Structure

Physi-Chem Properties

Molecular Weight:  470.14
Volume:  477.319
LogP:  4.174
LogD:  3.598
LogS:  -3.496
# Rotatable Bonds:  4
TPSA:  130.61
# H-Bond Aceptor:  7
# H-Bond Donor:  6
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.175
Synthetic Accessibility Score:  3.642
Fsp3:  0.071
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.911
MDCK Permeability:  7.1777767516323365e-06
Pgp-inhibitor:  0.627
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.195
20% Bioavailability (F20%):  0.943
30% Bioavailability (F30%):  0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.012
Plasma Protein Binding (PPB):  97.8355941772461%
Volume Distribution (VD):  0.67
Pgp-substrate:  2.495952606201172%

ADMET: Metabolism

CYP1A2-inhibitor:  0.699
CYP1A2-substrate:  0.285
CYP2C19-inhibitor:  0.697
CYP2C19-substrate:  0.048
CYP2C9-inhibitor:  0.785
CYP2C9-substrate:  0.981
CYP2D6-inhibitor:  0.278
CYP2D6-substrate:  0.912
CYP3A4-inhibitor:  0.71
CYP3A4-substrate:  0.186

ADMET: Excretion

Clearance (CL):  13.88
Half-life (T1/2):  0.751

ADMET: Toxicity

hERG Blockers:  0.204
Human Hepatotoxicity (H-HT):  0.21
Drug-inuced Liver Injury (DILI):  0.075
AMES Toxicity:  0.313
Rat Oral Acute Toxicity:  0.354
Maximum Recommended Daily Dose:  0.929
Skin Sensitization:  0.962
Carcinogencity:  0.068
Eye Corrosion:  0.003
Eye Irritation:  0.899
Respiratory Toxicity:  0.1

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

  Natural Product: NPC173203

Natural Product ID:  NPC173203
Common Name*:   4-[3-(3,5-Dihydroxyphenyl)-6-Hydroxy-4-[(E)-2-(4-Hydroxyphenyl)Ethenyl]-2,3-Dihydro-1-Benzofuran-2-Yl]Benzene-1,2-Diol
IUPAC Name:   4-[3-(3,5-dihydroxyphenyl)-6-hydroxy-4-[(E)-2-(4-hydroxyphenyl)ethenyl]-2,3-dihydro-1-benzofuran-2-yl]benzene-1,2-diol
Synonyms:  
Standard InCHIKey:  VJVQHVVOEFJLIO-DAFODLJHSA-N
Standard InCHI:  InChI=1S/C28H22O7/c29-19-6-2-15(3-7-19)1-4-16-9-22(32)14-25-26(16)27(18-10-20(30)13-21(31)11-18)28(35-25)17-5-8-23(33)24(34)12-17/h1-14,27-34H/b4-1+
SMILES:  Oc1cc(/C=C/c2ccc(cc2)O)c2c(c1)OC(C2c1cc(O)cc(c1)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL478595
PubChem CID:   5458896
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0040-4039(01)90945-1]
NPO25611 Smilax china Species Smilacaceae Eukaryota stems n.a. n.a. PMID[16252910]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[24704449]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. PMID[26967731]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22796 Cyperus rotundus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25611 Smilax china Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7132 Smilax glabra Species Smilacaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22796 Cyperus rotundus Species Cyperaceae 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
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 18238.96 nM PMID[530534]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 17579.24 nM PMID[530534]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 18793.17 nM PMID[530534]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 30902.95 nM PMID[530534]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 14962.36 nM PMID[530534]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 27101.92 nM PMID[530534]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 37068.07 nM PMID[530534]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 34355.79 nM PMID[530534]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 35075.19 nM PMID[530534]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 26668.59 nM PMID[530534]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 17218.69 nM PMID[530534]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 33496.54 nM PMID[530534]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 27797.13 nM PMID[530534]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 11641.26 nM PMID[530534]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 35892.19 nM PMID[530534]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 30974.19 nM PMID[530534]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 31768.74 nM PMID[530534]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 21627.19 nM PMID[530534]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 35563.13 nM PMID[530534]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 18578.04 nM PMID[530534]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 28973.44 nM PMID[530534]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 17619.76 nM PMID[530534]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 39174.19 nM PMID[530534]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 27101.92 nM PMID[530534]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 26977.39 nM PMID[530534]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 31915.38 nM PMID[530534]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 25585.86 nM PMID[530534]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 13458.6 nM PMID[530534]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 43451.02 nM PMID[530534]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 16826.74 nM PMID[530534]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 23659.2 nM PMID[530534]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 27039.58 nM PMID[530534]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 28379.19 nM PMID[530534]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 45603.69 nM PMID[530534]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 25409.73 nM PMID[530534]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 49545.02 nM PMID[530534]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 20044.72 nM PMID[530534]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 35892.19 nM PMID[530534]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 30619.63 nM PMID[530534]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 25292.98 nM PMID[530534]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 33342.64 nM PMID[530534]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 31260.79 nM PMID[530534]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 13091.82 nM PMID[530534]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 32508.73 nM PMID[530534]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 18155.16 nM PMID[530534]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 31695.67 nM PMID[530534]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 32583.67 nM PMID[530534]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 31405.09 nM PMID[530534]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 36559.48 nM PMID[530534]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 26363.31 nM PMID[530534]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 25292.98 nM PMID[530534]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 41783.04 nM PMID[530534]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 8336.81 nM PMID[530534]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 26001.6 nM PMID[530534]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 17579.24 nM PMID[530534]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 25061.09 nM PMID[530534]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 19498.45 nM PMID[530534]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 41304.75 nM PMID[530534]

☑ 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 NPC173203 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 NPC163508
0.9926 High Similarity NPC15659
0.9926 High Similarity NPC304894
0.9643 High Similarity NPC329836
0.9481 High Similarity NPC15109
0.9481 High Similarity NPC11727
0.9366 High Similarity NPC227516
0.9366 High Similarity NPC20757
0.9348 High Similarity NPC22317
0.9348 High Similarity NPC182509
0.9348 High Similarity NPC174787
0.9348 High Similarity NPC213607
0.9281 High Similarity NPC178054
0.927 High Similarity NPC141717
0.927 High Similarity NPC234952
0.9247 High Similarity NPC157333
0.9241 High Similarity NPC476391
0.9209 High Similarity NPC184797
0.9209 High Similarity NPC309124
0.9203 High Similarity NPC474390
0.9197 High Similarity NPC125579
0.9172 High Similarity NPC329343
0.9172 High Similarity NPC324517
0.9172 High Similarity NPC321972
0.9161 High Similarity NPC70409
0.9161 High Similarity NPC108811
0.9161 High Similarity NPC202742
0.9161 High Similarity NPC263940
0.9161 High Similarity NPC58190
0.9161 High Similarity NPC18185
0.9161 High Similarity NPC236202
0.9161 High Similarity NPC82917
0.9161 High Similarity NPC262911
0.9161 High Similarity NPC294558
0.9161 High Similarity NPC204770
0.9161 High Similarity NPC170103
0.9137 High Similarity NPC232164
0.9137 High Similarity NPC236306
0.9137 High Similarity NPC32630
0.9137 High Similarity NPC55947
0.9137 High Similarity NPC473739
0.9124 High Similarity NPC256307
0.9124 High Similarity NPC66840
0.9091 High Similarity NPC324492
0.9091 High Similarity NPC96576
0.9091 High Similarity NPC317053
0.9091 High Similarity NPC260397
0.9085 High Similarity NPC171932
0.9085 High Similarity NPC28440
0.9085 High Similarity NPC473108
0.9078 High Similarity NPC107161
0.9071 High Similarity NPC61783
0.9071 High Similarity NPC160283
0.9071 High Similarity NPC254759
0.9071 High Similarity NPC262189
0.9071 High Similarity NPC20520
0.9065 High Similarity NPC94994
0.9054 High Similarity NPC202104
0.9051 High Similarity NPC11060
0.9034 High Similarity NPC211561
0.9034 High Similarity NPC318373
0.9034 High Similarity NPC321657
0.9034 High Similarity NPC473266
0.9034 High Similarity NPC476969
0.9034 High Similarity NPC470826
0.9034 High Similarity NPC470098
0.9028 High Similarity NPC327412
0.9028 High Similarity NPC328567
0.9028 High Similarity NPC320970
0.9028 High Similarity NPC320671
0.9014 High Similarity NPC469630
0.9007 High Similarity NPC263261
0.9007 High Similarity NPC265075
0.9007 High Similarity NPC247291
0.9007 High Similarity NPC87725
0.9 High Similarity NPC292882
0.8993 High Similarity NPC162659
0.8993 High Similarity NPC265433
0.8993 High Similarity NPC270456
0.8993 High Similarity NPC248727
0.8978 High Similarity NPC474134
0.8978 High Similarity NPC131128
0.8973 High Similarity NPC477612
0.8951 High Similarity NPC93323
0.8951 High Similarity NPC114119
0.8951 High Similarity NPC471415
0.8951 High Similarity NPC280092
0.8951 High Similarity NPC470097
0.8951 High Similarity NPC45257
0.8951 High Similarity NPC12641
0.8944 High Similarity NPC277784
0.8936 High Similarity NPC27495
0.8936 High Similarity NPC472090
0.8936 High Similarity NPC472092
0.8936 High Similarity NPC266197
0.8936 High Similarity NPC472091
0.8936 High Similarity NPC291101
0.8929 High Similarity NPC211549
0.8921 High Similarity NPC112246
0.8921 High Similarity NPC470356
0.8921 High Similarity NPC474206
0.8921 High Similarity NPC112939
0.8921 High Similarity NPC473413
0.8921 High Similarity NPC151224
0.8921 High Similarity NPC94750
0.8921 High Similarity NPC121812
0.8921 High Similarity NPC164787
0.8913 High Similarity NPC158331
0.8897 High Similarity NPC16269
0.8897 High Similarity NPC471518
0.8897 High Similarity NPC471519
0.8897 High Similarity NPC21776
0.8889 High Similarity NPC149633
0.8889 High Similarity NPC181615
0.8881 High Similarity NPC85264
0.8881 High Similarity NPC274721
0.8881 High Similarity NPC477616
0.8881 High Similarity NPC155392
0.8881 High Similarity NPC102044
0.8881 High Similarity NPC135767
0.8881 High Similarity NPC47633
0.8873 High Similarity NPC470372
0.8873 High Similarity NPC471389
0.8873 High Similarity NPC472089
0.8873 High Similarity NPC311530
0.8865 High Similarity NPC245207
0.8865 High Similarity NPC319647
0.8865 High Similarity NPC184613
0.8865 High Similarity NPC70682
0.8865 High Similarity NPC260741
0.8865 High Similarity NPC127218
0.8865 High Similarity NPC25966
0.8865 High Similarity NPC22517
0.8857 High Similarity NPC227503
0.8857 High Similarity NPC230734
0.8857 High Similarity NPC474639
0.8857 High Similarity NPC302701
0.8857 High Similarity NPC16435
0.8857 High Similarity NPC269091
0.8857 High Similarity NPC306441
0.8851 High Similarity NPC279406
0.8851 High Similarity NPC44192
0.8851 High Similarity NPC226809
0.8851 High Similarity NPC233467
0.8851 High Similarity NPC322899
0.8851 High Similarity NPC272552
0.8851 High Similarity NPC160196
0.8851 High Similarity NPC469944
0.8851 High Similarity NPC226108
0.8851 High Similarity NPC134911
0.8851 High Similarity NPC46283
0.8849 High Similarity NPC317380
0.8849 High Similarity NPC287745
0.8841 High Similarity NPC185604
0.8841 High Similarity NPC61477
0.8841 High Similarity NPC261619
0.8841 High Similarity NPC219876
0.8841 High Similarity NPC175067
0.8841 High Similarity NPC126029
0.8841 High Similarity NPC204215
0.8841 High Similarity NPC15658
0.8841 High Similarity NPC78770
0.8836 High Similarity NPC281549
0.8828 High Similarity NPC211758
0.8828 High Similarity NPC233980
0.8828 High Similarity NPC71686
0.8828 High Similarity NPC87794
0.8828 High Similarity NPC176804
0.8819 High Similarity NPC473845
0.8819 High Similarity NPC63879
0.8819 High Similarity NPC317237
0.8819 High Similarity NPC50250
0.8819 High Similarity NPC44530
0.8819 High Similarity NPC277951
0.8811 High Similarity NPC472087
0.8811 High Similarity NPC475891
0.8811 High Similarity NPC2613
0.8811 High Similarity NPC204347
0.8811 High Similarity NPC183709
0.8811 High Similarity NPC59841
0.8811 High Similarity NPC472088
0.8808 High Similarity NPC125495
0.8808 High Similarity NPC470827
0.8803 High Similarity NPC55793
0.8794 High Similarity NPC176051
0.8794 High Similarity NPC326797
0.8794 High Similarity NPC276490
0.8794 High Similarity NPC103976
0.8794 High Similarity NPC477938
0.8794 High Similarity NPC474282
0.8794 High Similarity NPC48956
0.8794 High Similarity NPC107551
0.8794 High Similarity NPC102904
0.8792 High Similarity NPC20050
0.8792 High Similarity NPC306267
0.8792 High Similarity NPC224161
0.8786 High Similarity NPC99572
0.8786 High Similarity NPC234333
0.8786 High Similarity NPC47398
0.8786 High Similarity NPC134968

  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 NPC173203 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
0.8841 High Similarity NPD1613 Approved
0.8841 High Similarity NPD1612 Clinical (unspecified phase)
0.8686 High Similarity NPD1529 Clinical (unspecified phase)
0.8686 High Similarity NPD4908 Phase 1
0.8613 High Similarity NPD1530 Clinical (unspecified phase)
0.8561 High Similarity NPD4907 Clinical (unspecified phase)
0.8489 Intermediate Similarity NPD3027 Phase 3
0.8309 Intermediate Similarity NPD1610 Phase 2
0.8214 Intermediate Similarity NPD2861 Phase 2
0.8038 Intermediate Similarity NPD6234 Discontinued
0.8025 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8015 Intermediate Similarity NPD1548 Phase 1
0.7972 Intermediate Similarity NPD4625 Phase 3
0.7937 Intermediate Similarity NPD7199 Phase 2
0.7898 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD37 Approved
0.7834 Intermediate Similarity NPD1934 Approved
0.7805 Intermediate Similarity NPD7228 Approved
0.7801 Intermediate Similarity NPD4749 Approved
0.7799 Intermediate Similarity NPD4966 Approved
0.7799 Intermediate Similarity NPD4967 Phase 2
0.7799 Intermediate Similarity NPD4965 Approved
0.7791 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6166 Phase 2
0.7748 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7748 Intermediate Similarity NPD6674 Discontinued
0.7687 Intermediate Similarity NPD4060 Phase 1
0.7687 Intermediate Similarity NPD3620 Phase 2
0.7687 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7665 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD1511 Approved
0.7651 Intermediate Similarity NPD5844 Phase 1
0.7616 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD4160 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD6959 Discontinued
0.759 Intermediate Similarity NPD3818 Discontinued
0.7588 Intermediate Similarity NPD8053 Approved
0.7588 Intermediate Similarity NPD8054 Approved
0.7582 Intermediate Similarity NPD3892 Phase 2
0.758 Intermediate Similarity NPD1653 Approved
0.7578 Intermediate Similarity NPD3882 Suspended
0.7566 Intermediate Similarity NPD7037 Approved
0.7564 Intermediate Similarity NPD1512 Approved
0.7562 Intermediate Similarity NPD2801 Approved
0.7548 Intermediate Similarity NPD7212 Phase 2
0.7548 Intermediate Similarity NPD7213 Phase 3
0.7517 Intermediate Similarity NPD5735 Approved
0.75 Intermediate Similarity NPD7447 Phase 1
0.75 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD7466 Approved
0.7468 Intermediate Similarity NPD3750 Approved
0.7466 Intermediate Similarity NPD3018 Phase 2
0.7455 Intermediate Similarity NPD7229 Phase 3
0.7453 Intermediate Similarity NPD1465 Phase 2
0.7439 Intermediate Similarity NPD5494 Approved
0.7431 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7427 Intermediate Similarity NPD4577 Approved
0.7427 Intermediate Similarity NPD4578 Approved
0.7413 Intermediate Similarity NPD3705 Approved
0.7407 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7399 Intermediate Similarity NPD4663 Approved
0.7397 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7074 Phase 3
0.7391 Intermediate Similarity NPD5283 Phase 1
0.7362 Intermediate Similarity NPD7768 Phase 2
0.7353 Intermediate Similarity NPD3021 Approved
0.7353 Intermediate Similarity NPD3022 Approved
0.7349 Intermediate Similarity NPD6232 Discontinued
0.7349 Intermediate Similarity NPD3787 Discontinued
0.7337 Intermediate Similarity NPD7054 Approved
0.7321 Intermediate Similarity NPD7473 Discontinued
0.732 Intermediate Similarity NPD6099 Approved
0.732 Intermediate Similarity NPD6100 Approved
0.7317 Intermediate Similarity NPD3749 Approved
0.7315 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7240 Approved
0.731 Intermediate Similarity NPD2982 Phase 2
0.731 Intermediate Similarity NPD5327 Phase 3
0.731 Intermediate Similarity NPD2983 Phase 2
0.7294 Intermediate Similarity NPD7472 Approved
0.7292 Intermediate Similarity NPD1091 Approved
0.7285 Intermediate Similarity NPD5124 Phase 1
0.7285 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7279 Intermediate Similarity NPD6584 Phase 3
0.7273 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5763 Approved
0.7273 Intermediate Similarity NPD5762 Approved
0.7267 Intermediate Similarity NPD7549 Discontinued
0.7267 Intermediate Similarity NPD4380 Phase 2
0.7262 Intermediate Similarity NPD27 Approved
0.7262 Intermediate Similarity NPD2489 Approved
0.726 Intermediate Similarity NPD6696 Suspended
0.7257 Intermediate Similarity NPD7906 Approved
0.7255 Intermediate Similarity NPD5588 Approved
0.7251 Intermediate Similarity NPD6797 Phase 2
0.7246 Intermediate Similarity NPD228 Approved
0.7246 Intermediate Similarity NPD3051 Approved
0.7241 Intermediate Similarity NPD2981 Phase 2
0.7239 Intermediate Similarity NPD8455 Phase 2
0.7235 Intermediate Similarity NPD8156 Discontinued
0.7226 Intermediate Similarity NPD1549 Phase 2
0.7225 Intermediate Similarity NPD7312 Approved
0.7225 Intermediate Similarity NPD7313 Approved
0.7225 Intermediate Similarity NPD7311 Approved
0.7225 Intermediate Similarity NPD7310 Approved
0.7219 Intermediate Similarity NPD4140 Approved
0.7215 Intermediate Similarity NPD7041 Phase 2
0.7215 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD3094 Phase 2
0.7209 Intermediate Similarity NPD7251 Discontinued
0.7202 Intermediate Similarity NPD2970 Approved
0.7202 Intermediate Similarity NPD2969 Approved
0.72 Intermediate Similarity NPD6798 Discontinued
0.7197 Intermediate Similarity NPD2677 Approved
0.7195 Intermediate Similarity NPD3817 Phase 2
0.7184 Intermediate Similarity NPD7309 Approved
0.7176 Intermediate Similarity NPD8251 Approved
0.7176 Intermediate Similarity NPD8099 Discontinued
0.7176 Intermediate Similarity NPD8252 Approved
0.7172 Intermediate Similarity NPD422 Phase 1
0.7171 Intermediate Similarity NPD6355 Discontinued
0.717 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD6671 Approved
0.7161 Intermediate Similarity NPD7266 Discontinued
0.7153 Intermediate Similarity NPD5846 Approved
0.7153 Intermediate Similarity NPD6516 Phase 2
0.7143 Intermediate Similarity NPD8651 Approved
0.7143 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3748 Approved
0.7134 Intermediate Similarity NPD7819 Suspended
0.7125 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD4097 Suspended
0.7124 Intermediate Similarity NPD6353 Approved
0.711 Intermediate Similarity NPD6559 Discontinued
0.7107 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD2238 Phase 2
0.7105 Intermediate Similarity NPD1558 Phase 1
0.7099 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD4005 Discontinued
0.7091 Intermediate Similarity NPD2563 Approved
0.7091 Intermediate Similarity NPD2560 Approved
0.7091 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD6812 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD8127 Discontinued
0.7078 Intermediate Similarity NPD4536 Approved
0.7078 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD4538 Approved
0.7076 Intermediate Similarity NPD3751 Discontinued
0.7075 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD6583 Phase 3
0.7075 Intermediate Similarity NPD6582 Phase 2
0.707 Intermediate Similarity NPD1652 Phase 2
0.7069 Intermediate Similarity NPD7808 Phase 3
0.7063 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD4675 Approved
0.7055 Intermediate Similarity NPD3092 Approved
0.7055 Intermediate Similarity NPD4678 Approved
0.7044 Intermediate Similarity NPD5058 Phase 3
0.7042 Intermediate Similarity NPD7157 Approved
0.7039 Intermediate Similarity NPD6233 Phase 2
0.7032 Intermediate Similarity NPD1510 Phase 2
0.7032 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD5960 Phase 3
0.7032 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD8313 Approved
0.7029 Intermediate Similarity NPD2684 Approved
0.7029 Intermediate Similarity NPD8312 Approved
0.7027 Intermediate Similarity NPD7680 Approved
0.7025 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6331 Phase 2
0.7022 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD7095 Approved
0.7012 Intermediate Similarity NPD7411 Suspended
0.7012 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD1840 Phase 2
0.7007 Intermediate Similarity NPD968 Approved
0.7006 Intermediate Similarity NPD7831 Phase 2
0.7006 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7075 Discontinued
0.7006 Intermediate Similarity NPD7832 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7833 Phase 2
0.6995 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6993 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6988 Remote Similarity NPD5402 Approved
0.6987 Remote Similarity NPD2796 Approved
0.6981 Remote Similarity NPD6190 Approved
0.6978 Remote Similarity NPD4750 Phase 3

  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