Structure

Physi-Chem Properties

Molecular Weight:  740.17
Volume:  704.318
LogP:  4.138
LogD:  1.524
LogS:  -4.998
# Rotatable Bonds:  4
TPSA:  267.29
# H-Bond Aceptor:  15
# H-Bond Donor:  11
# Rings:  8
# Heavy Atoms:  15

MedChem Properties

QED Drug-Likeness Score:  0.07
Synthetic Accessibility Score:  5.075
Fsp3:  0.205
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:  -6.926
MDCK Permeability:  4.8269512262777425e-06
Pgp-inhibitor:  0.126
Pgp-substrate:  0.083
Human Intestinal Absorption (HIA):  0.857
20% Bioavailability (F20%):  0.994
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  89.1841812133789%
Volume Distribution (VD):  0.156
Pgp-substrate:  7.735718727111816%

ADMET: Metabolism

CYP1A2-inhibitor:  0.01
CYP1A2-substrate:  0.057
CYP2C19-inhibitor:  0.022
CYP2C19-substrate:  0.04
CYP2C9-inhibitor:  0.55
CYP2C9-substrate:  0.976
CYP2D6-inhibitor:  0.0
CYP2D6-substrate:  0.168
CYP3A4-inhibitor:  0.036
CYP3A4-substrate:  0.469

ADMET: Excretion

Clearance (CL):  11.379
Half-life (T1/2):  0.718

ADMET: Toxicity

hERG Blockers:  0.019
Human Hepatotoxicity (H-HT):  0.038
Drug-inuced Liver Injury (DILI):  0.941
AMES Toxicity:  0.326
Rat Oral Acute Toxicity:  0.968
Maximum Recommended Daily Dose:  0.988
Skin Sensitization:  0.963
Carcinogencity:  0.032
Eye Corrosion:  0.003
Eye Irritation:  0.919
Respiratory Toxicity:  0.017

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

  Natural Product: NPC9309

Natural Product ID:  NPC9309
Common Name*:   Cinchonain Iia
IUPAC Name:   (2R,3R,4S,10R)-2,10-bis(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-8-yl]-3,5-dihydroxy-3,4,9,10-tetrahydro-2H-pyrano[2,3-h]chromen-8-one
Synonyms:   Cinchonain IIa
Standard InCHIKey:  NWZBNZUABGSPSN-WRYDCQAKSA-N
Standard InCHI:  InChI=1S/C39H32O15/c40-19-4-1-14(7-23(19)44)17-11-30(50)52-29-13-27(48)33-34(35(51)37(54-39(33)31(17)29)16-3-6-21(42)25(46)9-16)32-26(47)12-22(43)18-10-28(49)36(53-38(18)32)15-2-5-20(41)24(45)8-15/h1-9,12-13,17,28,34-37,40-49,51H,10-11H2/t17-,28-,34+,35-,36-,37-/m1/s1
SMILES:  c1cc(c(cc1[C@H]1CC(=O)Oc2cc(c3[C@H](c4c(cc(c5C[C@H]([C@@H](c6ccc(c(c6)O)O)Oc45)O)O)O)[C@H]([C@@H](c4ccc(c(c4)O)O)Oc3c12)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL491581
PubChem CID:   11765545
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. leaf n.a. DOI[10.1021/np50070a005]
NPO23925 Iryanthera megistophylla Species Myristicaceae Eukaryota n.a. n.a. n.a. PMID[12398535]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[17944538]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota leaves Botanical Garden of Innsbruck, Austria n.a. PMID[20100662]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. leaf n.a. PMID[21443171]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. leaf n.a. PMID[21923134]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[22823026]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota leaves and stems Ha Long, Quang Ninh province, Vietnam 2014-Jul PMID[25769817]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. PMID[29792702]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25618 Eriobotrya japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14254 Kandelia candel Species Rhizophoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23925 Iryanthera megistophylla Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25618 Eriobotrya japonica Species Rosaceae 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
NPT1105 Organism Potato virus X Potato virus X Inhibition = 100.0 % PMID[503794]
NPT20 Organism Candida albicans Candida albicans MIC = 150.0 ug.mL-1 PMID[503794]

☑ 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 NPC9309 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
0.9615 High Similarity NPC7543
0.9615 High Similarity NPC98083
0.9615 High Similarity NPC94220
0.9615 High Similarity NPC24339
0.9615 High Similarity NPC166456
0.9494 High Similarity NPC109061
0.9371 High Similarity NPC124747
0.9371 High Similarity NPC177100
0.9371 High Similarity NPC155754
0.9371 High Similarity NPC139540
0.9363 High Similarity NPC165483
0.9329 High Similarity NPC98583
0.9268 High Similarity NPC65333
0.9268 High Similarity NPC100251
0.9108 High Similarity NPC226809
0.9108 High Similarity NPC279406
0.9074 High Similarity NPC12326
0.9051 High Similarity NPC224161
0.8994 High Similarity NPC46335
0.8976 High Similarity NPC180768
0.8944 High Similarity NPC4809
0.8944 High Similarity NPC73517
0.8944 High Similarity NPC147743
0.8941 High Similarity NPC125352
0.891 High Similarity NPC108811
0.891 High Similarity NPC204770
0.891 High Similarity NPC170103
0.891 High Similarity NPC294558
0.891 High Similarity NPC58190
0.891 High Similarity NPC82917
0.891 High Similarity NPC202742
0.891 High Similarity NPC262911
0.891 High Similarity NPC263940
0.891 High Similarity NPC18185
0.891 High Similarity NPC70409
0.891 High Similarity NPC236202
0.8889 High Similarity NPC106601
0.8889 High Similarity NPC86630
0.8889 High Similarity NPC471404
0.8889 High Similarity NPC205613
0.8889 High Similarity NPC151474
0.8889 High Similarity NPC321916
0.8889 High Similarity NPC159526
0.8889 High Similarity NPC212614
0.8868 High Similarity NPC226108
0.8868 High Similarity NPC134911
0.8868 High Similarity NPC46283
0.8868 High Similarity NPC469944
0.8868 High Similarity NPC44192
0.8868 High Similarity NPC322899
0.8868 High Similarity NPC272552
0.8861 High Similarity NPC477612
0.8846 High Similarity NPC96576
0.8841 High Similarity NPC476372
0.8841 High Similarity NPC476371
0.8837 High Similarity NPC318119
0.8834 High Similarity NPC24164
0.883 High Similarity NPC117668
0.8827 High Similarity NPC36077
0.881 High Similarity NPC186847
0.881 High Similarity NPC257667
0.881 High Similarity NPC472454
0.8797 High Similarity NPC211561
0.8795 High Similarity NPC471823
0.8795 High Similarity NPC224851
0.8793 High Similarity NPC269046
0.8779 High Similarity NPC129533
0.8779 High Similarity NPC123259
0.8773 High Similarity NPC36354
0.8773 High Similarity NPC185231
0.8758 High Similarity NPC8712
0.875 High Similarity NPC476365
0.8743 High Similarity NPC473818
0.8736 High Similarity NPC237202
0.8734 High Similarity NPC227516
0.8734 High Similarity NPC20757
0.8727 High Similarity NPC55121
0.8727 High Similarity NPC140346
0.8727 High Similarity NPC174311
0.8727 High Similarity NPC192258
0.8727 High Similarity NPC476200
0.872 High Similarity NPC476373
0.8712 High Similarity NPC125495
0.8712 High Similarity NPC156818
0.8712 High Similarity NPC38779
0.8712 High Similarity NPC160512
0.8712 High Similarity NPC68324
0.8712 High Similarity NPC289322
0.8712 High Similarity NPC114179
0.8698 High Similarity NPC212038
0.8698 High Similarity NPC262580
0.8698 High Similarity NPC81332
0.8698 High Similarity NPC289396
0.8698 High Similarity NPC271848
0.8696 High Similarity NPC306267
0.8696 High Similarity NPC20050
0.869 High Similarity NPC475212
0.8683 High Similarity NPC320741
0.8683 High Similarity NPC171985
0.8678 High Similarity NPC112380
0.8675 High Similarity NPC45943
0.8671 High Similarity NPC132111
0.8655 High Similarity NPC79736
0.8655 High Similarity NPC67629
0.865 High Similarity NPC250436
0.865 High Similarity NPC318432
0.865 High Similarity NPC88803
0.865 High Similarity NPC291948
0.865 High Similarity NPC104983
0.865 High Similarity NPC300845
0.8623 High Similarity NPC477840
0.8614 High Similarity NPC477841
0.8613 High Similarity NPC208797
0.8613 High Similarity NPC53680
0.8606 High Similarity NPC53889
0.8605 High Similarity NPC471789
0.8605 High Similarity NPC267549
0.8605 High Similarity NPC265380
0.8599 High Similarity NPC171932
0.8599 High Similarity NPC28440
0.8596 High Similarity NPC477082
0.8589 High Similarity NPC125709
0.8589 High Similarity NPC292385
0.8588 High Similarity NPC264302
0.858 High Similarity NPC7839
0.858 High Similarity NPC107627
0.858 High Similarity NPC142291
0.858 High Similarity NPC474656
0.8571 High Similarity NPC471403
0.8563 High Similarity NPC121290
0.8555 High Similarity NPC324742
0.8555 High Similarity NPC80956
0.8555 High Similarity NPC185275
0.8554 High Similarity NPC142252
0.8554 High Similarity NPC186228
0.8554 High Similarity NPC216916
0.8545 High Similarity NPC87317
0.8538 High Similarity NPC168789
0.8529 High Similarity NPC91043
0.8528 High Similarity NPC268484
0.8528 High Similarity NPC157333
0.8526 High Similarity NPC277331
0.8526 High Similarity NPC178054
0.8526 High Similarity NPC100482
0.8523 High Similarity NPC65489
0.8523 High Similarity NPC179947
0.8521 High Similarity NPC217781
0.8512 High Similarity NPC142614
0.8512 High Similarity NPC471788
0.8506 High Similarity NPC8940
0.8503 High Similarity NPC219927
0.85 High Similarity NPC281549
0.8494 Intermediate Similarity NPC42965
0.8491 Intermediate Similarity NPC268515
0.8491 Intermediate Similarity NPC102280
0.8491 Intermediate Similarity NPC248053
0.8491 Intermediate Similarity NPC40222
0.8491 Intermediate Similarity NPC155564
0.8485 Intermediate Similarity NPC323627
0.8485 Intermediate Similarity NPC470827
0.8485 Intermediate Similarity NPC322459
0.8485 Intermediate Similarity NPC318527
0.8485 Intermediate Similarity NPC324358
0.8481 Intermediate Similarity NPC475492
0.848 Intermediate Similarity NPC67134
0.848 Intermediate Similarity NPC4200
0.848 Intermediate Similarity NPC47140
0.8475 Intermediate Similarity NPC477081
0.8475 Intermediate Similarity NPC477083
0.8475 Intermediate Similarity NPC173872
0.8475 Intermediate Similarity NPC473618
0.8475 Intermediate Similarity NPC119094
0.8471 Intermediate Similarity NPC300307
0.8471 Intermediate Similarity NPC149300
0.8466 Intermediate Similarity NPC229817
0.8466 Intermediate Similarity NPC223720
0.8466 Intermediate Similarity NPC221140
0.8466 Intermediate Similarity NPC115203
0.8466 Intermediate Similarity NPC473686
0.8466 Intermediate Similarity NPC475352
0.8466 Intermediate Similarity NPC475220
0.8462 Intermediate Similarity NPC43065
0.8462 Intermediate Similarity NPC317671
0.8462 Intermediate Similarity NPC207575
0.8462 Intermediate Similarity NPC142707
0.8462 Intermediate Similarity NPC13481
0.8462 Intermediate Similarity NPC26536
0.8462 Intermediate Similarity NPC49983
0.8457 Intermediate Similarity NPC293227
0.8457 Intermediate Similarity NPC473631
0.8457 Intermediate Similarity NPC473717
0.8457 Intermediate Similarity NPC475662
0.8457 Intermediate Similarity NPC259707
0.8457 Intermediate Similarity NPC150977
0.8452 Intermediate Similarity NPC63438
0.8448 Intermediate Similarity NPC471030
0.8447 Intermediate Similarity NPC475250
0.8447 Intermediate Similarity NPC321657
0.8447 Intermediate Similarity NPC318373
0.8443 Intermediate Similarity NPC158188

  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 NPC9309 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
0.8698 High Similarity NPD7993 Clinical (unspecified phase)
0.865 High Similarity NPD4868 Clinical (unspecified phase)
0.8415 Intermediate Similarity NPD8455 Phase 2
0.8402 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD6166 Phase 2
0.8402 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8363 Intermediate Similarity NPD5844 Phase 1
0.8314 Intermediate Similarity NPD7074 Phase 3
0.8304 Intermediate Similarity NPD7228 Approved
0.8193 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.815 Intermediate Similarity NPD7054 Approved
0.8118 Intermediate Similarity NPD7199 Phase 2
0.8103 Intermediate Similarity NPD7472 Approved
0.8084 Intermediate Similarity NPD1465 Phase 2
0.8036 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD1934 Approved
0.8023 Intermediate Similarity NPD8313 Approved
0.8023 Intermediate Similarity NPD8312 Approved
0.8013 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD1613 Approved
0.8012 Intermediate Similarity NPD6959 Discontinued
0.8011 Intermediate Similarity NPD7251 Discontinued
0.8 Intermediate Similarity NPD6234 Discontinued
0.7977 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7966 Intermediate Similarity NPD7808 Phase 3
0.7955 Intermediate Similarity NPD6797 Phase 2
0.7943 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7941 Intermediate Similarity NPD7075 Discontinued
0.7931 Intermediate Similarity NPD7473 Discontinued
0.7927 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD37 Approved
0.7904 Intermediate Similarity NPD4380 Phase 2
0.7901 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7882 Intermediate Similarity NPD4967 Phase 2
0.7882 Intermediate Similarity NPD4965 Approved
0.7882 Intermediate Similarity NPD4966 Approved
0.7882 Intermediate Similarity NPD7768 Phase 2
0.787 Intermediate Similarity NPD7819 Suspended
0.7865 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD6232 Discontinued
0.7809 Intermediate Similarity NPD7240 Approved
0.7784 Intermediate Similarity NPD3818 Discontinued
0.7771 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7765 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD7411 Suspended
0.7746 Intermediate Similarity NPD5494 Approved
0.7735 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD3817 Phase 2
0.7701 Intermediate Similarity NPD8127 Discontinued
0.7692 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD1653 Approved
0.7661 Intermediate Similarity NPD2801 Approved
0.7657 Intermediate Similarity NPD7229 Phase 3
0.7657 Intermediate Similarity NPD3787 Discontinued
0.7651 Intermediate Similarity NPD1511 Approved
0.7643 Intermediate Similarity NPD4908 Phase 1
0.7636 Intermediate Similarity NPD6190 Approved
0.7602 Intermediate Similarity NPD6801 Discontinued
0.7595 Intermediate Similarity NPD3027 Phase 3
0.7592 Intermediate Similarity NPD7680 Approved
0.756 Intermediate Similarity NPD1512 Approved
0.7544 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7527 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD6559 Discontinued
0.7487 Intermediate Similarity NPD8151 Discontinued
0.7474 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD3882 Suspended
0.747 Intermediate Similarity NPD8166 Discontinued
0.747 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD6100 Approved
0.7439 Intermediate Similarity NPD6099 Approved
0.7438 Intermediate Similarity NPD6798 Discontinued
0.7429 Intermediate Similarity NPD3749 Approved
0.7427 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD7097 Phase 1
0.7418 Intermediate Similarity NPD7685 Pre-registration
0.7414 Intermediate Similarity NPD5402 Approved
0.7411 Intermediate Similarity NPD7783 Phase 2
0.7411 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD5124 Phase 1
0.7407 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD6355 Discontinued
0.7396 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD7266 Discontinued
0.7394 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD3751 Discontinued
0.7365 Intermediate Similarity NPD3750 Approved
0.7365 Intermediate Similarity NPD4628 Phase 3
0.7349 Intermediate Similarity NPD1549 Phase 2
0.7346 Intermediate Similarity NPD4060 Phase 1
0.7337 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7326 Intermediate Similarity NPD7458 Discontinued
0.731 Intermediate Similarity NPD5403 Approved
0.731 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD1610 Phase 2
0.7305 Intermediate Similarity NPD6674 Discontinued
0.7284 Intermediate Similarity NPD6233 Phase 2
0.7283 Intermediate Similarity NPD7549 Discontinued
0.7235 Intermediate Similarity NPD6799 Approved
0.7219 Intermediate Similarity NPD8150 Discontinued
0.7195 Intermediate Similarity NPD230 Phase 1
0.7193 Intermediate Similarity NPD5401 Approved
0.7188 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD6599 Discontinued
0.7169 Intermediate Similarity NPD7033 Discontinued
0.7152 Intermediate Similarity NPD1608 Approved
0.7143 Intermediate Similarity NPD2861 Phase 2
0.7143 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7390 Discontinued
0.7125 Intermediate Similarity NPD2797 Approved
0.7117 Intermediate Similarity NPD3268 Approved
0.7117 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD8054 Approved
0.7112 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7112 Intermediate Similarity NPD8053 Approved
0.7101 Intermediate Similarity NPD1652 Phase 2
0.7095 Intermediate Similarity NPD919 Approved
0.7093 Intermediate Similarity NPD2533 Approved
0.7093 Intermediate Similarity NPD2532 Approved
0.7093 Intermediate Similarity NPD2534 Approved
0.7083 Intermediate Similarity NPD6005 Phase 3
0.7083 Intermediate Similarity NPD6002 Phase 3
0.7083 Intermediate Similarity NPD6004 Phase 3
0.7083 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD3748 Approved
0.7066 Intermediate Similarity NPD1510 Phase 2
0.7059 Intermediate Similarity NPD4110 Phase 3
0.7059 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7003 Approved
0.7056 Intermediate Similarity NPD7435 Discontinued
0.7055 Intermediate Similarity NPD7095 Approved
0.7055 Intermediate Similarity NPD4625 Phase 3
0.7052 Intermediate Similarity NPD6273 Approved
0.7047 Intermediate Similarity NPD7667 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD8434 Phase 2
0.7029 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD3226 Approved
0.7024 Intermediate Similarity NPD2935 Discontinued
0.7024 Intermediate Similarity NPD2796 Approved
0.702 Intermediate Similarity NPD8319 Approved
0.702 Intermediate Similarity NPD7870 Phase 2
0.702 Intermediate Similarity NPD8320 Phase 1
0.702 Intermediate Similarity NPD7871 Phase 2
0.7 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6982 Remote Similarity NPD5762 Approved
0.6982 Remote Similarity NPD5763 Approved
0.697 Remote Similarity NPD7697 Approved
0.697 Remote Similarity NPD7698 Approved
0.697 Remote Similarity NPD7696 Phase 3
0.6962 Remote Similarity NPD17 Approved
0.6957 Remote Similarity NPD3225 Approved
0.6946 Remote Similarity NPD6653 Approved
0.6943 Remote Similarity NPD1548 Phase 1
0.6931 Remote Similarity NPD7874 Approved
0.6931 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6923 Remote Similarity NPD2438 Suspended
0.6923 Remote Similarity NPD1551 Phase 2
0.6919 Remote Similarity NPD7177 Discontinued
0.6915 Remote Similarity NPD7585 Approved
0.6915 Remote Similarity NPD7701 Phase 2
0.6914 Remote Similarity NPD7427 Discontinued
0.6904 Remote Similarity NPD6781 Approved
0.6904 Remote Similarity NPD6778 Approved
0.6904 Remote Similarity NPD6782 Approved
0.6904 Remote Similarity NPD6780 Approved
0.6904 Remote Similarity NPD6777 Approved
0.6904 Remote Similarity NPD6779 Approved
0.6904 Remote Similarity NPD6776 Approved
0.6897 Remote Similarity NPD7447 Phase 1
0.6897 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6894 Remote Similarity NPD4749 Approved
0.6879 Remote Similarity NPD6667 Approved
0.6879 Remote Similarity NPD6666 Approved
0.6875 Remote Similarity NPD422 Phase 1
0.6868 Remote Similarity NPD6746 Phase 2
0.6867 Remote Similarity NPD8032 Phase 2
0.6866 Remote Similarity NPD7583 Approved
0.6852 Remote Similarity NPD8651 Approved
0.6848 Remote Similarity NPD3926 Phase 2
0.6839 Remote Similarity NPD7212 Phase 2
0.6839 Remote Similarity NPD7213 Phase 3
0.6833 Remote Similarity NPD5353 Approved
0.6826 Remote Similarity NPD4140 Approved
0.6826 Remote Similarity NPD943 Approved
0.6826 Remote Similarity NPD1240 Approved
0.6824 Remote Similarity NPD5408 Approved
0.6824 Remote Similarity NPD5405 Approved
0.6824 Remote Similarity NPD5406 Approved
0.6824 Remote Similarity NPD5404 Approved
0.6818 Remote Similarity NPD920 Approved
0.6818 Remote Similarity NPD7501 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