPC143328
0.8598 High Similarity NPC181168
0.8598 High Similarity NPC163527
0.8598 High Similarity NPC115281
0.8596 High Similarity NPC469354
0.8589 High Similarity NPC234730
0.858 High Similarity NPC474514
0.8571 High Similarity NPC210642
0.8571 High Similarity NPC13985
0.8571 High Similarity NPC243891
0.8563 High Similarity NPC121290
0.8555 High Similarity NPC161609
0.8555 High Similarity NPC275690
0.8553 High Similarity NPC137352
0.8553 High Similarity NPC183083
0.8547 High Similarity NPC297574
0.8545 High Similarity NPC241600
0.8545 High Similarity NPC173726
0.8538 High Similarity NPC316539
0.8537 High Similarity NPC109765
0.8529 High Similarity NPC52598
0.8528 High Similarity NPC273578
0.8521 High Similarity NPC473531
0.8521 High Similarity NPC475453
0.8519 High Similarity NPC228662
0.8514 High Similarity NPC114120
0.8514 High Similarity NPC167045
0.8512 High Similarity NPC475738
0.8509 High Similarity NPC149505
0.8509 High Similarity NPC477381
0.8509 High Similarity NPC24425
0.8503 High Similarity NPC14030
0.8503 High Similarity NPC291957
0.8503 High Similarity NPC198796
0.85 High Similarity NPC102934
0.85 High Similarity NPC252402
0.8494 Intermediate Similarity NPC24627
0.8494 Intermediate Similarity NPC78944
0.8494 Intermediate Similarity NPC119910
0.8494 Intermediate Similarity NPC53889
0.8488 Intermediate Similarity NPC193377
0.8485 Intermediate Similarity NPC472860
0.8485 Intermediate Similarity NPC202495
0.8485 Intermediate Similarity NPC226759
0.8485 Intermediate Similarity NPC19600
0.8481 Intermediate Similarity NPC474036
0.8466 Intermediate Similarity NPC149735
0.8466 Intermediate Similarity NPC65591
0.8466 Intermediate Similarity NPC474656
0.8466 Intermediate Similarity NPC178574
0.8462 Intermediate Similarity NPC43065
0.8462 Intermediate Similarity NPC306475
0.8462 Intermediate Similarity NPC471923
0.8457 Intermediate Similarity NPC477700
0.8457 Intermediate Similarity NPC35924
0.8457 Intermediate Similarity NPC32079
0.8457 Intermediate Similarity NPC199172
0.8457 Intermediate Similarity NPC477379
0.8452 Intermediate Similarity NPC116759
0.8452 Intermediate Similarity NPC14294
0.8452 Intermediate Similarity NPC470898
0.8448 Intermediate Similarity NPC80956
0.8443 Intermediate Similarity NPC209411
0.8443 Intermediate Similarity NPC469889
0.8443 Intermediate Similarity NPC239890

  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 NPC320471 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
0.8696 High Similarity NPD37 Approved
0.8667 High Similarity NPD7199 Phase 2
0.8659 High Similarity NPD6234 Discontinued
0.865 High Similarity NPD4967 Phase 2
0.865 High Similarity NPD4966 Approved
0.865 High Similarity NPD4965 Approved
0.8616 High Similarity NPD6980 Clinical (unspecified phase)
0.8563 High Similarity NPD7184 Clinical (unspecified phase)
0.8412 Intermediate Similarity NPD7228 Approved
0.8363 Intermediate Similarity NPD5844 Phase 1
0.8353 Intermediate Similarity NPD7473 Discontinued
0.8313 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8304 Intermediate Similarity NPD3818 Discontinued
0.8284 Intermediate Similarity NPD6232 Discontinued
0.8218 Intermediate Similarity NPD7240 Approved
0.8199 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8136 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8114 Intermediate Similarity NPD6559 Discontinued
0.8103 Intermediate Similarity NPD7074 Phase 3
0.8046 Intermediate Similarity NPD7054 Approved
0.8036 Intermediate Similarity NPD3817 Phase 2
0.8 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7472 Approved
0.7976 Intermediate Similarity NPD7819 Suspended
0.7976 Intermediate Similarity NPD1465 Phase 2
0.7917 Intermediate Similarity NPD1934 Approved
0.791 Intermediate Similarity NPD7685 Pre-registration
0.7874 Intermediate Similarity NPD6166 Phase 2
0.7874 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7865 Intermediate Similarity NPD7808 Phase 3
0.7865 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7849 Intermediate Similarity NPD5494 Approved
0.7836 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7809 Intermediate Similarity NPD7251 Discontinued
0.7778 Intermediate Similarity NPD3882 Suspended
0.7765 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD8455 Phase 2
0.7753 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7753 Intermediate Similarity NPD6797 Phase 2
0.7733 Intermediate Similarity NPD7075 Discontinued
0.7722 Intermediate Similarity NPD8313 Approved
0.7722 Intermediate Similarity NPD8312 Approved
0.7717 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD3750 Approved
0.768 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD1653 Approved
0.7674 Intermediate Similarity NPD7768 Phase 2
0.7661 Intermediate Similarity NPD2801 Approved
0.7657 Intermediate Similarity NPD7229 Phase 3
0.763 Intermediate Similarity NPD3749 Approved
0.76 Intermediate Similarity NPD8127 Discontinued
0.7593 Intermediate Similarity NPD3748 Approved
0.7592 Intermediate Similarity NPD7680 Approved
0.7588 Intermediate Similarity NPD4380 Phase 2
0.7566 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7561 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7547 Intermediate Similarity NPD3764 Approved
0.7545 Intermediate Similarity NPD6799 Approved
0.7544 Intermediate Similarity NPD7411 Suspended
0.7542 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD7458 Discontinued
0.7529 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD3926 Phase 2
0.7514 Intermediate Similarity NPD5402 Approved
0.75 Intermediate Similarity NPD2532 Approved
0.75 Intermediate Similarity NPD2534 Approved
0.75 Intermediate Similarity NPD7266 Discontinued
0.75 Intermediate Similarity NPD8434 Phase 2
0.75 Intermediate Similarity NPD6801 Discontinued
0.75 Intermediate Similarity NPD6959 Discontinued
0.75 Intermediate Similarity NPD2533 Approved
0.7487 Intermediate Similarity NPD8151 Discontinued
0.7486 Intermediate Similarity NPD919 Approved
0.7486 Intermediate Similarity NPD3751 Discontinued
0.7485 Intermediate Similarity NPD6599 Discontinued
0.747 Intermediate Similarity NPD4628 Phase 3
0.7458 Intermediate Similarity NPD3787 Discontinued
0.744 Intermediate Similarity NPD1511 Approved
0.7438 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD6190 Approved
0.7412 Intermediate Similarity NPD5403 Approved
0.741 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD6674 Discontinued
0.7407 Intermediate Similarity NPD230 Phase 1
0.7407 Intermediate Similarity NPD6355 Discontinued
0.7407 Intermediate Similarity NPD1933 Approved
0.7396 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD5401 Approved
0.7375 Intermediate Similarity NPD3027 Phase 3
0.7374 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD7003 Approved
0.7365 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD5006 Approved
0.7358 Intermediate Similarity NPD5005 Approved
0.7353 Intermediate Similarity NPD6273 Approved
0.7353 Intermediate Similarity NPD1512 Approved
0.7333 Intermediate Similarity NPD2796 Approved
0.7333 Intermediate Similarity NPD2935 Discontinued
0.7329 Intermediate Similarity NPD6798 Discontinued
0.732 Intermediate Similarity NPD7435 Discontinued
0.7318 Intermediate Similarity NPD5242 Approved
0.7314 Intermediate Similarity NPD5353 Approved
0.7308 Intermediate Similarity NPD3705 Approved
0.7294 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7028 Phase 2
0.7273 Intermediate Similarity NPD1510 Phase 2
0.7262 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD1549 Phase 2
0.724 Intermediate Similarity NPD4420 Approved
0.7239 Intermediate Similarity NPD1613 Approved
0.7239 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD7783 Phase 2
0.7229 Intermediate Similarity NPD2438 Suspended
0.7225 Intermediate Similarity NPD3226 Approved
0.7207 Intermediate Similarity NPD1247 Approved
0.7195 Intermediate Similarity NPD447 Suspended
0.7193 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD7549 Discontinued
0.7186 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD6823 Phase 2
0.7178 Intermediate Similarity NPD6233 Phase 2
0.7165 Intermediate Similarity NPD6779 Approved
0.7165 Intermediate Similarity NPD6777 Approved
0.7165 Intermediate Similarity NPD6780 Approved
0.7165 Intermediate Similarity NPD6782 Approved
0.7165 Intermediate Similarity NPD6776 Approved
0.7165 Intermediate Similarity NPD6778 Approved
0.7165 Intermediate Similarity NPD6781 Approved
0.716 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD4110 Phase 3
0.7143 Intermediate Similarity NPD6386 Approved
0.7143 Intermediate Similarity NPD6385 Approved
0.7134 Intermediate Similarity NPD1240 Approved
0.7129 Intermediate Similarity NPD7930 Approved
0.7128 Intermediate Similarity NPD8150 Discontinued
0.7126 Intermediate Similarity NPD1551 Phase 2
0.711 Intermediate Similarity NPD920 Approved
0.7108 Intermediate Similarity NPD7097 Phase 1
0.7107 Intermediate Similarity NPD7870 Phase 2
0.7107 Intermediate Similarity NPD7871 Phase 2
0.71 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.71 Intermediate Similarity NPD7874 Approved
0.7099 Intermediate Similarity NPD4908 Phase 1
0.7099 Intermediate Similarity NPD6832 Phase 2
0.7099 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2346 Discontinued
0.7081 Intermediate Similarity NPD2798 Approved
0.7071 Intermediate Similarity NPD7999 Approved
0.7066 Intermediate Similarity NPD2799 Discontinued
0.7063 Intermediate Similarity NPD1283 Approved
0.7059 Intermediate Similarity NPD8166 Discontinued
0.7056 Intermediate Similarity NPD7698 Approved
0.7056 Intermediate Similarity NPD7696 Phase 3
0.7056 Intermediate Similarity NPD7697 Approved
0.7055 Intermediate Similarity NPD7095 Approved
0.7055 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD1607 Approved
0.7045 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD7039 Approved
0.7043 Intermediate Similarity NPD7038 Approved
0.7039 Intermediate Similarity NPD6971 Discontinued
0.7039 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4060 Phase 1
0.703 Intermediate Similarity NPD2979 Phase 3
0.7024 Intermediate Similarity NPD6099 Approved
0.7024 Intermediate Similarity NPD5406 Approved
0.7024 Intermediate Similarity NPD6100 Approved
0.7024 Intermediate Similarity NPD5405 Approved
0.7024 Intermediate Similarity NPD5408 Approved
0.7024 Intermediate Similarity NPD5404 Approved
0.7022 Intermediate Similarity NPD4288 Approved
0.702 Intermediate Similarity NPD8319 Approved
0.702 Intermediate Similarity NPD8320 Phase 1
0.7019 Intermediate Similarity NPD2797 Approved
0.7012 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1243 Approved
0.7 Intermediate Similarity NPD6843 Phase 3
0.7 Intermediate Similarity NPD6841 Approved
0.7 Intermediate Similarity NPD6842 Approved
0.7 Intermediate Similarity NPD7701 Phase 2
0.6994 Remote Similarity NPD642 Clinical (unspecified phase)
0.6982 Remote Similarity NPD5763 Approved
0.6982 Remote Similarity NPD5762 Approved
0.698 Remote Similarity NPD7801 Approved
0.6979 Remote Similarity NPD7296 Approved
0.6978 Remote Similarity NPD5711 Approved
0.6978 Remote Similarity NPD5710 Approved
0.6977 Remote Similarity NPD643 Clinical (unspecified phase)
0.6973 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6964 Remote Similarity NPD4308 Phase 3
0.6961 Remote Similarity NPD6746 Phase 2
0.6954 Remote Similarity NPD1940 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