Structure

Physi-Chem Properties

Molecular Weight:  236.18
Volume:  263.191
LogP:  3.256
LogD:  3.486
LogS:  -3.965
# Rotatable Bonds:  2
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.748
Synthetic Accessibility Score:  4.35
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.497
MDCK Permeability:  2.9935055863461457e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.021
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.181
Plasma Protein Binding (PPB):  88.43240356445312%
Volume Distribution (VD):  0.745
Pgp-substrate:  5.896999359130859%

ADMET: Metabolism

CYP1A2-inhibitor:  0.452
CYP1A2-substrate:  0.62
CYP2C19-inhibitor:  0.215
CYP2C19-substrate:  0.835
CYP2C9-inhibitor:  0.174
CYP2C9-substrate:  0.638
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.373
CYP3A4-inhibitor:  0.195
CYP3A4-substrate:  0.454

ADMET: Excretion

Clearance (CL):  6.112
Half-life (T1/2):  0.646

ADMET: Toxicity

hERG Blockers:  0.048
Human Hepatotoxicity (H-HT):  0.55
Drug-inuced Liver Injury (DILI):  0.169
AMES Toxicity:  0.044
Rat Oral Acute Toxicity:  0.013
Maximum Recommended Daily Dose:  0.403
Skin Sensitization:  0.934
Carcinogencity:  0.318
Eye Corrosion:  0.939
Eye Irritation:  0.928
Respiratory Toxicity:  0.862

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

  Natural Product: NPC80088

Natural Product ID:  NPC80088
Common Name*:   15-Oxo-Alpha-Cadinol
IUPAC Name:   (4aR,5R,8S,8aR)-5-hydroxy-5-methyl-8-propan-2-yl-4,4a,6,7,8,8a-hexahydro-3H-naphthalene-2-carbaldehyde
Synonyms:  
Standard InCHIKey:  FHFKLFYRFFKTRP-BYNSBNAKSA-N
Standard InCHI:  InChI=1S/C15H24O2/c1-10(2)12-6-7-15(3,17)14-5-4-11(9-16)8-13(12)14/h8-10,12-14,17H,4-7H2,1-3H3/t12-,13-,14+,15+/m0/s1
SMILES:  O=CC1=C[C@@H]2[C@@H](CC1)[C@](C)(O)CC[C@H]2C(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL462702
PubChem CID:   15548660
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO9348 Cananga odorata Species Annonaceae Eukaryota fruits n.a. n.a. PMID[11374955]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[12762792]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. PMID[21504145]
NPO9348 Cananga odorata Species Annonaceae Eukaryota flower buds Thailand n.a. PMID[24601675]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9348 Cananga odorata Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9348 Cananga odorata Species Annonaceae 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
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 Inhibition = 39.0 % PMID[490147]
NPT2 Others Unspecified Inhibition = 25.0 % PMID[490148]
NPT2 Others Unspecified Inhibition = 45.5 % PMID[490148]
NPT2 Others Unspecified Inhibition = 64.0 % PMID[490148]
NPT2 Others Unspecified Inhibition = 65.9 % PMID[490148]
NPT2 Others Unspecified Inhibition = 48.8 % PMID[490148]
NPT2 Others Unspecified Inhibition = 5.1 % PMID[490148]
NPT27 Others Unspecified Activity > 80.3 % PMID[490148]

☑ 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 NPC80088 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 NPC253561
0.96 High Similarity NPC119229
0.9467 High Similarity NPC472301
0.9189 High Similarity NPC76966
0.9189 High Similarity NPC186554
0.8947 High Similarity NPC207772
0.875 High Similarity NPC470812
0.8684 High Similarity NPC472305
0.8625 High Similarity NPC64600
0.8571 High Similarity NPC34110
0.8571 High Similarity NPC197659
0.8571 High Similarity NPC257666
0.8571 High Similarity NPC266193
0.8554 High Similarity NPC473229
0.8554 High Similarity NPC206060
0.8481 Intermediate Similarity NPC476809
0.8452 Intermediate Similarity NPC472983
0.8442 Intermediate Similarity NPC151622
0.8442 Intermediate Similarity NPC7629
0.8415 Intermediate Similarity NPC70685
0.8395 Intermediate Similarity NPC297398
0.8375 Intermediate Similarity NPC473217
0.8353 Intermediate Similarity NPC191684
0.8333 Intermediate Similarity NPC474925
0.8333 Intermediate Similarity NPC470428
0.8313 Intermediate Similarity NPC179591
0.8272 Intermediate Similarity NPC470813
0.825 Intermediate Similarity NPC172013
0.825 Intermediate Similarity NPC469637
0.8228 Intermediate Similarity NPC62336
0.8228 Intermediate Similarity NPC19443
0.8228 Intermediate Similarity NPC476949
0.8228 Intermediate Similarity NPC59436
0.8205 Intermediate Similarity NPC470525
0.8205 Intermediate Similarity NPC263582
0.8182 Intermediate Similarity NPC78527
0.8171 Intermediate Similarity NPC307258
0.8148 Intermediate Similarity NPC473420
0.8148 Intermediate Similarity NPC90055
0.8148 Intermediate Similarity NPC226068
0.8125 Intermediate Similarity NPC308038
0.8125 Intermediate Similarity NPC470429
0.8125 Intermediate Similarity NPC283789
0.8095 Intermediate Similarity NPC472974
0.8095 Intermediate Similarity NPC95594
0.8095 Intermediate Similarity NPC477579
0.8095 Intermediate Similarity NPC235341
0.8095 Intermediate Similarity NPC94755
0.8072 Intermediate Similarity NPC251170
0.8052 Intermediate Similarity NPC35656
0.8049 Intermediate Similarity NPC93590
0.8046 Intermediate Similarity NPC99380
0.8025 Intermediate Similarity NPC2482
0.8025 Intermediate Similarity NPC271104
0.8025 Intermediate Similarity NPC471514
0.8023 Intermediate Similarity NPC119416
0.8023 Intermediate Similarity NPC472973
0.8 Intermediate Similarity NPC275494
0.8 Intermediate Similarity NPC178852
0.8 Intermediate Similarity NPC471409
0.7976 Intermediate Similarity NPC470574
0.7975 Intermediate Similarity NPC250621
0.7949 Intermediate Similarity NPC470299
0.7931 Intermediate Similarity NPC183283
0.7931 Intermediate Similarity NPC134321
0.7931 Intermediate Similarity NPC128672
0.7931 Intermediate Similarity NPC85173
0.7927 Intermediate Similarity NPC116797
0.7927 Intermediate Similarity NPC121984
0.7917 Intermediate Similarity NPC282694
0.7917 Intermediate Similarity NPC79576
0.7917 Intermediate Similarity NPC194208
0.7907 Intermediate Similarity NPC48107
0.7907 Intermediate Similarity NPC328539
0.7907 Intermediate Similarity NPC472802
0.7907 Intermediate Similarity NPC158778
0.7907 Intermediate Similarity NPC471722
0.7901 Intermediate Similarity NPC281138
0.7901 Intermediate Similarity NPC170394
0.7901 Intermediate Similarity NPC152061
0.7889 Intermediate Similarity NPC5532
0.7889 Intermediate Similarity NPC469545
0.7889 Intermediate Similarity NPC61369
0.7882 Intermediate Similarity NPC73038
0.7882 Intermediate Similarity NPC158393
0.7882 Intermediate Similarity NPC472986
0.7882 Intermediate Similarity NPC472985
0.7882 Intermediate Similarity NPC72133
0.7875 Intermediate Similarity NPC97377
0.7867 Intermediate Similarity NPC4370
0.7867 Intermediate Similarity NPC263161
0.7867 Intermediate Similarity NPC290350
0.7857 Intermediate Similarity NPC476412
0.7848 Intermediate Similarity NPC476795
0.7848 Intermediate Similarity NPC114236
0.7841 Intermediate Similarity NPC172101
0.7841 Intermediate Similarity NPC472975
0.7841 Intermediate Similarity NPC272746
0.7841 Intermediate Similarity NPC472978
0.7841 Intermediate Similarity NPC116726
0.7831 Intermediate Similarity NPC103486
0.7831 Intermediate Similarity NPC48362
0.7821 Intermediate Similarity NPC247586
0.7816 Intermediate Similarity NPC275740
0.7816 Intermediate Similarity NPC184663
0.7816 Intermediate Similarity NPC86319
0.7805 Intermediate Similarity NPC148685
0.7805 Intermediate Similarity NPC824
0.7805 Intermediate Similarity NPC233352
0.7805 Intermediate Similarity NPC104120
0.7805 Intermediate Similarity NPC157895
0.7805 Intermediate Similarity NPC108955
0.7805 Intermediate Similarity NPC138492
0.7805 Intermediate Similarity NPC472478
0.7791 Intermediate Similarity NPC475740
0.7791 Intermediate Similarity NPC475772
0.7791 Intermediate Similarity NPC141292
0.7778 Intermediate Similarity NPC476808
0.7778 Intermediate Similarity NPC321514
0.7778 Intermediate Similarity NPC74410
0.7778 Intermediate Similarity NPC476245
0.7778 Intermediate Similarity NPC189485
0.7765 Intermediate Similarity NPC133954
0.7763 Intermediate Similarity NPC155198
0.7753 Intermediate Similarity NPC134826
0.775 Intermediate Similarity NPC242722
0.775 Intermediate Similarity NPC215481
0.775 Intermediate Similarity NPC180886
0.7738 Intermediate Similarity NPC110150
0.7738 Intermediate Similarity NPC251475
0.7738 Intermediate Similarity NPC470165
0.7738 Intermediate Similarity NPC169941
0.7738 Intermediate Similarity NPC66764
0.7727 Intermediate Similarity NPC474209
0.7727 Intermediate Similarity NPC328141
0.7727 Intermediate Similarity NPC126993
0.7727 Intermediate Similarity NPC472476
0.7727 Intermediate Similarity NPC475823
0.7722 Intermediate Similarity NPC22134
0.7711 Intermediate Similarity NPC327002
0.7711 Intermediate Similarity NPC55869
0.7711 Intermediate Similarity NPC278459
0.7701 Intermediate Similarity NPC131470
0.7701 Intermediate Similarity NPC474677
0.7701 Intermediate Similarity NPC471791
0.7701 Intermediate Similarity NPC471793
0.7701 Intermediate Similarity NPC471724
0.7701 Intermediate Similarity NPC292491
0.7701 Intermediate Similarity NPC310752
0.7701 Intermediate Similarity NPC143767
0.7701 Intermediate Similarity NPC104560
0.7692 Intermediate Similarity NPC242992
0.7692 Intermediate Similarity NPC164022
0.7692 Intermediate Similarity NPC474562
0.7692 Intermediate Similarity NPC84790
0.7692 Intermediate Similarity NPC23954
0.7692 Intermediate Similarity NPC192428
0.7683 Intermediate Similarity NPC472490
0.7674 Intermediate Similarity NPC475862
0.7674 Intermediate Similarity NPC476043
0.7674 Intermediate Similarity NPC213412
0.7674 Intermediate Similarity NPC6979
0.7674 Intermediate Similarity NPC474732
0.7674 Intermediate Similarity NPC474733
0.7674 Intermediate Similarity NPC94666
0.7674 Intermediate Similarity NPC473226
0.7674 Intermediate Similarity NPC31564
0.7674 Intermediate Similarity NPC325594
0.7674 Intermediate Similarity NPC474778
0.7674 Intermediate Similarity NPC74363
0.7674 Intermediate Similarity NPC194417
0.7674 Intermediate Similarity NPC145879
0.7667 Intermediate Similarity NPC472977
0.7667 Intermediate Similarity NPC472976
0.7667 Intermediate Similarity NPC23170
0.7667 Intermediate Similarity NPC196227
0.7667 Intermediate Similarity NPC299100
0.7667 Intermediate Similarity NPC471207
0.7667 Intermediate Similarity NPC471040
0.7667 Intermediate Similarity NPC103527
0.7662 Intermediate Similarity NPC469914
0.7654 Intermediate Similarity NPC203403
0.7654 Intermediate Similarity NPC325946
0.7654 Intermediate Similarity NPC165711
0.7654 Intermediate Similarity NPC74995
0.7647 Intermediate Similarity NPC237712
0.7647 Intermediate Similarity NPC85774
0.7647 Intermediate Similarity NPC30486
0.7647 Intermediate Similarity NPC214043
0.7647 Intermediate Similarity NPC329043
0.7647 Intermediate Similarity NPC321187
0.7647 Intermediate Similarity NPC40687
0.7647 Intermediate Similarity NPC58841
0.7647 Intermediate Similarity NPC473246
0.7647 Intermediate Similarity NPC161423
0.7647 Intermediate Similarity NPC227064
0.764 Intermediate Similarity NPC233455
0.764 Intermediate Similarity NPC131872
0.764 Intermediate Similarity NPC185936
0.764 Intermediate Similarity NPC65120

  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 NPC80088 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
0.8095 Intermediate Similarity NPD3618 Phase 1
0.7841 Intermediate Similarity NPD6079 Approved
0.7816 Intermediate Similarity NPD5328 Approved
0.7753 Intermediate Similarity NPD4202 Approved
0.7692 Intermediate Similarity NPD4697 Phase 3
0.7674 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD3133 Approved
0.7647 Intermediate Similarity NPD3666 Approved
0.7647 Intermediate Similarity NPD3665 Phase 1
0.764 Intermediate Similarity NPD7515 Phase 2
0.7619 Intermediate Similarity NPD4221 Approved
0.7619 Intermediate Similarity NPD3667 Approved
0.7619 Intermediate Similarity NPD4223 Phase 3
0.759 Intermediate Similarity NPD4695 Discontinued
0.75 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5222 Approved
0.75 Intermediate Similarity NPD5221 Approved
0.7473 Intermediate Similarity NPD7748 Approved
0.7471 Intermediate Similarity NPD5690 Phase 2
0.7447 Intermediate Similarity NPD4696 Approved
0.7447 Intermediate Similarity NPD5285 Approved
0.7447 Intermediate Similarity NPD5286 Approved
0.7442 Intermediate Similarity NPD4786 Approved
0.7442 Intermediate Similarity NPD4197 Approved
0.7419 Intermediate Similarity NPD4755 Approved
0.7419 Intermediate Similarity NPD5173 Approved
0.7416 Intermediate Similarity NPD4753 Phase 2
0.7386 Intermediate Similarity NPD3573 Approved
0.7368 Intermediate Similarity NPD5223 Approved
0.7356 Intermediate Similarity NPD5329 Approved
0.7292 Intermediate Similarity NPD5224 Approved
0.7292 Intermediate Similarity NPD5211 Phase 2
0.7292 Intermediate Similarity NPD5225 Approved
0.7292 Intermediate Similarity NPD4633 Approved
0.7292 Intermediate Similarity NPD5226 Approved
0.7273 Intermediate Similarity NPD5280 Approved
0.7273 Intermediate Similarity NPD7331 Phase 2
0.7273 Intermediate Similarity NPD4138 Approved
0.7273 Intermediate Similarity NPD4688 Approved
0.7273 Intermediate Similarity NPD5279 Phase 3
0.7273 Intermediate Similarity NPD4690 Approved
0.7273 Intermediate Similarity NPD4519 Discontinued
0.7273 Intermediate Similarity NPD4693 Phase 3
0.7273 Intermediate Similarity NPD5205 Approved
0.7273 Intermediate Similarity NPD4694 Approved
0.7273 Intermediate Similarity NPD4689 Approved
0.7273 Intermediate Similarity NPD4623 Approved
0.7263 Intermediate Similarity NPD4700 Approved
0.7234 Intermediate Similarity NPD7902 Approved
0.7216 Intermediate Similarity NPD5175 Approved
0.7216 Intermediate Similarity NPD5174 Approved
0.7204 Intermediate Similarity NPD4629 Approved
0.7204 Intermediate Similarity NPD5210 Approved
0.7143 Intermediate Similarity NPD7341 Phase 2
0.7143 Intermediate Similarity NPD5141 Approved
0.7143 Intermediate Similarity NPD3617 Approved
0.7059 Intermediate Similarity NPD4195 Approved
0.7045 Intermediate Similarity NPD3668 Phase 3
0.7041 Intermediate Similarity NPD4754 Approved
0.7021 Intermediate Similarity NPD5695 Phase 3
0.7 Intermediate Similarity NPD5697 Approved
0.6966 Remote Similarity NPD1694 Approved
0.6966 Remote Similarity NPD1696 Phase 3
0.6932 Remote Similarity NPD4788 Approved
0.6931 Remote Similarity NPD6011 Approved
0.6931 Remote Similarity NPD6899 Approved
0.6931 Remote Similarity NPD4729 Approved
0.6931 Remote Similarity NPD4730 Approved
0.6931 Remote Similarity NPD6881 Approved
0.6931 Remote Similarity NPD5128 Approved
0.6915 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6915 Remote Similarity NPD7900 Approved
0.6914 Remote Similarity NPD4691 Approved
0.69 Remote Similarity NPD5739 Approved
0.69 Remote Similarity NPD4768 Approved
0.69 Remote Similarity NPD7128 Approved
0.69 Remote Similarity NPD6402 Approved
0.69 Remote Similarity NPD6675 Approved
0.69 Remote Similarity NPD4767 Approved
0.6889 Remote Similarity NPD7146 Approved
0.6889 Remote Similarity NPD6684 Approved
0.6889 Remote Similarity NPD7521 Approved
0.6889 Remote Similarity NPD6409 Approved
0.6889 Remote Similarity NPD5330 Approved
0.6889 Remote Similarity NPD7334 Approved
0.6882 Remote Similarity NPD5281 Approved
0.6882 Remote Similarity NPD5284 Approved
0.6875 Remote Similarity NPD6084 Phase 2
0.6875 Remote Similarity NPD6083 Phase 2
0.6863 Remote Similarity NPD6013 Approved
0.6863 Remote Similarity NPD6012 Approved
0.6863 Remote Similarity NPD6014 Approved
0.686 Remote Similarity NPD7645 Phase 2
0.6832 Remote Similarity NPD5701 Approved
0.6818 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6809 Remote Similarity NPD6399 Phase 3
0.6804 Remote Similarity NPD5696 Approved
0.6796 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6796 Remote Similarity NPD5250 Approved
0.6796 Remote Similarity NPD5247 Approved
0.6796 Remote Similarity NPD4634 Approved
0.6796 Remote Similarity NPD7290 Approved
0.6796 Remote Similarity NPD5169 Approved
0.6796 Remote Similarity NPD7102 Approved
0.6796 Remote Similarity NPD5251 Approved
0.6796 Remote Similarity NPD6883 Approved
0.6796 Remote Similarity NPD5135 Approved
0.6796 Remote Similarity NPD5248 Approved
0.6796 Remote Similarity NPD5249 Phase 3
0.679 Remote Similarity NPD4137 Phase 3
0.6782 Remote Similarity NPD7525 Registered
0.6778 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6774 Remote Similarity NPD4096 Approved
0.6765 Remote Similarity NPD7320 Approved
0.6765 Remote Similarity NPD5168 Approved
0.6739 Remote Similarity NPD5737 Approved
0.6739 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6739 Remote Similarity NPD6903 Approved
0.6739 Remote Similarity NPD6672 Approved
0.6731 Remote Similarity NPD5215 Approved
0.6731 Remote Similarity NPD5127 Approved
0.6731 Remote Similarity NPD6869 Approved
0.6731 Remote Similarity NPD6617 Approved
0.6731 Remote Similarity NPD5216 Approved
0.6731 Remote Similarity NPD8130 Phase 1
0.6731 Remote Similarity NPD5217 Approved
0.6731 Remote Similarity NPD6649 Approved
0.6731 Remote Similarity NPD6650 Approved
0.6731 Remote Similarity NPD6847 Approved
0.6707 Remote Similarity NPD4747 Approved
0.6706 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6705 Remote Similarity NPD4139 Approved
0.6705 Remote Similarity NPD4692 Approved
0.6699 Remote Similarity NPD6372 Approved
0.6699 Remote Similarity NPD6373 Approved
0.6667 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6882 Approved
0.6667 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6667 Remote Similarity NPD8297 Approved
0.6667 Remote Similarity NPD4058 Approved
0.6633 Remote Similarity NPD7638 Approved
0.6632 Remote Similarity NPD5133 Approved
0.6604 Remote Similarity NPD4632 Approved
0.6591 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6588 Remote Similarity NPD6942 Approved
0.6588 Remote Similarity NPD7339 Approved
0.6571 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6566 Remote Similarity NPD7639 Approved
0.6566 Remote Similarity NPD7640 Approved
0.6562 Remote Similarity NPD6001 Approved
0.6559 Remote Similarity NPD5208 Approved
0.6559 Remote Similarity NPD4518 Approved
0.6542 Remote Similarity NPD5167 Approved
0.6538 Remote Similarity NPD368 Approved
0.6489 Remote Similarity NPD6101 Approved
0.6489 Remote Similarity NPD6673 Approved
0.6489 Remote Similarity NPD6904 Approved
0.6489 Remote Similarity NPD6080 Approved
0.6489 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6481 Remote Similarity NPD6274 Approved
0.6471 Remote Similarity NPD5733 Approved
0.6471 Remote Similarity NPD4687 Approved
0.6465 Remote Similarity NPD5290 Discontinued
0.6465 Remote Similarity NPD4225 Approved
0.6456 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6436 Remote Similarity NPD5091 Approved
0.6429 Remote Similarity NPD5276 Approved
0.6429 Remote Similarity NPD7614 Phase 1
0.6429 Remote Similarity NPD4243 Approved
0.6422 Remote Similarity NPD7115 Discovery
0.6422 Remote Similarity NPD6009 Approved
0.6422 Remote Similarity NPD6317 Approved
0.6421 Remote Similarity NPD5207 Approved
0.6421 Remote Similarity NPD5692 Phase 3
0.6408 Remote Similarity NPD6008 Approved
0.6364 Remote Similarity NPD6314 Approved
0.6364 Remote Similarity NPD6335 Approved
0.6364 Remote Similarity NPD287 Approved
0.6364 Remote Similarity NPD6313 Approved
0.6354 Remote Similarity NPD6050 Approved
0.6354 Remote Similarity NPD5694 Approved
0.6354 Remote Similarity NPD8035 Phase 2
0.6354 Remote Similarity NPD8034 Phase 2
0.6354 Remote Similarity NPD6411 Approved
0.6354 Remote Similarity NPD5693 Phase 1
0.6344 Remote Similarity NPD6098 Approved
0.633 Remote Similarity NPD6868 Approved
0.6306 Remote Similarity NPD7101 Approved
0.6306 Remote Similarity NPD7100 Approved
0.6289 Remote Similarity NPD5778 Approved
0.6289 Remote Similarity NPD5779 Approved
0.6279 Remote Similarity NPD4785 Approved
0.6279 Remote Similarity NPD4784 Approved
0.6279 Remote Similarity NPD6924 Approved
0.6279 Remote Similarity NPD6926 Approved
0.6265 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6262 Remote Similarity NPD4141 Clinical (unspecified phase)
0.625 Remote Similarity NPD6054 Approved
0.625 Remote Similarity NPD6319 Approved
0.6238 Remote Similarity NPD6404 Discontinued

  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