Structure

Physi-Chem Properties

Molecular Weight:  238.16
Volume:  254.685
LogP:  0.988
LogD:  0.784
LogS:  -1.297
# Rotatable Bonds:  1
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.683
Synthetic Accessibility Score:  4.428
Fsp3:  0.786
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.681
MDCK Permeability:  1.1668336810544133e-05
Pgp-inhibitor:  0.008
Pgp-substrate:  0.986
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.081
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.937
Plasma Protein Binding (PPB):  18.83359146118164%
Volume Distribution (VD):  1.173
Pgp-substrate:  63.84062194824219%

ADMET: Metabolism

CYP1A2-inhibitor:  0.03
CYP1A2-substrate:  0.684
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.866
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.309
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.215
CYP3A4-inhibitor:  0.043
CYP3A4-substrate:  0.354

ADMET: Excretion

Clearance (CL):  9.313
Half-life (T1/2):  0.613

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.271
Drug-inuced Liver Injury (DILI):  0.087
AMES Toxicity:  0.015
Rat Oral Acute Toxicity:  0.776
Maximum Recommended Daily Dose:  0.688
Skin Sensitization:  0.408
Carcinogencity:  0.744
Eye Corrosion:  0.494
Eye Irritation:  0.724
Respiratory Toxicity:  0.973

Download Data

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

  Natural Product: NPC157895

Natural Product ID:  NPC157895
Common Name*:   Laevinol D
IUPAC Name:   1-[(1R,2S,6R,8S,8aS)-2,6-dihydroxy-8,8a-dimethyl-2,3,4,6,7,8-hexahydro-1H-naphthalen-1-yl]ethanone
Synonyms:   laevinol D
Standard InCHIKey:  UCBOCFFXBGGPKI-PXSMZSCLSA-N
Standard InCHI:  InChI=1S/C14H22O3/c1-8-6-11(16)7-10-4-5-12(17)13(9(2)15)14(8,10)3/h7-8,11-13,16-17H,4-6H2,1-3H3/t8-,11+,12-,13-,14+/m0/s1
SMILES:  O[C@@H]1C[C@H](C)[C@@]2(C(=C1)CC[C@@H]([C@@H]2C(=O)C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL463357
PubChem CID:   5326387
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000129] Alcohols and polyols
          • [CHEMONTID:0001292] Cyclic alcohols and derivatives

*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
NPO6460 Lemnalia laevis Species Nephtheidae Eukaryota n.a. Formosan soft coral n.a. PMID[16378367]
NPO6460 Lemnalia laevis Species Nephtheidae 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
NPT168 Cell Line P388 Mus musculus ED50 > 5.0 ug ml-1 PMID[480509]
NPT139 Cell Line HT-29 Homo sapiens ED50 > 5.0 ug ml-1 PMID[480509]

☑ 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 NPC157895 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 NPC104120
1.0 High Similarity NPC148685
0.9342 High Similarity NPC308038
0.9333 High Similarity NPC74995
0.925 High Similarity NPC198761
0.9091 High Similarity NPC152061
0.9012 High Similarity NPC470955
0.8987 High Similarity NPC93590
0.8974 High Similarity NPC172013
0.8947 High Similarity NPC263582
0.8916 High Similarity NPC472970
0.8916 High Similarity NPC472971
0.8875 High Similarity NPC105173
0.8846 High Similarity NPC281138
0.8831 High Similarity NPC197659
0.878 High Similarity NPC194417
0.878 High Similarity NPC472985
0.878 High Similarity NPC472986
0.8718 High Similarity NPC62336
0.8659 High Similarity NPC52628
0.8625 High Similarity NPC14151
0.8608 High Similarity NPC7232
0.8588 High Similarity NPC230332
0.8554 High Similarity NPC82979
0.8554 High Similarity NPC473226
0.8554 High Similarity NPC472974
0.8519 High Similarity NPC48362
0.85 High Similarity NPC45495
0.8481 Intermediate Similarity NPC297996
0.8481 Intermediate Similarity NPC178852
0.8481 Intermediate Similarity NPC475994
0.8471 Intermediate Similarity NPC472983
0.8471 Intermediate Similarity NPC472973
0.8452 Intermediate Similarity NPC298904
0.8434 Intermediate Similarity NPC179006
0.8434 Intermediate Similarity NPC274724
0.8434 Intermediate Similarity NPC474083
0.8434 Intermediate Similarity NPC474853
0.8434 Intermediate Similarity NPC471224
0.8415 Intermediate Similarity NPC64600
0.8415 Intermediate Similarity NPC169941
0.8415 Intermediate Similarity NPC251475
0.8395 Intermediate Similarity NPC473420
0.8372 Intermediate Similarity NPC134321
0.8354 Intermediate Similarity NPC203403
0.8354 Intermediate Similarity NPC34110
0.8354 Intermediate Similarity NPC257666
0.8354 Intermediate Similarity NPC266193
0.8353 Intermediate Similarity NPC471791
0.8353 Intermediate Similarity NPC471793
0.8333 Intermediate Similarity NPC114236
0.8333 Intermediate Similarity NPC476043
0.8333 Intermediate Similarity NPC322159
0.8313 Intermediate Similarity NPC40687
0.8313 Intermediate Similarity NPC227132
0.8313 Intermediate Similarity NPC476412
0.8312 Intermediate Similarity NPC247586
0.8312 Intermediate Similarity NPC186042
0.8276 Intermediate Similarity NPC472978
0.8276 Intermediate Similarity NPC116726
0.8272 Intermediate Similarity NPC471514
0.8272 Intermediate Similarity NPC306095
0.8272 Intermediate Similarity NPC472301
0.8256 Intermediate Similarity NPC69627
0.8256 Intermediate Similarity NPC309603
0.8256 Intermediate Similarity NPC473100
0.8256 Intermediate Similarity NPC473999
0.825 Intermediate Similarity NPC239098
0.8235 Intermediate Similarity NPC272039
0.8235 Intermediate Similarity NPC220930
0.8228 Intermediate Similarity NPC470525
0.8228 Intermediate Similarity NPC250621
0.8228 Intermediate Similarity NPC472305
0.8214 Intermediate Similarity NPC133954
0.8214 Intermediate Similarity NPC15807
0.8214 Intermediate Similarity NPC79573
0.8214 Intermediate Similarity NPC70685
0.8214 Intermediate Similarity NPC476426
0.8214 Intermediate Similarity NPC470574
0.8182 Intermediate Similarity NPC69454
0.8182 Intermediate Similarity NPC477520
0.8171 Intermediate Similarity NPC226068
0.8171 Intermediate Similarity NPC116797
0.8161 Intermediate Similarity NPC48010
0.8161 Intermediate Similarity NPC128672
0.8161 Intermediate Similarity NPC473099
0.8148 Intermediate Similarity NPC19900
0.814 Intermediate Similarity NPC104560
0.814 Intermediate Similarity NPC471724
0.814 Intermediate Similarity NPC474854
0.8125 Intermediate Similarity NPC97377
0.8125 Intermediate Similarity NPC325946
0.8118 Intermediate Similarity NPC469994
0.8118 Intermediate Similarity NPC213412
0.8118 Intermediate Similarity NPC74363
0.8118 Intermediate Similarity NPC475862
0.8095 Intermediate Similarity NPC470812
0.8095 Intermediate Similarity NPC165064
0.809 Intermediate Similarity NPC196227
0.809 Intermediate Similarity NPC472976
0.809 Intermediate Similarity NPC472977
0.8077 Intermediate Similarity NPC275098
0.8072 Intermediate Similarity NPC151519
0.8072 Intermediate Similarity NPC38796
0.8072 Intermediate Similarity NPC212083
0.8072 Intermediate Similarity NPC158411
0.8068 Intermediate Similarity NPC73457
0.8068 Intermediate Similarity NPC63748
0.8068 Intermediate Similarity NPC475806
0.8068 Intermediate Similarity NPC6255
0.8068 Intermediate Similarity NPC233116
0.8068 Intermediate Similarity NPC472975
0.8068 Intermediate Similarity NPC473998
0.8068 Intermediate Similarity NPC172101
0.8068 Intermediate Similarity NPC471588
0.8052 Intermediate Similarity NPC34834
0.8049 Intermediate Similarity NPC233352
0.8049 Intermediate Similarity NPC2482
0.8049 Intermediate Similarity NPC824
0.8049 Intermediate Similarity NPC138492
0.8049 Intermediate Similarity NPC271104
0.8046 Intermediate Similarity NPC2983
0.8046 Intermediate Similarity NPC281524
0.8026 Intermediate Similarity NPC96484
0.8025 Intermediate Similarity NPC275494
0.8025 Intermediate Similarity NPC207772
0.8025 Intermediate Similarity NPC471409
0.8023 Intermediate Similarity NPC73064
0.8 Intermediate Similarity NPC167873
0.8 Intermediate Similarity NPC272617
0.8 Intermediate Similarity NPC7629
0.8 Intermediate Similarity NPC151622
0.8 Intermediate Similarity NPC271195
0.8 Intermediate Similarity NPC1973
0.8 Intermediate Similarity NPC471344
0.8 Intermediate Similarity NPC259286
0.8 Intermediate Similarity NPC476245
0.8 Intermediate Similarity NPC134067
0.7978 Intermediate Similarity NPC115021
0.7978 Intermediate Similarity NPC472930
0.7978 Intermediate Similarity NPC109305
0.7976 Intermediate Similarity NPC297398
0.7976 Intermediate Similarity NPC470948
0.7975 Intermediate Similarity NPC215050
0.7955 Intermediate Similarity NPC232202
0.7955 Intermediate Similarity NPC69622
0.7955 Intermediate Similarity NPC86372
0.7955 Intermediate Similarity NPC172361
0.7952 Intermediate Similarity NPC121984
0.7952 Intermediate Similarity NPC6663
0.7952 Intermediate Similarity NPC3915
0.7949 Intermediate Similarity NPC23954
0.7949 Intermediate Similarity NPC477792
0.7935 Intermediate Similarity NPC316598
0.7931 Intermediate Similarity NPC158778
0.7931 Intermediate Similarity NPC476796
0.7931 Intermediate Similarity NPC471722
0.7931 Intermediate Similarity NPC53454
0.7931 Intermediate Similarity NPC328539
0.7931 Intermediate Similarity NPC472802
0.7931 Intermediate Similarity NPC53911
0.7931 Intermediate Similarity NPC328313
0.7927 Intermediate Similarity NPC229204
0.7927 Intermediate Similarity NPC474113
0.7922 Intermediate Similarity NPC474248
0.7912 Intermediate Similarity NPC249954
0.7912 Intermediate Similarity NPC117133
0.7912 Intermediate Similarity NPC242848
0.7907 Intermediate Similarity NPC94755
0.7907 Intermediate Similarity NPC476104
0.7907 Intermediate Similarity NPC158393
0.7907 Intermediate Similarity NPC477579
0.7907 Intermediate Similarity NPC179591
0.7907 Intermediate Similarity NPC235341
0.7907 Intermediate Similarity NPC73038
0.7907 Intermediate Similarity NPC95594
0.7907 Intermediate Similarity NPC6979
0.7907 Intermediate Similarity NPC202394
0.7907 Intermediate Similarity NPC325594
0.7907 Intermediate Similarity NPC72133
0.7901 Intermediate Similarity NPC91594
0.7889 Intermediate Similarity NPC8993
0.7889 Intermediate Similarity NPC474529
0.7889 Intermediate Similarity NPC299100
0.7889 Intermediate Similarity NPC469406
0.7889 Intermediate Similarity NPC474690
0.7882 Intermediate Similarity NPC161423
0.7882 Intermediate Similarity NPC321187
0.7882 Intermediate Similarity NPC227064
0.7882 Intermediate Similarity NPC221758
0.7882 Intermediate Similarity NPC85774
0.7882 Intermediate Similarity NPC180834
0.7882 Intermediate Similarity NPC59453
0.7882 Intermediate Similarity NPC58841
0.7882 Intermediate Similarity NPC329043
0.7882 Intermediate Similarity NPC473246
0.7882 Intermediate Similarity NPC82902
0.7882 Intermediate Similarity NPC214043
0.7875 Intermediate Similarity NPC476795
0.7865 Intermediate Similarity NPC282616

  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 NPC157895 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
0.8118 Intermediate Similarity NPD3618 Phase 1
0.8072 Intermediate Similarity NPD3667 Approved
0.7882 Intermediate Similarity NPD3665 Phase 1
0.7882 Intermediate Similarity NPD4786 Approved
0.7882 Intermediate Similarity NPD3666 Approved
0.7882 Intermediate Similarity NPD3133 Approved
0.7841 Intermediate Similarity NPD5328 Approved
0.7701 Intermediate Similarity NPD5279 Phase 3
0.7667 Intermediate Similarity NPD6079 Approved
0.7667 Intermediate Similarity NPD7515 Phase 2
0.7582 Intermediate Similarity NPD4202 Approved
0.75 Intermediate Similarity NPD4623 Approved
0.75 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4519 Discontinued
0.7412 Intermediate Similarity NPD4695 Discontinued
0.7391 Intermediate Similarity NPD5778 Approved
0.7391 Intermediate Similarity NPD5779 Approved
0.734 Intermediate Similarity NPD5221 Approved
0.734 Intermediate Similarity NPD5222 Approved
0.734 Intermediate Similarity NPD4697 Phase 3
0.734 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD5211 Phase 2
0.7312 Intermediate Similarity NPD7748 Approved
0.7283 Intermediate Similarity NPD6411 Approved
0.7273 Intermediate Similarity NPD3668 Phase 3
0.7263 Intermediate Similarity NPD4755 Approved
0.7263 Intermediate Similarity NPD5173 Approved
0.7253 Intermediate Similarity NPD4753 Phase 2
0.7241 Intermediate Similarity NPD4221 Approved
0.7241 Intermediate Similarity NPD4223 Phase 3
0.7229 Intermediate Similarity NPD8264 Approved
0.7191 Intermediate Similarity NPD1694 Approved
0.7188 Intermediate Similarity NPD4225 Approved
0.7176 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5141 Approved
0.7113 Intermediate Similarity NPD5285 Approved
0.7113 Intermediate Similarity NPD5286 Approved
0.7113 Intermediate Similarity NPD4700 Approved
0.7113 Intermediate Similarity NPD4696 Approved
0.7093 Intermediate Similarity NPD7645 Phase 2
0.7083 Intermediate Similarity NPD7902 Approved
0.7079 Intermediate Similarity NPD4197 Approved
0.7065 Intermediate Similarity NPD6101 Approved
0.7065 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD4269 Approved
0.7045 Intermediate Similarity NPD4270 Approved
0.7041 Intermediate Similarity NPD5223 Approved
0.7021 Intermediate Similarity NPD6399 Phase 3
0.7013 Intermediate Similarity NPD368 Approved
0.7 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5329 Approved
0.7 Intermediate Similarity NPD1696 Phase 3
0.6977 Remote Similarity NPD3617 Approved
0.697 Remote Similarity NPD5225 Approved
0.697 Remote Similarity NPD5226 Approved
0.697 Remote Similarity NPD4633 Approved
0.697 Remote Similarity NPD5224 Approved
0.6941 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6939 Remote Similarity NPD7640 Approved
0.6939 Remote Similarity NPD7639 Approved
0.6923 Remote Similarity NPD6409 Approved
0.6923 Remote Similarity NPD4690 Approved
0.6923 Remote Similarity NPD4688 Approved
0.6923 Remote Similarity NPD5690 Phase 2
0.6923 Remote Similarity NPD7334 Approved
0.6923 Remote Similarity NPD5330 Approved
0.6923 Remote Similarity NPD7521 Approved
0.6923 Remote Similarity NPD6684 Approved
0.6923 Remote Similarity NPD4694 Approved
0.6923 Remote Similarity NPD7146 Approved
0.6923 Remote Similarity NPD4138 Approved
0.6923 Remote Similarity NPD4689 Approved
0.6923 Remote Similarity NPD4693 Phase 3
0.6923 Remote Similarity NPD5280 Approved
0.6923 Remote Similarity NPD5205 Approved
0.6916 Remote Similarity NPD7115 Discovery
0.69 Remote Similarity NPD4754 Approved
0.69 Remote Similarity NPD5174 Approved
0.69 Remote Similarity NPD5175 Approved
0.6875 Remote Similarity NPD5210 Approved
0.6875 Remote Similarity NPD4629 Approved
0.6854 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6837 Remote Similarity NPD7638 Approved
0.6827 Remote Similarity NPD4634 Approved
0.6824 Remote Similarity NPD6942 Approved
0.6824 Remote Similarity NPD7339 Approved
0.6818 Remote Similarity NPD7525 Registered
0.6818 Remote Similarity NPD4252 Approved
0.6818 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6813 Remote Similarity NPD5363 Approved
0.6809 Remote Similarity NPD5785 Approved
0.6778 Remote Similarity NPD4788 Approved
0.6774 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6774 Remote Similarity NPD6903 Approved
0.6771 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6771 Remote Similarity NPD7900 Approved
0.6765 Remote Similarity NPD6402 Approved
0.6765 Remote Similarity NPD7128 Approved
0.6765 Remote Similarity NPD4767 Approved
0.6765 Remote Similarity NPD5739 Approved
0.6765 Remote Similarity NPD6675 Approved
0.6765 Remote Similarity NPD4768 Approved
0.6742 Remote Similarity NPD4139 Approved
0.6742 Remote Similarity NPD4692 Approved
0.6739 Remote Similarity NPD5786 Approved
0.6737 Remote Similarity NPD7637 Suspended
0.6735 Remote Similarity NPD6083 Phase 2
0.6735 Remote Similarity NPD6084 Phase 2
0.6706 Remote Similarity NPD6926 Approved
0.6706 Remote Similarity NPD6924 Approved
0.6705 Remote Similarity NPD6929 Approved
0.6701 Remote Similarity NPD5695 Phase 3
0.6699 Remote Similarity NPD5701 Approved
0.6699 Remote Similarity NPD5697 Approved
0.6667 Remote Similarity NPD342 Phase 1
0.6667 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7331 Phase 2
0.6667 Remote Similarity NPD3573 Approved
0.6635 Remote Similarity NPD5128 Approved
0.6635 Remote Similarity NPD7320 Approved
0.6635 Remote Similarity NPD6881 Approved
0.6635 Remote Similarity NPD5168 Approved
0.6635 Remote Similarity NPD6011 Approved
0.6635 Remote Similarity NPD4729 Approved
0.6635 Remote Similarity NPD4730 Approved
0.6635 Remote Similarity NPD6899 Approved
0.6632 Remote Similarity NPD4096 Approved
0.6629 Remote Similarity NPD6931 Approved
0.6629 Remote Similarity NPD6930 Phase 2
0.6627 Remote Similarity NPD4137 Phase 3
0.6627 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6627 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6596 Remote Similarity NPD5737 Approved
0.6596 Remote Similarity NPD6672 Approved
0.6593 Remote Similarity NPD5362 Discontinued
0.6591 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6571 Remote Similarity NPD6012 Approved
0.6571 Remote Similarity NPD6014 Approved
0.6571 Remote Similarity NPD6373 Approved
0.6571 Remote Similarity NPD6372 Approved
0.6571 Remote Similarity NPD6013 Approved
0.6562 Remote Similarity NPD5284 Approved
0.6562 Remote Similarity NPD5281 Approved
0.6556 Remote Similarity NPD5369 Approved
0.6552 Remote Similarity NPD6933 Approved
0.6548 Remote Similarity NPD4691 Approved
0.6548 Remote Similarity NPD4747 Approved
0.6543 Remote Similarity NPD7341 Phase 2
0.6543 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6531 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6526 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6517 Remote Similarity NPD4195 Approved
0.6509 Remote Similarity NPD5249 Phase 3
0.6509 Remote Similarity NPD5169 Approved
0.6509 Remote Similarity NPD5248 Approved
0.6509 Remote Similarity NPD5250 Approved
0.6509 Remote Similarity NPD5251 Approved
0.6509 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6509 Remote Similarity NPD7102 Approved
0.6509 Remote Similarity NPD7290 Approved
0.6509 Remote Similarity NPD5247 Approved
0.6509 Remote Similarity NPD5135 Approved
0.6509 Remote Similarity NPD6883 Approved
0.6506 Remote Similarity NPD3621 Clinical (unspecified phase)
0.65 Remote Similarity NPD5696 Approved
0.6477 Remote Similarity NPD5776 Phase 2
0.6477 Remote Similarity NPD6925 Approved
0.6471 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6471 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5276 Approved
0.6449 Remote Similarity NPD5216 Approved
0.6449 Remote Similarity NPD5217 Approved
0.6449 Remote Similarity NPD6869 Approved
0.6449 Remote Similarity NPD6847 Approved
0.6449 Remote Similarity NPD6649 Approved
0.6449 Remote Similarity NPD5215 Approved
0.6449 Remote Similarity NPD8130 Phase 1
0.6449 Remote Similarity NPD5127 Approved
0.6449 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6449 Remote Similarity NPD6650 Approved
0.6449 Remote Similarity NPD6617 Approved
0.6444 Remote Similarity NPD7514 Phase 3
0.6444 Remote Similarity NPD7509 Discontinued
0.6444 Remote Similarity NPD7332 Phase 2
0.6437 Remote Similarity NPD8039 Approved
0.6437 Remote Similarity NPD3703 Phase 2
0.6429 Remote Similarity NPD6922 Approved
0.6429 Remote Similarity NPD3698 Phase 2
0.6429 Remote Similarity NPD5282 Discontinued
0.6429 Remote Similarity NPD6923 Approved
0.6421 Remote Similarity NPD4518 Approved
0.6413 Remote Similarity NPD7154 Phase 3
0.6413 Remote Similarity NPD6695 Phase 3
0.6404 Remote Similarity NPD7145 Approved
0.6392 Remote Similarity NPD8035 Phase 2
0.6392 Remote Similarity NPD8034 Phase 2
0.6389 Remote Similarity NPD6882 Approved
0.6389 Remote Similarity NPD8297 Approved
0.6383 Remote Similarity NPD6098 Approved
0.6381 Remote Similarity NPD6412 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