Structure

Physi-Chem Properties

Molecular Weight:  536.26
Volume:  527.418
LogP:  2.367
LogD:  1.126
LogS:  -4.22
# Rotatable Bonds:  6
TPSA:  156.66
# H-Bond Aceptor:  10
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.344
Synthetic Accessibility Score:  6.822
Fsp3:  0.857
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.355
MDCK Permeability:  7.226416346384212e-05
Pgp-inhibitor:  0.992
Pgp-substrate:  0.474
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.024
30% Bioavailability (F30%):  0.896

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.603
Plasma Protein Binding (PPB):  50.8416862487793%
Volume Distribution (VD):  0.475
Pgp-substrate:  30.314105987548828%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.942
CYP2C19-inhibitor:  0.011
CYP2C19-substrate:  0.564
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.017
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.079
CYP3A4-inhibitor:  0.322
CYP3A4-substrate:  0.279

ADMET: Excretion

Clearance (CL):  3.946
Half-life (T1/2):  0.175

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.407
Drug-inuced Liver Injury (DILI):  0.809
AMES Toxicity:  0.012
Rat Oral Acute Toxicity:  0.197
Maximum Recommended Daily Dose:  0.349
Skin Sensitization:  0.139
Carcinogencity:  0.075
Eye Corrosion:  0.003
Eye Irritation:  0.01
Respiratory Toxicity:  0.875

Download Data

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

  Natural Product: NPC297179

Natural Product ID:  NPC297179
Common Name*:   YYFUPACSPMCQHM-IAXDHZOFSA-N
IUPAC Name:   n.a.
Synonyms:   NSC-676836
Standard InCHIKey:  YYFUPACSPMCQHM-IAXDHZOFSA-N
Standard InCHI:  InChI=1S/C28H40O10/c1-7-26(34,12(2)3)10-18(30)38-20-19-14(5)21(31)28(35)24-25(6)15(13(4)8-16(29)22(25)32)9-17(37-23(20)33)27(19,24)11-36-28/h8,12,14-15,17,19-22,24,31-32,34-35H,7,9-11H2,1-6H3/t14-,15+,17-,19-,20-,21-,22-,24-,25-,26+,27+,28+/m1/s1
SMILES:  CC[C@](CC(=O)O[C@@H]1[C@H]2[C@@H](C)[C@H]([C@]3([C@@H]4[C@]5(C)[C@@H](C[C@H]([C@@]24CO3)OC1=O)C(=CC(=O)[C@H]5O)C)O)O)(C(C)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL553342
PubChem CID:   385564
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0002119] Quassinoids

*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
NPO14857 Pteris kiuschiuensis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8270 Elegia mucronata Species Restionaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14857 Pteris kiuschiuensis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4496 Eupatorium mohrii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8850 Castela peninsularis Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9712 Agrostis arundinacea Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14667 Cladonia boryi Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15055 Citrus limettioides Species Rutaceae 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. 10.0 nM PMID[527811]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 12.25 nM PMID[527811]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 18.75 nM PMID[527811]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 10.0 nM PMID[527811]

☑ 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 NPC297179 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
0.9815 High Similarity NPC152199
0.9815 High Similarity NPC134869
0.9815 High Similarity NPC235539
0.9722 High Similarity NPC474906
0.9722 High Similarity NPC18547
0.9636 High Similarity NPC204552
0.9636 High Similarity NPC188667
0.9537 High Similarity NPC11252
0.9537 High Similarity NPC289312
0.9474 High Similarity NPC470922
0.9464 High Similarity NPC112038
0.9459 High Similarity NPC17772
0.9455 High Similarity NPC40632
0.9455 High Similarity NPC96312
0.9455 High Similarity NPC328374
0.9455 High Similarity NPC251236
0.9444 High Similarity NPC201992
0.9381 High Similarity NPC102822
0.9381 High Similarity NPC477046
0.9375 High Similarity NPC469488
0.9369 High Similarity NPC122033
0.9369 High Similarity NPC287343
0.9369 High Similarity NPC470854
0.9369 High Similarity NPC97908
0.9369 High Similarity NPC474654
0.9364 High Similarity NPC473798
0.9292 High Similarity NPC109607
0.9292 High Similarity NPC107338
0.9279 High Similarity NPC259306
0.9279 High Similarity NPC470628
0.9279 High Similarity NPC474046
0.9273 High Similarity NPC7921
0.9273 High Similarity NPC208998
0.9273 High Similarity NPC51978
0.9273 High Similarity NPC49451
0.9204 High Similarity NPC470777
0.9204 High Similarity NPC476529
0.9204 High Similarity NPC475775
0.9189 High Similarity NPC469877
0.9189 High Similarity NPC470919
0.9167 High Similarity NPC293850
0.9107 High Similarity NPC173686
0.9107 High Similarity NPC16081
0.9091 High Similarity NPC146945
0.9091 High Similarity NPC171888
0.9052 High Similarity NPC265557
0.9052 High Similarity NPC91693
0.9052 High Similarity NPC105926
0.9052 High Similarity NPC18945
0.9052 High Similarity NPC67251
0.9027 High Similarity NPC309433
0.9018 High Similarity NPC143268
0.9018 High Similarity NPC45218
0.9018 High Similarity NPC323821
0.9018 High Similarity NPC268238
0.9009 High Similarity NPC474516
0.9009 High Similarity NPC302146
0.8974 High Similarity NPC476729
0.8974 High Similarity NPC24651
0.8966 High Similarity NPC312833
0.8947 High Similarity NPC251310
0.8947 High Similarity NPC470776
0.8938 High Similarity NPC474734
0.8938 High Similarity NPC207217
0.8908 High Similarity NPC188291
0.8899 High Similarity NPC144854
0.8899 High Similarity NPC3316
0.8898 High Similarity NPC285091
0.8879 High Similarity NPC470779
0.886 High Similarity NPC176513
0.886 High Similarity NPC473590
0.886 High Similarity NPC473968
0.886 High Similarity NPC470775
0.885 High Similarity NPC243354
0.8843 High Similarity NPC100390
0.8843 High Similarity NPC254614
0.8829 High Similarity NPC474567
0.8818 High Similarity NPC192813
0.8818 High Similarity NPC277017
0.8818 High Similarity NPC154608
0.8803 High Similarity NPC471965
0.8761 High Similarity NPC194273
0.875 High Similarity NPC475636
0.875 High Similarity NPC295220
0.875 High Similarity NPC471243
0.8739 High Similarity NPC143706
0.8739 High Similarity NPC472534
0.8739 High Similarity NPC87662
0.8729 High Similarity NPC202666
0.8729 High Similarity NPC471964
0.8729 High Similarity NPC14617
0.8729 High Similarity NPC471961
0.8729 High Similarity NPC262199
0.8729 High Similarity NPC227397
0.8729 High Similarity NPC478066
0.8718 High Similarity NPC75417
0.8716 High Similarity NPC475036
0.8707 High Similarity NPC319570
0.8689 High Similarity NPC102316
0.8678 High Similarity NPC54614
0.8678 High Similarity NPC309096
0.8667 High Similarity NPC470780
0.8655 High Similarity NPC177820
0.8655 High Similarity NPC470477
0.8655 High Similarity NPC247315
0.8655 High Similarity NPC471962
0.8655 High Similarity NPC473255
0.8655 High Similarity NPC471963
0.8655 High Similarity NPC30188
0.8644 High Similarity NPC40775
0.8644 High Similarity NPC235438
0.8644 High Similarity NPC249848
0.8644 High Similarity NPC107966
0.864 High Similarity NPC596
0.8636 High Similarity NPC102352
0.8629 High Similarity NPC262813
0.8621 High Similarity NPC286347
0.8618 High Similarity NPC478151
0.8607 High Similarity NPC172374
0.8607 High Similarity NPC301639
0.8607 High Similarity NPC264566
0.8607 High Similarity NPC262796
0.8607 High Similarity NPC478064
0.8607 High Similarity NPC475377
0.8607 High Similarity NPC475167
0.8607 High Similarity NPC45346
0.8607 High Similarity NPC478065
0.8607 High Similarity NPC476074
0.8607 High Similarity NPC134914
0.8607 High Similarity NPC173435
0.8607 High Similarity NPC329993
0.8596 High Similarity NPC198539
0.8596 High Similarity NPC194100
0.8596 High Similarity NPC255017
0.8596 High Similarity NPC320118
0.8583 High Similarity NPC225049
0.8583 High Similarity NPC469947
0.8583 High Similarity NPC181066
0.8583 High Similarity NPC47113
0.8583 High Similarity NPC174367
0.8571 High Similarity NPC27814
0.8571 High Similarity NPC235405
0.8571 High Similarity NPC30735
0.8571 High Similarity NPC281148
0.8571 High Similarity NPC218853
0.8571 High Similarity NPC474242
0.856 High Similarity NPC190065
0.856 High Similarity NPC141215
0.856 High Similarity NPC251998
0.856 High Similarity NPC471089
0.8559 High Similarity NPC275675
0.8547 High Similarity NPC472949
0.8547 High Similarity NPC39211
0.8547 High Similarity NPC309780
0.8547 High Similarity NPC180550
0.8547 High Similarity NPC6377
0.8547 High Similarity NPC114441
0.8547 High Similarity NPC35405
0.8547 High Similarity NPC208381
0.8547 High Similarity NPC473920
0.8547 High Similarity NPC11551
0.8547 High Similarity NPC475171
0.8547 High Similarity NPC473884
0.8547 High Similarity NPC127530
0.8547 High Similarity NPC469945
0.8547 High Similarity NPC268958
0.8547 High Similarity NPC214484
0.8547 High Similarity NPC157868
0.8537 High Similarity NPC478154
0.8537 High Similarity NPC478152
0.8537 High Similarity NPC254146
0.8537 High Similarity NPC478150
0.8537 High Similarity NPC6274
0.8537 High Similarity NPC478153
0.8537 High Similarity NPC33378
0.8534 High Similarity NPC470778
0.8534 High Similarity NPC477116
0.8534 High Similarity NPC146432
0.8534 High Similarity NPC27999
0.8534 High Similarity NPC224121
0.8525 High Similarity NPC264192
0.8522 High Similarity NPC247069
0.8522 High Similarity NPC102088
0.8519 High Similarity NPC472972
0.8512 High Similarity NPC476008
0.8512 High Similarity NPC470882
0.8509 High Similarity NPC474927
0.8509 High Similarity NPC90769
0.85 High Similarity NPC23275
0.8496 Intermediate Similarity NPC320383
0.8496 Intermediate Similarity NPC210005
0.8496 Intermediate Similarity NPC474786
0.8496 Intermediate Similarity NPC137104
0.8492 Intermediate Similarity NPC140045
0.8492 Intermediate Similarity NPC295885
0.8487 Intermediate Similarity NPC162574
0.8487 Intermediate Similarity NPC213952
0.8475 Intermediate Similarity NPC294112
0.8475 Intermediate Similarity NPC471406
0.8475 Intermediate Similarity NPC478051

  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 NPC297179 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
0.8729 High Similarity NPD8328 Phase 3
0.85 High Similarity NPD7492 Approved
0.8475 Intermediate Similarity NPD6054 Approved
0.8475 Intermediate Similarity NPD6059 Approved
0.8475 Intermediate Similarity NPD6319 Approved
0.8443 Intermediate Similarity NPD7736 Approved
0.843 Intermediate Similarity NPD6616 Approved
0.8376 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.8361 Intermediate Similarity NPD7078 Approved
0.8361 Intermediate Similarity NPD8293 Discontinued
0.8333 Intermediate Similarity NPD6370 Approved
0.825 Intermediate Similarity NPD6015 Approved
0.825 Intermediate Similarity NPD6016 Approved
0.819 Intermediate Similarity NPD8297 Approved
0.819 Intermediate Similarity NPD6882 Approved
0.8182 Intermediate Similarity NPD5988 Approved
0.8142 Intermediate Similarity NPD6675 Approved
0.8142 Intermediate Similarity NPD7128 Approved
0.8142 Intermediate Similarity NPD6402 Approved
0.8142 Intermediate Similarity NPD5739 Approved
0.8087 Intermediate Similarity NPD6373 Approved
0.8087 Intermediate Similarity NPD6372 Approved
0.8067 Intermediate Similarity NPD6009 Approved
0.8 Intermediate Similarity NPD6899 Approved
0.8 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6881 Approved
0.8 Intermediate Similarity NPD7320 Approved
0.7966 Intermediate Similarity NPD4632 Approved
0.7949 Intermediate Similarity NPD6649 Approved
0.7949 Intermediate Similarity NPD6650 Approved
0.7937 Intermediate Similarity NPD7319 Approved
0.7931 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7913 Intermediate Similarity NPD6412 Phase 2
0.7913 Intermediate Similarity NPD5701 Approved
0.7913 Intermediate Similarity NPD5697 Approved
0.7863 Intermediate Similarity NPD7102 Approved
0.7863 Intermediate Similarity NPD7290 Approved
0.7863 Intermediate Similarity NPD6883 Approved
0.7857 Intermediate Similarity NPD6033 Approved
0.784 Intermediate Similarity NPD7507 Approved
0.7797 Intermediate Similarity NPD8130 Phase 1
0.7797 Intermediate Similarity NPD6847 Approved
0.7797 Intermediate Similarity NPD6617 Approved
0.7797 Intermediate Similarity NPD6869 Approved
0.7778 Intermediate Similarity NPD6012 Approved
0.7778 Intermediate Similarity NPD6014 Approved
0.7778 Intermediate Similarity NPD6013 Approved
0.7712 Intermediate Similarity NPD4634 Approved
0.7692 Intermediate Similarity NPD6686 Approved
0.7692 Intermediate Similarity NPD6011 Approved
0.768 Intermediate Similarity NPD7604 Phase 2
0.7661 Intermediate Similarity NPD5983 Phase 2
0.7647 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7623 Intermediate Similarity NPD7115 Discovery
0.7559 Intermediate Similarity NPD6336 Discontinued
0.7522 Intermediate Similarity NPD6083 Phase 2
0.7522 Intermediate Similarity NPD6084 Phase 2
0.7522 Intermediate Similarity NPD4755 Approved
0.7521 Intermediate Similarity NPD6008 Approved
0.752 Intermediate Similarity NPD8513 Phase 3
0.752 Intermediate Similarity NPD8517 Approved
0.752 Intermediate Similarity NPD8516 Approved
0.752 Intermediate Similarity NPD8515 Approved
0.7479 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7411 Intermediate Similarity NPD7748 Approved
0.7398 Intermediate Similarity NPD6274 Approved
0.7391 Intermediate Similarity NPD4700 Approved
0.7391 Intermediate Similarity NPD4696 Approved
0.7391 Intermediate Similarity NPD5285 Approved
0.7391 Intermediate Similarity NPD5286 Approved
0.7387 Intermediate Similarity NPD7515 Phase 2
0.7381 Intermediate Similarity NPD6921 Approved
0.7368 Intermediate Similarity NPD7902 Approved
0.736 Intermediate Similarity NPD7516 Approved
0.736 Intermediate Similarity NPD7100 Approved
0.736 Intermediate Similarity NPD7101 Approved
0.7304 Intermediate Similarity NPD4225 Approved
0.728 Intermediate Similarity NPD7328 Approved
0.728 Intermediate Similarity NPD7327 Approved
0.728 Intermediate Similarity NPD6335 Approved
0.7273 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7265 Intermediate Similarity NPD5226 Approved
0.7265 Intermediate Similarity NPD4633 Approved
0.7265 Intermediate Similarity NPD5224 Approved
0.7265 Intermediate Similarity NPD5225 Approved
0.7265 Intermediate Similarity NPD5211 Phase 2
0.7244 Intermediate Similarity NPD6909 Approved
0.7244 Intermediate Similarity NPD8033 Approved
0.7244 Intermediate Similarity NPD6908 Approved
0.7236 Intermediate Similarity NPD8133 Approved
0.7232 Intermediate Similarity NPD6411 Approved
0.7227 Intermediate Similarity NPD4768 Approved
0.7227 Intermediate Similarity NPD4767 Approved
0.7207 Intermediate Similarity NPD5328 Approved
0.7203 Intermediate Similarity NPD5174 Approved
0.7203 Intermediate Similarity NPD5175 Approved
0.72 Intermediate Similarity NPD6317 Approved
0.7193 Intermediate Similarity NPD5695 Phase 3
0.7182 Intermediate Similarity NPD3573 Approved
0.7179 Intermediate Similarity NPD5223 Approved
0.7168 Intermediate Similarity NPD6399 Phase 3
0.7165 Intermediate Similarity NPD8377 Approved
0.7165 Intermediate Similarity NPD8294 Approved
0.7155 Intermediate Similarity NPD5696 Approved
0.7155 Intermediate Similarity NPD7638 Approved
0.7143 Intermediate Similarity NPD5141 Approved
0.7143 Intermediate Similarity NPD6314 Approved
0.7143 Intermediate Similarity NPD6313 Approved
0.713 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD5222 Approved
0.713 Intermediate Similarity NPD4697 Phase 3
0.713 Intermediate Similarity NPD5221 Approved
0.712 Intermediate Similarity NPD6868 Approved
0.7117 Intermediate Similarity NPD5737 Approved
0.7117 Intermediate Similarity NPD6672 Approved
0.7109 Intermediate Similarity NPD8380 Approved
0.7109 Intermediate Similarity NPD8335 Approved
0.7109 Intermediate Similarity NPD7503 Approved
0.7109 Intermediate Similarity NPD8379 Approved
0.7109 Intermediate Similarity NPD8378 Approved
0.7109 Intermediate Similarity NPD8296 Approved
0.7107 Intermediate Similarity NPD4730 Approved
0.7107 Intermediate Similarity NPD4729 Approved
0.7105 Intermediate Similarity NPD5282 Discontinued
0.7105 Intermediate Similarity NPD7900 Approved
0.7105 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD8074 Phase 3
0.7094 Intermediate Similarity NPD7640 Approved
0.7094 Intermediate Similarity NPD7639 Approved
0.708 Intermediate Similarity NPD6079 Approved
0.7073 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD5173 Approved
0.7068 Intermediate Similarity NPD5956 Approved
0.7059 Intermediate Similarity NPD4754 Approved
0.7054 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD6101 Approved
0.7025 Intermediate Similarity NPD5954 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD6067 Discontinued
0.6992 Remote Similarity NPD5248 Approved
0.6992 Remote Similarity NPD5249 Phase 3
0.6992 Remote Similarity NPD5251 Approved
0.6992 Remote Similarity NPD5250 Approved
0.6992 Remote Similarity NPD5247 Approved
0.6977 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6967 Remote Similarity NPD5128 Approved
0.6937 Remote Similarity NPD3618 Phase 1
0.6903 Remote Similarity NPD6673 Approved
0.6903 Remote Similarity NPD6080 Approved
0.6903 Remote Similarity NPD4753 Phase 2
0.6903 Remote Similarity NPD6904 Approved
0.6885 Remote Similarity NPD7899 Clinical (unspecified phase)
0.687 Remote Similarity NPD5778 Approved
0.687 Remote Similarity NPD5779 Approved
0.687 Remote Similarity NPD4202 Approved
0.6842 Remote Similarity NPD46 Approved
0.6842 Remote Similarity NPD6698 Approved
0.6814 Remote Similarity NPD7513 Clinical (unspecified phase)
0.68 Remote Similarity NPD5216 Approved
0.68 Remote Similarity NPD5217 Approved
0.68 Remote Similarity NPD5215 Approved
0.6794 Remote Similarity NPD8080 Discontinued
0.6786 Remote Similarity NPD6684 Approved
0.6786 Remote Similarity NPD6409 Approved
0.6786 Remote Similarity NPD7334 Approved
0.6786 Remote Similarity NPD5330 Approved
0.6786 Remote Similarity NPD7521 Approved
0.6786 Remote Similarity NPD7146 Approved
0.6783 Remote Similarity NPD7983 Approved
0.6765 Remote Similarity NPD7260 Phase 2
0.6757 Remote Similarity NPD4786 Approved
0.6754 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6752 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6746 Remote Similarity NPD6053 Discontinued
0.6727 Remote Similarity NPD3667 Approved
0.6721 Remote Similarity NPD8170 Clinical (unspecified phase)
0.672 Remote Similarity NPD5134 Clinical (unspecified phase)
0.672 Remote Similarity NPD5135 Approved
0.672 Remote Similarity NPD5169 Approved
0.672 Remote Similarity NPD6371 Approved
0.6714 Remote Similarity NPD6333 Approved
0.6714 Remote Similarity NPD6334 Approved
0.6667 Remote Similarity NPD6903 Approved
0.6667 Remote Similarity NPD5127 Approved
0.6643 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6638 Remote Similarity NPD8035 Phase 2
0.6638 Remote Similarity NPD5693 Phase 1
0.6638 Remote Similarity NPD8034 Phase 2
0.6638 Remote Similarity NPD6050 Approved
0.6637 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6637 Remote Similarity NPD6098 Approved
0.6612 Remote Similarity NPD5344 Discontinued
0.661 Remote Similarity NPD4629 Approved
0.661 Remote Similarity NPD1698 Clinical (unspecified phase)
0.661 Remote Similarity NPD5210 Approved
0.6607 Remote Similarity NPD3665 Phase 1
0.6607 Remote Similarity NPD3133 Approved
0.6607 Remote Similarity NPD3666 Approved
0.6594 Remote Similarity NPD6845 Suspended
0.6591 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6571 Remote Similarity NPD8387 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