Structure

Physi-Chem Properties

Molecular Weight:  396.38
Volume:  464.721
LogP:  8.733
LogD:  6.447
LogS:  -7.378
# Rotatable Bonds:  0
TPSA:  0.0
# H-Bond Aceptor:  0
# H-Bond Donor:  0
# Rings:  5
# Heavy Atoms:  0

MedChem Properties

QED Drug-Likeness Score:  0.359
Synthetic Accessibility Score:  4.643
Fsp3:  0.931
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:  -4.939
MDCK Permeability:  7.5042626122012734e-06
Pgp-inhibitor:  0.37
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.98
30% Bioavailability (F30%):  0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.028
Plasma Protein Binding (PPB):  97.25094604492188%
Volume Distribution (VD):  2.702
Pgp-substrate:  1.3487106561660767%

ADMET: Metabolism

CYP1A2-inhibitor:  0.097
CYP1A2-substrate:  0.508
CYP2C19-inhibitor:  0.143
CYP2C19-substrate:  0.961
CYP2C9-inhibitor:  0.185
CYP2C9-substrate:  0.195
CYP2D6-inhibitor:  0.489
CYP2D6-substrate:  0.414
CYP3A4-inhibitor:  0.91
CYP3A4-substrate:  0.876

ADMET: Excretion

Clearance (CL):  8.489
Half-life (T1/2):  0.023

ADMET: Toxicity

hERG Blockers:  0.966
Human Hepatotoxicity (H-HT):  0.154
Drug-inuced Liver Injury (DILI):  0.657
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.239
Maximum Recommended Daily Dose:  0.222
Skin Sensitization:  0.944
Carcinogencity:  0.132
Eye Corrosion:  0.908
Eye Irritation:  0.479
Respiratory Toxicity:  0.772

Download Data

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

  Natural Product: NPC469770

Natural Product ID:  NPC469770
Common Name*:   24-Nor-12-Ursene
IUPAC Name:   (4S,4aS,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,7,8,9,10,11,12,12a,14,14a-hexadecahydropicene
Synonyms:  
Standard InCHIKey:  KIGOXANJBVQEHO-KBCRJLLNSA-N
Standard InCHI:  InChI=1S/C29H48/c1-19-12-15-26(4)17-18-28(6)23(25(26)21(19)3)10-11-24-27(5)14-8-9-20(2)22(27)13-16-29(24,28)7/h10,19-22,24-25H,8-9,11-18H2,1-7H3/t19-,20+,21+,22+,24-,25+,26-,27+,28-,29-/m1/s1
SMILES:  C[C@@H]1CC[C@]2([C@@H]([C@H]1C)C1=CC[C@H]3[C@@]([C@@]1(CC2)C)(C)CC[C@@H]1[C@]3(C)CCC[C@@H]1C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1171157
PubChem CID:   49797798
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota whole plant Cholistan desert near district Bahawalpur (Punjab), Pakistan 2003-Oct PMID[20542692]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20954 Haloxylon salicornicum Species Chenopodiaceae 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
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 100.0 ug.mL-1 PMID[558125]

☑ 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 NPC469770 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
0.8824 High Similarity NPC17518
0.8824 High Similarity NPC22765
0.8276 Intermediate Similarity NPC474420
0.8276 Intermediate Similarity NPC474454
0.8276 Intermediate Similarity NPC474455
0.8269 Intermediate Similarity NPC124851
0.8235 Intermediate Similarity NPC86683
0.8182 Intermediate Similarity NPC127944
0.8095 Intermediate Similarity NPC296697
0.8095 Intermediate Similarity NPC82477
0.8095 Intermediate Similarity NPC142754
0.8095 Intermediate Similarity NPC39157
0.7969 Intermediate Similarity NPC286814
0.7937 Intermediate Similarity NPC220210
0.7937 Intermediate Similarity NPC20181
0.7931 Intermediate Similarity NPC474457
0.7931 Intermediate Similarity NPC474528
0.7931 Intermediate Similarity NPC474415
0.7931 Intermediate Similarity NPC475696
0.7895 Intermediate Similarity NPC123194
0.7843 Intermediate Similarity NPC192529
0.7797 Intermediate Similarity NPC469769
0.7727 Intermediate Similarity NPC190035
0.7692 Intermediate Similarity NPC202189
0.7667 Intermediate Similarity NPC475716
0.7647 Intermediate Similarity NPC193180
0.7612 Intermediate Similarity NPC474488
0.7547 Intermediate Similarity NPC114239
0.7547 Intermediate Similarity NPC241784
0.7547 Intermediate Similarity NPC13991
0.7547 Intermediate Similarity NPC296337
0.7463 Intermediate Similarity NPC225467
0.7451 Intermediate Similarity NPC103290
0.7358 Intermediate Similarity NPC248411
0.7308 Intermediate Similarity NPC190232
0.7308 Intermediate Similarity NPC105246
0.7288 Intermediate Similarity NPC470893
0.7286 Intermediate Similarity NPC27765
0.7286 Intermediate Similarity NPC122418
0.7286 Intermediate Similarity NPC106364
0.7286 Intermediate Similarity NPC290598
0.7286 Intermediate Similarity NPC120098
0.7286 Intermediate Similarity NPC265328
0.7286 Intermediate Similarity NPC30590
0.7241 Intermediate Similarity NPC474416
0.7231 Intermediate Similarity NPC222366
0.7231 Intermediate Similarity NPC476039
0.7231 Intermediate Similarity NPC286669
0.7188 Intermediate Similarity NPC469662
0.7183 Intermediate Similarity NPC157996
0.7183 Intermediate Similarity NPC34177
0.7183 Intermediate Similarity NPC40394
0.7183 Intermediate Similarity NPC101475
0.7164 Intermediate Similarity NPC138409
0.7164 Intermediate Similarity NPC184919
0.7143 Intermediate Similarity NPC138374
0.7143 Intermediate Similarity NPC17810
0.7143 Intermediate Similarity NPC34700
0.7121 Intermediate Similarity NPC197805
0.7121 Intermediate Similarity NPC176107
0.7083 Intermediate Similarity NPC158662
0.7083 Intermediate Similarity NPC474989
0.7083 Intermediate Similarity NPC98386
0.7083 Intermediate Similarity NPC470396
0.7083 Intermediate Similarity NPC196753
0.7083 Intermediate Similarity NPC300499
0.7083 Intermediate Similarity NPC99168
0.7083 Intermediate Similarity NPC253807
0.7083 Intermediate Similarity NPC22955
0.7083 Intermediate Similarity NPC230295
0.7069 Intermediate Similarity NPC473728
0.7042 Intermediate Similarity NPC112680
0.7031 Intermediate Similarity NPC202118
0.7031 Intermediate Similarity NPC197238
0.7018 Intermediate Similarity NPC200129
0.7015 Intermediate Similarity NPC94192
0.7015 Intermediate Similarity NPC20610
0.7 Intermediate Similarity NPC100334
0.7 Intermediate Similarity NPC211641
0.6986 Remote Similarity NPC53744
0.6986 Remote Similarity NPC16394
0.6986 Remote Similarity NPC291379
0.6984 Remote Similarity NPC317778
0.697 Remote Similarity NPC92327
0.6935 Remote Similarity NPC60772
0.6912 Remote Similarity NPC182815
0.6909 Remote Similarity NPC49088
0.6901 Remote Similarity NPC293803
0.6892 Remote Similarity NPC295131
0.6892 Remote Similarity NPC267517
0.6875 Remote Similarity NPC469728
0.6863 Remote Similarity NPC297643
0.6863 Remote Similarity NPC229262
0.6863 Remote Similarity NPC139717
0.6818 Remote Similarity NPC163678
0.6812 Remote Similarity NPC35734
0.6812 Remote Similarity NPC282593
0.6812 Remote Similarity NPC475728
0.6812 Remote Similarity NPC214770
0.6812 Remote Similarity NPC159577
0.6812 Remote Similarity NPC477856
0.6806 Remote Similarity NPC292589
0.6806 Remote Similarity NPC476308
0.68 Remote Similarity NPC3915
0.68 Remote Similarity NPC162632
0.68 Remote Similarity NPC242350
0.68 Remote Similarity NPC108476
0.68 Remote Similarity NPC263272
0.68 Remote Similarity NPC290495
0.68 Remote Similarity NPC274050
0.68 Remote Similarity NPC267691
0.68 Remote Similarity NPC195334
0.6786 Remote Similarity NPC323445
0.6774 Remote Similarity NPC11130
0.6769 Remote Similarity NPC474086
0.6765 Remote Similarity NPC216460
0.6765 Remote Similarity NPC32055
0.6761 Remote Similarity NPC219232
0.6761 Remote Similarity NPC128346
0.6724 Remote Similarity NPC476681
0.6719 Remote Similarity NPC176621
0.6719 Remote Similarity NPC311809
0.6716 Remote Similarity NPC279434
0.6716 Remote Similarity NPC259156
0.6716 Remote Similarity NPC323005
0.6716 Remote Similarity NPC43300
0.6716 Remote Similarity NPC242945
0.6714 Remote Similarity NPC470078
0.6714 Remote Similarity NPC265789
0.6714 Remote Similarity NPC21773
0.6714 Remote Similarity NPC115023
0.6712 Remote Similarity NPC107039
0.6712 Remote Similarity NPC472805
0.6712 Remote Similarity NPC90979
0.6712 Remote Similarity NPC471897
0.6712 Remote Similarity NPC471899
0.6711 Remote Similarity NPC304285
0.6711 Remote Similarity NPC69101
0.6711 Remote Similarity NPC286786
0.6711 Remote Similarity NPC47763
0.6711 Remote Similarity NPC163236
0.6711 Remote Similarity NPC310989
0.6711 Remote Similarity NPC251779
0.6667 Remote Similarity NPC34764
0.6667 Remote Similarity NPC190810
0.6667 Remote Similarity NPC76145
0.6667 Remote Similarity NPC177470
0.6667 Remote Similarity NPC139397
0.6623 Remote Similarity NPC253402
0.6623 Remote Similarity NPC132386
0.6623 Remote Similarity NPC159168
0.6623 Remote Similarity NPC70834
0.6623 Remote Similarity NPC200752
0.6622 Remote Similarity NPC110094
0.6622 Remote Similarity NPC280654
0.6622 Remote Similarity NPC260385
0.6622 Remote Similarity NPC72507
0.6622 Remote Similarity NPC115515
0.662 Remote Similarity NPC303613
0.662 Remote Similarity NPC251705
0.662 Remote Similarity NPC474228
0.662 Remote Similarity NPC471799
0.662 Remote Similarity NPC182717
0.662 Remote Similarity NPC474743
0.6618 Remote Similarity NPC193770
0.6615 Remote Similarity NPC60565
0.6604 Remote Similarity NPC227632
0.6604 Remote Similarity NPC62086
0.6604 Remote Similarity NPC78551
0.6579 Remote Similarity NPC116202
0.6575 Remote Similarity NPC89294
0.6571 Remote Similarity NPC265782
0.6571 Remote Similarity NPC145498
0.6571 Remote Similarity NPC251929
0.6571 Remote Similarity NPC2634
0.6571 Remote Similarity NPC260040
0.6571 Remote Similarity NPC40574
0.6571 Remote Similarity NPC307176
0.6567 Remote Similarity NPC107258
0.6562 Remote Similarity NPC472827
0.6545 Remote Similarity NPC86538
0.6545 Remote Similarity NPC60556
0.6545 Remote Similarity NPC109813
0.6538 Remote Similarity NPC312660
0.6538 Remote Similarity NPC96095
0.6538 Remote Similarity NPC238992
0.6538 Remote Similarity NPC180834
0.6533 Remote Similarity NPC199595
0.6533 Remote Similarity NPC231431
0.6528 Remote Similarity NPC476904
0.6528 Remote Similarity NPC471797
0.6522 Remote Similarity NPC188292
0.6522 Remote Similarity NPC310992
0.6522 Remote Similarity NPC208999
0.6522 Remote Similarity NPC160209
0.6522 Remote Similarity NPC260474
0.6522 Remote Similarity NPC476945
0.6515 Remote Similarity NPC283247
0.6508 Remote Similarity NPC173815
0.6508 Remote Similarity NPC470369

  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 NPC469770 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
0.7308 Intermediate Similarity NPD1799 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8262 Approved
0.6986 Remote Similarity NPD7645 Phase 2
0.6812 Remote Similarity NPD6938 Clinical (unspecified phase)
0.6812 Remote Similarity NPD6939 Phase 2
0.6765 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6714 Remote Similarity NPD4243 Approved
0.6667 Remote Similarity NPD319 Phase 1
0.6667 Remote Similarity NPD4137 Phase 3
0.6571 Remote Similarity NPD4747 Approved
0.6571 Remote Similarity NPD4691 Approved
0.6528 Remote Similarity NPD4784 Approved
0.6528 Remote Similarity NPD4785 Approved
0.6438 Remote Similarity NPD7339 Approved
0.6438 Remote Similarity NPD6942 Approved
0.6364 Remote Similarity NPD8028 Phase 2
0.6301 Remote Similarity NPD4058 Approved
0.6301 Remote Similarity NPD5733 Approved
0.6216 Remote Similarity NPD4190 Phase 3
0.6216 Remote Similarity NPD5275 Approved
0.6133 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6081 Remote Similarity NPD4687 Approved
0.6027 Remote Similarity NPD5276 Approved
0.6026 Remote Similarity NPD7525 Registered
0.6 Remote Similarity NPD7515 Phase 2
0.5972 Remote Similarity NPD6922 Approved
0.5972 Remote Similarity NPD6923 Approved
0.5909 Remote Similarity NPD287 Approved
0.5897 Remote Similarity NPD4195 Approved
0.589 Remote Similarity NPD7143 Approved
0.589 Remote Similarity NPD7144 Approved
0.5862 Remote Similarity NPD7748 Approved
0.5862 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5862 Remote Similarity NPD7900 Approved
0.5846 Remote Similarity NPD4219 Approved
0.5833 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5811 Remote Similarity NPD7150 Approved
0.5811 Remote Similarity NPD7151 Approved
0.5811 Remote Similarity NPD7152 Approved
0.5765 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5732 Remote Similarity NPD4786 Approved
0.5679 Remote Similarity NPD3667 Approved
0.5679 Remote Similarity NPD4221 Approved
0.5679 Remote Similarity NPD4223 Phase 3
0.5667 Remote Similarity NPD7902 Approved
0.5663 Remote Similarity NPD5329 Approved
0.5658 Remote Similarity NPD6924 Approved
0.5658 Remote Similarity NPD6926 Approved
0.5625 Remote Similarity NPD4695 Discontinued
0.56 Remote Similarity NPD5365 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