Structure

Physi-Chem Properties

Molecular Weight:  414.12
Volume:  371.805
LogP:  -0.986
LogD:  0.324
LogS:  -0.867
# Rotatable Bonds:  6
TPSA:  161.21
# H-Bond Aceptor:  11
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.283
Synthetic Accessibility Score:  4.909
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.858
MDCK Permeability:  0.00020816731557715684
Pgp-inhibitor:  0.0
Pgp-substrate:  0.187
Human Intestinal Absorption (HIA):  0.982
20% Bioavailability (F20%):  0.171
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.415
Plasma Protein Binding (PPB):  20.364131927490234%
Volume Distribution (VD):  0.327
Pgp-substrate:  65.92430877685547%

ADMET: Metabolism

CYP1A2-inhibitor:  0.007
CYP1A2-substrate:  0.033
CYP2C19-inhibitor:  0.013
CYP2C19-substrate:  0.069
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.052
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.105
CYP3A4-inhibitor:  0.017
CYP3A4-substrate:  0.205

ADMET: Excretion

Clearance (CL):  1.76
Half-life (T1/2):  0.451

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.085
Drug-inuced Liver Injury (DILI):  0.98
AMES Toxicity:  0.717
Rat Oral Acute Toxicity:  0.842
Maximum Recommended Daily Dose:  0.186
Skin Sensitization:  0.022
Carcinogencity:  0.961
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.757

Download Data

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

  Natural Product: NPC310804

Natural Product ID:  NPC310804
Common Name*:   IBIPGYWNOBGEMH-UHFFFAOYSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  IBIPGYWNOBGEMH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H22O11/c1-6(20)25-4-7-2-9-12-8(16(24)27-9)5-26-17(11(7)12)29-18-15(23)14(22)13(21)10(3-19)28-18/h2,5,9-15,17-19,21-23H,3-4H2,1H3
SMILES:  OCC1OC(OC2OC=C3C4C2C(=CC4OC3=O)COC(=O)C)C(C(C1O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1965021
PubChem CID:   233330
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. PMID[26767291]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. bark n.a. PMID[26767291]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15479 Oldenlandia diffusa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15479 Oldenlandia diffusa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15479 Oldenlandia diffusa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15479 Oldenlandia diffusa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16850 Eucommia ulmoides Species Eucommiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15479 Oldenlandia diffusa Species Rubiaceae 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. 100000.0 nM PMID[554417]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 1000.0 nM PMID[554417]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 57016.43 nM PMID[554417]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 10000.0 nM PMID[554417]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[554417]

☑ 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 NPC310804 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 NPC261117
0.9789 High Similarity NPC250545
0.9684 High Similarity NPC298255
0.9684 High Similarity NPC28304
0.9588 High Similarity NPC86095
0.9579 High Similarity NPC255677
0.9579 High Similarity NPC22149
0.9579 High Similarity NPC306344
0.9381 High Similarity NPC222062
0.9286 High Similarity NPC118761
0.9286 High Similarity NPC284929
0.9286 High Similarity NPC267869
0.9286 High Similarity NPC234304
0.9286 High Similarity NPC197541
0.9263 High Similarity NPC241911
0.899 High Similarity NPC195510
0.899 High Similarity NPC13171
0.8947 High Similarity NPC61201
0.8737 High Similarity NPC303451
0.8737 High Similarity NPC6414
0.8641 High Similarity NPC474285
0.8641 High Similarity NPC254538
0.8542 High Similarity NPC117596
0.8485 Intermediate Similarity NPC306041
0.8454 Intermediate Similarity NPC472124
0.8454 Intermediate Similarity NPC472126
0.8454 Intermediate Similarity NPC472125
0.8421 Intermediate Similarity NPC142583
0.8384 Intermediate Similarity NPC469543
0.8384 Intermediate Similarity NPC170204
0.8351 Intermediate Similarity NPC65665
0.8351 Intermediate Similarity NPC231710
0.8351 Intermediate Similarity NPC307699
0.8351 Intermediate Similarity NPC470573
0.8351 Intermediate Similarity NPC216826
0.8351 Intermediate Similarity NPC120021
0.8351 Intermediate Similarity NPC270908
0.835 Intermediate Similarity NPC475928
0.8265 Intermediate Similarity NPC9447
0.8252 Intermediate Similarity NPC471599
0.8252 Intermediate Similarity NPC106668
0.8235 Intermediate Similarity NPC244878
0.8235 Intermediate Similarity NPC473146
0.819 Intermediate Similarity NPC170432
0.8173 Intermediate Similarity NPC27687
0.8155 Intermediate Similarity NPC20673
0.8155 Intermediate Similarity NPC219038
0.8137 Intermediate Similarity NPC151093
0.8119 Intermediate Similarity NPC54731
0.8113 Intermediate Similarity NPC80338
0.8113 Intermediate Similarity NPC148270
0.8113 Intermediate Similarity NPC197813
0.8077 Intermediate Similarity NPC474730
0.8077 Intermediate Similarity NPC4899
0.8077 Intermediate Similarity NPC35185
0.8077 Intermediate Similarity NPC177013
0.8021 Intermediate Similarity NPC470658
0.802 Intermediate Similarity NPC101051
0.8 Intermediate Similarity NPC211455
0.8 Intermediate Similarity NPC188717
0.8 Intermediate Similarity NPC37240
0.7981 Intermediate Similarity NPC4637
0.7981 Intermediate Similarity NPC98859
0.7961 Intermediate Similarity NPC472015
0.7941 Intermediate Similarity NPC161293
0.7917 Intermediate Similarity NPC220167
0.7917 Intermediate Similarity NPC136699
0.789 Intermediate Similarity NPC193741
0.7879 Intermediate Similarity NPC104129
0.7879 Intermediate Similarity NPC249408
0.787 Intermediate Similarity NPC110701
0.787 Intermediate Similarity NPC475960
0.7864 Intermediate Similarity NPC472290
0.785 Intermediate Similarity NPC127235
0.7835 Intermediate Similarity NPC470124
0.7822 Intermediate Similarity NPC320552
0.7822 Intermediate Similarity NPC280390
0.781 Intermediate Similarity NPC3488
0.781 Intermediate Similarity NPC287539
0.78 Intermediate Similarity NPC327253
0.7788 Intermediate Similarity NPC473307
0.7788 Intermediate Similarity NPC49833
0.7788 Intermediate Similarity NPC249171
0.7778 Intermediate Similarity NPC137368
0.7757 Intermediate Similarity NPC474917
0.7748 Intermediate Similarity NPC475851
0.7748 Intermediate Similarity NPC475924
0.7745 Intermediate Similarity NPC63897
0.7736 Intermediate Similarity NPC80144
0.7732 Intermediate Similarity NPC266718
0.7723 Intermediate Similarity NPC472197
0.7723 Intermediate Similarity NPC477749
0.7714 Intermediate Similarity NPC469402
0.7699 Intermediate Similarity NPC277583
0.7692 Intermediate Similarity NPC153559
0.7692 Intermediate Similarity NPC304445
0.7692 Intermediate Similarity NPC236580
0.767 Intermediate Similarity NPC241407
0.767 Intermediate Similarity NPC291709
0.7664 Intermediate Similarity NPC473148
0.7647 Intermediate Similarity NPC238090
0.7647 Intermediate Similarity NPC472195
0.7647 Intermediate Similarity NPC472196
0.7642 Intermediate Similarity NPC67296
0.7624 Intermediate Similarity NPC118078
0.7624 Intermediate Similarity NPC473619
0.7619 Intermediate Similarity NPC124181
0.7619 Intermediate Similarity NPC37866
0.7596 Intermediate Similarity NPC256230
0.7593 Intermediate Similarity NPC307846
0.7593 Intermediate Similarity NPC305157
0.7573 Intermediate Similarity NPC71589
0.7573 Intermediate Similarity NPC475927
0.7573 Intermediate Similarity NPC256368
0.7573 Intermediate Similarity NPC2003
0.7573 Intermediate Similarity NPC25701
0.7573 Intermediate Similarity NPC475832
0.7573 Intermediate Similarity NPC159698
0.757 Intermediate Similarity NPC86077
0.7551 Intermediate Similarity NPC212363
0.7551 Intermediate Similarity NPC475035
0.7549 Intermediate Similarity NPC473321
0.7545 Intermediate Similarity NPC177524
0.7545 Intermediate Similarity NPC392
0.7545 Intermediate Similarity NPC219900
0.7525 Intermediate Similarity NPC477748
0.7524 Intermediate Similarity NPC476613
0.7524 Intermediate Similarity NPC476612
0.7523 Intermediate Similarity NPC153095
0.7523 Intermediate Similarity NPC223450
0.7523 Intermediate Similarity NPC243998
0.7521 Intermediate Similarity NPC473228
0.7521 Intermediate Similarity NPC470829
0.75 Intermediate Similarity NPC36954
0.75 Intermediate Similarity NPC475037
0.7477 Intermediate Similarity NPC473332
0.7477 Intermediate Similarity NPC476611
0.7476 Intermediate Similarity NPC320089
0.7476 Intermediate Similarity NPC476300
0.7476 Intermediate Similarity NPC179746
0.7476 Intermediate Similarity NPC475912
0.7476 Intermediate Similarity NPC81419
0.7475 Intermediate Similarity NPC21469
0.7453 Intermediate Similarity NPC307517
0.7453 Intermediate Similarity NPC198422
0.7453 Intermediate Similarity NPC81483
0.7453 Intermediate Similarity NPC40182
0.7453 Intermediate Similarity NPC61630
0.7453 Intermediate Similarity NPC187268
0.7453 Intermediate Similarity NPC90819
0.7453 Intermediate Similarity NPC169468
0.7451 Intermediate Similarity NPC80875
0.7451 Intermediate Similarity NPC474232
0.7451 Intermediate Similarity NPC202886
0.7429 Intermediate Similarity NPC474297
0.7426 Intermediate Similarity NPC473715
0.7414 Intermediate Similarity NPC475309
0.7414 Intermediate Similarity NPC13710
0.7407 Intermediate Similarity NPC304163
0.7407 Intermediate Similarity NPC201191
0.7404 Intermediate Similarity NPC294293
0.7404 Intermediate Similarity NPC477131
0.7379 Intermediate Similarity NPC30515
0.7379 Intermediate Similarity NPC133698
0.7379 Intermediate Similarity NPC184463
0.7379 Intermediate Similarity NPC470379
0.7379 Intermediate Similarity NPC470373
0.7379 Intermediate Similarity NPC472199
0.7379 Intermediate Similarity NPC208886
0.7379 Intermediate Similarity NPC12172
0.7379 Intermediate Similarity NPC131209
0.7368 Intermediate Similarity NPC293658
0.7368 Intermediate Similarity NPC264153
0.7368 Intermediate Similarity NPC474410
0.7364 Intermediate Similarity NPC239961
0.7364 Intermediate Similarity NPC85670
0.7364 Intermediate Similarity NPC469401
0.7364 Intermediate Similarity NPC41681
0.7358 Intermediate Similarity NPC474194
0.7358 Intermediate Similarity NPC58267
0.7358 Intermediate Similarity NPC263674
0.7358 Intermediate Similarity NPC261372
0.7353 Intermediate Similarity NPC50464
0.735 Intermediate Similarity NPC477071
0.735 Intermediate Similarity NPC475834
0.735 Intermediate Similarity NPC474179
0.7339 Intermediate Similarity NPC151516
0.7339 Intermediate Similarity NPC197736
0.7333 Intermediate Similarity NPC471142
0.7333 Intermediate Similarity NPC471141
0.7333 Intermediate Similarity NPC167893
0.7333 Intermediate Similarity NPC270013
0.7333 Intermediate Similarity NPC14961
0.7333 Intermediate Similarity NPC93869
0.7333 Intermediate Similarity NPC6765
0.7327 Intermediate Similarity NPC74139
0.7321 Intermediate Similarity NPC257853
0.732 Intermediate Similarity NPC127295
0.732 Intermediate Similarity NPC163362
0.7317 Intermediate Similarity NPC213634

  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 NPC310804 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
0.7545 Intermediate Similarity NPD6686 Approved
0.7282 Intermediate Similarity NPD46 Approved
0.7282 Intermediate Similarity NPD6698 Approved
0.7227 Intermediate Similarity NPD8513 Phase 3
0.7193 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD8517 Approved
0.7083 Intermediate Similarity NPD8515 Approved
0.7083 Intermediate Similarity NPD8516 Approved
0.6992 Remote Similarity NPD7507 Approved
0.6942 Remote Similarity NPD7503 Approved
0.6893 Remote Similarity NPD4249 Approved
0.6838 Remote Similarity NPD6053 Discontinued
0.6827 Remote Similarity NPD4250 Approved
0.6827 Remote Similarity NPD4251 Approved
0.6825 Remote Similarity NPD7319 Approved
0.6698 Remote Similarity NPD1695 Approved
0.6694 Remote Similarity NPD7328 Approved
0.6694 Remote Similarity NPD7327 Approved
0.6667 Remote Similarity NPD6371 Approved
0.6667 Remote Similarity NPD8033 Approved
0.6639 Remote Similarity NPD7516 Approved
0.6636 Remote Similarity NPD7838 Discovery
0.6602 Remote Similarity NPD6110 Phase 1
0.6585 Remote Similarity NPD8377 Approved
0.6585 Remote Similarity NPD8294 Approved
0.6574 Remote Similarity NPD7983 Approved
0.656 Remote Similarity NPD7830 Approved
0.656 Remote Similarity NPD7829 Approved
0.6552 Remote Similarity NPD6412 Phase 2
0.6545 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6535 Remote Similarity NPD8074 Phase 3
0.6532 Remote Similarity NPD8296 Approved
0.6532 Remote Similarity NPD8378 Approved
0.6532 Remote Similarity NPD8335 Approved
0.6532 Remote Similarity NPD8380 Approved
0.6532 Remote Similarity NPD8379 Approved
0.6518 Remote Similarity NPD4225 Approved
0.6476 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6455 Remote Similarity NPD5282 Discontinued
0.6442 Remote Similarity NPD7154 Phase 3
0.6429 Remote Similarity NPD7642 Approved
0.6423 Remote Similarity NPD7641 Discontinued
0.6381 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6364 Remote Similarity NPD8133 Approved
0.6328 Remote Similarity NPD8451 Approved
0.6321 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6286 Remote Similarity NPD5362 Discontinued
0.6279 Remote Similarity NPD8448 Approved
0.627 Remote Similarity NPD8444 Approved
0.6231 Remote Similarity NPD7736 Approved
0.6222 Remote Similarity NPD7966 Clinical (unspecified phase)
0.622 Remote Similarity NPD6370 Approved
0.621 Remote Similarity NPD7115 Discovery
0.621 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6195 Remote Similarity NPD7839 Suspended
0.6172 Remote Similarity NPD8328 Phase 3
0.6167 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6154 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8293 Discontinued
0.6136 Remote Similarity NPD8392 Approved
0.6136 Remote Similarity NPD8391 Approved
0.6136 Remote Similarity NPD8390 Approved
0.6126 Remote Similarity NPD7637 Suspended
0.6124 Remote Similarity NPD8341 Approved
0.6124 Remote Similarity NPD8299 Approved
0.6124 Remote Similarity NPD8342 Approved
0.6124 Remote Similarity NPD7492 Approved
0.6124 Remote Similarity NPD8340 Approved
0.6121 Remote Similarity NPD5344 Discontinued
0.6094 Remote Similarity NPD8080 Discontinued
0.6087 Remote Similarity NPD7638 Approved
0.608 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6077 Remote Similarity NPD6616 Approved
0.6071 Remote Similarity NPD5779 Approved
0.6071 Remote Similarity NPD5778 Approved
0.6066 Remote Similarity NPD2204 Approved
0.6063 Remote Similarity NPD6054 Approved
0.6036 Remote Similarity NPD5785 Approved
0.6034 Remote Similarity NPD7640 Approved
0.6034 Remote Similarity NPD7639 Approved
0.6031 Remote Similarity NPD7078 Approved
0.6016 Remote Similarity NPD6016 Approved
0.6016 Remote Similarity NPD6015 Approved
0.6016 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5985 Remote Similarity NPD8337 Approved
0.5985 Remote Similarity NPD8336 Approved
0.597 Remote Similarity NPD7260 Phase 2
0.5969 Remote Similarity NPD5988 Approved
0.5962 Remote Similarity NPD4268 Approved
0.5962 Remote Similarity NPD4271 Approved
0.5952 Remote Similarity NPD6009 Approved
0.5938 Remote Similarity NPD6319 Approved
0.5938 Remote Similarity NPD6059 Approved
0.5926 Remote Similarity NPD6845 Suspended
0.5902 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5888 Remote Similarity NPD6435 Approved
0.5887 Remote Similarity NPD6882 Approved
0.5882 Remote Similarity NPD1407 Approved
0.5872 Remote Similarity NPD5363 Approved
0.5854 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5849 Remote Similarity NPD4820 Approved
0.5849 Remote Similarity NPD4821 Approved
0.5849 Remote Similarity NPD4819 Approved
0.5849 Remote Similarity NPD4252 Approved
0.5849 Remote Similarity NPD4822 Approved
0.584 Remote Similarity NPD4632 Approved
0.5833 Remote Similarity NPD5332 Approved
0.5833 Remote Similarity NPD5331 Approved
0.5818 Remote Similarity NPD5786 Approved
0.581 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5809 Remote Similarity NPD8338 Approved
0.5804 Remote Similarity NPD6101 Approved
0.5804 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5794 Remote Similarity NPD4790 Discontinued
0.5789 Remote Similarity NPD6399 Phase 3
0.5785 Remote Similarity NPD6008 Approved
0.5769 Remote Similarity NPD8267 Approved
0.5769 Remote Similarity NPD8266 Approved
0.5769 Remote Similarity NPD8269 Approved
0.5769 Remote Similarity NPD8268 Approved
0.5763 Remote Similarity NPD6648 Approved
0.576 Remote Similarity NPD8297 Approved
0.5758 Remote Similarity NPD898 Approved
0.5758 Remote Similarity NPD897 Approved
0.5758 Remote Similarity NPD896 Approved
0.5741 Remote Similarity NPD4270 Approved
0.5741 Remote Similarity NPD5209 Approved
0.5741 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5741 Remote Similarity NPD4269 Approved
0.5727 Remote Similarity NPD1694 Approved
0.5702 Remote Similarity NPD6411 Approved
0.5701 Remote Similarity NPD5368 Approved
0.5691 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5682 Remote Similarity NPD6067 Discontinued
0.5682 Remote Similarity NPD7122 Discontinued
0.568 Remote Similarity NPD6650 Approved
0.568 Remote Similarity NPD6649 Approved
0.5648 Remote Similarity NPD5369 Approved
0.5645 Remote Similarity NPD6372 Approved
0.5645 Remote Similarity NPD6373 Approved
0.5625 Remote Similarity NPD7524 Approved
0.561 Remote Similarity NPD5697 Approved
0.561 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5607 Remote Similarity NPD7329 Approved
0.56 Remote Similarity NPD4247 Clinical (unspecified phase)
0.56 Remote Similarity NPD6421 Discontinued

  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