Structure

Physi-Chem Properties

Molecular Weight:  632.3
Volume:  643.997
LogP:  7.59
LogD:  3.64
LogS:  -4.556
# Rotatable Bonds:  2
TPSA:  127.07
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  7
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.223
Synthetic Accessibility Score:  5.859
Fsp3:  0.514
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.926
MDCK Permeability:  1.822405101847835e-05
Pgp-inhibitor:  0.902
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.689
20% Bioavailability (F20%):  0.421
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  99.92951202392578%
Volume Distribution (VD):  0.548
Pgp-substrate:  3.071277141571045%

ADMET: Metabolism

CYP1A2-inhibitor:  0.006
CYP1A2-substrate:  0.959
CYP2C19-inhibitor:  0.065
CYP2C19-substrate:  0.956
CYP2C9-inhibitor:  0.097
CYP2C9-substrate:  0.935
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.116
CYP3A4-inhibitor:  0.093
CYP3A4-substrate:  0.915

ADMET: Excretion

Clearance (CL):  1.527
Half-life (T1/2):  0.037

ADMET: Toxicity

hERG Blockers:  0.062
Human Hepatotoxicity (H-HT):  0.21
Drug-inuced Liver Injury (DILI):  0.941
AMES Toxicity:  0.083
Rat Oral Acute Toxicity:  0.998
Maximum Recommended Daily Dose:  0.999
Skin Sensitization:  0.912
Carcinogencity:  0.039
Eye Corrosion:  0.003
Eye Irritation:  0.901
Respiratory Toxicity:  0.403

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

  Natural Product: NPC470208

Natural Product ID:  NPC470208
Common Name*:   Tricitrinol B
IUPAC Name:   n.a.
Synonyms:   Tricitrinol B
Standard InCHIKey:  GIHKMCLRUJERAC-ITWOFJKESA-N
Standard InCHI:  InChI=1S/C37H44O9/c1-12-18(7)43-34(26-22(39)11-21(38)15(4)23(12)26)29-31(40)16(5)24-13(2)19(8)44-35-28(24)36(29)46-33-17(6)25-14(3)20(9)45-37(42-10)27(25)32(41)30(33)35/h11-14,18-20,34-35,37-41H,1-10H3/t12-,13-,14-,18-,19-,20-,34+,35-,37?/m1/s1
SMILES:  COC1O[C@H](C)[C@H](c2c1c(O)c1[C@@H]3O[C@H](C)[C@H](c4c3c(Oc1c2C)c(c(c4C)O)[C@H]1O[C@H](C)[C@H](c2c1c(O)cc(c2C)O)C)C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1822982
PubChem CID:   46840960
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes

*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
NPO33186 penicillium citrinum hgy1-5 Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[21761866]

☑ 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
NPT116 Cell Line HL-60 Homo sapiens IC50 = 3200.0 nM PMID[536931]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 4820.0 nM PMID[536931]
NPT91 Cell Line KB Homo sapiens IC50 = 3870.0 nM PMID[536931]
NPT1081 Cell Line BXPC-3 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT1097 Cell Line MKN-45 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT515 Cell Line SGC-7901 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT306 Cell Line PC-3 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT165 Cell Line HeLa Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT91 Cell Line KB Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT784 Cell Line MDA-MB-468 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT81 Cell Line A549 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT762 Cell Line A-431 Homo sapiens IC50 = 4830.0 nM PMID[536931]
NPT1059 Cell Line HMEC Homo sapiens IC50 = 7890.0 nM PMID[536931]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 5760.0 nM PMID[536931]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 7410.0 nM PMID[536931]
NPT91 Cell Line KB Homo sapiens IC50 = 4600.0 nM PMID[536931]
NPT91 Cell Line KB Homo sapiens Ratio IC50 = 0.94 n.a. PMID[536931]
NPT83 Cell Line MCF7 Homo sapiens Ratio IC50 = 1.28 n.a. PMID[536931]
NPT116 Cell Line HL-60 Homo sapiens Activity = 10.0 % PMID[536931]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 37.52 % PMID[536931]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 20.42 % PMID[536931]
NPT393 Cell Line HCT-116 Homo sapiens Activity = 42.06 % PMID[536931]
NPT1059 Cell Line HMEC Homo sapiens Ratio IC50 = 2.0 n.a. PMID[536931]
NPT165 Cell Line HeLa Homo sapiens Ratio IC50 = 2.0 n.a. PMID[536931]
NPT83 Cell Line MCF7 Homo sapiens Ratio IC50 = 2.0 n.a. PMID[536931]
NPT784 Cell Line MDA-MB-468 Homo sapiens Ratio IC50 = 2.0 n.a. PMID[536931]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 4830.0 nM PMID[536931]

☑ 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 NPC470208 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 NPC295573
0.8936 High Similarity NPC24913
0.8936 High Similarity NPC177712
0.8933 High Similarity NPC259707
0.8774 High Similarity NPC185231
0.875 High Similarity NPC476452
0.875 High Similarity NPC233467
0.875 High Similarity NPC59692
0.8741 High Similarity NPC473107
0.869 High Similarity NPC470308
0.869 High Similarity NPC470307
0.8684 High Similarity NPC471403
0.8667 High Similarity NPC174251
0.8667 High Similarity NPC153182
0.8652 High Similarity NPC25729
0.8652 High Similarity NPC474494
0.8621 High Similarity NPC471522
0.8618 High Similarity NPC260781
0.8618 High Similarity NPC218041
0.8618 High Similarity NPC469706
0.8618 High Similarity NPC162976
0.8618 High Similarity NPC118000
0.8618 High Similarity NPC182368
0.8618 High Similarity NPC145979
0.8618 High Similarity NPC9933
0.8618 High Similarity NPC185955
0.8618 High Similarity NPC225815
0.8618 High Similarity NPC469707
0.8618 High Similarity NPC205501
0.8618 High Similarity NPC214326
0.86 High Similarity NPC215678
0.86 High Similarity NPC155564
0.86 High Similarity NPC248053
0.86 High Similarity NPC102280
0.86 High Similarity NPC274454
0.8591 High Similarity NPC225445
0.859 High Similarity NPC147743
0.859 High Similarity NPC73517
0.859 High Similarity NPC4809
0.8571 High Similarity NPC200645
0.8571 High Similarity NPC106669
0.8571 High Similarity NPC475227
0.8562 High Similarity NPC473621
0.8542 High Similarity NPC469610
0.8535 High Similarity NPC106601
0.8535 High Similarity NPC86630
0.8535 High Similarity NPC471404
0.8535 High Similarity NPC159526
0.8535 High Similarity NPC151474
0.8535 High Similarity NPC205613
0.8535 High Similarity NPC212614
0.8531 High Similarity NPC8899
0.8523 High Similarity NPC116922
0.8514 High Similarity NPC210192
0.8506 High Similarity NPC21902
0.8506 High Similarity NPC226108
0.8506 High Similarity NPC44192
0.8506 High Similarity NPC272552
0.8506 High Similarity NPC46283
0.8506 High Similarity NPC322899
0.8506 High Similarity NPC134911
0.8506 High Similarity NPC469944
0.8483 Intermediate Similarity NPC476615
0.8483 Intermediate Similarity NPC476617
0.8483 Intermediate Similarity NPC476616
0.8481 Intermediate Similarity NPC1253
0.8481 Intermediate Similarity NPC100936
0.8477 Intermediate Similarity NPC14468
0.8477 Intermediate Similarity NPC471608
0.8472 Intermediate Similarity NPC321086
0.8472 Intermediate Similarity NPC469611
0.8467 Intermediate Similarity NPC177597
0.8467 Intermediate Similarity NPC475492
0.8446 Intermediate Similarity NPC273623
0.8425 Intermediate Similarity NPC137580
0.8421 Intermediate Similarity NPC111134
0.8421 Intermediate Similarity NPC15538
0.8421 Intermediate Similarity NPC112819
0.8421 Intermediate Similarity NPC473480
0.8421 Intermediate Similarity NPC133209
0.8421 Intermediate Similarity NPC6702
0.84 Intermediate Similarity NPC472451
0.8389 Intermediate Similarity NPC257095
0.8389 Intermediate Similarity NPC89686
0.8389 Intermediate Similarity NPC273932
0.8389 Intermediate Similarity NPC5155
0.8387 Intermediate Similarity NPC474442
0.8387 Intermediate Similarity NPC120633
0.8387 Intermediate Similarity NPC473018
0.838 Intermediate Similarity NPC473134
0.8377 Intermediate Similarity NPC472709
0.8377 Intermediate Similarity NPC218801
0.8377 Intermediate Similarity NPC183380
0.8377 Intermediate Similarity NPC472710
0.8366 Intermediate Similarity NPC280945
0.8344 Intermediate Similarity NPC470206
0.8344 Intermediate Similarity NPC470207
0.8333 Intermediate Similarity NPC49542
0.8333 Intermediate Similarity NPC78809
0.8333 Intermediate Similarity NPC5253
0.8333 Intermediate Similarity NPC139976
0.8333 Intermediate Similarity NPC20050
0.8333 Intermediate Similarity NPC230718
0.8333 Intermediate Similarity NPC128337
0.8333 Intermediate Similarity NPC224161
0.8333 Intermediate Similarity NPC84207
0.8333 Intermediate Similarity NPC306267
0.8313 Intermediate Similarity NPC48880
0.8312 Intermediate Similarity NPC44452
0.8312 Intermediate Similarity NPC107862
0.8312 Intermediate Similarity NPC180605
0.8312 Intermediate Similarity NPC148516
0.8312 Intermediate Similarity NPC177172
0.8312 Intermediate Similarity NPC321657
0.8312 Intermediate Similarity NPC318373
0.8312 Intermediate Similarity NPC122980
0.8311 Intermediate Similarity NPC87777
0.8311 Intermediate Similarity NPC472646
0.8311 Intermediate Similarity NPC71465
0.8311 Intermediate Similarity NPC262328
0.8311 Intermediate Similarity NPC134260
0.8299 Intermediate Similarity NPC11727
0.8299 Intermediate Similarity NPC125579
0.8299 Intermediate Similarity NPC15109
0.8299 Intermediate Similarity NPC37410
0.8289 Intermediate Similarity NPC161700
0.8289 Intermediate Similarity NPC277867
0.8289 Intermediate Similarity NPC149633
0.828 Intermediate Similarity NPC46335
0.8278 Intermediate Similarity NPC37793
0.8276 Intermediate Similarity NPC473309
0.8276 Intermediate Similarity NPC271945
0.8276 Intermediate Similarity NPC472590
0.8276 Intermediate Similarity NPC181497
0.8276 Intermediate Similarity NPC160623
0.8276 Intermediate Similarity NPC471517
0.8276 Intermediate Similarity NPC282508
0.8269 Intermediate Similarity NPC325860
0.8269 Intermediate Similarity NPC279406
0.8269 Intermediate Similarity NPC226809
0.8267 Intermediate Similarity NPC108674
0.8267 Intermediate Similarity NPC265075
0.8267 Intermediate Similarity NPC100482
0.8267 Intermediate Similarity NPC277331
0.8267 Intermediate Similarity NPC472791
0.8267 Intermediate Similarity NPC472792
0.8264 Intermediate Similarity NPC96719
0.8264 Intermediate Similarity NPC222108
0.8264 Intermediate Similarity NPC93962
0.8258 Intermediate Similarity NPC477612
0.8247 Intermediate Similarity NPC179809
0.8247 Intermediate Similarity NPC270751
0.8243 Intermediate Similarity NPC170328
0.8243 Intermediate Similarity NPC138350
0.8243 Intermediate Similarity NPC197723
0.8243 Intermediate Similarity NPC165482
0.8243 Intermediate Similarity NPC3293
0.8243 Intermediate Similarity NPC133463
0.8243 Intermediate Similarity NPC472648
0.8243 Intermediate Similarity NPC472647
0.8243 Intermediate Similarity NPC472649
0.8243 Intermediate Similarity NPC472800
0.8243 Intermediate Similarity NPC191462
0.8243 Intermediate Similarity NPC141717
0.8243 Intermediate Similarity NPC206525
0.8243 Intermediate Similarity NPC40664
0.8239 Intermediate Similarity NPC293801
0.8235 Intermediate Similarity NPC96576
0.8235 Intermediate Similarity NPC125755
0.8224 Intermediate Similarity NPC76176
0.8224 Intermediate Similarity NPC473108
0.8224 Intermediate Similarity NPC138227
0.8224 Intermediate Similarity NPC164183
0.8224 Intermediate Similarity NPC168579
0.8224 Intermediate Similarity NPC473845
0.8224 Intermediate Similarity NPC469313
0.8224 Intermediate Similarity NPC133251
0.8219 Intermediate Similarity NPC472798
0.8212 Intermediate Similarity NPC472353
0.8212 Intermediate Similarity NPC186033
0.8207 Intermediate Similarity NPC27187
0.8207 Intermediate Similarity NPC470225
0.8207 Intermediate Similarity NPC254000
0.8205 Intermediate Similarity NPC105073
0.8205 Intermediate Similarity NPC233886
0.8205 Intermediate Similarity NPC224528
0.8205 Intermediate Similarity NPC157081
0.8205 Intermediate Similarity NPC302915
0.8194 Intermediate Similarity NPC53986
0.8194 Intermediate Similarity NPC38664
0.8194 Intermediate Similarity NPC215300
0.8194 Intermediate Similarity NPC223912
0.8194 Intermediate Similarity NPC211561
0.8182 Intermediate Similarity NPC231712
0.8182 Intermediate Similarity NPC262911
0.8182 Intermediate Similarity NPC294558
0.8182 Intermediate Similarity NPC204770
0.8182 Intermediate Similarity NPC242774
0.8182 Intermediate Similarity NPC237546
0.8182 Intermediate Similarity NPC170103

  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 NPC470208 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
0.8462 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD4908 Phase 1
0.8146 Intermediate Similarity NPD6674 Discontinued
0.8138 Intermediate Similarity NPD4625 Phase 3
0.7975 Intermediate Similarity NPD6959 Discontinued
0.7959 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7952 Intermediate Similarity NPD7228 Approved
0.7847 Intermediate Similarity NPD4749 Approved
0.7832 Intermediate Similarity NPD1610 Phase 2
0.7716 Intermediate Similarity NPD8455 Phase 2
0.7674 Intermediate Similarity NPD8312 Approved
0.7674 Intermediate Similarity NPD8313 Approved
0.7669 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD37 Approved
0.7636 Intermediate Similarity NPD6234 Discontinued
0.7622 Intermediate Similarity NPD4966 Approved
0.7622 Intermediate Similarity NPD4965 Approved
0.7622 Intermediate Similarity NPD4967 Phase 2
0.7588 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7558 Intermediate Similarity NPD7240 Approved
0.7544 Intermediate Similarity NPD7074 Phase 3
0.7517 Intermediate Similarity NPD2861 Phase 2
0.75 Intermediate Similarity NPD7819 Suspended
0.75 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1613 Approved
0.7484 Intermediate Similarity NPD6100 Approved
0.7484 Intermediate Similarity NPD6099 Approved
0.7457 Intermediate Similarity NPD6559 Discontinued
0.744 Intermediate Similarity NPD7199 Phase 2
0.7438 Intermediate Similarity NPD7447 Phase 1
0.7431 Intermediate Similarity NPD1548 Phase 1
0.7405 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4060 Phase 1
0.7384 Intermediate Similarity NPD5844 Phase 1
0.7384 Intermediate Similarity NPD7054 Approved
0.7375 Intermediate Similarity NPD7213 Phase 3
0.7375 Intermediate Similarity NPD7212 Phase 2
0.7353 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD7472 Approved
0.7338 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD5124 Phase 1
0.7329 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD6696 Suspended
0.7314 Intermediate Similarity NPD7808 Phase 3
0.7308 Intermediate Similarity NPD4108 Discontinued
0.7305 Intermediate Similarity NPD7768 Phase 2
0.7278 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD7041 Phase 2
0.7267 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7263 Intermediate Similarity NPD7783 Phase 2
0.7262 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD7251 Discontinued
0.7256 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD1091 Approved
0.7209 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD6797 Phase 2
0.7195 Intermediate Similarity NPD1653 Approved
0.7193 Intermediate Similarity NPD7229 Phase 3
0.719 Intermediate Similarity NPD3027 Phase 3
0.7172 Intermediate Similarity NPD7340 Approved
0.7169 Intermediate Similarity NPD7411 Suspended
0.7168 Intermediate Similarity NPD7473 Discontinued
0.7166 Intermediate Similarity NPD7680 Approved
0.7158 Intermediate Similarity NPD8151 Discontinued
0.7143 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7097 Phase 1
0.7133 Intermediate Similarity NPD5327 Phase 3
0.7119 Intermediate Similarity NPD8453 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD5735 Approved
0.711 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD6166 Phase 2
0.711 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD7266 Discontinued
0.7093 Intermediate Similarity NPD6232 Discontinued
0.7083 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD3750 Approved
0.7081 Intermediate Similarity NPD7466 Approved
0.707 Intermediate Similarity NPD4097 Suspended
0.7066 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD7075 Discontinued
0.7051 Intermediate Similarity NPD4140 Approved
0.7012 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5762 Approved
0.7 Intermediate Similarity NPD5763 Approved
0.6994 Remote Similarity NPD3787 Discontinued
0.6984 Remote Similarity NPD7696 Phase 3
0.6984 Remote Similarity NPD7697 Approved
0.6984 Remote Similarity NPD7698 Approved
0.698 Remote Similarity NPD4626 Approved
0.6978 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6975 Remote Similarity NPD3892 Phase 2
0.6974 Remote Similarity NPD8651 Approved
0.6966 Remote Similarity NPD1398 Phase 1
0.6962 Remote Similarity NPD6353 Approved
0.6957 Remote Similarity NPD7037 Approved
0.6947 Remote Similarity NPD7870 Phase 2
0.6947 Remote Similarity NPD7871 Phase 2
0.6946 Remote Similarity NPD7458 Discontinued
0.6946 Remote Similarity NPD8158 Clinical (unspecified phase)
0.6944 Remote Similarity NPD8053 Approved
0.6944 Remote Similarity NPD8054 Approved
0.6932 Remote Similarity NPD3818 Discontinued
0.6923 Remote Similarity NPD4750 Phase 3
0.6923 Remote Similarity NPD6812 Clinical (unspecified phase)
0.6913 Remote Similarity NPD5691 Approved
0.6909 Remote Similarity NPD2532 Approved
0.6909 Remote Similarity NPD2534 Approved
0.6909 Remote Similarity NPD2533 Approved
0.6909 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6909 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6906 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6905 Remote Similarity NPD4380 Phase 2
0.6894 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6894 Remote Similarity NPD1552 Clinical (unspecified phase)
0.689 Remote Similarity NPD5058 Phase 3
0.6887 Remote Similarity NPD422 Phase 1
0.6887 Remote Similarity NPD3705 Approved
0.6883 Remote Similarity NPD6584 Phase 3
0.6882 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6882 Remote Similarity NPD1465 Phase 2
0.6871 Remote Similarity NPD7003 Approved
0.6871 Remote Similarity NPD6671 Approved
0.6867 Remote Similarity NPD5126 Approved
0.6867 Remote Similarity NPD5125 Phase 3
0.6852 Remote Similarity NPD1549 Phase 2
0.6852 Remote Similarity NPD970 Clinical (unspecified phase)
0.6851 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6848 Remote Similarity NPD7390 Discontinued
0.6842 Remote Similarity NPD6823 Phase 2
0.6839 Remote Similarity NPD7701 Phase 2
0.6836 Remote Similarity NPD3751 Discontinued
0.6835 Remote Similarity NPD3620 Phase 2
0.6835 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6833 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6825 Remote Similarity NPD6782 Approved
0.6825 Remote Similarity NPD6777 Approved
0.6825 Remote Similarity NPD6781 Approved
0.6825 Remote Similarity NPD6780 Approved
0.6825 Remote Similarity NPD6778 Approved
0.6825 Remote Similarity NPD6779 Approved
0.6825 Remote Similarity NPD6776 Approved
0.6824 Remote Similarity NPD1934 Approved
0.6813 Remote Similarity NPD4978 Clinical (unspecified phase)
0.681 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6806 Remote Similarity NPD7435 Discontinued
0.6798 Remote Similarity NPD8156 Discontinued
0.6782 Remote Similarity NPD5494 Approved
0.6776 Remote Similarity NPD1611 Approved
0.6771 Remote Similarity NPD8319 Approved
0.6771 Remote Similarity NPD8320 Phase 1
0.677 Remote Similarity NPD3748 Approved
0.6766 Remote Similarity NPD6090 Discontinued
0.6763 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6763 Remote Similarity NPD3749 Approved
0.6753 Remote Similarity NPD1283 Approved
0.6746 Remote Similarity NPD3226 Approved
0.6742 Remote Similarity NPD8251 Approved
0.6742 Remote Similarity NPD8099 Discontinued
0.6742 Remote Similarity NPD8252 Approved
0.674 Remote Similarity NPD7549 Discontinued
0.6735 Remote Similarity NPD7801 Approved
0.6731 Remote Similarity NPD3018 Phase 2
0.6728 Remote Similarity NPD2438 Suspended
0.6725 Remote Similarity NPD6801 Discontinued
0.6724 Remote Similarity NPD5709 Phase 3
0.672 Remote Similarity NPD7700 Phase 2
0.672 Remote Similarity NPD7699 Phase 2
0.6709 Remote Similarity NPD7985 Registered
0.6709 Remote Similarity NPD7294 Phase 1
0.6709 Remote Similarity NPD6798 Discontinued
0.6709 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6708 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6708 Remote Similarity NPD4536 Approved
0.6708 Remote Similarity NPD4538 Approved
0.6708 Remote Similarity NPD7119 Phase 2
0.6688 Remote Similarity NPD6582 Phase 2
0.6688 Remote Similarity NPD6583 Phase 3
0.6687 Remote Similarity NPD6355 Discontinued
0.6687 Remote Similarity NPD6666 Approved
0.6687 Remote Similarity NPD6667 Approved
0.6686 Remote Similarity NPD4666 Phase 3
0.6686 Remote Similarity NPD5929 Approved
0.6684 Remote Similarity NPD7874 Approved
0.6684 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6273 Approved
0.6667 Remote Similarity NPD4624 Approved
0.6667 Remote Similarity NPD8032 Phase 2
0.6667 Remote Similarity NPD2342 Discontinued
0.6667 Remote Similarity NPD7635 Approved
0.6667 Remote Similarity NPD7982 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7843 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