Structure

Physi-Chem Properties

Molecular Weight:  332.2
Volume:  353.422
LogP:  2.698
LogD:  2.739
LogS:  -4.108
# Rotatable Bonds:  2
TPSA:  71.44
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.623
Synthetic Accessibility Score:  4.632
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.908
MDCK Permeability:  2.5794530301936902e-05
Pgp-inhibitor:  0.487
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.524
30% Bioavailability (F30%):  0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.065
Plasma Protein Binding (PPB):  81.4127197265625%
Volume Distribution (VD):  0.501
Pgp-substrate:  12.161688804626465%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.725
CYP2C19-inhibitor:  0.21
CYP2C19-substrate:  0.698
CYP2C9-inhibitor:  0.174
CYP2C9-substrate:  0.288
CYP2D6-inhibitor:  0.008
CYP2D6-substrate:  0.114
CYP3A4-inhibitor:  0.767
CYP3A4-substrate:  0.573

ADMET: Excretion

Clearance (CL):  3.444
Half-life (T1/2):  0.827

ADMET: Toxicity

hERG Blockers:  0.002
Human Hepatotoxicity (H-HT):  0.178
Drug-inuced Liver Injury (DILI):  0.105
AMES Toxicity:  0.175
Rat Oral Acute Toxicity:  0.046
Maximum Recommended Daily Dose:  0.872
Skin Sensitization:  0.244
Carcinogencity:  0.118
Eye Corrosion:  0.041
Eye Irritation:  0.847
Respiratory Toxicity:  0.584

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

  Natural Product: NPC103486

Natural Product ID:  NPC103486
Common Name*:   Lonchophylloid A
IUPAC Name:   (4aR,4bS,7R,10aR)-3-hydroxy-7-(2-hydroxyacetyl)-1,1,4a,7-tetramethyl-4b,5,6,9,10,10a-hexahydrophenanthren-2-one
Synonyms:  
Standard InCHIKey:  JLXLDXALELIBKS-DZXDFRQDSA-N
Standard InCHI:  InChI=1S/C20H28O4/c1-18(2)15-6-5-12-9-19(3,16(23)11-21)8-7-13(12)20(15,4)10-14(22)17(18)24/h9-10,13,15,21-22H,5-8,11H2,1-4H3/t13-,15-,19+,20+/m0/s1
SMILES:  OCC(=O)[C@]1(C)CC[C@H]2C(=C1)CC[C@@H]1[C@]2(C)C=C(O)C(=O)C1(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL465959
PubChem CID:   10314714
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000258] Steroids and steroid derivatives
        • [CHEMONTID:0001194] Oxosteroids

*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
NPO2022 Ephemerantha lonchophylla n.a. n.a. n.a. n.a. n.a. n.a. PMID[10514302]
NPO2022 Ephemerantha lonchophylla n.a. n.a. n.a. n.a. n.a. n.a. PMID[9461658]
NPO2022 Ephemerantha lonchophylla n.a. n.a. n.a. 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
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens ED50 = 193.0 uM PMID[523564]

☑ 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 NPC103486 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
0.9359 High Similarity NPC55869
0.9231 High Similarity NPC108955
0.9136 High Similarity NPC263997
0.9136 High Similarity NPC8518
0.9136 High Similarity NPC132228
0.9114 High Similarity NPC116797
0.8961 High Similarity NPC470525
0.8902 High Similarity NPC32037
0.8902 High Similarity NPC241512
0.8902 High Similarity NPC6185
0.8875 High Similarity NPC225515
0.878 High Similarity NPC237712
0.875 High Similarity NPC2482
0.8736 High Similarity NPC23170
0.8734 High Similarity NPC30321
0.8734 High Similarity NPC62336
0.8734 High Similarity NPC189485
0.8718 High Similarity NPC92080
0.8718 High Similarity NPC263582
0.8675 High Similarity NPC474680
0.8659 High Similarity NPC105803
0.8659 High Similarity NPC53733
0.8642 High Similarity NPC474085
0.8642 High Similarity NPC121984
0.8625 High Similarity NPC27817
0.8625 High Similarity NPC472490
0.8608 High Similarity NPC476811
0.8605 High Similarity NPC129913
0.8571 High Similarity NPC94666
0.8571 High Similarity NPC472974
0.8571 High Similarity NPC327115
0.8554 High Similarity NPC473246
0.8554 High Similarity NPC476412
0.8537 High Similarity NPC48362
0.8519 High Similarity NPC472478
0.8506 High Similarity NPC99380
0.85 High Similarity NPC74410
0.8488 Intermediate Similarity NPC326627
0.8488 Intermediate Similarity NPC310010
0.8481 Intermediate Similarity NPC110725
0.8481 Intermediate Similarity NPC1254
0.8471 Intermediate Similarity NPC272039
0.8471 Intermediate Similarity NPC220930
0.8471 Intermediate Similarity NPC470523
0.8452 Intermediate Similarity NPC255174
0.8452 Intermediate Similarity NPC133652
0.8415 Intermediate Similarity NPC99308
0.8415 Intermediate Similarity NPC278459
0.8415 Intermediate Similarity NPC90055
0.8409 Intermediate Similarity NPC211230
0.8395 Intermediate Similarity NPC192329
0.8395 Intermediate Similarity NPC308038
0.8391 Intermediate Similarity NPC474209
0.8391 Intermediate Similarity NPC475823
0.8375 Intermediate Similarity NPC197659
0.8375 Intermediate Similarity NPC165711
0.8372 Intermediate Similarity NPC470524
0.8372 Intermediate Similarity NPC53454
0.8354 Intermediate Similarity NPC175079
0.8354 Intermediate Similarity NPC114236
0.8352 Intermediate Similarity NPC147954
0.8333 Intermediate Similarity NPC214043
0.8333 Intermediate Similarity NPC85774
0.8333 Intermediate Similarity NPC58841
0.8333 Intermediate Similarity NPC329043
0.8333 Intermediate Similarity NPC161423
0.8333 Intermediate Similarity NPC227064
0.8333 Intermediate Similarity NPC321187
0.8315 Intermediate Similarity NPC474882
0.8315 Intermediate Similarity NPC474328
0.8313 Intermediate Similarity NPC212083
0.8295 Intermediate Similarity NPC185936
0.8295 Intermediate Similarity NPC168027
0.8293 Intermediate Similarity NPC476809
0.8276 Intermediate Similarity NPC477973
0.8276 Intermediate Similarity NPC184663
0.8272 Intermediate Similarity NPC475994
0.8272 Intermediate Similarity NPC476808
0.8261 Intermediate Similarity NPC474720
0.8256 Intermediate Similarity NPC136548
0.8256 Intermediate Similarity NPC93778
0.825 Intermediate Similarity NPC26504
0.825 Intermediate Similarity NPC180886
0.8235 Intermediate Similarity NPC469948
0.8235 Intermediate Similarity NPC33663
0.8235 Intermediate Similarity NPC79573
0.8235 Intermediate Similarity NPC476426
0.8235 Intermediate Similarity NPC470574
0.8222 Intermediate Similarity NPC280725
0.8214 Intermediate Similarity NPC307258
0.8214 Intermediate Similarity NPC49019
0.8202 Intermediate Similarity NPC233118
0.8202 Intermediate Similarity NPC263780
0.8193 Intermediate Similarity NPC6663
0.8193 Intermediate Similarity NPC472684
0.8193 Intermediate Similarity NPC3915
0.8193 Intermediate Similarity NPC14151
0.8193 Intermediate Similarity NPC44963
0.8182 Intermediate Similarity NPC191684
0.8171 Intermediate Similarity NPC476177
0.8171 Intermediate Similarity NPC474113
0.8161 Intermediate Similarity NPC471722
0.8161 Intermediate Similarity NPC307298
0.8161 Intermediate Similarity NPC158778
0.8148 Intermediate Similarity NPC74995
0.8148 Intermediate Similarity NPC97377
0.814 Intermediate Similarity NPC145879
0.814 Intermediate Similarity NPC222613
0.814 Intermediate Similarity NPC51014
0.814 Intermediate Similarity NPC194417
0.814 Intermediate Similarity NPC474732
0.814 Intermediate Similarity NPC475022
0.814 Intermediate Similarity NPC118648
0.814 Intermediate Similarity NPC474778
0.814 Intermediate Similarity NPC472985
0.814 Intermediate Similarity NPC472986
0.814 Intermediate Similarity NPC229717
0.814 Intermediate Similarity NPC72133
0.814 Intermediate Similarity NPC474733
0.814 Intermediate Similarity NPC31564
0.814 Intermediate Similarity NPC20688
0.8118 Intermediate Similarity NPC53385
0.8118 Intermediate Similarity NPC144258
0.8111 Intermediate Similarity NPC196485
0.8111 Intermediate Similarity NPC245972
0.8095 Intermediate Similarity NPC151519
0.8095 Intermediate Similarity NPC310989
0.8095 Intermediate Similarity NPC93590
0.8095 Intermediate Similarity NPC302661
0.8095 Intermediate Similarity NPC238991
0.809 Intermediate Similarity NPC470036
0.809 Intermediate Similarity NPC19114
0.809 Intermediate Similarity NPC174167
0.809 Intermediate Similarity NPC472978
0.8072 Intermediate Similarity NPC45495
0.8072 Intermediate Similarity NPC18955
0.8072 Intermediate Similarity NPC172013
0.8068 Intermediate Similarity NPC275740
0.8068 Intermediate Similarity NPC474918
0.8068 Intermediate Similarity NPC472983
0.8068 Intermediate Similarity NPC86319
0.8068 Intermediate Similarity NPC5509
0.8068 Intermediate Similarity NPC31985
0.8068 Intermediate Similarity NPC477943
0.8068 Intermediate Similarity NPC474245
0.8068 Intermediate Similarity NPC112454
0.8068 Intermediate Similarity NPC472973
0.8068 Intermediate Similarity NPC119416
0.8068 Intermediate Similarity NPC65615
0.8068 Intermediate Similarity NPC123912
0.8068 Intermediate Similarity NPC1015
0.8068 Intermediate Similarity NPC68148
0.8049 Intermediate Similarity NPC59436
0.8049 Intermediate Similarity NPC275494
0.8049 Intermediate Similarity NPC476810
0.8049 Intermediate Similarity NPC471409
0.8046 Intermediate Similarity NPC58063
0.8046 Intermediate Similarity NPC472324
0.8046 Intermediate Similarity NPC475740
0.8025 Intermediate Similarity NPC250621
0.8023 Intermediate Similarity NPC474537
0.8023 Intermediate Similarity NPC469993
0.8023 Intermediate Similarity NPC474083
0.8022 Intermediate Similarity NPC147232
0.8 Intermediate Similarity NPC64600
0.8 Intermediate Similarity NPC291999
0.8 Intermediate Similarity NPC134826
0.8 Intermediate Similarity NPC102197
0.8 Intermediate Similarity NPC472930
0.8 Intermediate Similarity NPC474807
0.8 Intermediate Similarity NPC470299
0.8 Intermediate Similarity NPC250575
0.8 Intermediate Similarity NPC111323
0.8 Intermediate Similarity NPC297398
0.8 Intermediate Similarity NPC309309
0.8 Intermediate Similarity NPC147438
0.7978 Intermediate Similarity NPC46441
0.7978 Intermediate Similarity NPC113393
0.7978 Intermediate Similarity NPC85173
0.7976 Intermediate Similarity NPC136150
0.7976 Intermediate Similarity NPC189237
0.7976 Intermediate Similarity NPC471898
0.7976 Intermediate Similarity NPC473217
0.7955 Intermediate Similarity NPC206060
0.7955 Intermediate Similarity NPC58271
0.7955 Intermediate Similarity NPC328539
0.7955 Intermediate Similarity NPC472802
0.7955 Intermediate Similarity NPC230387
0.7955 Intermediate Similarity NPC473229
0.7955 Intermediate Similarity NPC131470
0.7955 Intermediate Similarity NPC72397
0.7955 Intermediate Similarity NPC143767
0.7955 Intermediate Similarity NPC471724
0.7952 Intermediate Similarity NPC152061
0.7952 Intermediate Similarity NPC7232
0.7952 Intermediate Similarity NPC476812
0.7952 Intermediate Similarity NPC475681
0.7952 Intermediate Similarity NPC19900
0.7935 Intermediate Similarity NPC96859
0.7935 Intermediate Similarity NPC117133

  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 NPC103486 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
0.9231 High Similarity NPD4695 Discontinued
0.8795 High Similarity NPD5279 Phase 3
0.8488 Intermediate Similarity NPD4753 Phase 2
0.8353 Intermediate Similarity NPD5690 Phase 2
0.8333 Intermediate Similarity NPD3666 Approved
0.8333 Intermediate Similarity NPD3665 Phase 1
0.8333 Intermediate Similarity NPD3133 Approved
0.8272 Intermediate Similarity NPD3617 Approved
0.8222 Intermediate Similarity NPD5210 Approved
0.8222 Intermediate Similarity NPD4629 Approved
0.814 Intermediate Similarity NPD4694 Approved
0.814 Intermediate Similarity NPD3618 Phase 1
0.814 Intermediate Similarity NPD5280 Approved
0.8132 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.8132 Intermediate Similarity NPD5222 Approved
0.8132 Intermediate Similarity NPD5221 Approved
0.8118 Intermediate Similarity NPD4197 Approved
0.8095 Intermediate Similarity NPD3667 Approved
0.8068 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.8043 Intermediate Similarity NPD5173 Approved
0.8023 Intermediate Similarity NPD5329 Approved
0.8022 Intermediate Similarity NPD5695 Phase 3
0.7935 Intermediate Similarity NPD4697 Phase 3
0.7907 Intermediate Similarity NPD4786 Approved
0.7889 Intermediate Similarity NPD6079 Approved
0.7889 Intermediate Similarity NPD7515 Phase 2
0.7882 Intermediate Similarity NPD4223 Phase 3
0.7882 Intermediate Similarity NPD4221 Approved
0.7872 Intermediate Similarity NPD5286 Approved
0.7872 Intermediate Similarity NPD5285 Approved
0.7872 Intermediate Similarity NPD4696 Approved
0.7865 Intermediate Similarity NPD5328 Approved
0.7849 Intermediate Similarity NPD6083 Phase 2
0.7849 Intermediate Similarity NPD6084 Phase 2
0.7849 Intermediate Similarity NPD4755 Approved
0.7789 Intermediate Similarity NPD5223 Approved
0.7753 Intermediate Similarity NPD6672 Approved
0.7753 Intermediate Similarity NPD5737 Approved
0.7727 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD5226 Approved
0.7708 Intermediate Similarity NPD5225 Approved
0.7708 Intermediate Similarity NPD5211 Phase 2
0.7708 Intermediate Similarity NPD4633 Approved
0.7708 Intermediate Similarity NPD5224 Approved
0.7684 Intermediate Similarity NPD4700 Approved
0.7647 Intermediate Similarity NPD8259 Clinical (unspecified phase)
0.7629 Intermediate Similarity NPD5175 Approved
0.7629 Intermediate Similarity NPD5174 Approved
0.7609 Intermediate Similarity NPD4202 Approved
0.7586 Intermediate Similarity NPD4788 Approved
0.7579 Intermediate Similarity NPD5696 Approved
0.7551 Intermediate Similarity NPD5141 Approved
0.7528 Intermediate Similarity NPD4623 Approved
0.7528 Intermediate Similarity NPD4519 Discontinued
0.7528 Intermediate Similarity NPD5205 Approved
0.7528 Intermediate Similarity NPD4689 Approved
0.7528 Intermediate Similarity NPD4690 Approved
0.7528 Intermediate Similarity NPD4688 Approved
0.7528 Intermediate Similarity NPD4693 Phase 3
0.7528 Intermediate Similarity NPD4138 Approved
0.7527 Intermediate Similarity NPD7748 Approved
0.75 Intermediate Similarity NPD5281 Approved
0.75 Intermediate Similarity NPD3668 Phase 3
0.75 Intermediate Similarity NPD5284 Approved
0.7449 Intermediate Similarity NPD4754 Approved
0.7419 Intermediate Similarity NPD5133 Approved
0.7407 Intermediate Similarity NPD4691 Approved
0.7403 Intermediate Similarity NPD2664 Clinical (unspecified phase)
0.74 Intermediate Similarity NPD5697 Approved
0.7391 Intermediate Similarity NPD4096 Approved
0.7391 Intermediate Similarity NPD5692 Phase 3
0.7333 Intermediate Similarity NPD7521 Approved
0.7333 Intermediate Similarity NPD7334 Approved
0.7333 Intermediate Similarity NPD5330 Approved
0.7333 Intermediate Similarity NPD7146 Approved
0.7333 Intermediate Similarity NPD6409 Approved
0.7333 Intermediate Similarity NPD6684 Approved
0.7327 Intermediate Similarity NPD5128 Approved
0.7327 Intermediate Similarity NPD4730 Approved
0.7327 Intermediate Similarity NPD6011 Approved
0.7327 Intermediate Similarity NPD5168 Approved
0.7327 Intermediate Similarity NPD6899 Approved
0.7327 Intermediate Similarity NPD6881 Approved
0.7327 Intermediate Similarity NPD4729 Approved
0.7326 Intermediate Similarity NPD4195 Approved
0.7317 Intermediate Similarity NPD5276 Approved
0.7312 Intermediate Similarity NPD5694 Approved
0.7312 Intermediate Similarity NPD6050 Approved
0.73 Intermediate Similarity NPD5739 Approved
0.73 Intermediate Similarity NPD7128 Approved
0.73 Intermediate Similarity NPD6675 Approved
0.73 Intermediate Similarity NPD4768 Approved
0.73 Intermediate Similarity NPD6402 Approved
0.73 Intermediate Similarity NPD4767 Approved
0.7292 Intermediate Similarity NPD7902 Approved
0.7284 Intermediate Similarity NPD4137 Phase 3
0.7283 Intermediate Similarity NPD6904 Approved
0.7283 Intermediate Similarity NPD6080 Approved
0.7283 Intermediate Similarity NPD6673 Approved
0.7273 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD6012 Approved
0.7255 Intermediate Similarity NPD6014 Approved
0.7255 Intermediate Similarity NPD6013 Approved
0.7234 Intermediate Similarity NPD6399 Phase 3
0.7228 Intermediate Similarity NPD5701 Approved
0.7195 Intermediate Similarity NPD4747 Approved
0.7188 Intermediate Similarity NPD7614 Phase 1
0.7184 Intermediate Similarity NPD7290 Approved
0.7184 Intermediate Similarity NPD5251 Approved
0.7184 Intermediate Similarity NPD5247 Approved
0.7184 Intermediate Similarity NPD5250 Approved
0.7184 Intermediate Similarity NPD5135 Approved
0.7184 Intermediate Similarity NPD6883 Approved
0.7184 Intermediate Similarity NPD4634 Approved
0.7184 Intermediate Similarity NPD7102 Approved
0.7184 Intermediate Similarity NPD5169 Approved
0.7184 Intermediate Similarity NPD5249 Phase 3
0.7184 Intermediate Similarity NPD5248 Approved
0.7184 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD6903 Approved
0.7174 Intermediate Similarity NPD4518 Approved
0.7174 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5091 Approved
0.7159 Intermediate Similarity NPD4692 Approved
0.7159 Intermediate Similarity NPD4139 Approved
0.7157 Intermediate Similarity NPD7320 Approved
0.7143 Intermediate Similarity NPD4687 Approved
0.7143 Intermediate Similarity NPD5733 Approved
0.7143 Intermediate Similarity NPD4058 Approved
0.7128 Intermediate Similarity NPD5693 Phase 1
0.7128 Intermediate Similarity NPD6411 Approved
0.7125 Intermediate Similarity NPD3704 Approved
0.7125 Intermediate Similarity NPD7331 Phase 2
0.7115 Intermediate Similarity NPD5217 Approved
0.7115 Intermediate Similarity NPD6649 Approved
0.7115 Intermediate Similarity NPD6847 Approved
0.7115 Intermediate Similarity NPD8130 Phase 1
0.7115 Intermediate Similarity NPD6650 Approved
0.7115 Intermediate Similarity NPD6617 Approved
0.7115 Intermediate Similarity NPD5216 Approved
0.7115 Intermediate Similarity NPD5215 Approved
0.7115 Intermediate Similarity NPD5127 Approved
0.7115 Intermediate Similarity NPD6869 Approved
0.7087 Intermediate Similarity NPD6372 Approved
0.7087 Intermediate Similarity NPD6373 Approved
0.7065 Intermediate Similarity NPD3573 Approved
0.7048 Intermediate Similarity NPD8297 Approved
0.7048 Intermediate Similarity NPD6882 Approved
0.7033 Intermediate Similarity NPD1696 Phase 3
0.7 Intermediate Similarity NPD7341 Phase 2
0.6981 Remote Similarity NPD4632 Approved
0.6979 Remote Similarity NPD5282 Discontinued
0.6979 Remote Similarity NPD7900 Approved
0.6979 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6977 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6098 Approved
0.6952 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6916 Remote Similarity NPD5167 Approved
0.6915 Remote Similarity NPD6101 Approved
0.6915 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6907 Remote Similarity NPD5654 Approved
0.6893 Remote Similarity NPD6412 Phase 2
0.686 Remote Similarity NPD7339 Approved
0.686 Remote Similarity NPD6942 Approved
0.6852 Remote Similarity NPD6274 Approved
0.6852 Remote Similarity NPD6868 Approved
0.6842 Remote Similarity NPD5207 Approved
0.6837 Remote Similarity NPD7732 Phase 3
0.6809 Remote Similarity NPD5208 Approved
0.6789 Remote Similarity NPD6009 Approved
0.6789 Remote Similarity NPD6317 Approved
0.6786 Remote Similarity NPD4789 Approved
0.6768 Remote Similarity NPD5959 Approved
0.6747 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6742 Remote Similarity NPD7645 Phase 2
0.6735 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6335 Approved
0.6727 Remote Similarity NPD6313 Approved
0.6727 Remote Similarity NPD6314 Approved
0.6707 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6705 Remote Similarity NPD4756 Discovery
0.67 Remote Similarity NPD7638 Approved
0.6667 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7100 Approved
0.6667 Remote Similarity NPD7525 Registered
0.6667 Remote Similarity NPD6686 Approved
0.6667 Remote Similarity NPD1694 Approved
0.6667 Remote Similarity NPD7101 Approved
0.6667 Remote Similarity NPD4522 Approved
0.6634 Remote Similarity NPD7639 Approved
0.6634 Remote Similarity NPD6404 Discontinued
0.6634 Remote Similarity NPD7640 Approved
0.663 Remote Similarity NPD3527 Clinical (unspecified phase)
0.6629 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6607 Remote Similarity NPD6319 Approved
0.6607 Remote Similarity NPD6054 Approved
0.6593 Remote Similarity NPD8028 Phase 2
0.6585 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6552 Remote Similarity NPD6926 Approved
0.6552 Remote Similarity NPD6924 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