Structure

Physi-Chem Properties

Molecular Weight:  304.09
Volume:  296.545
LogP:  2.518
LogD:  2.499
LogS:  -3.072
# Rotatable Bonds:  1
TPSA:  100.13
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.718
Synthetic Accessibility Score:  4.36
Fsp3:  0.312
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.144
MDCK Permeability:  6.567469426954631e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.891
Human Intestinal Absorption (HIA):  0.05
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.044
Plasma Protein Binding (PPB):  85.06493377685547%
Volume Distribution (VD):  1.147
Pgp-substrate:  13.012186050415039%

ADMET: Metabolism

CYP1A2-inhibitor:  0.97
CYP1A2-substrate:  0.891
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.39
CYP2C9-inhibitor:  0.114
CYP2C9-substrate:  0.378
CYP2D6-inhibitor:  0.163
CYP2D6-substrate:  0.175
CYP3A4-inhibitor:  0.287
CYP3A4-substrate:  0.538

ADMET: Excretion

Clearance (CL):  1.361
Half-life (T1/2):  0.66

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.21
Drug-inuced Liver Injury (DILI):  0.987
AMES Toxicity:  0.311
Rat Oral Acute Toxicity:  0.059
Maximum Recommended Daily Dose:  0.051
Skin Sensitization:  0.756
Carcinogencity:  0.03
Eye Corrosion:  0.014
Eye Irritation:  0.181
Respiratory Toxicity:  0.505

Download Data

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

  Natural Product: NPC471456

Natural Product ID:  NPC471456
Common Name*:   Bombamalone A
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  JYUFSZQBCUGFJN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H16O6/c1-6(2)7-5-8(17)10-11-9(7)13(18)16(3,20)14(21-4)12(11)22-15(10)19/h5-6,17,20H,1-4H3
SMILES:  COC1=C2OC(=O)c3c2c(C(=O)C1(C)O)c(cc3O)C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL250449
PubChem CID:   23642715
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0002441] Naphthols 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
NPO29953 Bombax malabaricum Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[17764148]
NPO29953 Bombax malabaricum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29953 Bombax malabaricum Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT2511 Cell Line HGC-27 Homo sapiens IC50 > 10000.0 nM PMID[510827]

☑ 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 NPC471456 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
0.9167 High Similarity NPC117985
0.9 High Similarity NPC473094
0.8944 High Similarity NPC473096
0.8944 High Similarity NPC473095
0.8903 High Similarity NPC478231
0.8839 High Similarity NPC115249
0.8839 High Similarity NPC184284
0.8839 High Similarity NPC76041
0.8782 High Similarity NPC137301
0.8782 High Similarity NPC192189
0.8766 High Similarity NPC198927
0.8758 High Similarity NPC53362
0.8758 High Similarity NPC166583
0.875 High Similarity NPC144843
0.8742 High Similarity NPC47623
0.8726 High Similarity NPC317585
0.8726 High Similarity NPC478221
0.8726 High Similarity NPC208173
0.8726 High Similarity NPC478230
0.8726 High Similarity NPC170189
0.8726 High Similarity NPC472890
0.8726 High Similarity NPC69043
0.872 High Similarity NPC473113
0.8716 High Similarity NPC471452
0.871 High Similarity NPC472891
0.8679 High Similarity NPC470339
0.8675 High Similarity NPC314271
0.8675 High Similarity NPC322112
0.8671 High Similarity NPC474360
0.8667 High Similarity NPC168471
0.8627 High Similarity NPC474309
0.8625 High Similarity NPC472055
0.8625 High Similarity NPC243701
0.8616 High Similarity NPC478226
0.8616 High Similarity NPC246466
0.8616 High Similarity NPC478225
0.8616 High Similarity NPC472889
0.8599 High Similarity NPC478224
0.8598 High Similarity NPC191653
0.859 High Similarity NPC179178
0.8589 High Similarity NPC62444
0.8581 High Similarity NPC94781
0.858 High Similarity NPC249181
0.8571 High Similarity NPC260946
0.8571 High Similarity NPC263817
0.8553 High Similarity NPC478027
0.8553 High Similarity NPC472050
0.8544 High Similarity NPC471695
0.8528 High Similarity NPC191930
0.8526 High Similarity NPC280753
0.8526 High Similarity NPC44378
0.8519 High Similarity NPC94796
0.8509 High Similarity NPC470810
0.8509 High Similarity NPC475107
0.8509 High Similarity NPC43490
0.8506 High Similarity NPC75694
0.8506 High Similarity NPC475923
0.8506 High Similarity NPC474630
0.85 High Similarity NPC263483
0.85 High Similarity NPC476930
0.8497 Intermediate Similarity NPC159721
0.8491 Intermediate Similarity NPC234485
0.8491 Intermediate Similarity NPC79998
0.8487 Intermediate Similarity NPC149533
0.8481 Intermediate Similarity NPC271681
0.8477 Intermediate Similarity NPC275356
0.8476 Intermediate Similarity NPC20237
0.8476 Intermediate Similarity NPC476255
0.8471 Intermediate Similarity NPC119929
0.8471 Intermediate Similarity NPC182693
0.8471 Intermediate Similarity NPC31132
0.8471 Intermediate Similarity NPC158866
0.8471 Intermediate Similarity NPC150928
0.8466 Intermediate Similarity NPC476931
0.8457 Intermediate Similarity NPC317544
0.8452 Intermediate Similarity NPC473023
0.8452 Intermediate Similarity NPC120536
0.8442 Intermediate Similarity NPC42540
0.8442 Intermediate Similarity NPC471451
0.8442 Intermediate Similarity NPC151607
0.8438 Intermediate Similarity NPC150227
0.8438 Intermediate Similarity NPC478223
0.8434 Intermediate Similarity NPC313717
0.8434 Intermediate Similarity NPC315306
0.8431 Intermediate Similarity NPC82913
0.8428 Intermediate Similarity NPC301233
0.8428 Intermediate Similarity NPC127172
0.8428 Intermediate Similarity NPC312482
0.8428 Intermediate Similarity NPC472799
0.8424 Intermediate Similarity NPC193222
0.8424 Intermediate Similarity NPC283041
0.8418 Intermediate Similarity NPC240768
0.8418 Intermediate Similarity NPC205918
0.8418 Intermediate Similarity NPC200773
0.8415 Intermediate Similarity NPC189689
0.8411 Intermediate Similarity NPC112135
0.8408 Intermediate Similarity NPC478219
0.8408 Intermediate Similarity NPC84142
0.84 Intermediate Similarity NPC158481
0.84 Intermediate Similarity NPC326847
0.8397 Intermediate Similarity NPC5568
0.8397 Intermediate Similarity NPC8817
0.8397 Intermediate Similarity NPC137296
0.8395 Intermediate Similarity NPC313368
0.8393 Intermediate Similarity NPC162248
0.8387 Intermediate Similarity NPC473692
0.8385 Intermediate Similarity NPC77679
0.8385 Intermediate Similarity NPC190020
0.8385 Intermediate Similarity NPC29552
0.8385 Intermediate Similarity NPC473395
0.8385 Intermediate Similarity NPC84935
0.8377 Intermediate Similarity NPC471731
0.8377 Intermediate Similarity NPC478202
0.8377 Intermediate Similarity NPC66593
0.8377 Intermediate Similarity NPC21873
0.8375 Intermediate Similarity NPC199926
0.8375 Intermediate Similarity NPC478133
0.8366 Intermediate Similarity NPC37530
0.8366 Intermediate Similarity NPC472603
0.8366 Intermediate Similarity NPC478217
0.8366 Intermediate Similarity NPC313123
0.8365 Intermediate Similarity NPC51824
0.8365 Intermediate Similarity NPC113608
0.8365 Intermediate Similarity NPC470338
0.8365 Intermediate Similarity NPC268992
0.8365 Intermediate Similarity NPC478220
0.8365 Intermediate Similarity NPC470340
0.8365 Intermediate Similarity NPC180388
0.8365 Intermediate Similarity NPC470337
0.8364 Intermediate Similarity NPC165460
0.8364 Intermediate Similarity NPC476056
0.8354 Intermediate Similarity NPC56204
0.8354 Intermediate Similarity NPC475717
0.8354 Intermediate Similarity NPC164762
0.8344 Intermediate Similarity NPC470479
0.8344 Intermediate Similarity NPC172329
0.8344 Intermediate Similarity NPC194579
0.8344 Intermediate Similarity NPC2569
0.8344 Intermediate Similarity NPC470359
0.8344 Intermediate Similarity NPC478134
0.8344 Intermediate Similarity NPC37139
0.8343 Intermediate Similarity NPC312630
0.8343 Intermediate Similarity NPC324220
0.8333 Intermediate Similarity NPC476139
0.8333 Intermediate Similarity NPC290803
0.8333 Intermediate Similarity NPC476152
0.8333 Intermediate Similarity NPC470357
0.8333 Intermediate Similarity NPC476229
0.8333 Intermediate Similarity NPC136878
0.8333 Intermediate Similarity NPC225173
0.8333 Intermediate Similarity NPC163846
0.8333 Intermediate Similarity NPC475080
0.8323 Intermediate Similarity NPC471305
0.8323 Intermediate Similarity NPC103910
0.8323 Intermediate Similarity NPC29932
0.8313 Intermediate Similarity NPC95715
0.8312 Intermediate Similarity NPC471733
0.8312 Intermediate Similarity NPC11314
0.8303 Intermediate Similarity NPC211592
0.8303 Intermediate Similarity NPC316262
0.8303 Intermediate Similarity NPC314653
0.8302 Intermediate Similarity NPC215921
0.8302 Intermediate Similarity NPC70016
0.8302 Intermediate Similarity NPC91809
0.8302 Intermediate Similarity NPC133856
0.8301 Intermediate Similarity NPC472601
0.8301 Intermediate Similarity NPC165172
0.8301 Intermediate Similarity NPC327187
0.8301 Intermediate Similarity NPC99441
0.8301 Intermediate Similarity NPC472600
0.8294 Intermediate Similarity NPC77179
0.8294 Intermediate Similarity NPC221820
0.8294 Intermediate Similarity NPC23553
0.8293 Intermediate Similarity NPC478229
0.8291 Intermediate Similarity NPC77325
0.8291 Intermediate Similarity NPC270160
0.8291 Intermediate Similarity NPC474310
0.8291 Intermediate Similarity NPC120171
0.8291 Intermediate Similarity NPC233267
0.8291 Intermediate Similarity NPC291049
0.8291 Intermediate Similarity NPC4423
0.8291 Intermediate Similarity NPC237440
0.8289 Intermediate Similarity NPC126739
0.8289 Intermediate Similarity NPC197666
0.8289 Intermediate Similarity NPC221104
0.8289 Intermediate Similarity NPC191835
0.8282 Intermediate Similarity NPC470358
0.8282 Intermediate Similarity NPC286422
0.828 Intermediate Similarity NPC125801
0.828 Intermediate Similarity NPC210320
0.8278 Intermediate Similarity NPC86524
0.8278 Intermediate Similarity NPC50455
0.8278 Intermediate Similarity NPC291454
0.8274 Intermediate Similarity NPC472620
0.8274 Intermediate Similarity NPC118128
0.8274 Intermediate Similarity NPC294501
0.8272 Intermediate Similarity NPC201127
0.8272 Intermediate Similarity NPC474637
0.8272 Intermediate Similarity NPC302258
0.8272 Intermediate Similarity NPC143328

  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 NPC471456 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
0.8506 High Similarity NPD2533 Approved
0.8506 High Similarity NPD2532 Approved
0.8506 High Similarity NPD2534 Approved
0.8253 Intermediate Similarity NPD7473 Discontinued
0.8182 Intermediate Similarity NPD6232 Discontinued
0.8117 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD8150 Discontinued
0.795 Intermediate Similarity NPD3226 Approved
0.7879 Intermediate Similarity NPD3882 Suspended
0.7857 Intermediate Similarity NPD5711 Approved
0.7857 Intermediate Similarity NPD5710 Approved
0.7831 Intermediate Similarity NPD7075 Discontinued
0.7812 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7809 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6599 Discontinued
0.7758 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD7819 Suspended
0.7756 Intermediate Similarity NPD2935 Discontinued
0.7722 Intermediate Similarity NPD2800 Approved
0.7711 Intermediate Similarity NPD3817 Phase 2
0.7692 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7684 Intermediate Similarity NPD8434 Phase 2
0.7651 Intermediate Similarity NPD2801 Approved
0.764 Intermediate Similarity NPD6799 Approved
0.7613 Intermediate Similarity NPD230 Phase 1
0.7598 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD2346 Discontinued
0.759 Intermediate Similarity NPD1934 Approved
0.759 Intermediate Similarity NPD6801 Discontinued
0.7588 Intermediate Similarity NPD6959 Discontinued
0.758 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD4380 Phase 2
0.7546 Intermediate Similarity NPD1512 Approved
0.7532 Intermediate Similarity NPD3764 Approved
0.7532 Intermediate Similarity NPD5408 Approved
0.7532 Intermediate Similarity NPD5404 Approved
0.7532 Intermediate Similarity NPD5405 Approved
0.7532 Intermediate Similarity NPD5406 Approved
0.7531 Intermediate Similarity NPD7390 Discontinued
0.753 Intermediate Similarity NPD7411 Suspended
0.7529 Intermediate Similarity NPD5844 Phase 1
0.7529 Intermediate Similarity NPD5494 Approved
0.7528 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD3749 Approved
0.75 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6559 Discontinued
0.75 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD1247 Approved
0.7485 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD3818 Discontinued
0.7471 Intermediate Similarity NPD919 Approved
0.7471 Intermediate Similarity NPD6234 Discontinued
0.7469 Intermediate Similarity NPD3300 Phase 2
0.7468 Intermediate Similarity NPD2799 Discontinued
0.7457 Intermediate Similarity NPD2403 Approved
0.7457 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD6166 Phase 2
0.7456 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD4628 Phase 3
0.7453 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD1607 Approved
0.7423 Intermediate Similarity NPD1511 Approved
0.7416 Intermediate Similarity NPD8313 Approved
0.7416 Intermediate Similarity NPD8312 Approved
0.7394 Intermediate Similarity NPD7435 Discontinued
0.7381 Intermediate Similarity NPD37 Approved
0.7368 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7356 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD8320 Phase 1
0.7354 Intermediate Similarity NPD8319 Approved
0.7353 Intermediate Similarity NPD4966 Approved
0.7353 Intermediate Similarity NPD4967 Phase 2
0.7353 Intermediate Similarity NPD4965 Approved
0.7346 Intermediate Similarity NPD3750 Approved
0.7342 Intermediate Similarity NPD6651 Approved
0.7337 Intermediate Similarity NPD1465 Phase 2
0.7337 Intermediate Similarity NPD6535 Approved
0.7337 Intermediate Similarity NPD6534 Approved
0.733 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD6776 Approved
0.7326 Intermediate Similarity NPD6777 Approved
0.7326 Intermediate Similarity NPD6779 Approved
0.7326 Intermediate Similarity NPD6780 Approved
0.7326 Intermediate Similarity NPD6781 Approved
0.7326 Intermediate Similarity NPD6778 Approved
0.7326 Intermediate Similarity NPD6782 Approved
0.7325 Intermediate Similarity NPD943 Approved
0.7325 Intermediate Similarity NPD4060 Phase 1
0.7325 Intermediate Similarity NPD1240 Approved
0.7301 Intermediate Similarity NPD6190 Approved
0.7294 Intermediate Similarity NPD5402 Approved
0.7289 Intermediate Similarity NPD920 Approved
0.7284 Intermediate Similarity NPD1243 Approved
0.7278 Intermediate Similarity NPD447 Suspended
0.7273 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD1471 Phase 3
0.725 Intermediate Similarity NPD1510 Phase 2
0.7247 Intermediate Similarity NPD6797 Phase 2
0.7247 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7700 Phase 2
0.7219 Intermediate Similarity NPD7699 Phase 2
0.7212 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD1470 Approved
0.7207 Intermediate Similarity NPD7251 Discontinued
0.7205 Intermediate Similarity NPD6100 Approved
0.7205 Intermediate Similarity NPD6099 Approved
0.7202 Intermediate Similarity NPD7458 Discontinued
0.72 Intermediate Similarity NPD3926 Phase 2
0.72 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD7074 Phase 3
0.7175 Intermediate Similarity NPD7228 Approved
0.7175 Intermediate Similarity NPD3751 Discontinued
0.7171 Intermediate Similarity NPD1201 Approved
0.7169 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD7808 Phase 3
0.7165 Intermediate Similarity NPD7874 Approved
0.7165 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2344 Approved
0.7152 Intermediate Similarity NPD4626 Approved
0.7151 Intermediate Similarity NPD7768 Phase 2
0.7143 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1283 Approved
0.7135 Intermediate Similarity NPD7054 Approved
0.7134 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD8166 Discontinued
0.7134 Intermediate Similarity NPD7003 Approved
0.7133 Intermediate Similarity NPD9545 Approved
0.712 Intermediate Similarity NPD7697 Approved
0.712 Intermediate Similarity NPD7696 Phase 3
0.712 Intermediate Similarity NPD7698 Approved
0.7117 Intermediate Similarity NPD1549 Phase 2
0.7114 Intermediate Similarity NPD9493 Approved
0.7113 Intermediate Similarity NPD8151 Discontinued
0.7101 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7099 Intermediate Similarity NPD1551 Phase 2
0.7095 Intermediate Similarity NPD7472 Approved
0.7089 Intermediate Similarity NPD3268 Approved
0.7089 Intermediate Similarity NPD2313 Discontinued
0.7086 Intermediate Similarity NPD7199 Phase 2
0.7083 Intermediate Similarity NPD7871 Phase 2
0.7083 Intermediate Similarity NPD7870 Phase 2
0.7083 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD5403 Approved
0.7079 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6355 Discontinued
0.7062 Intermediate Similarity NPD7701 Phase 2
0.7048 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD3787 Discontinued
0.7045 Intermediate Similarity NPD7229 Phase 3
0.7041 Intermediate Similarity NPD7801 Approved
0.7037 Intermediate Similarity NPD3748 Approved
0.7013 Intermediate Similarity NPD9269 Phase 2
0.7 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD2979 Phase 3
0.6994 Remote Similarity NPD2438 Suspended
0.6994 Remote Similarity NPD2796 Approved
0.6988 Remote Similarity NPD2309 Approved
0.6987 Remote Similarity NPD1164 Approved
0.6983 Remote Similarity NPD7799 Discontinued
0.6981 Remote Similarity NPD411 Approved
0.6974 Remote Similarity NPD5691 Approved
0.6964 Remote Similarity NPD5401 Approved
0.6961 Remote Similarity NPD5953 Discontinued
0.6954 Remote Similarity NPD7783 Phase 2
0.6954 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6951 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6951 Remote Similarity NPD5763 Approved
0.6951 Remote Similarity NPD5762 Approved
0.6948 Remote Similarity NPD1281 Approved
0.6946 Remote Similarity NPD7236 Approved
0.6944 Remote Similarity NPD7286 Phase 2
0.6923 Remote Similarity NPD6765 Approved
0.6923 Remote Similarity NPD6764 Approved
0.6923 Remote Similarity NPD7685 Pre-registration
0.6918 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6915 Remote Similarity NPD6212 Phase 3
0.6915 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6915 Remote Similarity NPD6213 Phase 3
0.6903 Remote Similarity NPD9717 Approved
0.6903 Remote Similarity NPD1608 Approved
0.6902 Remote Similarity NPD8407 Phase 2
0.6894 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6891 Remote Similarity NPD6823 Phase 2
0.6885 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6879 Remote Similarity NPD1203 Approved
0.6875 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6872 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6863 Remote Similarity NPD9268 Approved
0.685 Remote Similarity NPD7930 Approved
0.6848 Remote Similarity NPD6002 Phase 3
0.6848 Remote Similarity NPD6004 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