Structure

Physi-Chem Properties

Molecular Weight:  712.22
Volume:  656.378
LogP:  0.295
LogD:  -0.15
LogS:  -1.959
# Rotatable Bonds:  13
TPSA:  280.82
# H-Bond Aceptor:  18
# H-Bond Donor:  9
# Rings:  5
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.049
Synthetic Accessibility Score:  5.388
Fsp3:  0.562
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.55
MDCK Permeability:  9.944094927050173e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.987
Human Intestinal Absorption (HIA):  0.951
20% Bioavailability (F20%):  0.351
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.171
Plasma Protein Binding (PPB):  66.33631134033203%
Volume Distribution (VD):  0.432
Pgp-substrate:  27.981714248657227%

ADMET: Metabolism

CYP1A2-inhibitor:  0.017
CYP1A2-substrate:  0.017
CYP2C19-inhibitor:  0.037
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.009
CYP2C9-substrate:  0.04
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.092
CYP3A4-inhibitor:  0.037
CYP3A4-substrate:  0.043

ADMET: Excretion

Clearance (CL):  0.925
Half-life (T1/2):  0.939

ADMET: Toxicity

hERG Blockers:  0.05
Human Hepatotoxicity (H-HT):  0.088
Drug-inuced Liver Injury (DILI):  0.882
AMES Toxicity:  0.219
Rat Oral Acute Toxicity:  0.54
Maximum Recommended Daily Dose:  0.088
Skin Sensitization:  0.882
Carcinogencity:  0.627
Eye Corrosion:  0.003
Eye Irritation:  0.061
Respiratory Toxicity:  0.607

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

  Natural Product: NPC69367

Natural Product ID:  NPC69367
Common Name*:   6''-O-Trans-Caffeoylgenipin Gentiobioside
IUPAC Name:   methyl (1S,4aS,7aS)-1-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Synonyms:  
Standard InCHIKey:  CSRRWPAMFHNUSX-DALANRPMSA-N
Standard InCHI:  InChI=1S/C32H40O18/c1-44-29(43)16-10-46-30(22-14(9-33)4-5-15(16)22)50-32-28(42)26(40)24(38)20(49-32)12-47-31-27(41)25(39)23(37)19(48-31)11-45-21(36)7-3-13-2-6-17(34)18(35)8-13/h2-4,6-8,10,15,19-20,22-28,30-35,37-42H,5,9,11-12H2,1H3/b7-3+/t15-,19-,20-,22-,23-,24-,25+,26+,27-,28-,30+,31-,32+/m1/s1
SMILES:  COC(=O)C1=CO[C@H]([C@@H]2C(=CC[C@H]12)CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](COC(=O)/C=C/c3ccc(c(c3)O)O)O2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2316917
PubChem CID:   71552449
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0004081] Iridoid O-glycosides

*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
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[16309325]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. Seoul, Korea 2000-Jun PMID[16643034]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[18505286]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[19650637]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[23305920]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[32141747]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9518 Gardenia jasminoides 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
NPT113 Cell Line RAW264.7 Mus musculus IC50 > 100000.0 nM PMID[545705]

☑ 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 NPC69367 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
0.9507 High Similarity NPC293154
0.9324 High Similarity NPC203664
0.9184 High Similarity NPC23677
0.9091 High Similarity NPC220936
0.9091 High Similarity NPC31745
0.9034 High Similarity NPC296643
0.9013 High Similarity NPC475484
0.8912 High Similarity NPC202391
0.8912 High Similarity NPC296659
0.891 High Similarity NPC145847
0.8896 High Similarity NPC187205
0.8889 High Similarity NPC476376
0.8854 High Similarity NPC109990
0.8844 High Similarity NPC475213
0.8844 High Similarity NPC152796
0.8839 High Similarity NPC179914
0.8836 High Similarity NPC47471
0.8836 High Similarity NPC476377
0.8811 High Similarity NPC471883
0.8803 High Similarity NPC473285
0.8784 High Similarity NPC296954
0.8784 High Similarity NPC196063
0.8784 High Similarity NPC300894
0.8784 High Similarity NPC141455
0.8784 High Similarity NPC63304
0.8767 High Similarity NPC475530
0.8767 High Similarity NPC473799
0.8759 High Similarity NPC65262
0.8759 High Similarity NPC101686
0.8759 High Similarity NPC469364
0.875 High Similarity NPC476870
0.8732 High Similarity NPC254819
0.8718 High Similarity NPC469384
0.8716 High Similarity NPC76406
0.8716 High Similarity NPC476380
0.8716 High Similarity NPC476381
0.8716 High Similarity NPC269141
0.8716 High Similarity NPC264632
0.8716 High Similarity NPC476378
0.8716 High Similarity NPC476397
0.8716 High Similarity NPC175214
0.8716 High Similarity NPC205864
0.8716 High Similarity NPC119537
0.8716 High Similarity NPC96795
0.8716 High Similarity NPC476375
0.8716 High Similarity NPC298257
0.8716 High Similarity NPC247032
0.8716 High Similarity NPC476384
0.8716 High Similarity NPC112
0.8716 High Similarity NPC105005
0.8707 High Similarity NPC476385
0.8707 High Similarity NPC134405
0.8699 High Similarity NPC81515
0.8699 High Similarity NPC68092
0.8699 High Similarity NPC476383
0.8699 High Similarity NPC220942
0.8699 High Similarity NPC472350
0.8699 High Similarity NPC205195
0.8699 High Similarity NPC64141
0.8699 High Similarity NPC197316
0.8699 High Similarity NPC89105
0.8693 High Similarity NPC106818
0.869 High Similarity NPC472132
0.8667 High Similarity NPC229505
0.8658 High Similarity NPC64195
0.8658 High Similarity NPC77922
0.8658 High Similarity NPC473281
0.8654 High Similarity NPC286919
0.8654 High Similarity NPC475663
0.8636 High Similarity NPC246893
0.8636 High Similarity NPC87403
0.8634 High Similarity NPC21956
0.863 High Similarity NPC260425
0.8627 High Similarity NPC478249
0.8627 High Similarity NPC269914
0.8618 High Similarity NPC96599
0.8611 High Similarity NPC254398
0.8609 High Similarity NPC18789
0.8601 High Similarity NPC219677
0.86 High Similarity NPC262182
0.86 High Similarity NPC287615
0.86 High Similarity NPC216819
0.86 High Similarity NPC83743
0.8592 High Similarity NPC229784
0.8592 High Similarity NPC477294
0.8592 High Similarity NPC477293
0.8581 High Similarity NPC472127
0.8581 High Similarity NPC472128
0.8562 High Similarity NPC117346
0.8562 High Similarity NPC240592
0.8562 High Similarity NPC470572
0.8562 High Similarity NPC188393
0.8562 High Similarity NPC470934
0.8553 High Similarity NPC201148
0.8553 High Similarity NPC199311
0.8553 High Similarity NPC80732
0.8553 High Similarity NPC476011
0.8553 High Similarity NPC192763
0.8553 High Similarity NPC3460
0.8553 High Similarity NPC215095
0.8553 High Similarity NPC261122
0.8553 High Similarity NPC28651
0.8553 High Similarity NPC300262
0.8553 High Similarity NPC210611
0.8552 High Similarity NPC169398
0.8544 High Similarity NPC138993
0.8544 High Similarity NPC478265
0.8543 High Similarity NPC119773
0.8543 High Similarity NPC474268
0.8543 High Similarity NPC476865
0.8543 High Similarity NPC143246
0.8543 High Similarity NPC475539
0.8542 High Similarity NPC473924
0.8533 High Similarity NPC184464
0.8533 High Similarity NPC476867
0.8533 High Similarity NPC251062
0.8523 High Similarity NPC265648
0.8523 High Similarity NPC222433
0.8521 High Similarity NPC232880
0.8509 High Similarity NPC282551
0.8503 High Similarity NPC78363
0.8497 Intermediate Similarity NPC94871
0.8497 Intermediate Similarity NPC306890
0.8497 Intermediate Similarity NPC476398
0.8497 Intermediate Similarity NPC473427
0.8497 Intermediate Similarity NPC478242
0.8497 Intermediate Similarity NPC259347
0.8497 Intermediate Similarity NPC470933
0.8497 Intermediate Similarity NPC476386
0.8497 Intermediate Similarity NPC471062
0.8487 Intermediate Similarity NPC473149
0.8477 Intermediate Similarity NPC252292
0.8477 Intermediate Similarity NPC100998
0.8477 Intermediate Similarity NPC476866
0.8477 Intermediate Similarity NPC475528
0.8477 Intermediate Similarity NPC476869
0.8477 Intermediate Similarity NPC476382
0.8477 Intermediate Similarity NPC476864
0.8477 Intermediate Similarity NPC34587
0.8477 Intermediate Similarity NPC476868
0.8477 Intermediate Similarity NPC34927
0.8467 Intermediate Similarity NPC186296
0.8467 Intermediate Similarity NPC40305
0.8452 Intermediate Similarity NPC478268
0.8451 Intermediate Similarity NPC476873
0.8446 Intermediate Similarity NPC328273
0.8446 Intermediate Similarity NPC321638
0.8446 Intermediate Similarity NPC321184
0.8446 Intermediate Similarity NPC171134
0.8446 Intermediate Similarity NPC226005
0.8442 Intermediate Similarity NPC257970
0.8442 Intermediate Similarity NPC12006
0.8442 Intermediate Similarity NPC147224
0.8442 Intermediate Similarity NPC476871
0.8442 Intermediate Similarity NPC470927
0.8438 Intermediate Similarity NPC246024
0.8435 Intermediate Similarity NPC157554
0.8431 Intermediate Similarity NPC473138
0.8431 Intermediate Similarity NPC28776
0.8431 Intermediate Similarity NPC308178
0.8428 Intermediate Similarity NPC474936
0.8425 Intermediate Similarity NPC287597
0.8425 Intermediate Similarity NPC34293
0.8425 Intermediate Similarity NPC886
0.8421 Intermediate Similarity NPC212808
0.8421 Intermediate Similarity NPC473867
0.8421 Intermediate Similarity NPC473147
0.8411 Intermediate Similarity NPC110063
0.8397 Intermediate Similarity NPC478241
0.8397 Intermediate Similarity NPC89693
0.8397 Intermediate Similarity NPC229548
0.8397 Intermediate Similarity NPC471874
0.8395 Intermediate Similarity NPC301910
0.8395 Intermediate Similarity NPC130730
0.8389 Intermediate Similarity NPC202700
0.8387 Intermediate Similarity NPC143480
0.8387 Intermediate Similarity NPC158546
0.8387 Intermediate Similarity NPC289021
0.8387 Intermediate Similarity NPC85192
0.8387 Intermediate Similarity NPC7145
0.8387 Intermediate Similarity NPC125823
0.8377 Intermediate Similarity NPC478236
0.8377 Intermediate Similarity NPC90896
0.8377 Intermediate Similarity NPC283839
0.8377 Intermediate Similarity NPC478234
0.8375 Intermediate Similarity NPC471869
0.8366 Intermediate Similarity NPC232992
0.8354 Intermediate Similarity NPC478248
0.8354 Intermediate Similarity NPC478266
0.8333 Intermediate Similarity NPC289967
0.8333 Intermediate Similarity NPC472611
0.8333 Intermediate Similarity NPC154262
0.8333 Intermediate Similarity NPC180586
0.8333 Intermediate Similarity NPC159387
0.8333 Intermediate Similarity NPC472612
0.8333 Intermediate Similarity NPC137501
0.8333 Intermediate Similarity NPC7518
0.8323 Intermediate Similarity NPC471873
0.8322 Intermediate Similarity NPC471881
0.8322 Intermediate Similarity NPC100389

  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 NPC69367 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
0.8699 High Similarity NPD7266 Discontinued
0.8476 Intermediate Similarity NPD7685 Pre-registration
0.7871 Intermediate Similarity NPD6190 Approved
0.7849 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7811 Intermediate Similarity NPD7472 Approved
0.7799 Intermediate Similarity NPD1653 Approved
0.7798 Intermediate Similarity NPD7228 Approved
0.7751 Intermediate Similarity NPD7054 Approved
0.7719 Intermediate Similarity NPD7251 Discontinued
0.7674 Intermediate Similarity NPD7808 Phase 3
0.7661 Intermediate Similarity NPD6797 Phase 2
0.7602 Intermediate Similarity NPD7074 Phase 3
0.7485 Intermediate Similarity NPD3818 Discontinued
0.7485 Intermediate Similarity NPD6234 Discontinued
0.7471 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD8166 Discontinued
0.7455 Intermediate Similarity NPD8455 Phase 2
0.7438 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7414 Intermediate Similarity NPD7240 Approved
0.7403 Intermediate Similarity NPD230 Phase 1
0.7396 Intermediate Similarity NPD7199 Phase 2
0.7396 Intermediate Similarity NPD8127 Discontinued
0.7394 Intermediate Similarity NPD37 Approved
0.7365 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD4966 Approved
0.7365 Intermediate Similarity NPD4965 Approved
0.7365 Intermediate Similarity NPD4967 Phase 2
0.733 Intermediate Similarity NPD8313 Approved
0.733 Intermediate Similarity NPD8312 Approved
0.7321 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD6166 Phase 2
0.7069 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD7680 Approved
0.7037 Intermediate Similarity NPD4628 Phase 3
0.7025 Intermediate Similarity NPD6653 Approved
0.7022 Intermediate Similarity NPD6559 Discontinued
0.7006 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.6982 Remote Similarity NPD1934 Approved
0.6975 Remote Similarity NPD6674 Discontinued
0.6964 Remote Similarity NPD4380 Phase 2
0.6949 Remote Similarity NPD5844 Phase 1
0.6941 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6941 Remote Similarity NPD1465 Phase 2
0.6923 Remote Similarity NPD3027 Phase 3
0.6913 Remote Similarity NPD9545 Approved
0.6903 Remote Similarity NPD9494 Approved
0.6901 Remote Similarity NPD3817 Phase 2
0.6867 Remote Similarity NPD1357 Approved
0.6864 Remote Similarity NPD7028 Phase 2
0.6842 Remote Similarity NPD3705 Approved
0.6842 Remote Similarity NPD1091 Approved
0.6842 Remote Similarity NPD2801 Approved
0.6821 Remote Similarity NPD7075 Discontinued
0.6805 Remote Similarity NPD7458 Discontinued
0.6797 Remote Similarity NPD9269 Phase 2
0.6795 Remote Similarity NPD5736 Approved
0.6792 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6792 Remote Similarity NPD1613 Approved
0.677 Remote Similarity NPD7097 Phase 1
0.6769 Remote Similarity NPD8151 Discontinued
0.6766 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6766 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6763 Remote Similarity NPD3882 Suspended
0.675 Remote Similarity NPD6355 Discontinued
0.6744 Remote Similarity NPD7819 Suspended
0.6743 Remote Similarity NPD5494 Approved
0.6742 Remote Similarity NPD7473 Discontinued
0.6739 Remote Similarity NPD8150 Discontinued
0.6736 Remote Similarity NPD8320 Phase 1
0.6736 Remote Similarity NPD8319 Approved
0.673 Remote Similarity NPD6663 Approved
0.6727 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6727 Remote Similarity NPD4110 Phase 3
0.6727 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6721 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6707 Remote Similarity NPD1511 Approved
0.6707 Remote Similarity NPD970 Clinical (unspecified phase)
0.6706 Remote Similarity NPD3455 Phase 2
0.6705 Remote Similarity NPD5353 Approved
0.6705 Remote Similarity NPD5402 Approved
0.6704 Remote Similarity NPD3751 Discontinued
0.6704 Remote Similarity NPD7799 Discontinued
0.6667 Remote Similarity NPD6232 Discontinued
0.6667 Remote Similarity NPD3764 Approved
0.6667 Remote Similarity NPD4978 Clinical (unspecified phase)
0.6649 Remote Similarity NPD8434 Phase 2
0.6647 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6646 Remote Similarity NPD5763 Approved
0.6646 Remote Similarity NPD5762 Approved
0.6627 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6273 Approved
0.6627 Remote Similarity NPD1512 Approved
0.6626 Remote Similarity NPD7033 Discontinued
0.6625 Remote Similarity NPD6233 Phase 2
0.6624 Remote Similarity NPD5647 Approved
0.6623 Remote Similarity NPD5536 Phase 2
0.6609 Remote Similarity NPD8443 Clinical (unspecified phase)
0.66 Remote Similarity NPD7930 Approved
0.6598 Remote Similarity NPD7435 Discontinued
0.6597 Remote Similarity NPD7700 Phase 2
0.6597 Remote Similarity NPD7699 Phase 2
0.659 Remote Similarity NPD6801 Discontinued
0.6588 Remote Similarity NPD5403 Approved
0.6584 Remote Similarity NPD3620 Phase 2
0.6584 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6582 Remote Similarity NPD2861 Phase 2
0.6575 Remote Similarity NPD8470 Clinical (unspecified phase)
0.6573 Remote Similarity NPD3787 Discontinued
0.6566 Remote Similarity NPD1652 Phase 2
0.6562 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6545 Remote Similarity NPD6004 Phase 3
0.6545 Remote Similarity NPD6005 Phase 3
0.6545 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6545 Remote Similarity NPD6002 Phase 3
0.6545 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6543 Remote Similarity NPD447 Suspended
0.6543 Remote Similarity NPD5124 Phase 1
0.6543 Remote Similarity NPD1933 Approved
0.6543 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6541 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6536 Remote Similarity NPD9268 Approved
0.6533 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6533 Remote Similarity NPD7783 Phase 2
0.6532 Remote Similarity NPD6385 Approved
0.6532 Remote Similarity NPD6386 Approved
0.6531 Remote Similarity NPD7999 Approved
0.6531 Remote Similarity NPD3021 Approved
0.6531 Remote Similarity NPD3022 Approved
0.6527 Remote Similarity NPD3750 Approved
0.6519 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6513 Remote Similarity NPD7697 Approved
0.6513 Remote Similarity NPD7696 Phase 3
0.6513 Remote Similarity NPD7698 Approved
0.6507 Remote Similarity NPD1358 Approved
0.65 Remote Similarity NPD7095 Approved
0.6497 Remote Similarity NPD3225 Approved
0.6485 Remote Similarity NPD9570 Approved
0.6485 Remote Similarity NPD2935 Discontinued
0.6482 Remote Similarity NPD7874 Approved
0.6482 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6481 Remote Similarity NPD4060 Phase 1
0.6481 Remote Similarity NPD826 Approved
0.6481 Remote Similarity NPD825 Approved
0.6478 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6477 Remote Similarity NPD7768 Phase 2
0.6474 Remote Similarity NPD1608 Approved
0.6471 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5401 Approved
0.6467 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6465 Remote Similarity NPD7701 Phase 2
0.646 Remote Similarity NPD3268 Approved
0.646 Remote Similarity NPD6798 Discontinued
0.6456 Remote Similarity NPD3094 Phase 2
0.6456 Remote Similarity NPD6362 Approved
0.6456 Remote Similarity NPD2797 Approved
0.6443 Remote Similarity NPD969 Suspended
0.6443 Remote Similarity NPD6781 Approved
0.6443 Remote Similarity NPD6782 Approved
0.6443 Remote Similarity NPD6776 Approved
0.6443 Remote Similarity NPD6780 Approved
0.6443 Remote Similarity NPD6777 Approved
0.6443 Remote Similarity NPD6779 Approved
0.6443 Remote Similarity NPD228 Approved
0.6443 Remote Similarity NPD6778 Approved
0.644 Remote Similarity NPD6534 Approved
0.644 Remote Similarity NPD6535 Approved
0.6438 Remote Similarity NPD3134 Approved
0.6437 Remote Similarity NPD7411 Suspended
0.6425 Remote Similarity NPD5619 Clinical (unspecified phase)
0.6421 Remote Similarity NPD7296 Approved
0.6416 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6412 Remote Similarity NPD4357 Discontinued
0.6412 Remote Similarity NPD6799 Approved
0.6409 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6407 Remote Similarity NPD2424 Discontinued
0.6396 Remote Similarity NPD7870 Phase 2
0.6396 Remote Similarity NPD7871 Phase 2
0.6387 Remote Similarity NPD5126 Approved
0.6387 Remote Similarity NPD1778 Approved
0.6387 Remote Similarity NPD5125 Phase 3
0.6386 Remote Similarity NPD2438 Suspended
0.6382 Remote Similarity NPD7585 Approved
0.638 Remote Similarity NPD943 Approved
0.638 Remote Similarity NPD4140 Approved
0.6378 Remote Similarity NPD7039 Approved
0.6378 Remote Similarity NPD7038 Approved
0.6378 Remote Similarity NPD6823 Phase 2
0.6374 Remote Similarity NPD2534 Approved
0.6374 Remote Similarity NPD2532 Approved
0.6374 Remote Similarity NPD2533 Approved
0.6368 Remote Similarity NPD7801 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