Structure

Physi-Chem Properties

Molecular Weight:  730.26
Volume:  738.26
LogP:  5.033
LogD:  4.047
LogS:  -4.275
# Rotatable Bonds:  20
TPSA:  179.67
# H-Bond Aceptor:  13
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  13

MedChem Properties

QED Drug-Likeness Score:  0.055
Synthetic Accessibility Score:  3.851
Fsp3:  0.25
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.35
MDCK Permeability:  6.046216003596783e-05
Pgp-inhibitor:  0.955
Pgp-substrate:  0.134
Human Intestinal Absorption (HIA):  0.043
20% Bioavailability (F20%):  0.991
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  100.52050018310547%
Volume Distribution (VD):  0.358
Pgp-substrate:  4.350338935852051%

ADMET: Metabolism

CYP1A2-inhibitor:  0.269
CYP1A2-substrate:  0.935
CYP2C19-inhibitor:  0.827
CYP2C19-substrate:  0.152
CYP2C9-inhibitor:  0.883
CYP2C9-substrate:  0.964
CYP2D6-inhibitor:  0.59
CYP2D6-substrate:  0.935
CYP3A4-inhibitor:  0.838
CYP3A4-substrate:  0.893

ADMET: Excretion

Clearance (CL):  11.05
Half-life (T1/2):  0.9

ADMET: Toxicity

hERG Blockers:  0.59
Human Hepatotoxicity (H-HT):  0.142
Drug-inuced Liver Injury (DILI):  0.102
AMES Toxicity:  0.254
Rat Oral Acute Toxicity:  0.056
Maximum Recommended Daily Dose:  0.841
Skin Sensitization:  0.97
Carcinogencity:  0.127
Eye Corrosion:  0.003
Eye Irritation:  0.019
Respiratory Toxicity:  0.113

Download Data

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

  Natural Product: NPC143120

Natural Product ID:  NPC143120
Common Name*:   Threo-Carolignan E
IUPAC Name:   3-[4-[(1S,2S)-1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxypropan-2-yl]oxy-3-methoxyphenyl]propyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:  
Standard InCHIKey:  CXFBVHGWTGTGBR-QYQWMRSMSA-N
Standard InCHI:  InChI=1S/C40H42O13/c1-47-33-20-26(7-13-29(33)41)10-17-38(44)51-19-5-6-25-9-16-32(36(22-25)50-4)53-37(40(46)28-12-15-31(43)35(23-28)49-3)24-52-39(45)18-11-27-8-14-30(42)34(21-27)48-2/h7-18,20-23,37,40-43,46H,5-6,19,24H2,1-4H3/b17-10+,18-11+/t37-,40-/m0/s1
SMILES:  COc1cc(ccc1O)/C=C/C(=O)OCCCc1ccc(c(c1)OC)O[C@@H](COC(=O)/C=C/c1ccc(c(c1)OC)O)[C@H](c1ccc(c(c1)OC)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3589244
PubChem CID:   5274622
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO13813 Durio carinatus Species Malvaceae Eukaryota n.a. stem n.a. DOI[10.1021/np100332v]
NPO18913 Hibiscus ficulneus Species Malvaceae Eukaryota n.a. n.a. n.a. PMID[26026364]
NPO23035 Clematis montana Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22589 Clematis armandii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13813 Durio carinatus Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18913 Hibiscus ficulneus Species Malvaceae 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
NPT71 Cell Line HEK293 Homo sapiens IC50 = 6300.0 nM PMID[492898]
NPT71 Cell Line HEK293 Homo sapiens IC50 = 26400.0 nM PMID[492898]
NPT2170 Cell Line RKO Homo sapiens IC50 = 36100.0 nM PMID[492898]
NPT660 Cell Line SW480 Homo sapiens IC50 > 40000.0 nM PMID[492898]
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 40000.0 nM PMID[492898]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 40000.0 nM PMID[492898]

☑ 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 NPC143120 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 NPC274960
1.0 High Similarity NPC473909
0.9716 High Similarity NPC475250
0.9348 High Similarity NPC126206
0.9315 High Similarity NPC115203
0.9275 High Similarity NPC471665
0.9275 High Similarity NPC471664
0.927 High Similarity NPC135127
0.9252 High Similarity NPC469888
0.9214 High Similarity NPC106055
0.9214 High Similarity NPC110699
0.9085 High Similarity NPC67467
0.9073 High Similarity NPC476373
0.9067 High Similarity NPC125495
0.9048 High Similarity NPC85192
0.9048 High Similarity NPC125823
0.9048 High Similarity NPC7145
0.9048 High Similarity NPC143480
0.9028 High Similarity NPC34927
0.9028 High Similarity NPC252292
0.9028 High Similarity NPC100998
0.9028 High Similarity NPC34587
0.9028 High Similarity NPC476382
0.9021 High Similarity NPC478239
0.9014 High Similarity NPC470372
0.9013 High Similarity NPC7191
0.9013 High Similarity NPC149873
0.9 High Similarity NPC120852
0.9 High Similarity NPC11411
0.8993 High Similarity NPC237594
0.8993 High Similarity NPC249791
0.8993 High Similarity NPC476387
0.8993 High Similarity NPC119060
0.8986 High Similarity NPC478268
0.898 High Similarity NPC476871
0.8973 High Similarity NPC80732
0.8973 High Similarity NPC199311
0.8973 High Similarity NPC192763
0.8973 High Similarity NPC3460
0.8973 High Similarity NPC215095
0.8973 High Similarity NPC201148
0.8973 High Similarity NPC261122
0.8973 High Similarity NPC210611
0.8973 High Similarity NPC300262
0.8973 High Similarity NPC187398
0.8973 High Similarity NPC252402
0.8973 High Similarity NPC476348
0.8973 High Similarity NPC102934
0.8973 High Similarity NPC28651
0.8966 High Similarity NPC40222
0.8966 High Similarity NPC268515
0.8966 High Similarity NPC476865
0.8954 High Similarity NPC476371
0.8954 High Similarity NPC476372
0.8951 High Similarity NPC140502
0.8951 High Similarity NPC157816
0.8929 High Similarity NPC214729
0.8919 High Similarity NPC300329
0.8912 High Similarity NPC476386
0.8912 High Similarity NPC106138
0.8912 High Similarity NPC473427
0.8912 High Similarity NPC259347
0.8912 High Similarity NPC476398
0.8912 High Similarity NPC306890
0.8912 High Similarity NPC94871
0.8912 High Similarity NPC471062
0.8912 High Similarity NPC470933
0.8905 High Similarity NPC83062
0.8904 High Similarity NPC232992
0.8904 High Similarity NPC476347
0.8897 High Similarity NPC476866
0.8897 High Similarity NPC476869
0.8897 High Similarity NPC476868
0.8897 High Similarity NPC476864
0.8882 High Similarity NPC478269
0.8881 High Similarity NPC186406
0.8874 High Similarity NPC470896
0.8874 High Similarity NPC473275
0.8873 High Similarity NPC260842
0.8865 High Similarity NPC471719
0.8859 High Similarity NPC163598
0.8859 High Similarity NPC264875
0.8859 High Similarity NPC120774
0.8851 High Similarity NPC470927
0.8851 High Similarity NPC205727
0.8851 High Similarity NPC120426
0.8851 High Similarity NPC21184
0.8851 High Similarity NPC259576
0.8851 High Similarity NPC470934
0.8851 High Similarity NPC294522
0.8851 High Similarity NPC257970
0.8851 High Similarity NPC221091
0.8851 High Similarity NPC188393
0.8836 High Similarity NPC199928
0.8828 High Similarity NPC476867
0.8828 High Similarity NPC160378
0.8828 High Similarity NPC232228
0.8819 High Similarity NPC193722
0.8819 High Similarity NPC278469
0.8816 High Similarity NPC470827
0.8811 High Similarity NPC267291
0.8803 High Similarity NPC474390
0.8784 High Similarity NPC176903
0.8784 High Similarity NPC30688
0.8782 High Similarity NPC59516
0.8768 High Similarity NPC86030
0.8768 High Similarity NPC5851
0.8767 High Similarity NPC163898
0.8767 High Similarity NPC287615
0.8767 High Similarity NPC216819
0.8767 High Similarity NPC262182
0.8767 High Similarity NPC83743
0.8766 High Similarity NPC216916
0.8766 High Similarity NPC478267
0.8759 High Similarity NPC118787
0.8759 High Similarity NPC147821
0.8759 High Similarity NPC319625
0.8759 High Similarity NPC111247
0.8759 High Similarity NPC41706
0.8759 High Similarity NPC163332
0.8759 High Similarity NPC292056
0.8759 High Similarity NPC183181
0.8758 High Similarity NPC470828
0.875 High Similarity NPC83375
0.875 High Similarity NPC224876
0.8741 High Similarity NPC100389
0.8733 High Similarity NPC289967
0.8733 High Similarity NPC472611
0.8733 High Similarity NPC472612
0.8732 High Similarity NPC77861
0.8723 High Similarity NPC309744
0.8716 High Similarity NPC226153
0.8716 High Similarity NPC472969
0.8716 High Similarity NPC304048
0.8699 High Similarity NPC292443
0.8699 High Similarity NPC110063
0.8696 High Similarity NPC72529
0.8686 High Similarity NPC120225
0.8686 High Similarity NPC191037
0.8686 High Similarity NPC178284
0.8686 High Similarity NPC213552
0.8686 High Similarity NPC58607
0.8684 High Similarity NPC131532
0.8681 High Similarity NPC262189
0.8681 High Similarity NPC266197
0.8681 High Similarity NPC202700
0.8681 High Similarity NPC22317
0.8681 High Similarity NPC291101
0.8675 High Similarity NPC475141
0.8671 High Similarity NPC138738
0.8671 High Similarity NPC470413
0.8662 High Similarity NPC93783
0.8658 High Similarity NPC470826
0.8658 High Similarity NPC473266
0.8658 High Similarity NPC98809
0.8658 High Similarity NPC476394
0.8658 High Similarity NPC470098
0.8654 High Similarity NPC45943
0.8649 High Similarity NPC15577
0.8649 High Similarity NPC99183
0.8639 High Similarity NPC138915
0.8621 High Similarity NPC476385
0.8621 High Similarity NPC476377
0.8621 High Similarity NPC134405
0.8621 High Similarity NPC47471
0.8618 High Similarity NPC473736
0.8613 High Similarity NPC194519
0.8613 High Similarity NPC289459
0.8611 High Similarity NPC89105
0.8611 High Similarity NPC81515
0.8611 High Similarity NPC476383
0.8611 High Similarity NPC68092
0.8611 High Similarity NPC64141
0.8611 High Similarity NPC472350
0.8611 High Similarity NPC22517
0.8611 High Similarity NPC197316
0.8601 High Similarity NPC37468
0.8601 High Similarity NPC471988
0.8601 High Similarity NPC186418
0.8601 High Similarity NPC157554
0.86 High Similarity NPC477612
0.8592 High Similarity NPC111635
0.8592 High Similarity NPC67247
0.8592 High Similarity NPC170694
0.8591 High Similarity NPC478237
0.8591 High Similarity NPC281549
0.859 High Similarity NPC12326
0.8582 High Similarity NPC7903
0.8582 High Similarity NPC16208
0.8582 High Similarity NPC184447
0.8582 High Similarity NPC35932
0.8582 High Similarity NPC160991
0.8581 High Similarity NPC241846
0.8581 High Similarity NPC93610
0.8571 High Similarity NPC133984
0.8571 High Similarity NPC28440
0.8571 High Similarity NPC171932
0.8571 High Similarity NPC471876
0.8562 High Similarity NPC473873
0.8562 High Similarity NPC473792

  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 NPC143120 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
0.8611 High Similarity NPD7266 Discontinued
0.8269 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD3027 Phase 3
0.817 Intermediate Similarity NPD1653 Approved
0.811 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8069 Intermediate Similarity NPD1613 Approved
0.8069 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD6190 Approved
0.795 Intermediate Similarity NPD8127 Discontinued
0.7943 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD6166 Phase 2
0.7914 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD8455 Phase 2
0.7793 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD7054 Approved
0.7771 Intermediate Similarity NPD5844 Phase 1
0.7755 Intermediate Similarity NPD6233 Phase 2
0.7738 Intermediate Similarity NPD7685 Pre-registration
0.7736 Intermediate Similarity NPD1934 Approved
0.7733 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD7472 Approved
0.7725 Intermediate Similarity NPD7074 Phase 3
0.7724 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD4628 Phase 3
0.7661 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD3817 Phase 2
0.7619 Intermediate Similarity NPD7095 Approved
0.7607 Intermediate Similarity NPD6234 Discontinued
0.7605 Intermediate Similarity NPD7228 Approved
0.7605 Intermediate Similarity NPD3818 Discontinued
0.7597 Intermediate Similarity NPD8166 Discontinued
0.7593 Intermediate Similarity NPD7768 Phase 2
0.7588 Intermediate Similarity NPD7808 Phase 3
0.7588 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD4060 Phase 1
0.7578 Intermediate Similarity NPD2801 Approved
0.7578 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD6798 Discontinued
0.7551 Intermediate Similarity NPD4908 Phase 1
0.755 Intermediate Similarity NPD7097 Phase 1
0.7544 Intermediate Similarity NPD8313 Approved
0.7544 Intermediate Similarity NPD8312 Approved
0.7533 Intermediate Similarity NPD4340 Discontinued
0.7532 Intermediate Similarity NPD6674 Discontinued
0.7529 Intermediate Similarity NPD7251 Discontinued
0.7518 Intermediate Similarity NPD228 Approved
0.7516 Intermediate Similarity NPD37 Approved
0.7515 Intermediate Similarity NPD7199 Phase 2
0.7485 Intermediate Similarity NPD4965 Approved
0.7485 Intermediate Similarity NPD4966 Approved
0.7485 Intermediate Similarity NPD4967 Phase 2
0.7485 Intermediate Similarity NPD3882 Suspended
0.7471 Intermediate Similarity NPD6797 Phase 2
0.7469 Intermediate Similarity NPD1465 Phase 2
0.7464 Intermediate Similarity NPD7843 Approved
0.745 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD5536 Phase 2
0.7439 Intermediate Similarity NPD7075 Discontinued
0.7427 Intermediate Similarity NPD7038 Approved
0.7427 Intermediate Similarity NPD7039 Approved
0.7423 Intermediate Similarity NPD5402 Approved
0.7421 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD1652 Phase 2
0.7419 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD7549 Discontinued
0.7375 Intermediate Similarity NPD3687 Approved
0.7375 Intermediate Similarity NPD3686 Approved
0.7368 Intermediate Similarity NPD6653 Approved
0.7365 Intermediate Similarity NPD2861 Phase 2
0.7365 Intermediate Similarity NPD6232 Discontinued
0.7361 Intermediate Similarity NPD3496 Discontinued
0.7351 Intermediate Similarity NPD1558 Phase 1
0.7351 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD3620 Phase 2
0.7342 Intermediate Similarity NPD1511 Approved
0.7338 Intermediate Similarity NPD5535 Approved
0.7337 Intermediate Similarity NPD7473 Discontinued
0.7333 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD5403 Approved
0.731 Intermediate Similarity NPD422 Phase 1
0.7305 Intermediate Similarity NPD7157 Approved
0.7303 Intermediate Similarity NPD230 Phase 1
0.7303 Intermediate Similarity NPD6355 Discontinued
0.7303 Intermediate Similarity NPD5124 Phase 1
0.7303 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD5763 Approved
0.729 Intermediate Similarity NPD5762 Approved
0.7286 Intermediate Similarity NPD5283 Phase 1
0.7284 Intermediate Similarity NPD4380 Phase 2
0.7278 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD4110 Phase 3
0.7261 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7256 Intermediate Similarity NPD7819 Suspended
0.725 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD6273 Approved
0.725 Intermediate Similarity NPD1512 Approved
0.7239 Intermediate Similarity NPD7411 Suspended
0.7237 Intermediate Similarity NPD4140 Approved
0.7226 Intermediate Similarity NPD1358 Approved
0.7225 Intermediate Similarity NPD6559 Discontinued
0.7212 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD2983 Phase 2
0.7211 Intermediate Similarity NPD2982 Phase 2
0.7208 Intermediate Similarity NPD4536 Approved
0.7208 Intermediate Similarity NPD4538 Approved
0.7208 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD6801 Discontinued
0.7192 Intermediate Similarity NPD1091 Approved
0.7192 Intermediate Similarity NPD3705 Approved
0.719 Intermediate Similarity NPD447 Suspended
0.7188 Intermediate Similarity NPD5401 Approved
0.7188 Intermediate Similarity NPD7446 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD6584 Phase 3
0.7174 Intermediate Similarity NPD2684 Approved
0.7172 Intermediate Similarity NPD5846 Approved
0.7172 Intermediate Similarity NPD6516 Phase 2
0.7171 Intermediate Similarity NPD4062 Phase 3
0.7162 Intermediate Similarity NPD3225 Approved
0.7162 Intermediate Similarity NPD8651 Approved
0.7161 Intermediate Similarity NPD7033 Discontinued
0.7153 Intermediate Similarity NPD1548 Phase 1
0.7152 Intermediate Similarity NPD3750 Approved
0.7151 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2981 Phase 2
0.7134 Intermediate Similarity NPD6386 Approved
0.7134 Intermediate Similarity NPD6385 Approved
0.7133 Intermediate Similarity NPD9494 Approved
0.7133 Intermediate Similarity NPD3018 Phase 2
0.7126 Intermediate Similarity NPD7240 Approved
0.7125 Intermediate Similarity NPD6799 Approved
0.7117 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD2935 Discontinued
0.7103 Intermediate Similarity NPD1357 Approved
0.7101 Intermediate Similarity NPD6959 Discontinued
0.7091 Intermediate Similarity NPD7945 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD3060 Approved
0.7081 Intermediate Similarity NPD3536 Discontinued
0.7078 Intermediate Similarity NPD5735 Approved
0.7075 Intermediate Similarity NPD1610 Phase 2
0.7063 Intermediate Similarity NPD7440 Discontinued
0.7063 Intermediate Similarity NPD5058 Phase 3
0.7056 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD5960 Phase 3
0.7051 Intermediate Similarity NPD5588 Approved
0.7048 Intermediate Similarity NPD6818 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD5494 Approved
0.7029 Intermediate Similarity NPD3134 Approved
0.7027 Intermediate Similarity NPD1608 Approved
0.7019 Intermediate Similarity NPD4357 Discontinued
0.7012 Intermediate Similarity NPD3455 Phase 2
0.7006 Intermediate Similarity NPD6032 Approved
0.7006 Intermediate Similarity NPD8054 Approved
0.7006 Intermediate Similarity NPD8053 Approved
0.7 Intermediate Similarity NPD2797 Approved
0.7 Intermediate Similarity NPD3021 Approved
0.7 Intermediate Similarity NPD3022 Approved
0.6994 Remote Similarity NPD3751 Discontinued
0.6993 Remote Similarity NPD3764 Approved
0.6986 Remote Similarity NPD5585 Approved
0.6981 Remote Similarity NPD4236 Phase 3
0.6981 Remote Similarity NPD4237 Approved
0.6981 Remote Similarity NPD4162 Approved
0.698 Remote Similarity NPD6583 Phase 3
0.698 Remote Similarity NPD6582 Phase 2
0.6978 Remote Similarity NPD290 Approved
0.6975 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6975 Remote Similarity NPD4123 Phase 3
0.6974 Remote Similarity NPD6832 Phase 2
0.6974 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1933 Approved
0.6959 Remote Similarity NPD3787 Discontinued
0.6959 Remote Similarity NPD1535 Discovery
0.6952 Remote Similarity NPD7680 Approved
0.6946 Remote Similarity NPD2977 Approved
0.6946 Remote Similarity NPD2978 Approved
0.6944 Remote Similarity NPD6671 Approved
0.6939 Remote Similarity NPD1778 Approved
0.6939 Remote Similarity NPD4626 Approved
0.6933 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6927 Remote Similarity NPD8434 Phase 2
0.6923 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6971 Discontinued
0.6918 Remote Similarity NPD2424 Discontinued
0.6918 Remote Similarity NPD1549 Phase 2
0.6918 Remote Similarity NPD1894 Discontinued
0.6913 Remote Similarity NPD1481 Phase 2
0.6909 Remote Similarity NPD7458 Discontinued
0.6909 Remote Similarity NPD3226 Approved
0.6906 Remote Similarity NPD968 Approved
0.6905 Remote Similarity NPD6374 Clinical (unspecified phase)
0.6903 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6899 Remote Similarity NPD1551 Phase 2

  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