Structure

Physi-Chem Properties

Molecular Weight:  500.24
Volume:  504.565
LogP:  2.294
LogD:  1.411
LogS:  -3.626
# Rotatable Bonds:  4
TPSA:  144.52
# H-Bond Aceptor:  8
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.314
Synthetic Accessibility Score:  4.734
Fsp3:  0.643
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:  -5.383
MDCK Permeability:  1.781924584065564e-05
Pgp-inhibitor:  0.01
Pgp-substrate:  0.475
Human Intestinal Absorption (HIA):  0.672
20% Bioavailability (F20%):  0.983
30% Bioavailability (F30%):  0.339

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.97
Plasma Protein Binding (PPB):  86.04994201660156%
Volume Distribution (VD):  0.508
Pgp-substrate:  12.934869766235352%

ADMET: Metabolism

CYP1A2-inhibitor:  0.01
CYP1A2-substrate:  0.91
CYP2C19-inhibitor:  0.046
CYP2C19-substrate:  0.529
CYP2C9-inhibitor:  0.055
CYP2C9-substrate:  0.792
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.124
CYP3A4-inhibitor:  0.285
CYP3A4-substrate:  0.419

ADMET: Excretion

Clearance (CL):  5.517
Half-life (T1/2):  0.145

ADMET: Toxicity

hERG Blockers:  0.027
Human Hepatotoxicity (H-HT):  0.253
Drug-inuced Liver Injury (DILI):  0.034
AMES Toxicity:  0.016
Rat Oral Acute Toxicity:  0.852
Maximum Recommended Daily Dose:  0.907
Skin Sensitization:  0.025
Carcinogencity:  0.818
Eye Corrosion:  0.003
Eye Irritation:  0.009
Respiratory Toxicity:  0.837

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

  Natural Product: NPC161151

Natural Product ID:  NPC161151
Common Name*:   (17-Acetyl-3,8,14,17-Tetrahydroxy-10,13-Dimethyl-1,2,3,4,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-12-Yl) 4-Hydroxybenzoate
IUPAC Name:   (17-acetyl-3,8,14,17-tetrahydroxy-10,13-dimethyl-1,2,3,4,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-12-yl) 4-hydroxybenzoate
Synonyms:  
Standard InCHIKey:  IMRGSWAJVVVYOW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C28H36O8/c1-16(29)26(33)12-13-28(35)25(26,3)22(36-23(32)17-4-6-19(30)7-5-17)15-21-24(2)10-9-20(31)14-18(24)8-11-27(21,28)34/h4-8,20-22,30-31,33-35H,9-15H2,1-3H3
SMILES:  CC(=O)C1(CCC2(C1(C)C(CC1C3(C)CCC(CC3=CCC21O)O)OC(=O)c1ccc(cc1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1989993
PubChem CID:   435955
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0003569] Pregnane steroids
          • [CHEMONTID:0001468] Gluco/mineralocorticoids, progestogins and derivatives

*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
NPO23745 Cynanchum wallichii Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14232 Cynanchum otophyllum Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]

☑ 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 27039.58 nM PMID[448906]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 46238.1 nM PMID[448906]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 75162.29 nM PMID[448906]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 80167.81 nM PMID[448906]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[448906]

☑ 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 NPC161151 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
0.8982 High Similarity NPC475613
0.8742 High Similarity NPC132599
0.8742 High Similarity NPC473632
0.8742 High Similarity NPC469730
0.8671 High Similarity NPC279442
0.8625 High Similarity NPC473611
0.8608 High Similarity NPC477483
0.8608 High Similarity NPC325032
0.858 High Similarity NPC472807
0.8571 High Similarity NPC70344
0.8563 High Similarity NPC469419
0.8563 High Similarity NPC469458
0.8563 High Similarity NPC88176
0.8563 High Similarity NPC149002
0.8563 High Similarity NPC469396
0.8553 High Similarity NPC101043
0.8553 High Similarity NPC306799
0.8553 High Similarity NPC471103
0.8545 High Similarity NPC266365
0.8544 High Similarity NPC250046
0.8544 High Similarity NPC60509
0.8544 High Similarity NPC81698
0.85 High Similarity NPC116292
0.85 High Similarity NPC327962
0.85 High Similarity NPC179128
0.85 High Similarity NPC87630
0.85 High Similarity NPC267469
0.8491 Intermediate Similarity NPC7095
0.8491 Intermediate Similarity NPC198455
0.8491 Intermediate Similarity NPC161239
0.8491 Intermediate Similarity NPC165260
0.8471 Intermediate Similarity NPC127857
0.8466 Intermediate Similarity NPC159692
0.8462 Intermediate Similarity NPC202428
0.8462 Intermediate Similarity NPC266545
0.8457 Intermediate Similarity NPC106895
0.8452 Intermediate Similarity NPC200726
0.8452 Intermediate Similarity NPC469459
0.8447 Intermediate Similarity NPC134685
0.8447 Intermediate Similarity NPC11588
0.8447 Intermediate Similarity NPC229545
0.8447 Intermediate Similarity NPC248265
0.8438 Intermediate Similarity NPC473719
0.8438 Intermediate Similarity NPC51602
0.8434 Intermediate Similarity NPC477627
0.8421 Intermediate Similarity NPC195972
0.8402 Intermediate Similarity NPC177362
0.8397 Intermediate Similarity NPC182869
0.8395 Intermediate Similarity NPC228204
0.8395 Intermediate Similarity NPC114357
0.8395 Intermediate Similarity NPC26033
0.8395 Intermediate Similarity NPC21410
0.8395 Intermediate Similarity NPC155329
0.8395 Intermediate Similarity NPC259144
0.8395 Intermediate Similarity NPC282239
0.8395 Intermediate Similarity NPC473670
0.8395 Intermediate Similarity NPC472549
0.8393 Intermediate Similarity NPC211592
0.8391 Intermediate Similarity NPC102367
0.8385 Intermediate Similarity NPC283875
0.8385 Intermediate Similarity NPC138641
0.8385 Intermediate Similarity NPC469647
0.8385 Intermediate Similarity NPC35160
0.8385 Intermediate Similarity NPC162569
0.8385 Intermediate Similarity NPC22571
0.8385 Intermediate Similarity NPC469648
0.8385 Intermediate Similarity NPC142654
0.8383 Intermediate Similarity NPC477491
0.8375 Intermediate Similarity NPC470245
0.8375 Intermediate Similarity NPC473214
0.8375 Intermediate Similarity NPC112216
0.8375 Intermediate Similarity NPC125033
0.8364 Intermediate Similarity NPC476077
0.8363 Intermediate Similarity NPC477617
0.8363 Intermediate Similarity NPC148185
0.8344 Intermediate Similarity NPC477894
0.8344 Intermediate Similarity NPC11410
0.8343 Intermediate Similarity NPC186746
0.8333 Intermediate Similarity NPC158333
0.8333 Intermediate Similarity NPC27377
0.8333 Intermediate Similarity NPC87448
0.8333 Intermediate Similarity NPC97947
0.8333 Intermediate Similarity NPC472030
0.8333 Intermediate Similarity NPC41481
0.8333 Intermediate Similarity NPC265395
0.8333 Intermediate Similarity NPC237549
0.8333 Intermediate Similarity NPC257213
0.8333 Intermediate Similarity NPC242262
0.8333 Intermediate Similarity NPC472576
0.8333 Intermediate Similarity NPC256142
0.8333 Intermediate Similarity NPC304876
0.8333 Intermediate Similarity NPC472005
0.8333 Intermediate Similarity NPC118080
0.8333 Intermediate Similarity NPC119252
0.8333 Intermediate Similarity NPC219419
0.8333 Intermediate Similarity NPC1173
0.8333 Intermediate Similarity NPC473414
0.8333 Intermediate Similarity NPC291599
0.8333 Intermediate Similarity NPC249471
0.8333 Intermediate Similarity NPC472022
0.8323 Intermediate Similarity NPC293568
0.8323 Intermediate Similarity NPC470153
0.8323 Intermediate Similarity NPC161955
0.8323 Intermediate Similarity NPC472398
0.8323 Intermediate Similarity NPC117943
0.8323 Intermediate Similarity NPC197037
0.8313 Intermediate Similarity NPC472938
0.8313 Intermediate Similarity NPC473215
0.8313 Intermediate Similarity NPC55744
0.8313 Intermediate Similarity NPC472937
0.8313 Intermediate Similarity NPC472936
0.8313 Intermediate Similarity NPC476975
0.8303 Intermediate Similarity NPC471968
0.8302 Intermediate Similarity NPC478263
0.8302 Intermediate Similarity NPC312393
0.8293 Intermediate Similarity NPC472393
0.8291 Intermediate Similarity NPC241951
0.8291 Intermediate Similarity NPC470152
0.8291 Intermediate Similarity NPC475759
0.8284 Intermediate Similarity NPC40138
0.8282 Intermediate Similarity NPC251139
0.8282 Intermediate Similarity NPC221249
0.8282 Intermediate Similarity NPC114410
0.8282 Intermediate Similarity NPC469456
0.8282 Intermediate Similarity NPC112523
0.8276 Intermediate Similarity NPC469418
0.8276 Intermediate Similarity NPC260300
0.8272 Intermediate Similarity NPC145649
0.8272 Intermediate Similarity NPC472939
0.8272 Intermediate Similarity NPC233581
0.8272 Intermediate Similarity NPC472548
0.8269 Intermediate Similarity NPC171207
0.8269 Intermediate Similarity NPC100913
0.8269 Intermediate Similarity NPC472547
0.8269 Intermediate Similarity NPC275592
0.8269 Intermediate Similarity NPC90614
0.8269 Intermediate Similarity NPC97667
0.8263 Intermediate Similarity NPC208676
0.8263 Intermediate Similarity NPC130489
0.8261 Intermediate Similarity NPC476173
0.8261 Intermediate Similarity NPC91730
0.825 Intermediate Similarity NPC208293
0.825 Intermediate Similarity NPC75295
0.825 Intermediate Similarity NPC258856
0.8249 Intermediate Similarity NPC96194
0.8249 Intermediate Similarity NPC299855
0.8242 Intermediate Similarity NPC471102
0.8239 Intermediate Similarity NPC472575
0.8239 Intermediate Similarity NPC472568
0.8239 Intermediate Similarity NPC472556
0.8239 Intermediate Similarity NPC96903
0.8239 Intermediate Similarity NPC184817
0.8239 Intermediate Similarity NPC470157
0.8239 Intermediate Similarity NPC25491
0.8239 Intermediate Similarity NPC469349
0.8239 Intermediate Similarity NPC200471
0.8239 Intermediate Similarity NPC177940
0.8239 Intermediate Similarity NPC158663
0.8239 Intermediate Similarity NPC171525
0.8239 Intermediate Similarity NPC472571
0.8239 Intermediate Similarity NPC478264
0.8239 Intermediate Similarity NPC471100
0.8239 Intermediate Similarity NPC471107
0.8239 Intermediate Similarity NPC174982
0.8239 Intermediate Similarity NPC470159
0.8239 Intermediate Similarity NPC70403
0.8239 Intermediate Similarity NPC472572
0.8239 Intermediate Similarity NPC29704
0.8239 Intermediate Similarity NPC476973
0.8239 Intermediate Similarity NPC471104
0.8239 Intermediate Similarity NPC473088
0.8235 Intermediate Similarity NPC477488
0.8232 Intermediate Similarity NPC217091
0.8229 Intermediate Similarity NPC108191
0.8229 Intermediate Similarity NPC93685
0.8228 Intermediate Similarity NPC163087
0.8225 Intermediate Similarity NPC109990
0.8225 Intermediate Similarity NPC471861
0.8222 Intermediate Similarity NPC475299
0.8221 Intermediate Similarity NPC158546
0.8221 Intermediate Similarity NPC289021
0.8221 Intermediate Similarity NPC77719
0.8217 Intermediate Similarity NPC16912
0.8214 Intermediate Similarity NPC471134
0.8208 Intermediate Similarity NPC469393
0.8205 Intermediate Similarity NPC477592
0.8205 Intermediate Similarity NPC170718
0.8204 Intermediate Similarity NPC165234
0.8204 Intermediate Similarity NPC475536
0.8202 Intermediate Similarity NPC189704
0.8199 Intermediate Similarity NPC470330
0.8198 Intermediate Similarity NPC472803
0.8194 Intermediate Similarity NPC182217
0.8194 Intermediate Similarity NPC70680
0.8194 Intermediate Similarity NPC233350
0.8193 Intermediate Similarity NPC88007
0.8193 Intermediate Similarity NPC195954
0.8193 Intermediate Similarity NPC194499
0.8187 Intermediate Similarity NPC473094
0.8187 Intermediate Similarity NPC474935

  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 NPC161151 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
0.8471 Intermediate Similarity NPD7236 Approved
0.8323 Intermediate Similarity NPD7239 Suspended
0.8229 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8079 Intermediate Similarity NPD8434 Phase 2
0.7978 Intermediate Similarity NPD8150 Discontinued
0.7977 Intermediate Similarity NPD7799 Discontinued
0.795 Intermediate Similarity NPD6190 Approved
0.7898 Intermediate Similarity NPD7685 Pre-registration
0.787 Intermediate Similarity NPD7057 Phase 3
0.787 Intermediate Similarity NPD7058 Phase 2
0.7778 Intermediate Similarity NPD8166 Discontinued
0.7758 Intermediate Similarity NPD6273 Approved
0.7751 Intermediate Similarity NPD5760 Phase 2
0.7751 Intermediate Similarity NPD5761 Phase 2
0.7705 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD8127 Discontinued
0.7669 Intermediate Similarity NPD4628 Phase 3
0.7616 Intermediate Similarity NPD7075 Discontinued
0.7598 Intermediate Similarity NPD6764 Approved
0.7598 Intermediate Similarity NPD6765 Approved
0.7595 Intermediate Similarity NPD6663 Approved
0.7579 Intermediate Similarity NPD7497 Discontinued
0.7564 Intermediate Similarity NPD5736 Approved
0.7558 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD3764 Approved
0.7528 Intermediate Similarity NPD5844 Phase 1
0.7514 Intermediate Similarity NPD7473 Discontinued
0.75 Intermediate Similarity NPD8360 Approved
0.75 Intermediate Similarity NPD8368 Discontinued
0.75 Intermediate Similarity NPD8361 Approved
0.7473 Intermediate Similarity NPD8407 Phase 2
0.7471 Intermediate Similarity NPD4380 Phase 2
0.7444 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD6785 Approved
0.7432 Intermediate Similarity NPD6784 Approved
0.7412 Intermediate Similarity NPD7458 Discontinued
0.7405 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD8435 Approved
0.7391 Intermediate Similarity NPD230 Phase 1
0.7384 Intermediate Similarity NPD6801 Discontinued
0.7381 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6599 Discontinued
0.736 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD6166 Phase 2
0.736 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD6232 Discontinued
0.7341 Intermediate Similarity NPD7819 Suspended
0.7333 Intermediate Similarity NPD8470 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD3094 Phase 2
0.7306 Intermediate Similarity NPD7435 Discontinued
0.7299 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD5402 Approved
0.7297 Intermediate Similarity NPD8424 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD37 Approved
0.7278 Intermediate Similarity NPD7228 Approved
0.7278 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5763 Approved
0.7273 Intermediate Similarity NPD6234 Discontinued
0.7273 Intermediate Similarity NPD5762 Approved
0.7268 Intermediate Similarity NPD8320 Phase 1
0.7268 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD8319 Approved
0.7263 Intermediate Similarity NPD8485 Approved
0.7257 Intermediate Similarity NPD4966 Approved
0.7257 Intermediate Similarity NPD4965 Approved
0.7257 Intermediate Similarity NPD4967 Phase 2
0.7249 Intermediate Similarity NPD6534 Approved
0.7249 Intermediate Similarity NPD6535 Approved
0.7246 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD3750 Approved
0.7241 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7228 Intermediate Similarity NPD8312 Approved
0.7228 Intermediate Similarity NPD8313 Approved
0.7225 Intermediate Similarity NPD7700 Phase 2
0.7225 Intermediate Similarity NPD7411 Suspended
0.7225 Intermediate Similarity NPD7699 Phase 2
0.7216 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD3817 Phase 2
0.7191 Intermediate Similarity NPD7199 Phase 2
0.7182 Intermediate Similarity NPD3818 Discontinued
0.7182 Intermediate Similarity NPD3751 Discontinued
0.7176 Intermediate Similarity NPD2534 Approved
0.7176 Intermediate Similarity NPD2533 Approved
0.7176 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD2532 Approved
0.7168 Intermediate Similarity NPD7028 Phase 2
0.716 Intermediate Similarity NPD7961 Discontinued
0.7159 Intermediate Similarity NPD3882 Suspended
0.715 Intermediate Similarity NPD6778 Approved
0.715 Intermediate Similarity NPD6782 Approved
0.715 Intermediate Similarity NPD6777 Approved
0.715 Intermediate Similarity NPD8486 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD6781 Approved
0.715 Intermediate Similarity NPD6776 Approved
0.715 Intermediate Similarity NPD6779 Approved
0.715 Intermediate Similarity NPD6780 Approved
0.7143 Intermediate Similarity NPD7003 Approved
0.7143 Intermediate Similarity NPD9545 Approved
0.7135 Intermediate Similarity NPD5494 Approved
0.712 Intermediate Similarity NPD7251 Discontinued
0.7119 Intermediate Similarity NPD3749 Approved
0.7118 Intermediate Similarity NPD6799 Approved
0.7117 Intermediate Similarity NPD4140 Approved
0.711 Intermediate Similarity NPD3226 Approved
0.7104 Intermediate Similarity NPD7074 Phase 3
0.7095 Intermediate Similarity NPD6959 Discontinued
0.7093 Intermediate Similarity NPD5403 Approved
0.7086 Intermediate Similarity NPD1934 Approved
0.7085 Intermediate Similarity NPD7874 Approved
0.7085 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD7808 Phase 3
0.7079 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD6355 Discontinued
0.7072 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD3092 Approved
0.7066 Intermediate Similarity NPD6005 Phase 3
0.7066 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6002 Phase 3
0.7066 Intermediate Similarity NPD7266 Discontinued
0.7066 Intermediate Similarity NPD6004 Phase 3
0.7065 Intermediate Similarity NPD6797 Phase 2
0.7062 Intermediate Similarity NPD7768 Phase 2
0.7059 Intermediate Similarity NPD3300 Phase 2
0.7051 Intermediate Similarity NPD3019 Approved
0.7051 Intermediate Similarity NPD2932 Approved
0.7049 Intermediate Similarity NPD7054 Approved
0.7045 Intermediate Similarity NPD2801 Approved
0.7045 Intermediate Similarity NPD1465 Phase 2
0.7044 Intermediate Similarity NPD8404 Phase 2
0.7041 Intermediate Similarity NPD7696 Phase 3
0.7041 Intermediate Similarity NPD7698 Approved
0.7041 Intermediate Similarity NPD7697 Approved
0.7027 Intermediate Similarity NPD6559 Discontinued
0.7024 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD7472 Approved
0.7006 Intermediate Similarity NPD6100 Approved
0.7006 Intermediate Similarity NPD2935 Discontinued
0.7006 Intermediate Similarity NPD6099 Approved
0.7005 Intermediate Similarity NPD7871 Phase 2
0.7005 Intermediate Similarity NPD7870 Phase 2
0.6994 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6985 Remote Similarity NPD7701 Phase 2
0.6977 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6977 Remote Similarity NPD5401 Approved
0.697 Remote Similarity NPD5735 Approved
0.6965 Remote Similarity NPD7801 Approved
0.6961 Remote Similarity NPD3787 Discontinued
0.6951 Remote Similarity NPD8032 Phase 2
0.6946 Remote Similarity NPD1510 Phase 2
0.6946 Remote Similarity NPD3748 Approved
0.6946 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6936 Remote Similarity NPD1512 Approved
0.6935 Remote Similarity NPD7240 Approved
0.6933 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6928 Remote Similarity NPD6653 Approved
0.6923 Remote Similarity NPD7741 Discontinued
0.6923 Remote Similarity NPD3091 Approved
0.6923 Remote Similarity NPD1549 Phase 2
0.6919 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6919 Remote Similarity NPD7390 Discontinued
0.6909 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6909 Remote Similarity NPD3620 Phase 2
0.6905 Remote Similarity NPD5404 Approved
0.6905 Remote Similarity NPD5405 Approved
0.6905 Remote Similarity NPD5408 Approved
0.6905 Remote Similarity NPD5406 Approved
0.6899 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6882 Remote Similarity NPD2800 Approved
0.6866 Remote Similarity NPD8151 Discontinued
0.6864 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6864 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6854 Remote Similarity NPD8455 Phase 2
0.6848 Remote Similarity NPD6233 Phase 2
0.6845 Remote Similarity NPD651 Clinical (unspecified phase)
0.6845 Remote Similarity NPD7033 Discontinued
0.6845 Remote Similarity NPD2799 Discontinued
0.6829 Remote Similarity NPD7095 Approved
0.6826 Remote Similarity NPD1607 Approved
0.6826 Remote Similarity NPD6651 Approved
0.6821 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6821 Remote Similarity NPD1511 Approved
0.6818 Remote Similarity NPD6823 Phase 2
0.6809 Remote Similarity NPD5028 Approved
0.6809 Remote Similarity NPD4955 Approved
0.6809 Remote Similarity NPD36 Approved
0.6809 Remote Similarity NPD5026 Approved
0.6809 Remote Similarity NPD4954 Approved
0.6809 Remote Similarity NPD5034 Approved
0.6807 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6807 Remote Similarity NPD1240 Approved
0.6807 Remote Similarity NPD943 Approved
0.6805 Remote Similarity NPD2796 Approved
0.679 Remote Similarity NPD1470 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