Structure

Physi-Chem Properties

Molecular Weight:  502.32
Volume:  528.758
LogP:  4.49
LogD:  4.017
LogS:  -4.822
# Rotatable Bonds:  0
TPSA:  57.69
# H-Bond Aceptor:  5
# H-Bond Donor:  0
# Rings:  8
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.45
Synthetic Accessibility Score:  7.295
Fsp3:  0.781
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.496
MDCK Permeability:  7.2015927798929624e-06
Pgp-inhibitor:  0.049
Pgp-substrate:  0.989
Human Intestinal Absorption (HIA):  0.231
20% Bioavailability (F20%):  0.216
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.911
Plasma Protein Binding (PPB):  57.91099548339844%
Volume Distribution (VD):  3.517
Pgp-substrate:  31.35601234436035%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.127
CYP2C19-inhibitor:  0.722
CYP2C19-substrate:  0.915
CYP2C9-inhibitor:  0.888
CYP2C9-substrate:  0.158
CYP2D6-inhibitor:  0.196
CYP2D6-substrate:  0.216
CYP3A4-inhibitor:  0.945
CYP3A4-substrate:  0.919

ADMET: Excretion

Clearance (CL):  14.261
Half-life (T1/2):  0.227

ADMET: Toxicity

hERG Blockers:  0.395
Human Hepatotoxicity (H-HT):  0.253
Drug-inuced Liver Injury (DILI):  0.121
AMES Toxicity:  0.039
Rat Oral Acute Toxicity:  0.952
Maximum Recommended Daily Dose:  0.967
Skin Sensitization:  0.464
Carcinogencity:  0.899
Eye Corrosion:  0.003
Eye Irritation:  0.008
Respiratory Toxicity:  0.936

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

  Natural Product: NPC143173

Natural Product ID:  NPC143173
Common Name*:   Complanadines C
IUPAC Name:   n.a.
Synonyms:   Complanadines C
Standard InCHIKey:  WIKLMEPVJASSRU-YSXVRAOPSA-N
Standard InCHI:  InChI=1S/C32H42N2O3/c1-18-9-20-12-28(35)24-5-3-7-33-17-22(11-26(20)31(24,33)15-18)23-14-27-21-10-19(2)16-32(27)25(29(36)13-21)6-4-8-34(32)30(23)37/h14,17-21,24-27H,3-13,15-16H2,1-2H3/t18-,19-,20+,21+,24-,25-,26-,27-,31+,32+/m1/s1
SMILES:  C[C@@H]1C[C@H]2CC(=O)[C@H]3CCCN4C=C(C[C@H]2[C@]34C1)C1=C[C@@H]2[C@H]3C[C@@H](C)C[C@@]42[C@H](CCCN4C1=O)C(=O)C3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL388789
PubChem CID:   44421961
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
NPO19825 Litsea japonica Species Lauraceae Eukaryota leaves n.a. n.a. PMID[14575444]
NPO16934 Nephthea chabrolii Species Nephtheidae Eukaryota n.a. Formosan soft coral n.a. PMID[16309317]
NPO7688 Artemisia selengensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO19076 Gaillardia pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19364 Aconitum chasmanthum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19364 Aconitum chasmanthum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19076 Gaillardia pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19076 Gaillardia pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18023 Vitex quinata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21360 Cordia corymbosa Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19076 Gaillardia pulchella Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19869 Fusicolla aquaeductuum Species Nectriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19565 Crocus chrysanthus Species Iridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15450 Minuria leptophylla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19364 Aconitum chasmanthum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16934 Nephthea chabrolii Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18518 Haematomma nemetzii Species Haematommataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19825 Litsea japonica Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18499 Podium complanatum Species Sphecidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11060 Doris luteorosea Species Dorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9799 Hebeloma longicaudum Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17577 Azalea ovata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO19234 Hymenopappus newberryi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19298 Gerbera crocea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17341 Gambeya africana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7688 Artemisia selengensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17887 Penstemon centranthifolius Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19696 Othonna quercifolia Species Asteraceae 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
NPT137 Cell Line L1210 Mus musculus IC50 > 10.0 ug.mL-1 PMID[537649]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 0.52 ug.mL-1 PMID[537649]
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 2.05 ug.mL-1 PMID[537649]

☑ 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 NPC143173 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
0.6667 Remote Similarity NPC474001
0.6607 Remote Similarity NPC473056
0.6606 Remote Similarity NPC311769
0.6606 Remote Similarity NPC182106
0.6606 Remote Similarity NPC76283
0.6577 Remote Similarity NPC259252
0.6545 Remote Similarity NPC157479
0.6514 Remote Similarity NPC135639
0.6514 Remote Similarity NPC143344
0.6514 Remote Similarity NPC234822
0.6514 Remote Similarity NPC61321
0.6514 Remote Similarity NPC78058
0.6491 Remote Similarity NPC247316
0.6471 Remote Similarity NPC58200
0.6455 Remote Similarity NPC147513
0.6423 Remote Similarity NPC274895
0.6355 Remote Similarity NPC268580
0.6355 Remote Similarity NPC127430
0.6355 Remote Similarity NPC120699
0.633 Remote Similarity NPC255430
0.6293 Remote Similarity NPC476754
0.6226 Remote Similarity NPC320667
0.6226 Remote Similarity NPC214125
0.6216 Remote Similarity NPC207048
0.621 Remote Similarity NPC476918
0.6207 Remote Similarity NPC476753
0.6207 Remote Similarity NPC476752
0.6179 Remote Similarity NPC476328
0.6179 Remote Similarity NPC476926
0.6168 Remote Similarity NPC308050
0.6132 Remote Similarity NPC63284
0.6091 Remote Similarity NPC90150
0.6087 Remote Similarity NPC249312
0.608 Remote Similarity NPC476920
0.608 Remote Similarity NPC476276
0.608 Remote Similarity NPC476919
0.6077 Remote Similarity NPC473573
0.6076 Remote Similarity NPC475248
0.6076 Remote Similarity NPC63047
0.6071 Remote Similarity NPC116881
0.6071 Remote Similarity NPC57163
0.6036 Remote Similarity NPC215474
0.6033 Remote Similarity NPC477964
0.6019 Remote Similarity NPC244256
0.6019 Remote Similarity NPC86452
0.6 Remote Similarity NPC190035
0.6 Remote Similarity NPC246904
0.6 Remote Similarity NPC250632
0.6 Remote Similarity NPC184033
0.5985 Remote Similarity NPC79698
0.5983 Remote Similarity NPC145707
0.5968 Remote Similarity NPC469958
0.5963 Remote Similarity NPC28529
0.5938 Remote Similarity NPC44733
0.5935 Remote Similarity NPC152718
0.5935 Remote Similarity NPC226509
0.5909 Remote Similarity NPC474006
0.5859 Remote Similarity NPC63511
0.5854 Remote Similarity NPC77703
0.5854 Remote Similarity NPC34193
0.5849 Remote Similarity NPC225467
0.5845 Remote Similarity NPC473962
0.584 Remote Similarity NPC476921
0.5827 Remote Similarity NPC24596
0.581 Remote Similarity NPC286814
0.5783 Remote Similarity NPC286994
0.5775 Remote Similarity NPC126458
0.5766 Remote Similarity NPC267203
0.5766 Remote Similarity NPC77890
0.5766 Remote Similarity NPC132858
0.5739 Remote Similarity NPC34811
0.5738 Remote Similarity NPC91036
0.5714 Remote Similarity NPC142754
0.5714 Remote Similarity NPC296697
0.5714 Remote Similarity NPC39157
0.5714 Remote Similarity NPC82477
0.5691 Remote Similarity NPC140685
0.5669 Remote Similarity NPC230677
0.5669 Remote Similarity NPC185929
0.5669 Remote Similarity NPC167336
0.5656 Remote Similarity NPC247220
0.5648 Remote Similarity NPC474488
0.5641 Remote Similarity NPC43308
0.5631 Remote Similarity NPC476559
0.5631 Remote Similarity NPC206660
0.5619 Remote Similarity NPC220210
0.5619 Remote Similarity NPC20181
0.56 Remote Similarity NPC476922
0.56 Remote Similarity NPC100810
0.56 Remote Similarity NPC144714

  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 NPC143173 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
0.6029 Remote Similarity NPD3547 Approved
0.6029 Remote Similarity NPD3550 Clinical (unspecified phase)
0.6029 Remote Similarity NPD3549 Approved
0.5968 Remote Similarity NPD7812 Clinical (unspecified phase)
0.5946 Remote Similarity NPD8028 Phase 2
0.592 Remote Similarity NPD7333 Discontinued
0.5917 Remote Similarity NPD5349 Clinical (unspecified phase)
0.5909 Remote Similarity NPD7679 Phase 2
0.5909 Remote Similarity NPD7155 Clinical (unspecified phase)
0.58 Remote Similarity NPD8239 Clinical (unspecified phase)
0.5766 Remote Similarity NPD529 Approved
0.5758 Remote Similarity NPD3551 Approved
0.5705 Remote Similarity NPD6566 Discontinued
0.5702 Remote Similarity NPD3527 Clinical (unspecified phase)
0.5664 Remote Similarity NPD2754 Discontinued
0.5646 Remote Similarity NPD7541 Clinical (unspecified phase)
0.563 Remote Similarity NPD6934 Discontinued
0.562 Remote Similarity NPD5769 Clinical (unspecified phase)
0.5615 Remote Similarity NPD4063 Clinical (unspecified phase)

  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